4,4′-Bipyridyl adduct of an iodo­antimonate anion linked by a 4,4′-bipyridinium cation

Charmant, J.P.H.; Norman, N.C.; Orpen, A.G.; Starbuck, J.

doi:10.1107/S1600536803022347

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4,4′-Bipyridyl adduct of an iodoantimonate anion linked by a 4,4′-bipyridinium cation

J. P. H. Charmant, N. C. Norman, A. G. Orpen and J. Starbuck

The crystal structure of the title iodoantimonate complex, 4,4′-bipyridinium(2+) di-μ-iodo-bis[(4,4′-bipyridyl)triiodoantimony(III)], formulated as [4,4′-H₂bipy]²⁺[Sb₂I₈(4,4′-bipy)₂]²⁻ or (C₁₀H₁₀N₂)[Sb₂I₈(C₁₀H₈N₂)₂], contains layers of hydrogen-bonded ribbon polymers in which anionic dimetal complexes are linked through hydrogen bonding with 4,4′-H₂bipy cations. The complex is isostructural with its bismuth analogue.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022347/br6118sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022347/br6118Isup2.hkl Contains datablock I

CCDC reference: 226647

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.011 Å
R factor = 0.041
wR factor = 0.079
Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact  C1'    ..  C2'      =       2.83 Ang.

Author Response: This contact is between two atoms that both have partial occupancies of less than 50%.


Alert level B
CHEMW01_ALERT_1_B  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.95 <> 1.05
            Calculated formula weight =  1729.3115
            Formula weight given      =  1629.2600
CHEMW03_ALERT_2_B WARNING: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.95 <> 1.05
           From the CIF: _cell_formula_units_Z                    2
           From the CIF: _chemical_formula_weight          1629.26
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   30.00  360.33
           H         1.01   26.00   26.21
           N        14.01    6.00   84.04
           Sb      121.75    2.00  243.50
           I       126.90    8.00 1015.24
           Calculated formula weight             1729.32
DENSD01_ALERT_1_B  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.95 <> 1.05
            Crystal density given    =      2.608
            Calculated crystal density =      2.457
PLAT043_ALERT_1_B Check Reported Molecular Weight ................    1629.26
PLAT046_ALERT_1_B Reported Z, MW and D(calc) are Inconsistent ....       2.46
PLAT432_ALERT_2_B Short Inter X...Y Contact  C2'    ..  C2'      =       3.02 Ang.

Author Response: This contact is between two atoms that both have partial occupancies of less than 50%.


Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.528     0.710
            Tmin and Tmax expected:      0.449     0.710
            RR =      1.175
            Please check that your absorption correction is appropriate.
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
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 ............       2.00 Ratio
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.19
PLAT213_ALERT_2_C Atom C2'     has ADP max/min Ratio .............       3.30 prolat
PLAT213_ALERT_2_C Atom C5'     has ADP max/min Ratio .............       3.30 prolat
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C1'
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C4'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C13
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.37
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.82
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H10 N2

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4,4'-bipyridinium(2+) di-µ-iodo-bis[(4,4'-bipyridyl)triiodoantimony(III)] top

