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

The Hg atom in the title compound, (C₁₄H₁₈N₂)[HgBrCl₃], is coordinated by four halogen atoms in a tetra­hedral geometry. The four halogen atoms are each disordered between Br and Cl, with the Br:Cl ratios being 0.218 (2):0.782 (2), 0.136 (2):0.864 (2), 0.090 (2):0.910 (2) and 0.556 (2):0.444 (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 = 0.031
• wR factor = 0.081
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.58
PLAT301_ALERT_3_B Main Residue  Disorder .........................      50.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  Br1    ..  C10     ..       3.21 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.096     0.415
            Tmin(prime) and Tmax expected:      0.101     0.344
            RR(prime) =      0.789
            Please check that your absorption correction is appropriate.
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 .....................       0.83
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      44.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  Br2    ..  C5      ..       3.27 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  Br2    ..  C4      ..       3.31 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      0.829
            Tmax scaled      0.344 Tmin scaled      0.080
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        130

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   8 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
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The preceding study reports the structure of the tetrahedral dibromidodichloridomercurate(II), which was isolated as a 1,2-ethanedipyridinium salt (Wang et al., 2007). Replacing the cation by 1,4-butanedipyridinium furnishes a similar tetrahalomercurate. The anion of the salt is composed of one bromine and three chlorine atoms which are disordered (Fig. 1); the metal atom shows tetrahedral coordination. Selected bond distances are listed in Table 1.

Related literature

For related tetrahalogenomercurates, see: Wang 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 dichloride (0.054 g, 0.2 mmol) in DMF (10 ml). The mixture was set aside for the formation of colourless crystals in 30% yield after several days. CH&N elemental analysis for C₁₄H₁₈BrCl₃HgN₂. Calculated: C 27.97, H 3.02, N 4.46%; found C 27.08, H 2.77, N 4.49%.

S3. Refinement

