1,1'-(Butane-1,4-di­yl)dipyridinium dibromidodiiodidomercurate(II)

The Hg atom in the title compound, (C₁₄H₁₈N₂)[HgBr₂I₂], is coordinated by four halogen atoms in a tetra­hedral geometry. The four halogen atoms are disordered between I and Br, with the I:Br ratios being 0.824 (2):0.176 (2), 0.614 (2):0.386 (2), 0.325 (2):0.675 (2) and 0.237 (2):0.763 (2). The cation is disordered over two orientations and each was refined with an occupancy of 0.50.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma]() = 0.000 Å
• Disorder in main residue
• R factor = 0.035
• wR factor = 0.091
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSTM02_ALERT_3_A  The ratio of expected to reported Tmax/Tmin(RR') is < 0.50
            Tmin and Tmax reported:      0.059     0.165
            Tmin(prime) and Tmax expected:      0.046     0.061
            RR(prime) =      0.476
            Please check that your absorption correction is appropriate.

Author Response: The range is given by SADABS, and a heavy-atom model is assumed. That the range is large is in agreement with the presence of heavy atoms although a crystal of similar dimensions was used (for which the range is expected to be nearly unity). There is a lot of refundant reflections for the orthorhombic crystal.

PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large .............       0.25

Author Response: As above.

Alert level B
PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving .   ?
PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving .   ?
PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving .   ?
PLAT301_ALERT_3_B Main Residue  Disorder .........................      50.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  I3     ..  C5'     ..       3.33 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.37
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.02
PLAT128_ALERT_4_C Non-standard setting of Space group Pnma    ....    Pbca
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C7'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      44.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  I4     ..  C2      ..       3.40 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.372
            Tmax scaled      0.061 Tmin scaled      0.022

Author Response: The range is given by SADABS, and a heavy-atom model is assumed. That the range is large is in agreement with the presence of heavy atoms although a crystal of similar dimensions was used (for which the range is expected to be nearly unity). There is a lot of refundant reflections for the orthorhombic crystal.

PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        226

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The preceding study reports the structure of 1,2-butanedipyridinium bromotrichloromercurate(II) (Niu et al., 2007). Replacing the mercuric dichloride reactant by mercuric diiodide furnishes a similar tetrahalogenomercurate. The anion of the salt is composed two bromines and two chlorines that are disordered (Fig. 1); the metal atom shows tetrahedral coordination. Selected bond distances are given in Table 1.

Related literature

For the related butanedipyridinium bromidotrichloridomercurate, see: Niu et al. (2007).

S2. Experimental

The salt was synthesized from the reaction of butane-1,4-dipyridinium dibromide (0.026 g, 0.1 mmol) in methanol (5 ml) and mercuric diiodide (0.091 g, 0.2 mmol) in DMF (10 ml). The mixture was set aside for the formation of colorless crystals in 30% yield after several days.

S3. Refinement

The four halogen atoms lie in general positions. Initial attempts to refine the structure with either four iodines or four bromines gave unacceptably high R-indices and large peaks/deep holes. The four halogen atoms were then refined as four (I+Br) mixtures; one attempt had the mixtures to have the same displacement parameters as well as sharing the same sites. A second attempt allowed the components having the same displacement parameters only. The second led to a formulation consisting of approximately two I and two Br atoms. The use of a restraint that fixed the number of I and Br atoms as exactly two I and two Br led to occupancies of 0.824 (2), 0.614 (2), 0.325 (2) and 0.237 (2), respectively, for I1, I2, I3 and I4, and 0.176 (2), 0.386 (2), 0.675 (2) and 0.763 (2), respectively, for Br1, Br2, Br3 and Br4.

The formulation is in fair agreement with CH&N elemental analysis, and furthermore, there were neither large peaks nor deep holes in the difference Fourier map; the final difference Fourier map had a large peak at 0.77 Å from Hg1. Other formulations led to somewhat larger peaks/deep holes.

