9,10-Bis(dichloro­ethyl­amino­meth­yl)anthracene

The title compound, C₂₄H₂₈Cl₄N₂, was obtained by the reaction of 9,10-dichloro­methyl­anthracene and dichloro­ethyl­amine. The mol­ecule is centrosymmetric, with the substituents above and below the anthracene plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.089
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT410_ALERT_2_C Short Intra H...H Contact  H5A    ..  H11     ..       1.92 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

9,10-Bis(dichloroethylaminomethyl)anthracene

Crystal data

C24H28Cl4N2	Dx = 1.358 Mg m^−3
Mr = 486.28	Melting point: 162 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3505 (12) Å	Cell parameters from 2134 reflections
b = 10.6953 (10) Å	θ = 3.1–25.1°
c = 8.3412 (8) Å	µ = 0.51 mm^−1
β = 92.879 (1)°	T = 293 K
V = 1189.52 (19) Å^3	Block, yellow
Z = 2	0.22 × 0.20 × 0.16 mm
F(000) = 508

Data collection

Bruker SMART CCD area-detector diffractometer	2093 independent reflections
Radiation source: fine-focus sealed tube	1669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.891, Tmax = 0.921	k = −12→12
6278 measured reflections	l = −7→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.408P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2093 reflections	Δρmax = 0.25 e Å^−3
137 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0134 (15)

Special details

Experimental. ¹H NMR (300 MHZ, CDCl₃, δ, p.p.m.): 3.483 (t, 8H, CH₂), 3.992 (t, 8H, CH₂), 4.70 (s, 4H, CH₂), 7.50–7.55 (m, 4H, AnH), 8.34–8.39 (m, 4H, AnH).

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.31311 (4)	0.58536 (6)	0.11368 (6)	0.0739 (2)
Cl2	0.43369 (5)	0.28429 (6)	0.63139 (8)	0.0828 (2)
N1	0.28120 (10)	0.51499 (14)	0.58006 (17)	0.0439 (4)
C1	0.30892 (18)	0.5031 (2)	0.2998 (2)	0.0631 (6)
H1A	0.2608	0.4354	0.2882	0.076*
H1B	0.3742	0.4670	0.3268	0.076*
C2	0.28016 (14)	0.58725 (18)	0.4317 (2)	0.0480 (4)
H2A	0.3271	0.6562	0.4430	0.058*
H2B	0.2137	0.6212	0.4078	0.058*
C3	0.37449 (14)	0.5251 (2)	0.6764 (2)	0.0539 (5)
H3A	0.3685	0.5925	0.7531	0.065*
H3B	0.4280	0.5467	0.6069	0.065*
C4	0.40266 (15)	0.4070 (2)	0.7658 (3)	0.0649 (6)
H4A	0.3471	0.3806	0.8283	0.078*
H4B	0.4596	0.4234	0.8395	0.078*
C5	0.19394 (12)	0.53235 (19)	0.6777 (2)	0.0470 (4)
H5A	0.1969	0.6153	0.7247	0.056*
H5B	0.1974	0.4722	0.7648	0.056*
C6	0.09445 (12)	0.51724 (16)	0.5842 (2)	0.0413 (4)
C7	0.06525 (12)	0.39764 (16)	0.5287 (2)	0.0417 (4)
C8	0.12792 (14)	0.29072 (18)	0.5557 (2)	0.0513 (5)
H8	0.1903	0.3007	0.6089	0.062*
C9	0.09895 (16)	0.17556 (19)	0.5063 (2)	0.0587 (5)
H9	0.1411	0.1075	0.5266	0.070*
C10	0.00580 (17)	0.15792 (19)	0.4244 (3)	0.0593 (5)
H10	−0.0134	0.0783	0.3903	0.071*
C11	−0.05615 (15)	0.25555 (18)	0.3946 (2)	0.0527 (5)
H11	−0.1177	0.2416	0.3403	0.063*
C12	−0.03016 (12)	0.38025 (16)	0.4440 (2)	0.0415 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0780 (4)	0.1004 (5)	0.0436 (3)	0.0086 (3)	0.0058 (2)	0.0132 (3)
Cl2	0.0764 (4)	0.0783 (4)	0.0935 (5)	0.0169 (3)	0.0014 (3)	0.0056 (3)
N1	0.0356 (8)	0.0567 (9)	0.0393 (8)	−0.0015 (7)	0.0006 (6)	0.0055 (7)
C1	0.0807 (15)	0.0655 (13)	0.0428 (11)	0.0061 (11)	0.0008 (10)	0.0045 (9)
C2	0.0444 (10)	0.0538 (11)	0.0459 (10)	0.0017 (8)	0.0045 (8)	0.0063 (9)
C3	0.0380 (10)	0.0707 (13)	0.0526 (11)	−0.0048 (9)	−0.0024 (8)	−0.0009 (10)
C4	0.0466 (11)	0.0925 (17)	0.0547 (12)	0.0057 (11)	−0.0056 (9)	0.0074 (11)
C5	0.0412 (10)	0.0599 (11)	0.0399 (10)	−0.0022 (8)	0.0012 (7)	−0.0007 (9)
C6	0.0366 (9)	0.0512 (10)	0.0362 (9)	−0.0028 (8)	0.0039 (7)	0.0007 (8)
C7	0.0382 (9)	0.0486 (10)	0.0387 (9)	0.0001 (8)	0.0065 (7)	0.0024 (8)
C8	0.0462 (10)	0.0543 (11)	0.0535 (11)	0.0043 (9)	0.0034 (8)	0.0044 (9)
C9	0.0625 (13)	0.0511 (12)	0.0631 (13)	0.0113 (10)	0.0090 (10)	0.0051 (10)
C10	0.0723 (14)	0.0438 (11)	0.0623 (13)	−0.0035 (10)	0.0084 (11)	−0.0035 (10)
C11	0.0512 (11)	0.0528 (11)	0.0541 (12)	−0.0083 (9)	0.0026 (9)	−0.0029 (9)
C12	0.0396 (9)	0.0469 (10)	0.0385 (9)	−0.0036 (8)	0.0074 (7)	−0.0006 (8)