The four halogens lie in general positions. Initial attempts to refine the structure with either four bromines or four chlorines gave unacceptably high R-indices and large peaks/deep holes. The four halogen atoms were then refined as four (Br+Cl) mixtures; one attempt had the mixtures to have the same displacement parameters as well as sharing the same site. A second attempt had the components having the same displacement parameters only. The second led to a formulation consisting of approximately one Br and three Cl atoms. The use of a restraint that fixed the number of Br and Cl atoms as exactly 1 Br and 3 Cl led to occupancies of 0.218 (2), 0.136 (2), 0.090 (2) and 0.556 (2), respectively, Br1, Br2, Br3 and Br4, and 0.782 (2), 0.864 (2), 0.910 (2) and 0.444 (2), respectively, for Cl1, Cl2, Cl3 and Cl4. The formulation is in good agreement with CH&N elemental analysis, and furthermore, there were neither large peaks nor deep holes in the difference Fourier map. 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 occupancy could not be refined. 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][HgBrCl3]. Displacement ellipsoids are drawn at the 50% probability level. The bromine and chlorine atoms are disordered; the figure depicts the anion as an [HgX4]^2- species. Hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data

(C14H18N2)[HgBrCl3]	F(000) = 1128
Mr = 601.15	Dx = 2.111 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4607 reflections
a = 15.9912 (8) Å	θ = 2.7–26.4°
b = 8.7769 (5) Å	µ = 10.67 mm^−1
c = 14.3189 (9) Å	T = 295 K
β = 109.760 (1)°	Block, colourless
V = 1891.4 (2) Å^3	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	3316 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→15
Tmin = 0.096, Tmax = 0.415	k = −10→10
11857 measured reflections	l = −17→17

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.263P] where P = (Fo^2 + 2Fc^2)/3
3316 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.77 e Å^−3
130 restraints	Δρmin = −0.84 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Hg1	0.254133 (15)	0.47282 (3)	0.529270 (15)	0.05327 (11)
Br1	0.180 (3)	0.253 (4)	0.411 (2)	0.0635 (18)	0.218 (2)
Br2	0.415 (3)	0.435 (4)	0.623 (3)	0.0563 (12)	0.136 (2)
Br3	0.2771 (14)	0.660 (2)	0.4126 (18)	0.0577 (7)	0.090 (2)
Br4	0.1650 (4)	0.5446 (5)	0.6389 (4)	0.0643 (7)	0.556 (2)
Cl1	0.1756 (17)	0.251 (3)	0.4255 (15)	0.0635 (18)	0.782 (2)
Cl2	0.4166 (11)	0.4121 (14)	0.6159 (11)	0.0563 (12)	0.864 (2)
Cl3	0.2607 (3)	0.6920 (5)	0.4159 (4)	0.0577 (7)	0.910 (2)
Cl4	0.1718 (14)	0.5153 (17)	0.6513 (14)	0.0643 (7)	0.444 (2)
