Bis(phenanthridinium) hexa­chloridoplatinate(IV) dimethyl sulfoxide disolvate

The asymmetric unit of the title compound, (C₁₃H₁₀N)₂[PtCl₆]·2C₂H₆OS, contains one independent protonated phenanthridinium cation, half of a centrosymmetric [PtCl₆]²⁻anion and one dimethyl sulfoxide solvent mol­ecule. Intra­molecular N—H...O and inter­molecular C—H...Cl hydrogen-bonding inter­actions seem to be effective in the stabilization of the structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.045
• wR factor = 0.096
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   295.000
            Value of melting point given =     0.000
PLAT083_ALERT_2_C SHELXL Second Parameter in WGHT unusually Large.      16.00
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Pt1
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_4_C Crystal Probably too Large for Beam Size .......       0.80 mm

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: The synthesis and characterization of the compound has been made by N. Safari, V. Amani and A. Abedi. The diffraction data of the compound has been collected by O. B\"uy\"ukg\"ung\"or. The crystallography and preparation for publication have been carried out by S. Karaca and M. Akkurt.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

S1. Comment

In recent years, there has been considerable interest in proton transfer systems and their structures (Zafar et al., 2000; Abedi et al., 2008). Several proton transfer systems using H₂[PtCl₆] with proton acceptor molecules, such as [HpyBr-3]₂[PtCl₆].2H₂O, (II), and [HpyI-3]₂[PtCl₆].2H₂O, (III), (Zordan et al., 2005), [BMIM]₂[PtCl₆], (IV), and [EMIM]₂[PtCl₆], (V), (Hasan et al., 2001), {(DABCO)H₂[PtCl₆]}, (VI), (Juan et al.,1998), {p-C₆H₄(CH₂ImMe)₂[PtCl₆]}, (VII), (Li & Liu, 2003), [het][PtCl₆].2H₂O, (VIII), (Hu et al., 2003), [9-MeGuaH]₂[PtCl₆].2H₂O, (IX), (Terzis & Mentzafos, 1983), [HpyCl-3]₃[PtCl₆]Cl, (X), (Zordan et al., 2004), [2,9-dmphen.H]₂[PtCl₆], (XI), (Yousefi et al., 2007), [H₂DA18C6][PtCl₆].2H₂O, (XII), (Yousefi et al., 2007a), [2,6-dmpy.H]₂[PtCl₆], (XIII), (Amani et al., 2008), [TBA]₃[PtCl₆]Cl, (XIV), (Yousefi et al., 2007b) and [2,4,6-dmpy.H]₂[PtCl₆], (XV), (Kalateh et al., 2008) [where hpy is halo-pyridinium, BMIM⁺ is 1-n-butyl-3-methylimidazolium, EMIM⁺ is1-ethyl-3-methylimidazolium, DABCO is 1,4-diazabicyclooctane, Im is imidazolium, het is 2-(α-hydroxyethyl) thiamine, 9-MeGuaH is 9-methylguaninium, 2,9-dmphen.H is 2,9-dimethyl-1,10-phenanthrolinium, H₂DA18C6 is 1,10-Diazonia-18-crown-6,2,6-dmpy.H is 2,6-dimethylpyridinium, TBA is tribenzylammonium and 2,4,6-dmpy.H is 2,4,6-dimethylpyridinium] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of the title compound (I), (Fig. 1) contains one independent protonated phenanthridinium cation and one half PtCl^2-₆ anion, and one dimethyl sulfoxide solvate. The Pt ion has an octahedral coordination (Table 1). In cation, the bond lengths and angles are normal. In PtCl^2-₆ anion, the Pt—Cl bond lengths and Cl—Pt—Cl bond angles are also within normal ranges, as in (III) to (XV).

The intramolecular N—H···O and intermolecular C—H···Cl hydrogen bonding interactions (Table 1) seem to be effective in the stabilization of the structure (Fig. 2).

