catena-Poly[[[dichloridomercury(II)]-μ-1,4-bis­(3-pyridyl­amino­meth­yl)benzene-κ²N:N′] N,N-dimethyl­formamide monosolvate]

The crystal structure of the polymeric title compound, {[HgCl₂(C₁₈H₁₈N₄)]·C₃H₇NO}_n, features an N-heterocyclic ligand which links adjacent HgCl₂ units into a helical chain running along the b axis. The coordination geometry of the Hg^II atom is a distorted tetra­hedron. The dimethyl­formamide mol­ecule is disordered over two positions in a 1:1 ratio, and is linked to the complex mol­ecules via N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.013 Å
• Disorder in solvent or counterion
• R factor = 0.051
• wR factor = 0.167
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT973_ALERT_2_B Large Calcd. Positive Residual Density on    Hg1       1.52 eA-3

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     --  C14     ..        5.7 su
PLAT234_ALERT_4_C Large Hirshfeld Difference C4     --  C5      ..       0.17 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C8     --  C9      ..       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C14    --  C15     ..       0.16 Ang.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Hg1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT245_ALERT_2_C U(iso) H19     Smaller than U(eq) C21'    by ...      0.031 AngSq
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........         O1
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O1'
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C7     -C12           1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0133 Ang
PLAT411_ALERT_2_C Short Inter H...H Contact  H4     ..  H19'    ..       2.10 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          9
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         77

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          5
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Hg1    --  N4_b    ..        7.2 su
PLAT244_ALERT_4_G Low   'Solvent' Ueq as Compared to Neighbors of          N5
PLAT244_ALERT_4_G Low   'Solvent' Ueq as Compared to Neighbors of         N5'
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................        100 Perc.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          !
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         42

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  18 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

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

---

S1. Comment

1,4-Bis(2-pyridylaminomethyl)benzene is a flexible N-heterocycle whose pyridyl and amino N-atoms are capable for forming coordination polymers (Zhu et al., 2007). The crystal structure of HgCl₂(C₁₈H₁₈N₄)^.DMF features the N-heterocycle linking adjacent HgCl₂ units into a helical chain (Scheme I, Fig. 1). The geometry of Hg^II is a tetrahedron. The lattice DMF molecule is disordered in two positions in a 1:1 ratio. The N-heterocycle forms an N–H···O hydrogen bond to the solvent molecule at an N···O distance of 2.99 (3) and 3.03 (3) Å; the hydrogen bond probably stabilizes the solvent molecule so that it is not lost during crystallization.

Related literature

For the structure of the N-heterocyclic ligand, see: Zhu et al. (2007).

S2. Experimental

A THF solution (10 ml) of mercuric chloride (2 mmol) was mixed with a DMF solution (5 ml) of 1,4-bis(3-pyridylaminomethyl)benzene (2 mmol). The solution was filtered and sent aside for the grown of colorless crystals.

S3. Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atoms similar treated (N–H 0.86 Å).

The lattice DMF molecule is disordered over two sites; the disorder could not be refined, and was assumed to be a 1:1 type of disorder. The C–O distances were restrained to 1.25±0.01 Å, the C_carbonyl–N distances to 1.35±0.01 Å and the N–C_methyl distances to 1.45±0.01 Å. Each component was retrained to planar, with a maximum deviation of 0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones, and the anisotropic temperature factors were restrained to be nearly isotropic.

The final difference Fourier map had peaks/holes in the vicinity of Hg1.