N1	0.5444 (6)	0.0632 (18)	0.3892 (8)	0.0415 (18)	0.50
C1	0.5126 (7)	0.2014 (16)	0.4108 (11)	0.049 (2)	0.50
H1	0.5517	0.2820	0.4356	0.059*	0.50
C2	0.4226 (8)	0.2193 (12)	0.3955 (13)	0.047 (3)	0.50
H2	0.4014	0.3118	0.4100	0.057*	0.50
C3	0.3643 (6)	0.0990 (12)	0.3585 (9)	0.045 (3)	0.50
H3	0.3041	0.1109	0.3482	0.054*	0.50
C4	0.3960 (8)	−0.0393 (12)	0.3368 (10)	0.047 (3)	0.50
H4	0.3570	−0.1198	0.3121	0.056*	0.50
C5	0.4861 (8)	−0.0572 (14)	0.3522 (10)	0.045 (2)	0.50
H5	0.5073	−0.1497	0.3377	0.054*	0.50
N2	0.8831 (4)	−0.0935 (9)	0.3268 (6)	0.051 (2)	0.50
C6	0.9378 (8)	−0.1770 (12)	0.4066 (7)	0.071 (2)	0.50
H6	0.9134	−0.2292	0.4479	0.085*	0.50
C7	1.0288 (7)	−0.1824 (17)	0.4249 (8)	0.056 (2)	0.50
H7	1.0654	−0.2382	0.4783	0.067*	0.50
C8	1.0651 (4)	−0.1044 (18)	0.3632 (10)	0.058 (3)	0.50
H8	1.1260	−0.1080	0.3754	0.070*	0.50
C9	1.0104 (7)	−0.0209 (15)	0.2834 (9)	0.074 (2)	0.50
H9	1.0348	0.0313	0.2421	0.089*	0.50
C10	0.9194 (7)	−0.0155 (10)	0.2651 (6)	0.058 (3)	0.50
H10	0.8828	0.0403	0.2117	0.070*	0.50
C11	0.6368 (10)	0.020 (4)	0.4005 (15)	0.055 (3)	0.50
H11A	0.6758	0.0525	0.4654	0.066*	0.50
H11B	0.6407	−0.0897	0.3971	0.066*	0.50
C12	0.6673 (6)	0.0893 (13)	0.3235 (9)	0.060 (3)	0.50
H12A	0.6549	0.1977	0.3197	0.072*	0.50
H12B	0.6347	0.0447	0.2595	0.072*	0.50
C13	0.7646 (6)	0.0649 (11)	0.3455 (9)	0.065 (2)	0.50
H13A	0.7945	0.0679	0.4167	0.078*	0.50
H13B	0.7879	0.1473	0.3164	0.078*	0.50
C14	0.7849 (5)	−0.0846 (11)	0.3060 (8)	0.058 (2)	0.50
H14A	0.7659	−0.1685	0.3381	0.069*	0.50
H14B	0.7535	−0.0911	0.2352	0.069*	0.50
N1'	0.5395 (6)	0.0366 (18)	0.3852 (8)	0.0415 (18)	0.50
C1'	0.5296 (7)	0.1906 (17)	0.4015 (11)	0.049 (2)	0.50
H1'	0.5785	0.2553	0.4171	0.059*	0.50
C2'	0.4467 (8)	0.2480 (12)	0.3944 (13)	0.047 (3)	0.50
H2'	0.4401	0.3511	0.4053	0.057*	0.50
C3'	0.3737 (6)	0.1514 (12)	0.3711 (10)	0.045 (3)	0.50
H3'	0.3182	0.1898	0.3664	0.054*	0.50
C4'	0.3835 (7)	−0.0027 (12)	0.3549 (10)	0.047 (3)	0.50
H4'	0.3346	−0.0673	0.3393	0.056*	0.50
C5'	0.4664 (8)	−0.0601 (13)	0.3619 (10)	0.045 (2)	0.50
H5'	0.4730	−0.1632	0.3510	0.054*	0.50
N2'	0.8955 (4)	−0.0307 (10)	0.3618 (6)	0.051 (2)	0.50
C6'	0.9442 (8)	−0.1532 (12)	0.4144 (7)	0.071 (2)	0.50
H6'	0.9242	−0.2062	0.4590	0.085*	0.50
C7'	1.0227 (8)	−0.1965 (15)	0.4003 (9)	0.056 (2)	0.50
H7'	1.0552	−0.2785	0.4355	0.067*	0.50
C8'	1.0525 (5)	−0.1173 (17)	0.3336 (10)	0.058 (3)	0.50
H8'	1.1051	−0.1463	0.3242	0.070*	0.50
C9'	1.0039 (8)	0.0051 (14)	0.2810 (9)	0.074 (2)	0.50
H9'	1.0239	0.0581	0.2363	0.089*	0.50
C10'	0.9254 (7)	0.0485 (10)	0.2951 (7)	0.058 (3)	0.50