Related literature

For related literature, see: Abedi et al. (2008); Amani et al. (2008); Hasan et al. (2001); Hu et al. (2003); Juan et al. (1998); Kalateh et al. (2008); Li & Liu (2003); Terzis & Mentzafos (1983); Yousefi, Ahmadi et al. (2007); Yousefi, Teimouri et al. (2007a,b); Zafar et al. (2000); Zordan & Brammer (2004); Zordan et al. (2005).

S2. Experimental

For the preparation of the title compound, (I), a solution of phenanthridine (0.27 g,1.48 mmol) in ethanol (10 ml) was added to a solution of H₂PtCl₆.6H₂O, (0.38 g, 0.74 mmol) in ethanol (10 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by ethanol diffusion in a solution of orange precipitated in DMSO after one week [yield; 0.51 g, 74.7%, m.p. < 573 K].

S3. Refinement

The C-bound H-atoms were placed in calculated positions with C—H = 0.93 Å and C—H 0.96 Å, and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2U_eq (ring C) and U_iso(H) = 1.5U_eq (methyl C). The N-bound H-atom was found from a difference Fourier map and refined freely. In the final Fourier map, the highest and deepest peaks were located 1.13 and 0.47 Å from atom S1, respectively.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. ORTEP-3 view of the title molecule, with the atom-numbering scheme and 50% probability displacement ellipsoids
	Fig. 2. View of the packing and hydrogen bonding interactions. For clarity, H atoms not involved in hydrogen bonds have been omitted.

Bis(phenanthridinium) hexachloridoplatinate(IV) dimethyl sulfoxide disolvate

Crystal data

(C13H10N)2[PtCl6]·2C2H6OS	F(000) = 1816
Mr = 924.50	Dx = 1.828 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 46774 reflections
a = 24.3695 (11) Å	θ = 1.4–27.3°
b = 7.9061 (3) Å	µ = 4.81 mm^−1
c = 17.4322 (6) Å	T = 295 K
V = 3358.6 (2) Å^3	Prism, yellow
Z = 4	0.80 × 0.35 × 0.09 mm