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the polymeric chain structure of HgCl2(C18H18N4)^.DMF at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary. radius.

catena-Poly[[[dichloridomercury(II)]-µ-1,4-bis(3- pyridylaminomethyl)benzene-κ²N:N'] N,N-dimethylformamide monosolvate]

Crystal data

[HgCl2(C18H18N4)]·C3H7NO	F(000) = 1232
Mr = 634.95	Dx = 1.737 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10259 reflections
a = 8.4851 (9) Å	θ = 3.2–27.5°
b = 15.1215 (14) Å	µ = 6.58 mm^−1
c = 19.490 (2) Å	T = 293 K
β = 103.826 (2)°	Prism, colorless
V = 2428.2 (4) Å^3	0.15 × 0.11 × 0.11 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP diffractometer	5479 independent reflections
Radiation source: fine-focus sealed tube	2593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
ω scan	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.439, Tmax = 0.531	k = −19→19
22980 measured reflections	l = −25→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0656P)^2] where P = (Fo^2 + 2Fc^2)/3
5479 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 1.26 e Å^−3
42 restraints	Δρmin = −1.31 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Hg1	0.65054 (5)	0.63785 (2)	0.73300 (2)	0.0944 (2)
Cl1	0.3880 (4)	0.5916 (3)	0.7371 (2)	0.1488 (12)
Cl2	0.7868 (4)	0.77413 (15)	0.72364 (19)	0.1366 (11)
N1	0.7052 (9)	0.5581 (4)	0.6351 (4)	0.0845 (19)
N2	0.5616 (9)	0.3645 (4)	0.5347 (5)	0.097 (2)
H2N	0.4912	0.3482	0.5589	0.116*
N3	1.2859 (9)	0.1242 (4)	0.5624 (4)	0.089 (2)
H3N	1.2888	0.1819	0.5685	0.106*
N4	1.6587 (8)	0.0700 (4)	0.6783 (3)	0.0778 (18)
C1	0.6262 (10)	0.4841 (5)	0.6124 (5)	0.077 (2)
H1	0.5528	0.4619	0.6366	0.092*
C2	0.6491 (10)	0.4383 (5)	0.5535 (5)	0.078 (2)
C3	0.7569 (11)	0.4741 (7)	0.5156 (5)	0.097 (3)
H3	0.7720	0.4457	0.4753	0.117*
C4	0.8377 (13)	0.5496 (7)	0.5381 (6)	0.105 (3)
H4	0.9108	0.5734	0.5144	0.126*
C5	0.8089 (11)	0.5909 (6)	0.5976 (6)	0.098 (3)
H5	0.8631	0.6435	0.6127	0.118*
C6	0.5810 (12)	0.3099 (7)	0.4743 (5)	0.108 (3)
H6A	0.5769	0.3485	0.4342	0.130*
H6B	0.4894	0.2698	0.4617	0.130*
C7	0.7345 (10)	0.2565 (5)	0.4868 (5)	0.077 (2)