H10'	0.8929	0.1304	0.2598	0.070*	0.50
C11'	0.6329 (11)	−0.004 (4)	0.3962 (13)	0.055 (3)	0.50
H11C	0.6735	0.0614	0.4456	0.066*	0.50
H11D	0.6447	−0.1086	0.4186	0.066*	0.50
C12'	0.6475 (5)	0.0143 (14)	0.2997 (8)	0.060 (3)	0.50
H12C	0.6470	0.1219	0.2840	0.072*	0.50
H12D	0.5991	−0.0341	0.2479	0.072*	0.50
C13'	0.7332 (5)	−0.0535 (14)	0.3013 (8)	0.065 (2)	0.50
H13C	0.7332	−0.1614	0.3161	0.078*	0.50
H13D	0.7383	−0.0435	0.2359	0.078*	0.50
C14'	0.8112 (5)	0.0193 (12)	0.3753 (8)	0.058 (2)	0.50
H14C	0.8126	−0.0073	0.4416	0.069*	0.50
H14D	0.8058	0.1291	0.3684	0.069*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.05137 (18)	0.04907 (17)	0.06456 (16)	−0.00278 (9)	0.02638 (13)	−0.00031 (10)
Br1	0.068 (3)	0.0608 (8)	0.076 (5)	−0.0161 (14)	0.043 (3)	−0.018 (3)
Br2	0.0542 (9)	0.047 (4)	0.061 (2)	0.011 (3)	0.0108 (12)	−0.007 (2)
Br3	0.047 (2)	0.055 (2)	0.0626 (8)	−0.0058 (11)	0.0074 (12)	0.0138 (13)
Br4	0.0685 (12)	0.0632 (19)	0.0745 (16)	0.0078 (13)	0.0418 (12)	0.0016 (11)
Cl1	0.068 (3)	0.0608 (8)	0.076 (5)	−0.0161 (14)	0.043 (3)	−0.018 (3)
Cl2	0.0542 (9)	0.047 (4)	0.061 (2)	0.011 (3)	0.0108 (12)	−0.007 (2)
Cl3	0.047 (2)	0.055 (2)	0.0626 (8)	−0.0058 (11)	0.0074 (12)	0.0138 (13)
Cl4	0.0685 (12)	0.0632 (19)	0.0745 (16)	0.0078 (13)	0.0418 (12)	0.0016 (11)
N1	0.034 (3)	0.041 (5)	0.047 (2)	−0.001 (2)	0.011 (2)	−0.004 (2)
C1	0.039 (5)	0.057 (4)	0.058 (4)	0.012 (4)	0.024 (3)	−0.008 (3)
C2	0.032 (6)	0.052 (5)	0.064 (3)	0.006 (4)	0.023 (5)	0.005 (4)
C3	0.040 (4)	0.047 (8)	0.050 (4)	0.006 (4)	0.019 (3)	−0.003 (5)
C4	0.035 (4)	0.062 (6)	0.058 (5)	0.005 (4)	0.036 (4)	−0.001 (4)
C5	0.027 (5)	0.057 (4)	0.061 (4)	0.003 (3)	0.028 (4)	0.012 (3)
N2	0.023 (3)	0.063 (7)	0.058 (6)	−0.016 (4)	0.003 (4)	−0.006 (4)
C6	0.056 (4)	0.074 (5)	0.079 (4)	0.006 (4)	0.019 (3)	0.020 (4)
C7	0.045 (4)	0.052 (4)	0.057 (6)	0.003 (3)	−0.002 (4)	−0.014 (4)
C8	0.037 (4)	0.076 (5)	0.057 (8)	−0.005 (4)	0.011 (4)	−0.018 (5)
C9	0.052 (4)	0.088 (6)	0.089 (4)	−0.001 (4)	0.033 (4)	0.020 (4)
C10	0.046 (4)	0.070 (7)	0.060 (6)	0.003 (5)	0.021 (4)	0.008 (5)
C11	0.039 (3)	0.059 (7)	0.063 (3)	0.004 (3)	0.011 (3)	−0.004 (4)
C12	0.043 (5)	0.070 (7)	0.066 (5)	−0.003 (5)	0.018 (4)	0.003 (5)
C13	0.057 (5)	0.072 (5)	0.069 (5)	0.002 (4)	0.025 (5)	−0.008 (4)
C14	0.044 (5)	0.064 (5)	0.064 (4)	−0.003 (4)	0.017 (4)	0.000 (4)
N1'	0.034 (3)	0.041 (5)	0.047 (2)	−0.001 (2)	0.011 (2)	−0.004 (2)
C1'	0.039 (5)	0.057 (4)	0.058 (4)	0.012 (4)	0.024 (3)	−0.008 (3)
C2'	0.032 (6)	0.052 (5)	0.064 (3)	0.006 (4)	0.023 (5)	0.005 (4)