The cation is disordered over two orientations and each was refined with an occupancy of 0.50. The pyridyl rings were refined as rigid hexagons (C—C = C—N = 1.39 Å). The C(sp^3)—C(sp3) and N—C(sp³) distances were restrained to 1.50 (1) Å, and the 1,3-related distances to 2.45 (1) Å; additionally, the alphatic carbon atom bonded to the nitrogen atom was retrained to lie on the plane of the ring. The displacement parameters of the primed atoms were set to those of the unprimed ones and they were restrained to be nearly isotropic. C-bound H atoms were generated geometrically (C–H 0.93 and 0.97 Å), and were included in the refinement in the riding-model approximation, with U(H) set to 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

Fig. 1. The molecular structure of [C14H18N2][HgBr2I2]. Displacement ellipsoids are drawn at the 50% probability level. The bromine and iodine atoms are disordered; the figure depicts the anion as an [HgX4]^2- species. Hydrogen atoms are drawn as spheres of arbitrary radius. Only one of the components of the disordered cation is shown.

1,1'-(Butane-1,4-diyl)dipyridinium dibromidodiiodidomercurate(II)

Crystal data

(C14H18N2)[HgBr2I2]	F(000) = 2976
Mr = 828.51	Dx = 2.598 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5589 reflections
a = 16.0181 (8) Å	θ = 2.4–22.3°
b = 15.3290 (7) Å	µ = 13.95 mm^−1
c = 17.2550 (8) Å	T = 295 K
V = 4236.8 (3) Å^3	Block, colourless
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEX area-detector diffractometer	3722 independent reflections
Radiation source: fine-focus sealed tube	2713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.059, Tmax = 0.165	k = −18→18
31877 measured reflections	l = −20→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 2.7056P] where P = (Fo^2 + 2Fc^2)/3
3722 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 1.03 e Å^−3
226 restraints	Δρmin = −0.51 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Hg1	0.59858 (2)	0.751573 (19)	0.866623 (17)	0.05914 (13)
I1	0.68911 (13)	0.67185 (13)	0.75380 (15)	0.0712 (4)	0.824 (2)