C8	0.7897 (12)	0.2164 (6)	0.5502 (6)	0.100 (3)
H8	0.7379	0.2257	0.5866	0.120*
C9	0.9204 (13)	0.1631 (7)	0.5601 (5)	0.101 (3)
H9	0.9559	0.1349	0.6035	0.121*
C10	1.0050 (10)	0.1482 (5)	0.5074 (5)	0.073 (2)
C11	0.9536 (11)	0.1896 (6)	0.4447 (5)	0.085 (2)
H11	1.0070	0.1811	0.4087	0.102*
C12	0.8207 (12)	0.2447 (6)	0.4349 (5)	0.093 (3)
H12	0.7875	0.2749	0.3923	0.111*
C13	1.1469 (10)	0.0856 (6)	0.5190 (6)	0.098 (3)
H13A	1.1204	0.0317	0.5408	0.118*
H13B	1.1685	0.0701	0.4738	0.118*
C14	1.5277 (9)	0.1115 (5)	0.6468 (4)	0.0675 (19)
H14	1.5119	0.1688	0.6610	0.081*
C15	1.4147 (9)	0.0755 (5)	0.5950 (4)	0.0700 (19)
C16	1.4362 (11)	−0.0123 (5)	0.5778 (5)	0.083 (2)
H16	1.3588	−0.0406	0.5429	0.100*
C17	1.5701 (12)	−0.0560 (6)	0.6123 (5)	0.092 (3)
H17	1.5835	−0.1152	0.6020	0.111*
C18	1.6827 (11)	−0.0152 (5)	0.6607 (5)	0.083 (2)
H18	1.7778	−0.0446	0.6825	0.100*
O1	0.300 (4)	0.314 (2)	0.6094 (14)	0.110 (3)	0.50
N5	0.181 (3)	0.3560 (13)	0.7007 (11)	0.085 (3)	0.50
C19	0.303 (3)	0.3275 (14)	0.6732 (14)	0.128 (6)	0.50
H19	0.4011	0.3163	0.7053	0.154*	0.50
C20	0.025 (3)	0.375 (2)	0.6545 (18)	0.197 (11)	0.50
H20A	0.0333	0.4262	0.6267	0.295*	0.50
H20B	−0.0525	0.3856	0.6823	0.295*	0.50
H20C	−0.0096	0.3252	0.6239	0.295*	0.50
C21	0.180 (5)	0.380 (2)	0.7725 (13)	0.185 (9)	0.50
H21A	0.1230	0.4349	0.7723	0.278*	0.50
H21B	0.2899	0.3868	0.7998	0.278*	0.50
H21C	0.1273	0.3346	0.7931	0.278*	0.50
O1'	0.323 (4)	0.309 (2)	0.6172 (14)	0.110 (3)	0.50
N5'	0.181 (3)	0.3701 (11)	0.6889 (12)	0.085 (3)	0.50
C19'	0.200 (3)	0.3494 (13)	0.6242 (13)	0.128 (6)	0.50
H19'	0.1203	0.3654	0.5844	0.154*	0.50
C20'	0.052 (4)	0.416 (2)	0.712 (2)	0.197 (11)	0.50
H20D	−0.0339	0.3751	0.7128	0.295*	0.50
H20E	0.0113	0.4629	0.6793	0.295*	0.50
H20F	0.0940	0.4398	0.7580	0.295*	0.50
C21'	0.308 (3)	0.344 (2)	0.7492 (15)	0.185 (9)	0.50
H21D	0.3351	0.2828	0.7443	0.278*	0.50
H21E	0.2704	0.3509	0.7917	0.278*	0.50
H21F	0.4020	0.3798	0.7517	0.278*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.0921 (3)	0.0868 (3)	0.0909 (3)	0.00588 (18)	−0.0045 (2)	−0.00621 (18)
Cl1	0.096 (2)	0.202 (3)	0.142 (3)	−0.024 (2)	0.017 (2)	−0.030 (3)
Cl2	0.139 (3)	0.0719 (13)	0.172 (3)	0.0028 (14)	−0.015 (2)	0.0193 (16)