C3'	0.040 (4)	0.047 (8)	0.050 (4)	0.006 (4)	0.019 (3)	−0.003 (5)
C4'	0.035 (4)	0.062 (6)	0.058 (5)	0.005 (4)	0.036 (4)	−0.001 (4)
C5'	0.027 (5)	0.057 (4)	0.061 (4)	0.003 (3)	0.028 (4)	0.012 (3)
N2'	0.023 (3)	0.063 (7)	0.058 (6)	−0.016 (4)	0.003 (4)	−0.006 (4)
C6'	0.056 (4)	0.074 (5)	0.079 (4)	0.006 (4)	0.019 (3)	0.020 (4)
C7'	0.045 (4)	0.052 (4)	0.057 (6)	0.003 (3)	−0.002 (4)	−0.014 (4)
C8'	0.037 (4)	0.076 (5)	0.057 (8)	−0.005 (4)	0.011 (4)	−0.018 (5)
C9'	0.052 (4)	0.088 (6)	0.089 (4)	−0.001 (4)	0.033 (4)	0.020 (4)
C10'	0.046 (4)	0.070 (7)	0.060 (6)	0.003 (5)	0.021 (4)	0.008 (5)
C11'	0.039 (3)	0.059 (7)	0.063 (3)	0.004 (3)	0.011 (3)	−0.004 (4)
C12'	0.043 (5)	0.070 (7)	0.066 (5)	−0.003 (5)	0.018 (4)	0.003 (5)
C13'	0.057 (5)	0.072 (5)	0.069 (5)	0.002 (4)	0.025 (5)	−0.008 (4)
C14'	0.044 (5)	0.064 (5)	0.064 (4)	−0.003 (4)	0.017 (4)	0.000 (4)

Geometric parameters (Å, º)

Hg1—Cl1	2.51 (2)	C13—H13A	0.97
Hg1—Br1	2.58 (4)	C13—H13B	0.97
Hg1—Cl2	2.529 (15)	C14—H14A	0.97
Hg1—Br2	2.49 (4)	C14—H14B	0.97
Hg1—Cl3	2.543 (5)	N1'—C1'	1.39
Hg1—Br3	2.46 (2)	N1'—C5'	1.39
Hg1—Cl4	2.545 (18)	N1'—C11'	1.491 (8)
Hg1—Br4	2.530 (5)	C1'—C2'	1.39
N1—C1	1.39	C1'—H1'	0.93
N1—C5	1.39	C2'—C3'	1.39
N1—C11	1.479 (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'	1.492 (8)
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	1.498 (8)	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'	1.486 (9)
C9—C10	1.39	C11'—H11C	0.97
C9—H9	0.93	C11'—H11D	0.97
C10—H10	0.93	C12'—C13'	1.487 (8)
C11—C12	1.478 (9)	C12'—H12C	0.97
C11—H11A	0.97	C12'—H12D	0.97
C11—H11B	0.97	C13'—C14'	1.481 (8)
C12—C13	1.494 (8)	C13'—H13C	0.97
C12—H12A	0.97	C13'—H13D	0.97
C12—H12B	0.97	C14'—H14C	0.97
C13—C14	1.506 (8)	C14'—H14D	0.97
Cl2—Hg1—Br2	5.1 (9)	C13—C12—H12B	109.3
Cl2—Hg1—Cl3	102.4 (4)	H12A—C12—H12B	108.0
Br2—Hg1—Cl3	100.6 (11)	C12—C13—C14	112.8 (7)
Cl2—Hg1—Br3	96.3 (6)	C12—C13—H13A	109.0
Br2—Hg1—Br3	95.1 (12)	C14—C13—H13A	109.0
Cl3—Hg1—Br3	8.9 (4)	C12—C13—H13B	109.0
Cl2—Hg1—Cl4	112.2 (6)	C14—C13—H13B	109.0
Br2—Hg1—Cl4	109.4 (10)	H13A—C13—H13B	107.8
Cl3—Hg1—Cl4	118.0 (3)	N2—C14—C13	108.4 (6)
Br3—Hg1—Cl4	126.8 (5)	N2—C14—H14A	110.0
Cl2—Hg1—Br4	116.7 (3)	C13—C14—H14A	110.0
Br2—Hg1—Br4	113.4 (9)	N2—C14—H14B	110.0
Cl3—Hg1—Br4	111.18 (10)	C13—C14—H14B	110.0
Br3—Hg1—Br4	120.0 (4)	H14A—C14—H14B	108.4
Cl4—Hg1—Br4	7.0 (4)	C1'—N1'—C5'	120.0
Cl2—Hg1—Cl1	110.7 (7)	C1'—N1'—C11'	112.4 (16)
Br2—Hg1—Cl1	115.8 (9)	C5'—N1'—C11'	127.6 (16)
Cl3—Hg1—Cl1	109.2 (5)	C2'—C1'—N1'	120.0
Br3—Hg1—Cl1	106.0 (7)	C2'—C1'—H1'	120.0