I2	0.5676 (4)	0.9215 (4)	0.8189 (3)	0.0717 (8)	0.614 (2)
I3	0.677 (4)	0.744 (4)	1.007 (3)	0.0732 (18)	0.325 (2)
I4	0.4457 (13)	0.6720 (11)	0.8836 (11)	0.0691 (8)	0.237 (2)
Br1	0.6735 (11)	0.6560 (12)	0.7524 (12)	0.0712 (4)	0.176 (2)
Br2	0.5830 (10)	0.9228 (10)	0.8330 (7)	0.0717 (8)	0.386 (2)
Br3	0.674 (3)	0.743 (3)	1.000 (2)	0.0732 (18)	0.675 (2)
Br4	0.4489 (6)	0.6863 (4)	0.8958 (5)	0.0691 (8)	0.763 (2)
N1	0.6643 (7)	0.4418 (11)	0.5603 (7)	0.0511 (19)	0.50
C1	0.7070 (9)	0.5169 (11)	0.5387 (7)	0.062 (3)	0.50
H1	0.6879	0.5504	0.4974	0.074*	0.50
C2	0.7784 (8)	0.5420 (10)	0.5788 (10)	0.065 (4)	0.50
H2	0.8070	0.5922	0.5643	0.078*	0.50
C3	0.8070 (8)	0.4919 (12)	0.6405 (9)	0.065 (3)	0.50
H3	0.8547	0.5087	0.6673	0.078*	0.50
C4	0.7643 (12)	0.4168 (12)	0.6621 (9)	0.071 (3)	0.50
H4	0.7835	0.3833	0.7034	0.085*	0.50
C5	0.6930 (11)	0.3918 (10)	0.6220 (9)	0.065 (3)	0.50
H5	0.6644	0.3415	0.6364	0.077*	0.50
N2	0.5665 (12)	0.1988 (7)	0.3523 (6)	0.064 (3)	0.50
C6	0.6475 (11)	0.1667 (10)	0.3470 (13)	0.082 (4)	0.50
H6	0.6907	0.2033	0.3317	0.098*	0.50
C7	0.6638 (9)	0.0798 (11)	0.3645 (15)	0.105 (4)	0.50
H7	0.7179	0.0583	0.3609	0.126*	0.50
C8	0.5991 (11)	0.0251 (7)	0.3874 (11)	0.088 (4)	0.50
H8	0.6100	−0.0330	0.3991	0.105*	0.50
C9	0.5182 (10)	0.0572 (9)	0.3927 (11)	0.084 (4)	0.50
H9	0.4749	0.0205	0.4080	0.101*	0.50
C10	0.5019 (9)	0.1440 (10)	0.3752 (10)	0.075 (3)	0.50
H10	0.4477	0.1655	0.3788	0.090*	0.50
C11	0.5890 (10)	0.4165 (18)	0.5171 (11)	0.059 (3)	0.50
H11A	0.5599	0.4687	0.5005	0.071*	0.50
H11B	0.5521	0.3844	0.5514	0.071*	0.50
C12	0.6080 (10)	0.361 (2)	0.4477 (13)	0.055 (3)	0.50
H12A	0.6348	0.3076	0.4638	0.066*	0.50
H12B	0.6456	0.3923	0.4133	0.066*	0.50
C13	0.5274 (9)	0.3414 (10)	0.4065 (8)	0.063 (4)	0.50
H13A	0.4909	0.3094	0.4412	0.076*	0.50
H13B	0.4999	0.3957	0.3931	0.076*	0.50
C14	0.5405 (11)	0.2897 (8)	0.3354 (7)	0.063 (4)	0.50
H14A	0.5829	0.3176	0.3039	0.075*	0.50
H14B	0.4891	0.2887	0.3057	0.075*	0.50
N1'	0.6530 (7)	0.4378 (11)	0.5467 (7)	0.0511 (19)	0.50
C1'	0.6846 (9)	0.5220 (10)	0.5408 (8)	0.062 (3)	0.50
H1'	0.6626	0.5605	0.5045	0.074*	0.50