N1	0.071 (5)	0.083 (4)	0.092 (5)	0.005 (4)	0.007 (4)	−0.001 (4)
N2	0.065 (5)	0.099 (5)	0.123 (7)	0.002 (4)	0.014 (5)	−0.031 (5)
N3	0.066 (5)	0.072 (4)	0.116 (6)	0.005 (3)	−0.003 (4)	−0.016 (4)
N4	0.079 (5)	0.073 (4)	0.065 (4)	−0.009 (3)	−0.014 (3)	−0.005 (3)
C1	0.062 (5)	0.080 (5)	0.081 (5)	0.007 (4)	0.002 (4)	0.002 (4)
C2	0.062 (5)	0.078 (5)	0.089 (6)	0.013 (4)	0.010 (5)	−0.010 (5)
C3	0.078 (7)	0.114 (8)	0.097 (7)	0.020 (5)	0.014 (6)	−0.012 (6)
C4	0.107 (8)	0.103 (7)	0.113 (8)	0.004 (6)	0.041 (7)	0.005 (6)
C5	0.072 (6)	0.086 (6)	0.126 (8)	−0.002 (5)	0.004 (6)	0.003 (6)
C6	0.096 (7)	0.108 (7)	0.101 (7)	0.026 (6)	−0.016 (6)	−0.034 (6)
C7	0.064 (5)	0.081 (5)	0.082 (6)	0.013 (4)	0.005 (5)	−0.010 (4)
C8	0.092 (7)	0.113 (7)	0.101 (7)	0.036 (6)	0.037 (6)	0.020 (6)
C9	0.113 (8)	0.122 (7)	0.066 (6)	0.029 (6)	0.017 (6)	0.021 (5)
C10	0.057 (5)	0.070 (4)	0.080 (6)	0.007 (4)	−0.006 (4)	−0.007 (4)
C11	0.083 (6)	0.100 (6)	0.075 (6)	0.016 (5)	0.023 (5)	−0.007 (5)
C12	0.104 (8)	0.107 (6)	0.063 (5)	0.025 (5)	0.012 (5)	−0.002 (5)
C13	0.066 (6)	0.090 (6)	0.119 (8)	0.007 (5)	−0.017 (5)	−0.029 (5)
C14	0.058 (5)	0.068 (4)	0.056 (4)	0.010 (3)	−0.027 (3)	−0.004 (3)
C15	0.063 (5)	0.069 (4)	0.068 (5)	0.012 (4)	−0.004 (4)	0.003 (4)
C16	0.086 (6)	0.067 (4)	0.083 (6)	0.007 (4)	−0.006 (5)	−0.011 (4)
C17	0.094 (7)	0.070 (5)	0.099 (7)	0.009 (5)	−0.006 (6)	−0.006 (5)
C18	0.082 (6)	0.070 (5)	0.083 (6)	0.007 (4)	−0.009 (5)	−0.003 (4)
O1	0.108 (7)	0.101 (4)	0.125 (6)	0.006 (5)	0.035 (5)	−0.011 (4)
N5	0.083 (5)	0.087 (6)	0.082 (6)	0.010 (4)	0.015 (5)	0.016 (5)
C19	0.125 (10)	0.134 (9)	0.122 (10)	0.015 (7)	0.023 (8)	0.009 (8)
C20	0.188 (13)	0.210 (14)	0.193 (14)	0.023 (9)	0.047 (10)	−0.009 (9)
C21	0.189 (12)	0.195 (12)	0.177 (12)	0.005 (9)	0.054 (9)	0.000 (9)
O1'	0.108 (7)	0.101 (4)	0.125 (6)	0.006 (5)	0.035 (5)	−0.011 (4)
N5'	0.083 (5)	0.087 (6)	0.082 (6)	0.010 (4)	0.015 (5)	0.016 (5)
C19'	0.125 (10)	0.134 (9)	0.122 (10)	0.015 (7)	0.023 (8)	0.009 (8)
C20'	0.188 (13)	0.210 (14)	0.193 (14)	0.023 (9)	0.047 (10)	−0.009 (9)
C21'	0.189 (12)	0.195 (12)	0.177 (12)	0.005 (9)	0.054 (9)	0.000 (9)