Cl4—Hg1—Cl1	104.4 (6)	N1'—C1'—H1'	120.0
Br4—Hg1—Cl1	106.6 (5)	C1'—C2'—C3'	120.0
Cl2—Hg1—Br1	109.3 (9)	C1'—C2'—H2'	120.0
Br2—Hg1—Br1	114.4 (11)	C3'—C2'—H2'	120.0
Cl3—Hg1—Br1	104.8 (8)	C4'—C3'—C2'	120.0
Br3—Hg1—Br1	101.2 (9)	C4'—C3'—H3'	120.0
Cl4—Hg1—Br1	109.5 (8)	C2'—C3'—H3'	120.0
Br4—Hg1—Br1	111.5 (7)	C3'—C4'—C5'	120.0
Cl1—Hg1—Br1	5.4 (10)	C3'—C4'—H4'	120.0
C1—N1—C5	120.0	C5'—C4'—H4'	120.0
C1—N1—C11	128.6 (16)	C4'—C5'—N1'	120.0
C5—N1—C11	111.4 (16)	C4'—C5'—H5'	120.0
C2—C1—N1	120.0	N1'—C5'—H5'	120.0
C2—C1—H1	120.0	C6'—N2'—C10'	120.0
N1—C1—H1	120.0	C6'—N2'—C14'	121.5 (8)
C1—C2—C3	120.0	C10'—N2'—C14'	118.5 (8)
C1—C2—H2	120.0	N2'—C6'—C7'	120.0
C3—C2—H2	120.0	N2'—C6'—H6'	120.0
C4—C3—C2	120.0	C7'—C6'—H6'	120.0
C4—C3—H3	120.0	C8'—C7'—C6'	120.0
C2—C3—H3	120.0	C8'—C7'—H7'	120.0
C5—C4—C3	120.0	C6'—C7'—H7'	120.0
C5—C4—H4	120.0	C7'—C8'—C9'	120.0
C3—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	121.1 (8)	C9'—C10'—N2'	120.0
C10—N2—C14	118.9 (8)	C9'—C10'—H10'	120.0
N2—C6—C7	120.0	N2'—C10'—H10'	120.0
N2—C6—H6	120.0	C12'—C11'—N1'	110.0 (7)
C7—C6—H6	120.0	C12'—C11'—H11C	109.7
C8—C7—C6	120.0	N1'—C11'—H11C	109.7
C8—C7—H7	120.0	C12'—C11'—H11D	109.7
C6—C7—H7	120.0	N1'—C11'—H11D	109.7
C9—C8—C7	120.0	H11C—C11'—H11D	108.2
C9—C8—H8	120.0	C11'—C12'—C13'	112.1 (8)
C7—C8—H8	120.0	C11'—C12'—H12C	109.2
C8—C9—C10	120.0	C13'—C12'—H12C	109.2
C8—C9—H9	120.0	C11'—C12'—H12D	109.2
C10—C9—H9	120.0	C13'—C12'—H12D	109.2
C9—C10—N2	120.0	H12C—C12'—H12D	107.9
C9—C10—H10	120.0	C14'—C13'—C12'	112.8 (7)
N2—C10—H10	120.0	C14'—C13'—H13C	109.0
C12—C11—N1	112.6 (8)	C12'—C13'—H13C	109.0
C12—C11—H11A	109.1	C14'—C13'—H13D	109.0
N1—C11—H11A	109.1	C12'—C13'—H13D	109.0
C12—C11—H11B	109.1	H13C—C13'—H13D	107.8
N1—C11—H11B	109.1	C13'—C14'—N2'	111.1 (6)
H11A—C11—H11B	107.8	C13'—C14'—H14C	109.4
C11—C12—C13	111.5 (8)	N2'—C14'—H14C	109.4
C11—C12—H12A	109.3	C13'—C14'—H14D	109.4
C13—C12—H12A	109.3	N2'—C14'—H14D	109.4
C11—C12—H12B	109.3	H14C—C14'—H14D	108.0
C11—N1—C1—C2	−179.6 (3)	C11'—N1'—C1'—C2'	−179.8 (2)
C11—N1—C5—C4	179.7 (2)	C11'—N1'—C5'—C4'	179.8 (3)
C14—N2—C6—C7	−179.4 (3)	C14'—N2'—C6'—C7'	−179.8 (3)
C14—N2—C10—C9	179.4 (3)	C14'—N2'—C10'—C9'	179.8 (3)
C1—N1—C11—C12	−74 (2)	C1'—N1'—C11'—C12'	−89 (2)
C5—N1—C11—C12	106 (2)	C5'—N1'—C11'—C12'	91 (2)
N1—C11—C12—C13	171.0 (16)	N1'—C11'—C12'—C13'	−168.6 (16)
C11—C12—C13—C14	86.6 (17)	C11'—C12'—C13'—C14'	−61.7 (19)
C6—N2—C14—C13	100.1 (10)	C12'—C13'—C14'—N2'	−169.3 (9)
C10—N2—C14—C13	−79.3 (10)	C6'—N2'—C14'—C13'	−93.4 (11)
C12—C13—C14—N2	176.8 (9)	C10'—N2'—C14'—C13'	86.8 (11)