C2'	0.7490 (8)	0.5488 (9)	0.5893 (10)	0.065 (4)	0.50
H2'	0.7701	0.6051	0.5854	0.078*	0.50
C3'	0.7818 (8)	0.4913 (12)	0.6437 (9)	0.065 (3)	0.50
H3'	0.8249	0.5092	0.6761	0.078*	0.50
C4'	0.7502 (12)	0.4071 (11)	0.6495 (9)	0.071 (3)	0.50
H4'	0.7722	0.3686	0.6859	0.085*	0.50
C5'	0.6859 (11)	0.3803 (9)	0.6010 (9)	0.065 (3)	0.50
H5'	0.6647	0.3240	0.6049	0.077*	0.50
N2'	0.5766 (12)	0.1750 (6)	0.3511 (6)	0.064 (3)	0.50
C6'	0.6585 (11)	0.1463 (10)	0.3439 (12)	0.082 (4)	0.50
H6'	0.6984	0.1821	0.3212	0.098*	0.50
C7'	0.6807 (9)	0.0640 (11)	0.3706 (15)	0.105 (4)	0.50
H7'	0.7355	0.0447	0.3658	0.126*	0.50
C8'	0.6210 (11)	0.0104 (8)	0.4046 (11)	0.088 (4)	0.50
H8'	0.6359	−0.0447	0.4225	0.105*	0.50
C9'	0.5391 (10)	0.0391 (9)	0.4118 (10)	0.084 (4)	0.50
H9'	0.4992	0.0033	0.4345	0.101*	0.50
C10'	0.5169 (9)	0.1215 (10)	0.3851 (10)	0.075 (3)	0.50
H10'	0.4620	0.1407	0.3899	0.090*	0.50
C11'	0.5849 (10)	0.4077 (18)	0.4962 (11)	0.059 (3)	0.50
H11C	0.5580	0.4580	0.4730	0.071*	0.50
H11D	0.5437	0.3776	0.5275	0.071*	0.50
C12'	0.6136 (11)	0.3480 (19)	0.4332 (13)	0.055 (3)	0.50
H12C	0.6360	0.2948	0.4553	0.066*	0.50
H12D	0.6572	0.3759	0.4031	0.066*	0.50
C13'	0.5401 (10)	0.3271 (9)	0.3818 (9)	0.063 (4)	0.50
H13C	0.4954	0.3030	0.4132	0.076*	0.50
H13D	0.5198	0.3804	0.3582	0.076*	0.50
C14'	0.5622 (11)	0.2640 (8)	0.3201 (7)	0.063 (4)	0.50
H14C	0.6122	0.2838	0.2939	0.075*	0.50
H14D	0.5174	0.2620	0.2823	0.075*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.0614 (2)	0.0609 (2)	0.0551 (2)	0.00344 (15)	0.00333 (15)	−0.00355 (15)
I1	0.0754 (10)	0.0702 (10)	0.0680 (4)	−0.0013 (5)	0.0145 (7)	−0.0171 (6)
I2	0.104 (2)	0.0568 (4)	0.0548 (18)	0.0035 (12)	0.0093 (11)	−0.0019 (12)
I3	0.070 (2)	0.0910 (6)	0.058 (5)	0.0138 (12)	−0.011 (3)	−0.002 (3)
I4	0.0619 (9)	0.055 (2)	0.090 (3)	−0.0031 (15)	0.0052 (15)	−0.0088 (13)
Br1	0.0754 (10)	0.0702 (10)	0.0680 (4)	−0.0013 (5)	0.0145 (7)	−0.0171 (6)
Br2	0.104 (2)	0.0568 (4)	0.0548 (18)	0.0035 (12)	0.0093 (11)	−0.0019 (12)
Br3	0.070 (2)	0.0910 (6)	0.058 (5)	0.0138 (12)	−0.011 (3)	−0.002 (3)
Br4	0.0619 (9)	0.055 (2)	0.090 (3)	−0.0031 (15)	0.0052 (15)	−0.0088 (13)