Data collection

Stoe IPDS-2 diffractometer	3533 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2992 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.106
Detector resolution: 6.67 pixels mm^-1	θmax = 26.8°, θmin = 1.7°
ω scans	h = −30→30
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→10
Tmin = 0.114, Tmax = 0.671	l = −22→20
33029 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0192P)^2 + 15.6678P] where P = (Fo^2 + 2Fc^2)/3
3533 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 2.20 e Å^−3
0 restraints	Δρmin = −1.01 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
N1	0.3026 (2)	0.7872 (7)	0.9147 (3)	0.0450 (17)
C1	0.2284 (2)	0.9236 (7)	0.8111 (3)	0.0380 (17)
C2	0.1935 (3)	0.9962 (8)	0.7558 (4)	0.051 (2)
C3	0.2148 (3)	1.0700 (9)	0.6916 (4)	0.057 (3)
C4	0.2715 (3)	1.0779 (9)	0.6797 (4)	0.059 (3)
C5	0.3067 (3)	1.0107 (9)	0.7327 (4)	0.052 (2)
C6	0.2855 (2)	0.9333 (8)	0.7987 (3)	0.0417 (17)
C7	0.3209 (3)	0.8621 (8)	0.8539 (4)	0.048 (2)
C8	0.2463 (3)	0.7702 (8)	0.9301 (3)	0.0403 (17)
C9	0.2309 (3)	0.6859 (9)	0.9972 (4)	0.049 (2)
C10	0.1764 (3)	0.6683 (9)	1.0126 (4)	0.056 (2)
C11	0.1378 (3)	0.7337 (9)	0.9637 (5)	0.060 (3)
C12	0.1527 (3)	0.8186 (8)	0.8981 (4)	0.051 (2)
C13	0.2085 (2)	0.8394 (7)	0.8797 (3)	0.0383 (17)
S1	0.42059 (10)	0.6422 (3)	1.04509 (15)	0.0776 (8)
O1	0.3643 (2)	0.7031 (10)	1.0318 (4)	0.099 (3)
C14	0.4292 (4)	0.6686 (12)	1.1452 (5)	0.080 (3)
C15	0.4641 (5)	0.7984 (15)	1.0151 (6)	0.111 (5)
Pt1	1.00000	0.67772 (4)	0.25000	0.0358 (1)
Cl1	0.95124 (7)	0.8825 (2)	0.18305 (10)	0.0533 (5)
Cl2	1.04739 (6)	0.4687 (2)	0.31590 (9)	0.0509 (5)
Cl3	1.06735 (7)	0.6805 (2)	0.15568 (9)	0.0525 (5)
HN1	0.325 (4)	0.753 (11)	0.948 (5)	0.09 (3)*
H2	0.15570	0.99380	0.76300	0.0610*
H3	0.19120	1.11580	0.65520	0.0690*
H4	0.28520	1.12890	0.63560	0.0710*
H5	0.34440	1.01640	0.72490	0.0620*
H7	0.35860	0.86920	0.84640	0.0580*
H9	0.25720	0.64290	1.03050	0.0590*
H10	0.16530	0.61150	1.05660	0.0670*
H11	0.10070	0.72030	0.97510	0.0710*
H12	0.12590	0.86250	0.86580	0.0610*
H14A	0.40670	0.58810	1.17200	0.1200*
H14B	0.41840	0.78110	1.15950	0.1200*
H14C	0.46700	0.65100	1.15850	0.1200*
H15A	0.46470	0.80150	0.96010	0.1660*
H15B	0.50040	0.77600	1.03400	0.1660*
H15C	0.45170	0.90540	1.03450	0.1660*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.030 (3)	0.053 (3)	0.052 (3)	−0.001 (2)	−0.008 (2)	−0.008 (3)
C1	0.036 (3)	0.037 (3)	0.041 (3)	0.002 (2)	−0.004 (2)	−0.009 (2)
C2	0.043 (3)	0.056 (4)	0.054 (4)	0.007 (3)	−0.005 (3)	−0.007 (3)
C3	0.062 (5)	0.059 (4)	0.051 (4)	0.011 (4)	−0.007 (4)	−0.001 (3)
C4	0.074 (5)	0.057 (4)	0.046 (4)	0.004 (4)	0.013 (4)	0.000 (3)
C5	0.051 (4)	0.061 (4)	0.044 (4)	−0.005 (3)	0.008 (3)	−0.009 (3)
C6	0.034 (3)	0.047 (3)	0.044 (3)	0.005 (3)	0.001 (3)	−0.013 (3)
C7	0.026 (3)	0.057 (4)	0.061 (4)	0.002 (3)	−0.002 (3)	−0.012 (3)
C8	0.036 (3)	0.043 (3)	0.042 (3)	0.002 (3)	−0.001 (3)	−0.013 (3)
C9	0.053 (4)	0.053 (4)	0.042 (3)	−0.002 (3)	−0.006 (3)	−0.004 (3)
C10	0.059 (4)	0.055 (4)	0.053 (4)	−0.005 (4)	0.006 (4)	0.000 (3)
C11	0.040 (4)	0.061 (4)	0.078 (5)	0.000 (3)	0.018 (4)	0.003 (4)
C12	0.035 (3)	0.054 (4)	0.064 (4)	0.005 (3)	0.002 (3)	0.000 (3)
C13	0.032 (3)	0.041 (3)	0.042 (3)	0.004 (2)	−0.001 (2)	−0.013 (3)
S1	0.0602 (13)	0.0891 (16)	0.0836 (15)	−0.0018 (11)	−0.0189 (11)	−0.0056 (12)
O1	0.049 (3)	0.170 (7)	0.077 (4)	0.013 (4)	−0.021 (3)	0.027 (4)
C14	0.072 (6)	0.106 (7)	0.062 (5)	−0.016 (5)	−0.017 (4)	0.030 (5)
C15	0.095 (8)	0.166 (11)	0.071 (6)	−0.051 (8)	0.009 (6)	−0.023 (7)
Pt1	0.0247 (2)	0.0484 (2)	0.0342 (2)	0.0000	0.0005 (1)	0.0000
Cl1	0.0434 (9)	0.0616 (9)	0.0548 (9)	0.0150 (8)	−0.0025 (7)	0.0076 (8)
Cl2	0.0390 (8)	0.0611 (9)	0.0527 (9)	0.0007 (7)	−0.0073 (7)	0.0160 (8)
Cl3	0.0396 (8)	0.0715 (10)	0.0463 (8)	0.0082 (8)	0.0145 (7)	0.0067 (8)