Crystal data top

(C₁₀H₈N)[Sb₂I₈(C₁₀H₈N₂)₂]	F(000) = 1548
M_r = 1629.26	D_x = 2.608 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5693 reflections
a = 9.6444 (19) Å	θ = 2–27°
b = 12.678 (2) Å	µ = 6.86 mm⁻¹
c = 18.097 (2) Å	T = 173 K
β = 95.570 (16)°	Block, orange
V = 2202.3 (6) Å³	0.20 × 0.10 × 0.05 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	5038 independent reflections
Radiation source: fine-focus sealed tube	3230 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 8.192 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
Frames, each covering 0.3° in ω scans	h = −12→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→16
T_min = 0.528, T_max = 0.710	l = −23→23
13744 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0291P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
5038 reflections	Δρ_max = 1.35 e Å⁻³
234 parameters	Δρ_min = −1.56 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00028 (5)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3904 (13)	0.7885 (10)	0.4554 (7)	0.045 (4)	0.659 (11)
H1	0.3067	0.7649	0.4736	0.054*	0.659 (11)
C2	0.3837 (13)	0.8477 (9)	0.3923 (7)	0.041 (4)	0.659 (11)
H2	0.2962	0.8629	0.3657	0.049*	0.659 (11)
C1'	0.483 (4)	0.872 (2)	0.4949 (15)	0.079 (9)	0.341 (11)
H1'	0.4646	0.9037	0.5405	0.095*	0.341 (11)
C2'	0.476 (3)	0.932 (2)	0.4313 (14)	0.067 (9)	0.341 (11)
H2'	0.4467	1.0039	0.4323	0.080*	0.341 (11)
C3	0.5127 (8)	0.8878 (6)	0.3659 (4)	0.0357 (18)
C4	0.6268 (13)	0.8487 (12)	0.4027 (8)	0.050 (4)	0.659 (11)
H4	0.7137	0.8613	0.3837	0.061*	0.659 (11)
C5	0.6258 (15)	0.7900 (12)	0.4678 (8)	0.047 (4)	0.659 (11)
H5	0.7122	0.7704	0.4937	0.056*	0.659 (11)
C4'	0.574 (4)	0.799 (2)	0.3654 (16)	0.079 (9)	0.341 (11)
H4'	0.6088	0.7718	0.3218	0.095*	0.341 (11)
C5'	0.588 (4)	0.743 (2)	0.4339 (16)	0.067 (9)	0.341 (11)
H5'	0.6538	0.6864	0.4385	0.080*	0.341 (11)
C6	0.3932 (9)	1.0762 (6)	0.2124 (4)	0.041 (2)
H6	0.3145	1.1192	0.1979	0.049*
C7	0.3950 (8)	1.0165 (6)	0.2759 (4)	0.0374 (19)
H7	0.3181	1.0189	0.3049	0.045*
C8	0.5072 (8)	0.9534 (6)	0.2976 (4)	0.0330 (18)
C9	0.6159 (9)	0.9530 (7)	0.2535 (4)	0.047 (2)
H9	0.6956	0.9104	0.2664	0.057*
C10	0.6084 (10)	1.0147 (7)	0.1904 (5)	0.054 (2)
H10	0.6838	1.0138	0.1603	0.065*
N1	0.5164 (8)	0.7625 (5)	0.4931 (4)	0.0454 (18)
N2	0.4993 (7)	1.0750 (5)	0.1708 (3)	0.0368 (16)
Sb1	0.51916 (5)	0.62082 (4)	0.59623 (3)	0.03187 (14)
I1	0.32731 (6)	0.75800 (4)	0.66135 (3)	0.04248 (15)
I2	0.26512 (6)	0.51266 (4)	0.49351 (3)	0.04121 (15)
I3	0.76038 (6)	0.72265 (4)	0.66929 (3)	0.04023 (15)
I4	0.50347 (6)	0.45484 (5)	0.70763 (3)	0.05013 (18)
C11	0.4969 (10)	1.2577 (7)	0.0049 (5)	0.052 (2)
H11	0.4969	1.1972	−0.0261	0.063*
C12	0.4971 (9)	1.3563 (6)	−0.0272 (5)	0.048 (2)
H12	0.4965	1.3626	−0.0796	0.057*
C13	0.4983 (8)	1.4463 (6)	0.0163 (4)	0.0386 (19)
C14	0.4958 (12)	1.4304 (7)	0.0915 (5)	0.069 (3)
H14	0.4939	1.4895	0.1237	0.082*
C15	0.4959 (12)	1.3307 (8)	0.1206 (5)	0.074 (3)
H15	0.4953	1.3230	0.1728	0.089*
N3	0.4968 (8)	1.2442 (6)	0.0790 (4)	0.059 (2)
H3	0.4973	1.1809	0.0989	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.032 (7)	0.066 (10)	0.037 (7)	−0.001 (7)	0.006 (6)	0.023 (7)
C2	0.040 (7)	0.037 (8)	0.045 (7)	0.007 (6)	−0.006 (6)	0.015 (6)
C1'	0.17 (3)	0.037 (12)	0.036 (11)	0.031 (15)	0.028 (14)	−0.002 (9)
C2'	0.12 (2)	0.046 (13)	0.042 (12)	0.046 (14)	0.045 (13)	0.030 (10)
C3	0.035 (4)	0.035 (5)	0.037 (4)	0.008 (4)	0.001 (4)	−0.001 (4)
C4	0.029 (7)	0.061 (10)	0.062 (10)	0.007 (7)	0.012 (7)	0.033 (8)
C5	0.033 (8)	0.064 (11)	0.042 (8)	0.000 (7)	−0.002 (7)	0.009 (7)
C4'	0.17 (3)	0.037 (12)	0.036 (11)	0.031 (15)	0.028 (14)	−0.002 (9)
C5'	0.12 (2)	0.046 (13)	0.042 (12)	0.046 (14)	0.045 (13)	0.030 (10)
C6	0.049 (5)	0.033 (4)	0.040 (5)	0.009 (4)	−0.002 (4)	0.006 (4)
C7	0.039 (5)	0.034 (4)	0.038 (4)	−0.002 (4)	0.000 (4)	0.008 (4)
C8	0.041 (5)	0.028 (4)	0.029 (4)	−0.004 (4)	−0.003 (4)	0.000 (3)
C9	0.045 (5)	0.065 (6)	0.033 (4)	0.013 (5)	0.004 (4)	0.014 (4)
C10	0.050 (5)	0.077 (7)	0.039 (5)	0.007 (5)	0.017 (4)	0.001 (5)
N1	0.056 (5)	0.048 (4)	0.033 (4)	0.014 (4)	0.004 (4)	0.004 (3)
N2	0.040 (4)	0.039 (4)	0.031 (4)	−0.002 (3)	0.000 (3)	−0.002 (3)
Sb1	0.0387 (3)	0.0343 (3)	0.0220 (2)	−0.0001 (2)	−0.0001 (2)	0.0004 (2)
I1	0.0436 (3)	0.0458 (3)	0.0382 (3)	0.0017 (3)	0.0044 (2)	−0.0080 (2)
I2	0.0432 (3)	0.0464 (3)	0.0327 (3)	0.0038 (3)	−0.0029 (2)	−0.0106 (2)
I3	0.0435 (3)	0.0378 (3)	0.0380 (3)	−0.0052 (3)	−0.0033 (2)	−0.0037 (2)
I4	0.0458 (3)	0.0664 (4)	0.0374 (3)	−0.0049 (3)	−0.0002 (3)	0.0195 (3)
C11	0.073 (6)	0.041 (5)	0.045 (5)	0.002 (5)	0.013 (5)	0.010 (4)
C12	0.064 (6)	0.047 (5)	0.034 (4)	0.003 (5)	0.015 (4)	0.004 (4)
C13	0.047 (5)	0.039 (5)	0.030 (4)	0.000 (4)	0.007 (4)	0.007 (4)
C14	0.128 (10)	0.046 (6)	0.031 (5)	−0.017 (6)	0.004 (6)	0.010 (4)
C15	0.131 (10)	0.062 (7)	0.028 (5)	−0.014 (7)	0.002 (6)	0.003 (5)
N3	0.082 (6)	0.047 (5)	0.047 (5)	−0.006 (4)	0.004 (4)	0.011 (4)