N1	0.053 (4)	0.054 (3)	0.047 (4)	0.008 (3)	0.003 (3)	0.001 (3)
C1	0.059 (6)	0.055 (4)	0.072 (5)	0.007 (5)	0.004 (5)	0.004 (4)
C2	0.066 (7)	0.066 (5)	0.063 (5)	−0.005 (5)	0.015 (6)	−0.007 (4)
C3	0.059 (6)	0.071 (5)	0.064 (5)	0.003 (5)	0.002 (5)	−0.013 (4)
C4	0.080 (6)	0.070 (5)	0.063 (5)	0.004 (5)	−0.011 (5)	−0.001 (4)
C5	0.079 (5)	0.056 (5)	0.059 (7)	0.004 (4)	0.006 (5)	−0.002 (5)
N2	0.069 (5)	0.069 (6)	0.054 (4)	−0.015 (5)	−0.008 (4)	−0.004 (4)
C6	0.078 (6)	0.087 (7)	0.081 (5)	−0.013 (5)	0.011 (5)	−0.005 (5)
C7	0.103 (7)	0.106 (7)	0.106 (6)	0.008 (5)	0.007 (5)	−0.010 (5)
C8	0.097 (7)	0.078 (6)	0.088 (7)	0.002 (5)	−0.016 (6)	0.000 (5)
C9	0.087 (7)	0.080 (6)	0.086 (7)	−0.013 (5)	−0.010 (5)	0.004 (5)
C10	0.068 (6)	0.074 (6)	0.082 (6)	−0.005 (5)	−0.002 (5)	−0.001 (5)
C11	0.052 (4)	0.067 (5)	0.058 (7)	0.001 (4)	0.002 (4)	−0.003 (5)
C12	0.054 (4)	0.055 (6)	0.055 (6)	0.001 (4)	0.003 (4)	0.001 (4)
C13	0.064 (5)	0.062 (5)	0.064 (7)	−0.002 (4)	−0.001 (5)	−0.003 (5)
C14	0.064 (6)	0.065 (6)	0.058 (5)	0.009 (5)	−0.011 (5)	0.001 (5)
N1'	0.053 (4)	0.054 (3)	0.047 (4)	0.008 (3)	0.003 (3)	0.001 (3)
C1'	0.059 (6)	0.055 (4)	0.072 (5)	0.007 (5)	0.004 (5)	0.004 (4)
C2'	0.066 (7)	0.066 (5)	0.063 (5)	−0.005 (5)	0.015 (6)	−0.007 (4)
C3'	0.059 (6)	0.071 (5)	0.064 (5)	0.003 (5)	0.002 (5)	−0.013 (4)
C4'	0.080 (6)	0.070 (5)	0.063 (5)	0.004 (5)	−0.011 (5)	−0.001 (4)
C5'	0.079 (5)	0.056 (5)	0.059 (7)	0.004 (4)	0.006 (5)	−0.002 (5)
N2'	0.069 (5)	0.069 (6)	0.054 (4)	−0.015 (5)	−0.008 (4)	−0.004 (4)
C6'	0.078 (6)	0.087 (7)	0.081 (5)	−0.013 (5)	0.011 (5)	−0.005 (5)
C7'	0.103 (7)	0.106 (7)	0.106 (6)	0.008 (5)	0.007 (5)	−0.010 (5)
C8'	0.097 (7)	0.078 (6)	0.088 (7)	0.002 (5)	−0.016 (6)	0.000 (5)
C9'	0.087 (7)	0.080 (6)	0.086 (7)	−0.013 (5)	−0.010 (5)	0.004 (5)
C10'	0.068 (6)	0.074 (6)	0.082 (6)	−0.005 (5)	−0.002 (5)	−0.001 (5)
C11'	0.052 (4)	0.067 (5)	0.058 (7)	0.001 (4)	0.002 (4)	−0.003 (5)
C12'	0.054 (4)	0.055 (6)	0.055 (6)	0.001 (4)	0.003 (4)	0.001 (4)
C13'	0.064 (5)	0.062 (5)	0.064 (7)	−0.002 (4)	−0.001 (5)	−0.003 (5)
C14'	0.064 (6)	0.065 (6)	0.058 (5)	0.009 (5)	−0.011 (5)	0.001 (5)