Geometric parameters (Å, º)

Pt1—Cl1^i	2.3228 (17)	C8—C13	1.386 (8)
Pt1—Cl2^i	2.3204 (16)	C9—C10	1.362 (10)
Pt1—Cl3^i	2.3233 (16)	C10—C11	1.371 (11)
Pt1—Cl3	2.3233 (16)	C11—C12	1.375 (11)
Pt1—Cl1	2.3228 (17)	C12—C13	1.407 (9)
Pt1—Cl2	2.3204 (16)	C2—H2	0.9300
S1—C14	1.770 (9)	C3—H3	0.9300
S1—C15	1.710 (12)	C4—H4	0.9300
S1—O1	1.472 (6)	C5—H5	0.9300
N1—C7	1.293 (9)	C7—H7	0.9300
N1—C8	1.405 (9)	C9—H9	0.9300
N1—HN1	0.84 (9)	C10—H10	0.9300
C1—C6	1.410 (7)	C11—H11	0.9300
C1—C2	1.408 (9)	C12—H12	0.9300
C1—C13	1.452 (7)	C14—H14B	0.9600
C2—C3	1.365 (10)	C14—H14A	0.9600
C3—C4	1.399 (10)	C14—H14C	0.9600
C4—C5	1.368 (10)	C15—H15C	0.9600
C5—C6	1.402 (9)	C15—H15A	0.9600
C6—C7	1.410 (9)	C15—H15B	0.9600
C8—C9	1.398 (9)
Cl1···Cl1^i	3.331 (2)	C8···O1	3.420 (9)
Cl1···Cl2^i	3.272 (2)	C8···C6^ix	3.598 (8)
Cl1···Cl3^i	3.265 (2)	C8···C9^viii	3.533 (9)
Cl1···Cl3	3.284 (2)	C8···C1^ix	3.492 (8)
Cl2···Cl1^i	3.272 (2)	C9···O1	3.309 (9)
Cl2···Cl3^i	3.297 (2)	C9···C8^ix	3.533 (9)
Cl2···Cl3	3.293 (2)	C10···Cl3^xi	3.646 (7)
Cl2···C7^ii	3.540 (7)	C13···C6^ix	3.511 (8)
Cl2···Cl2^i	3.258 (2)	C2···H12	2.7400
Cl3···Cl2	3.293 (2)	C2···H14A^xii	2.9200
Cl3···Cl1	3.284 (2)	C4···H10^xii	3.0400
Cl3···Cl1^i	3.265 (2)	C10···H3^xiii	3.0400
Cl3···C10^iii	3.646 (7)	C12···H2	2.7300
Cl3···Cl2^i	3.297 (2)	HN1···H9	2.3600
Cl1···H15A^iv	2.9100	HN1···S1	3.01 (9)
Cl1···H14C^v	2.9400	HN1···O1	1.79 (9)
Cl1···H2^vi	2.9400	H2···H12	2.1900
Cl1···H7^iv	3.0500	H2···H14A^xii	2.2900
Cl1···H12^vi	2.8900	H2···C12	2.7300
Cl2···H7^ii	2.6800	H2···Cl1^vi	2.9400
Cl2···H15A^ii	3.1200	H3···C10^xiv	3.0400
Cl2···H5^ii	3.0800	H5···H7	2.4400
Cl3···H15C^vii	3.0700	H5···Cl2^x	3.0800
Cl3···H10^iii	3.0000	H5···Cl3^x	2.9200
Cl3···H5^ii	2.9200	H7···Cl1^xv	3.0500
S1···HN1	3.01 (9)	H7···H5	2.4400
O1···N1	2.621 (8)	H7···Cl2^x	2.6800