Geometric parameters (Å, º) top

C1—C2	1.362 (15)	C7—H7	0.9500
C1—N1	1.375 (13)	C8—C9	1.379 (11)
C1—H1	0.9500	C9—C10	1.380 (11)
C2—C3	1.466 (14)	C9—H9	0.9500
C2—H2	0.9500	C10—N2	1.321 (10)
C1'—C2'	1.38 (3)	C10—H10	0.9500
C1'—N1	1.43 (2)	Sb1—N1	2.588 (7)
C1'—H1'	0.9500	Sb1—I3	2.8687 (8)
C2'—C3	1.39 (3)	Sb1—I1	2.8741 (8)
C2'—H2'	0.9500	Sb1—I4	2.9283 (8)
C3—C4'	1.27 (3)	Sb1—I2	3.2334 (9)
C3—C4	1.326 (14)	Sb1—I2ⁱ	3.2381 (9)
C3—C8	1.486 (10)	I2—Sb1ⁱ	3.2381 (9)
C4—C5	1.393 (18)	C11—N3	1.352 (10)
C4—H4	0.9500	C11—C12	1.378 (10)
C5—N1	1.241 (15)	C11—H11	0.9500
C5—H5	0.9500	C12—C13	1.386 (10)
C4'—C5'	1.43 (4)	C12—H12	0.9500
C4'—H4'	0.9500	C13—C14	1.379 (10)
C5'—N1	1.36 (3)	C13—C13ⁱⁱ	1.486 (14)
C5'—H5'	0.9500	C14—C15	1.368 (12)
C6—N2	1.327 (10)	C14—H14	0.9500
C6—C7	1.376 (10)	C15—N3	1.331 (11)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.371 (10)	N3—H3	0.8800