Geometric parameters (Å, º)

Hg1—Br1	2.73 (2)	C13—H13A	0.97
Hg1—Br2	2.70 (2)	C13—H13B	0.97
Hg1—Br3	2.61 (4)	C14—H14A	0.97
Hg1—Br4	2.646 (9)	C14—H14B	0.97
Hg1—I1	2.718 (2)	N1'—C1'	1.39
Hg1—I2	2.777 (6)	N1'—C5'	1.39
Hg1—I3	2.72 (5)	N1'—C11'	1.470 (8)
Hg1—I4	2.75 (2)	C1'—C2'	1.39
N1—C1	1.39	C1'—H1'	0.93
N1—C5	1.39	C2'—C3'	1.39
N1—C11	1.470 (8)	C2'—H2'	0.93
C1—C2	1.39	C3'—C4'	1.39
C1—H1	0.93	C3'—H3'	0.93
C2—C3	1.39	C4'—C5'	1.39
C2—H2	0.93	C4'—H4'	0.93
C3—C4	1.39	C5'—H5'	0.93
C3—H3	0.93	N2'—C6'	1.39
C4—C5	1.39	N2'—C10'	1.39
C4—H4	0.93	N2'—C14'	1.483 (9)
C5—H5	0.93	C6'—C7'	1.39
N2—C6	1.39	C6'—H6'	0.93
N2—C10	1.39	C7'—C8'	1.39
N2—C14	1.484 (9)	C7'—H7'	0.93
C6—C7	1.39	C8'—C9'	1.39
C6—H6	0.93	C8'—H8'	0.93
C7—C8	1.39	C9'—C10'	1.39
C7—H7	0.93	C9'—H9'	0.93
C8—C9	1.39	C10'—H10'	0.93
C8—H8	0.93	C11'—C12'	1.493 (9)
C9—C10	1.39	C11'—H11C	0.97
C9—H9	0.93	C11'—H11D	0.97
C10—H10	0.93	C12'—C13'	1.509 (9)
C11—C12	1.496 (9)	C12'—H12C	0.97
C11—H11A	0.97	C12'—H12D	0.97
C11—H11B	0.97	C13'—C14'	1.481 (8)
C12—C13	1.506 (9)	C13'—H13C	0.97
C12—H12A	0.97	C13'—H13D	0.97
C12—H12B	0.97	C14'—H14C	0.97
C13—C14	1.475 (8)	C14'—H14D	0.97
Br3—Hg1—I3	0 (2)	C13—C12—H12B	110.0
Br3—Hg1—Br4	103.6 (10)	H12A—C12—H12B	108.3
I3—Hg1—Br4	103.4 (13)	C14—C13—C12	112.4 (8)
Br3—Hg1—I4	107.4 (11)	C14—C13—H13A	109.1
I3—Hg1—I4	107.2 (14)	C12—C13—H13A	109.1
Br4—Hg1—I4	6.2 (4)	C14—C13—H13B	109.1
Br3—Hg1—I1	111.3 (10)	C12—C13—H13B	109.1
I3—Hg1—I1	111.6 (13)	H13A—C13—H13B	107.9
Br4—Hg1—I1	116.73 (12)	C13—C14—N2	112.4 (8)
I4—Hg1—I1	110.6 (3)	C13—C14—H14A	109.1
Br3—Hg1—Br1	114.1 (11)	N2—C14—H14A	109.1
I3—Hg1—Br1	114.4 (13)	C13—C14—H14B	109.1
Br4—Hg1—Br1	109.4 (3)	N2—C14—H14B	109.1
I4—Hg1—Br1	103.3 (4)	H14A—C14—H14B	107.9
I1—Hg1—Br1	7.4 (3)	C1'—N1'—C5'	120.0
Br3—Hg1—I2	112.9 (9)	C1'—N1'—C11'	121.2 (15)
I3—Hg1—I2	112.8 (12)	C5'—N1'—C11'	118.8 (15)
Br4—Hg1—I2	104.5 (2)	N1'—C1'—C2'	120.0
I4—Hg1—I2	106.8 (4)	N1'—C1'—H1'	120.0
I1—Hg1—I2	107.74 (13)	C2'—C1'—H1'	120.0
Br1—Hg1—I2	111.6 (4)	C3'—C2'—C1'	120.0
Br3—Hg1—Br2	106.2 (10)	C3'—C2'—H2'	120.0
I3—Hg1—Br2	106.1 (12)	C1'—C2'—H2'	120.0
Br4—Hg1—Br2	108.9 (4)	C4'—C3'—C2'	120.0
I4—Hg1—Br2	111.8 (5)	C4'—C3'—H3'	120.0
I1—Hg1—Br2	109.4 (3)	C2'—C3'—H3'	120.0
Br1—Hg1—Br2	114.0 (5)	C3'—C4'—C5'	120.0
I2—Hg1—Br2	7.1 (3)	C3'—C4'—H4'	120.0