O1···C9	3.309 (9)	H9···O1	2.6500
O1···C8	3.420 (9)	H9···HN1	2.3600
O1···HN1	1.79 (9)	H10···C4^xvi	3.0400
O1···H9	2.6500	H10···Cl3^xi	3.0000
N1···O1	2.621 (8)	H11···H15B^xvii	2.4500
C1···C8^viii	3.492 (8)	H12···C2	2.7400
C1···C4^ix	3.566 (9)	H12···H2	2.1900
C2···C7^viii	3.379 (9)	H12···Cl1^vi	2.8900
C2···C6^viii	3.573 (9)	H14A···C2^xvi	2.9200
C3···C6^viii	3.426 (9)	H14A···H2^xvi	2.2900
C3···C5^viii	3.596 (10)	H14B···H15C	2.5200
C4···C1^viii	3.566 (9)	H14C···H15B	2.5200
C5···C3^ix	3.596 (10)	H14C···Cl1^xviii	2.9400
C6···C3^ix	3.426 (9)	H15A···Cl2^x	3.1200
C6···C13^viii	3.511 (8)	H15A···Cl1^xv	2.9100
C6···C2^ix	3.573 (9)	H15B···H14C	2.5200
C6···C8^viii	3.598 (8)	H15B···H11^xix	2.4500
C7···C2^ix	3.379 (9)	H15C···H14B	2.5200
C7···Cl2^x	3.540 (7)	H15C···Cl3^xx	3.0700
Cl1^i—Pt1—Cl2	89.60 (6)	C9—C10—C11	120.5 (7)
Cl2—Pt1—Cl2^i	89.18 (6)	C10—C11—C12	121.4 (7)
Cl2—Pt1—Cl3^i	90.46 (5)	C11—C12—C13	120.1 (6)
Cl1^i—Pt1—Cl3	89.29 (6)	C1—C13—C8	118.8 (5)
Cl2^i—Pt1—Cl3	90.46 (5)	C1—C13—C12	124.4 (5)
Cl3—Pt1—Cl3^i	178.92 (6)	C8—C13—C12	116.9 (5)
Cl1^i—Pt1—Cl2^i	178.75 (6)	C1—C2—H2	120.00
Cl1^i—Pt1—Cl3^i	89.96 (6)	C3—C2—H2	120.00
Cl2^i—Pt1—Cl3^i	90.32 (5)	C2—C3—H3	119.00
Cl2—Pt1—Cl3	90.32 (5)	C4—C3—H3	120.00
Cl1—Pt1—Cl1^i	91.62 (6)	C3—C4—H4	120.00
Cl1—Pt1—Cl2	178.75 (6)	C5—C4—H4	120.00
Cl1—Pt1—Cl3	89.96 (6)	C6—C5—H5	120.00
Cl1—Pt1—Cl2^i	89.60 (6)	C4—C5—H5	120.00
Cl1—Pt1—Cl3^i	89.29 (6)	N1—C7—H7	119.00
O1—S1—C14	103.1 (4)	C6—C7—H7	119.00
O1—S1—C15	107.1 (5)	C8—C9—H9	121.00
C14—S1—C15	98.2 (5)	C10—C9—H9	121.00
C7—N1—C8	122.5 (5)	C11—C10—H10	120.00
C8—N1—HN1	118 (6)	C9—C10—H10	120.00
C7—N1—HN1	119 (6)	C12—C11—H11	119.00
C2—C1—C13	123.3 (5)	C10—C11—H11	119.00
C2—C1—C6	118.0 (5)	C13—C12—H12	120.00
C6—C1—C13	118.7 (5)	C11—C12—H12	120.00
C1—C2—C3	120.4 (6)	S1—C14—H14A	109.00
C2—C3—C4	121.1 (7)	S1—C14—H14B	109.00