Geometric parameters (Å, º)

Cl1—C1	1.787 (2)	C5—H5A	0.970
Cl2—C4	1.788 (2)	C5—H5B	0.970
N1—C3	1.452 (2)	C6—C12^i	1.405 (2)
N1—C2	1.459 (2)	C6—C7	1.409 (2)
N1—C5	1.466 (2)	C7—C8	1.428 (3)
C1—C2	1.487 (3)	C7—C12	1.437 (2)
C1—H1A	0.970	C8—C9	1.349 (3)
C1—H1B	0.970	C8—H8	0.930
C2—H2A	0.970	C9—C10	1.401 (3)
C2—H2B	0.970	C9—H9	0.930
C3—C4	1.505 (3)	C10—C11	1.347 (3)
C3—H3A	0.970	C10—H10	0.930
C3—H3B	0.970	C11—C12	1.433 (3)
C4—H4A	0.970	C11—H11	0.930
C4—H4B	0.970	C12—C6^i	1.405 (2)
C5—C6	1.515 (2)
C3—N1—C2	113.68 (14)	N1—C5—C6	113.66 (14)
C3—N1—C5	111.51 (14)	N1—C5—H5A	108.8
C2—N1—C5	115.48 (14)	C6—C5—H5A	108.8
C2—C1—Cl1	111.44 (15)	N1—C5—H5B	108.8
C2—C1—H1A	109.3	C6—C5—H5B	108.8
Cl1—C1—H1A	109.3	H5A—C5—H5B	107.7
C2—C1—H1B	109.3	C12^i—C6—C7	119.79 (15)
Cl1—C1—H1B	109.3	C12^i—C6—C5	121.04 (16)
H1A—C1—H1B	108.0	C7—C6—C5	119.15 (15)
N1—C2—C1	108.39 (16)	C6—C7—C8	121.65 (16)
N1—C2—H2A	110.0	C6—C7—C12	120.20 (15)
C1—C2—H2A	110.0	C8—C7—C12	118.15 (16)
N1—C2—H2B	110.0	C9—C8—C7	121.73 (18)
C1—C2—H2B	110.0	C9—C8—H8	119.1
H2A—C2—H2B	108.4	C7—C8—H8	119.1
N1—C3—C4	113.46 (16)	C8—C9—C10	120.38 (19)
N1—C3—H3A	108.9	C8—C9—H9	119.8
C4—C3—H3A	108.9	C10—C9—H9	119.8
N1—C3—H3B	108.9	C11—C10—C9	120.46 (19)
C4—C3—H3B	108.9	C11—C10—H10	119.8
H3A—C3—H3B	107.7	C9—C10—H10	119.8
C3—C4—Cl2	111.43 (15)	C10—C11—C12	122.05 (18)
C3—C4—H4A	109.3	C10—C11—H11	119.0
Cl2—C4—H4A	109.3	C12—C11—H11	119.0
C3—C4—H4B	109.3	C6^i—C12—C11	122.74 (16)
Cl2—C4—H4B	109.3	C6^i—C12—C7	120.02 (15)
H4A—C4—H4B	108.0	C11—C12—C7	117.23 (16)
C3—N1—C2—C1	95.39 (19)	C5—C6—C7—C12	178.09 (15)
C5—N1—C2—C1	−133.89 (17)	C6—C7—C8—C9	178.25 (18)
Cl1—C1—C2—N1	−178.33 (13)	C12—C7—C8—C9	−1.0 (3)
C2—N1—C3—C4	−146.04 (17)	C7—C8—C9—C10	0.7 (3)
C5—N1—C3—C4	81.3 (2)	C8—C9—C10—C11	−0.3 (3)
N1—C3—C4—Cl2	67.44 (19)	C9—C10—C11—C12	0.2 (3)
C3—N1—C5—C6	−177.53 (15)	C10—C11—C12—C6^i	−179.14 (18)
C2—N1—C5—C6	50.7 (2)	C10—C11—C12—C7	−0.5 (3)
N1—C5—C6—C12^i	−112.04 (18)	C6—C7—C12—C6^i	0.3 (3)
N1—C5—C6—C7	69.6 (2)	C8—C7—C12—C6^i	179.56 (15)
C12^i—C6—C7—C8	−179.54 (16)	C6—C7—C12—C11	−178.41 (16)
C5—C6—C7—C8	−1.2 (2)	C8—C7—C12—C11	0.9 (2)
C12^i—C6—C7—C12	−0.3 (3)

Symmetry code: (i) −x, −y+1, −z+1.