Geometric parameters (Å, º)

Hg1—N1	2.395 (7)	C11—H11	0.9300
Hg1—N4^i	2.308 (6)	C12—H12	0.9300
Hg1—Cl1	2.355 (3)	C13—H13A	0.9700
Hg1—Cl2	2.391 (3)	C13—H13B	0.9700
N1—C1	1.325 (10)	C14—C15	1.331 (10)
N1—C5	1.364 (11)	C14—H14	0.9300
N2—C2	1.342 (10)	C15—C16	1.392 (10)
N2—C6	1.479 (11)	C16—C17	1.346 (12)
N2—H2N	0.8800	C16—H16	0.9300
N3—C15	1.345 (10)	C17—C18	1.324 (11)
N3—C13	1.404 (10)	C17—H17	0.9300
N3—H3N	0.8800	C18—H18	0.9300
N4—C14	1.296 (9)	O1—C19	1.253 (10)
N4—C18	1.361 (9)	N5—C19	1.344 (10)
N4—Hg1^ii	2.308 (6)	N5—C20	1.440 (10)
C1—C2	1.392 (11)	N5—C21	1.448 (10)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.414 (12)	C20—H20A	0.9600
C3—C4	1.351 (13)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.390 (13)	C21—H21A	0.9600
C4—H4	0.9300	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.502 (11)	O1'—C19'	1.250 (10)
C6—H6A	0.9700	N5'—C19'	1.346 (10)
C6—H6B	0.9700	N5'—C20'	1.448 (10)
C7—C8	1.356 (12)	N5'—C21'	1.449 (10)
C7—C12	1.394 (11)	C19'—H19'	0.9300
C8—C9	1.347 (12)	C20'—H20D	0.9600
C8—H8	0.9300	C20'—H20E	0.9600
C9—C10	1.405 (12)	C20'—H20F	0.9600
C9—H9	0.9300	C21'—H21D	0.9600
C10—C11	1.348 (11)	C21'—H21E	0.9600
C10—C13	1.506 (11)	C21'—H21F	0.9600
C11—C12	1.378 (11)
N4^i—Hg1—Cl1	110.0 (2)	C10—C11—C12	118.9 (8)
N4^i—Hg1—Cl2	100.07 (18)	C10—C11—H11	120.6
Cl1—Hg1—Cl2	137.49 (12)	C12—C11—H11	120.6
N4^i—Hg1—N1	97.9 (2)	C11—C12—C7	122.1 (8)
Cl1—Hg1—N1	104.0 (2)	C11—C12—H12	119.0
Cl2—Hg1—N1	100.6 (2)	C7—C12—H12	119.0
C1—N1—C5	117.9 (8)	N3—C13—C10	110.8 (7)
C1—N1—Hg1	120.9 (6)	N3—C13—H13A	109.5
C5—N1—Hg1	121.1 (6)	C10—C13—H13A	109.5
C2—N2—C6	121.5 (8)	N3—C13—H13B	109.5
C2—N2—H2N	119.2	C10—C13—H13B	109.5
C6—N2—H2N	119.2	H13A—C13—H13B	108.1
C15—N3—C13	121.9 (7)	N4—C14—C15	122.8 (7)
C15—N3—H3N	119.0	N4—C14—H14	118.6
C13—N3—H3N	119.0	C15—C14—H14	118.6
C14—N4—C18	120.1 (7)	C14—C15—N3	119.4 (7)
C14—N4—Hg1^ii	120.6 (5)	C14—C15—C16	117.4 (7)
C18—N4—Hg1^ii	119.3 (5)	N3—C15—C16	123.2 (8)
N1—C1—C2	122.4 (8)	C17—C16—C15	119.4 (8)
N1—C1—H1	118.8	C17—C16—H16	120.3
C2—C1—H1	118.8	C15—C16—H16	120.3
N2—C2—C1	117.5 (8)	C18—C17—C16	120.4 (8)
N2—C2—C3	124.0 (8)	C18—C17—H17	119.8
C1—C2—C3	118.4 (8)	C16—C17—H17	119.8
C4—C3—C2	119.7 (9)	C17—C18—N4	119.7 (8)
C4—C3—H3	120.1	C17—C18—H18	120.2
C2—C3—H3	120.1	N4—C18—H18	120.2
C3—C4—C5	118.3 (9)	C19—N5—C20	120 (3)
C3—C4—H4	120.9	C19—N5—C21	130 (3)