C3—C4—C5	120.1 (7)	S1—C14—H14C	110.00
C4—C5—C6	119.5 (6)	H14A—C14—H14B	109.00
C1—C6—C5	120.9 (5)	H14A—C14—H14C	110.00
C5—C6—C7	120.6 (5)	H14B—C14—H14C	110.00
C1—C6—C7	118.5 (5)	S1—C15—H15A	109.00
N1—C7—C6	122.1 (6)	S1—C15—H15B	109.00
C9—C8—C13	122.7 (6)	S1—C15—H15C	109.00
N1—C8—C9	117.9 (6)	H15A—C15—H15B	109.00
N1—C8—C13	119.4 (5)	H15A—C15—H15C	110.00
C8—C9—C10	118.4 (7)	H15B—C15—H15C	109.00
C7—N1—C8—C9	179.5 (6)	C4—C5—C6—C1	0.1 (10)
C7—N1—C8—C13	−1.7 (9)	C4—C5—C6—C7	179.6 (6)
C8—N1—C7—C6	0.4 (10)	C1—C6—C7—N1	0.7 (9)
C6—C1—C2—C3	1.4 (9)	C5—C6—C7—N1	−178.8 (6)
C13—C1—C2—C3	−178.4 (6)	N1—C8—C9—C10	−179.8 (6)
C13—C1—C6—C7	−0.6 (8)	C13—C8—C9—C10	1.4 (10)
C2—C1—C13—C8	179.2 (6)	N1—C8—C13—C1	1.7 (8)
C2—C1—C13—C12	1.0 (9)	N1—C8—C13—C12	−179.9 (5)
C6—C1—C13—C8	−0.6 (8)	C9—C8—C13—C1	−179.5 (6)
C6—C1—C13—C12	−178.8 (6)	C9—C8—C13—C12	−1.2 (9)
C2—C1—C6—C5	−0.9 (9)	C8—C9—C10—C11	−0.8 (11)
C2—C1—C6—C7	179.6 (6)	C9—C10—C11—C12	−0.1 (11)
C13—C1—C6—C5	178.9 (6)	C10—C11—C12—C13	0.3 (11)
C1—C2—C3—C4	−1.1 (10)	C11—C12—C13—C1	178.6 (6)
C2—C3—C4—C5	0.2 (11)	C11—C12—C13—C8	0.4 (9)
C3—C4—C5—C6	0.3 (10)

Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+3/2, −y+3/2, z−1/2; (iii) x+1, y, z−1; (iv) x+1/2, −y+3/2, −z+1; (v) −x+3/2, y+1/2, z−1; (vi) −x+1, −y+2, −z+1; (vii) −x+3/2, y−1/2, z−1; (viii) −x+1/2, y+1/2, z; (ix) −x+1/2, y−1/2, z; (x) −x+3/2, −y+3/2, z+1/2; (xi) x−1, y, z+1; (xii) −x+1/2, −y+3/2, z−1/2; (xiii) x, −y+2, z+1/2; (xiv) x, −y+2, z−1/2; (xv) x−1/2, −y+3/2, −z+1; (xvi) −x+1/2, −y+3/2, z+1/2; (xvii) x−1/2, −y+3/2, −z+2; (xviii) −x+3/2, y−1/2, z+1; (xix) x+1/2, −y+3/2, −z+2; (xx) −x+3/2, y+1/2, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1	0.84 (9)	1.79 (9)	2.621 (8)	169 (8)
C7—H7···Cl2^x	0.93	2.68	3.540 (7)	154

Symmetry code: (x) −x+3/2, −y+3/2, z+1/2.