C1—N1—C5	120.0	C5'—C4'—H4'	120.0
C1—N1—C11	119.1 (16)	C4'—C5'—N1'	120.0
C5—N1—C11	120.9 (16)	C4'—C5'—H5'	120.0
N1—C1—C2	120.0	N1'—C5'—H5'	120.0
N1—C1—H1	120.0	C6'—N2'—C10'	120.0
C2—C1—H1	120.0	C6'—N2'—C14'	114.0 (13)
C3—C2—C1	120.0	C10'—N2'—C14'	126.0 (13)
C3—C2—H2	120.0	N2'—C6'—C7'	120.0
C1—C2—H2	120.0	N2'—C6'—H6'	120.0
C2—C3—C4	120.0	C7'—C6'—H6'	120.0
C2—C3—H3	120.0	C8'—C7'—C6'	120.0
C4—C3—H3	120.0	C8'—C7'—H7'	120.0
C3—C4—C5	120.0	C6'—C7'—H7'	120.0
C3—C4—H4	120.0	C7'—C8'—C9'	120.0
C5—C4—H4	120.0	C7'—C8'—H8'	120.0
C4—C5—N1	120.0	C9'—C8'—H8'	120.0
C4—C5—H5	120.0	C10'—C9'—C8'	120.0
N1—C5—H5	120.0	C10'—C9'—H9'	120.0
C6—N2—C10	120.0	C8'—C9'—H9'	120.0
C6—N2—C14	125.6 (14)	C9'—C10'—N2'	120.0
C10—N2—C14	114.4 (14)	C9'—C10'—H10'	120.0
N2—C6—C7	120.0	N2'—C10'—H10'	120.0
N2—C6—H6	120.0	N1'—C11'—C12'	113.3 (8)
C7—C6—H6	120.0	N1'—C11'—H11C	108.9
C6—C7—C8	120.0	C12'—C11'—H11C	108.9
C6—C7—H7	120.0	N1'—C11'—H11D	108.9
C8—C7—H7	120.0	C12'—C11'—H11D	108.9
C9—C8—C7	120.0	H11C—C11'—H11D	107.7
C9—C8—H8	120.0	C11'—C12'—C13'	108.6 (8)
C7—C8—H8	120.0	C11'—C12'—H12C	110.0
C8—C9—C10	120.0	C13'—C12'—H12C	110.0
C8—C9—H9	120.0	C11'—C12'—H12D	110.0
C10—C9—H9	120.0	C13'—C12'—H12D	110.0
C9—C10—N2	120.0	H12C—C12'—H12D	108.4
C9—C10—H10	120.0	C14'—C13'—C12'	112.0 (8)
N2—C10—H10	120.0	C14'—C13'—H13C	109.2
N1—C11—C12	112.8 (7)	C12'—C13'—H13C	109.2
N1—C11—H11A	109.0	C14'—C13'—H13D	109.2
C12—C11—H11A	109.0	C12'—C13'—H13D	109.2
N1—C11—H11B	109.0	H13C—C13'—H13D	107.9
C12—C11—H11B	109.0	C13'—C14'—N2'	112.3 (8)
H11A—C11—H11B	107.8	C13'—C14'—H14C	109.2
C11—C12—C13	108.6 (8)	N2'—C14'—H14C	109.2
C11—C12—H12A	110.0	C13'—C14'—H14D	109.2
C13—C12—H12A	110.0	N2'—C14'—H14D	109.2
C11—C12—H12B	110.0	H14C—C14'—H14D	107.9
C11—N1—C1—C2	180.0 (3)	C11'—N1'—C1'—C2'	180.0 (3)
C11—N1—C5—C4	180.0 (3)	C11'—N1'—C5'—C4'	−180.0 (3)
C14—N2—C6—C7	180.0 (3)	C14'—N2'—C6'—C7'	180.0 (2)
C14—N2—C10—C9	−180.0 (2)	C14'—N2'—C10'—C9'	−180.0 (3)
C1—N1—C11—C12	87 (2)	C1'—N1'—C11'—C12'	105 (2)
C5—N1—C11—C12	−93 (2)	C5'—N1'—C11'—C12'	−75 (2)
N1—C11—C12—C13	−178 (2)	N1'—C11'—C12'—C13'	−176 (2)
C11—C12—C13—C14	178 (2)	C11'—C12'—C13'—C14'	−177 (2)
C12—C13—C14—N2	70 (2)	C12'—C13'—C14'—N2'	71 (2)
C6—N2—C14—C13	−102.0 (14)	C6'—N2'—C14'—C13'	−113.9 (13)
C10—N2—C14—C13	78.0 (14)	C10'—N2'—C14'—C13'	66.0 (13)