C5—C4—H4	120.9	C20—N5—C21	110 (3)
N1—C5—C4	123.3 (9)	O1—C19—N5	128 (3)
N1—C5—H5	118.4	O1—C19—H19	116.2
C4—C5—H5	118.4	N5—C19—H19	116.2
N2—C6—C7	115.3 (8)	C19'—N5'—C20'	132 (3)
N2—C6—H6A	108.4	C19'—N5'—C21'	118 (2)
C7—C6—H6A	108.4	C20'—N5'—C21'	111 (2)
N2—C6—H6B	108.4	O1'—C19'—N5'	121 (3)
C7—C6—H6B	108.4	O1'—C19'—H19'	119.7
H6A—C6—H6B	107.5	N5'—C19'—H19'	119.7
C8—C7—C12	118.5 (8)	N5'—C20'—H20D	109.5
C8—C7—C6	119.1 (8)	N5'—C20'—H20E	109.5
C12—C7—C6	122.4 (9)	H20D—C20'—H20E	109.5
C9—C8—C7	119.4 (8)	N5'—C20'—H20F	109.5
C9—C8—H8	120.3	H20D—C20'—H20F	109.5
C7—C8—H8	120.3	H20E—C20'—H20F	109.5
C8—C9—C10	122.6 (9)	N5'—C21'—H21D	109.5
C8—C9—H9	118.7	N5'—C21'—H21E	109.5
C10—C9—H9	118.7	H21D—C21'—H21E	109.5
C11—C10—C9	118.5 (7)	N5'—C21'—H21F	109.5
C11—C10—C13	120.1 (8)	H21D—C21'—H21F	109.5
C9—C10—C13	121.4 (8)	H21E—C21'—H21F	109.5
N4^i—Hg1—N1—C1	90.8 (6)	C8—C9—C10—C13	−177.7 (10)
Cl1—Hg1—N1—C1	−22.2 (7)	C9—C10—C11—C12	0.1 (13)
Cl2—Hg1—N1—C1	−167.3 (6)	C13—C10—C11—C12	178.2 (8)
N4^i—Hg1—N1—C5	−94.4 (7)	C10—C11—C12—C7	−2.3 (15)
Cl1—Hg1—N1—C5	152.6 (6)	C8—C7—C12—C11	4.0 (15)
Cl2—Hg1—N1—C5	7.5 (7)	C6—C7—C12—C11	−174.4 (9)
C5—N1—C1—C2	1.8 (12)	C15—N3—C13—C10	162.7 (8)
Hg1—N1—C1—C2	176.8 (6)	C11—C10—C13—N3	105.7 (10)
C6—N2—C2—C1	−178.2 (7)	C9—C10—C13—N3	−76.3 (12)
C6—N2—C2—C3	4.8 (14)	C18—N4—C14—C15	−2.5 (12)
N1—C1—C2—N2	−179.4 (8)	Hg1^ii—N4—C14—C15	179.4 (6)
N1—C1—C2—C3	−2.1 (13)	N4—C14—C15—N3	−176.6 (8)
N2—C2—C3—C4	178.9 (9)	N4—C14—C15—C16	4.0 (12)
C1—C2—C3—C4	1.8 (14)	C13—N3—C15—C14	−165.7 (8)
C2—C3—C4—C5	−1.4 (15)	C13—N3—C15—C16	13.6 (14)
C1—N1—C5—C4	−1.3 (14)	C14—C15—C16—C17	−1.8 (13)
Hg1—N1—C5—C4	−176.3 (7)	N3—C15—C16—C17	178.9 (9)
C3—C4—C5—N1	1.1 (16)	C15—C16—C17—C18	−1.9 (15)
C2—N2—C6—C7	73.2 (12)	C16—C17—C18—N4	3.5 (14)
N2—C6—C7—C8	40.2 (13)	C14—N4—C18—C17	−1.4 (12)
N2—C6—C7—C12	−141.5 (9)	Hg1^ii—N4—C18—C17	176.7 (7)
C12—C7—C8—C9	−3.4 (15)	C20—N5—C19—O1	0.0 (2)
C6—C7—C8—C9	175.0 (10)	C21—N5—C19—O1	−174 (3)
C7—C8—C9—C10	1.3 (17)	C20'—N5'—C19'—O1'	180.0 (4)
C8—C9—C10—C11	0.4 (15)	C21'—N5'—C19'—O1'	0.0 (3)

Symmetry codes: (i) −x+5/2, y+1/2, −z+3/2; (ii) −x+5/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.88	2.15	3.03 (3)	174
N2—H2N···O1′	0.88	2.11	2.99 (3)	180
N3—H3N···O1^iii	0.88	2.14	3.01 (3)	166
N3—H3N···O1′^iii	0.88	2.13	2.98 (3)	162

Symmetry code: (iii) x+1, y, z.