C2—C1—N1	121.1 (11)	C9—C10—H10	119.1
C2—C1—H1	119.5	C5—N1—C1	119.4 (10)
N1—C1—H1	119.5	C5'—N1—C1'	109.5 (17)
C1—C2—C3	119.4 (10)	C5—N1—Sb1	120.8 (8)
C1—C2—H2	120.3	C5'—N1—Sb1	118.0 (11)
C3—C2—H2	120.3	C1—N1—Sb1	118.1 (7)
C2'—C1'—N1	121 (2)	C1'—N1—Sb1	130.2 (11)
C2'—C1'—H1'	119.5	C10—N2—C6	119.5 (7)
N1—C1'—H1'	119.5	C10—N2—H3	123.8
C1'—C2'—C3	119 (2)	C6—N2—H3	115.5
C1'—C2'—H2'	120.3	N1—Sb1—I3	88.35 (16)
C3—C2'—H2'	120.3	N1—Sb1—I1	85.05 (16)
C4'—C3—C2'	121.6 (17)	I3—Sb1—I1	93.68 (2)
C4—C3—C2	113.3 (9)	N1—Sb1—I4	175.90 (17)
C4'—C3—C8	117.9 (15)	I3—Sb1—I4	95.73 (2)
C4—C3—C8	126.0 (9)	I1—Sb1—I4	94.25 (2)
C2'—C3—C8	119.3 (11)	N1—Sb1—I2	85.73 (16)
C2—C3—C8	120.1 (7)	I3—Sb1—I2	172.38 (2)
C3—C4—C5	123.4 (12)	I1—Sb1—I2	90.59 (2)
C3—C4—H4	118.3	I4—Sb1—I2	90.24 (2)
C5—C4—H4	118.3	N1—Sb1—I2ⁱ	87.90 (16)
N1—C5—C4	122.6 (12)	I3—Sb1—I2ⁱ	86.25 (2)
N1—C5—H5	118.7	I1—Sb1—I2ⁱ	172.95 (2)
C4—C5—H5	118.7	I4—Sb1—I2ⁱ	92.77 (2)
C3—C4'—C5'	116 (2)	I2—Sb1—I2ⁱ	88.74 (2)
C3—C4'—H4'	121.9	Sb1—I2—Sb1ⁱ	91.26 (2)
C5'—C4'—H4'	121.9	N3—C11—C12	122.2 (8)
N1—C5'—C4'	125 (3)	N3—C11—H11	118.9
N1—C5'—H5'	117.3	C12—C11—H11	118.9
C4'—C5'—H5'	117.3	C11—C12—C13	120.5 (8)
N2—C6—C7	121.3 (7)	C11—C12—H12	119.8
N2—C6—H6	119.4	C13—C12—H12	119.8
C7—C6—H6	119.4	C14—C13—C12	116.2 (7)
C8—C7—C6	120.4 (8)	C14—C13—C13ⁱⁱ	122.0 (9)
C8—C7—H7	119.8	C12—C13—C13ⁱⁱ	121.8 (9)
C6—C7—H7	119.8	C15—C14—C13	121.0 (9)
C7—C8—C9	117.3 (7)	C15—C14—H14	119.5
C7—C8—C3	121.9 (7)	C13—C14—H14	119.5
C9—C8—C3	120.8 (7)	N3—C15—C14	122.9 (9)
C8—C9—C10	119.7 (8)	N3—C15—H15	118.6
C8—C9—H9	120.1	C14—C15—H15	118.6
C10—C9—H9	120.1	C15—N3—C11	117.2 (8)
N2—C10—C9	121.7 (8)	C15—N3—H3	121.4
N2—C10—H10	119.1	C11—N3—H3	121.4

N1—C1—C2—C3	−2.5 (19)	C4'—C5'—N1—Sb1	165 (3)
N1—C1'—C2'—C3	−5 (5)	C2—C1—N1—C5	−2.7 (19)
C1'—C2'—C3—C4'	−12 (5)	C2—C1—N1—C5'	−40 (2)
C1'—C2'—C3—C4	−47 (3)	C2—C1—N1—C1'	67.7 (17)
C1'—C2'—C3—C2	69 (3)	C2—C1—N1—Sb1	−168.2 (10)
C1'—C2'—C3—C8	−179 (3)	C2'—C1'—N1—C5	57 (3)
C1—C2—C3—C4'	53.3 (19)	C2'—C1'—N1—C5'	23 (4)
C1—C2—C3—C4	8.7 (17)	C2'—C1'—N1—C1	−67 (3)
C1—C2—C3—C2'	−68.9 (16)	C2'—C1'—N1—Sb1	−174 (2)
C1—C2—C3—C8	−179.4 (10)	C9—C10—N2—C6	−0.4 (13)
C4'—C3—C4—C5	−86 (3)	C9—C10—N2—H3	166.4
C2'—C3—C4—C5	51 (2)	C7—C6—N2—C10	0.5 (12)
C2—C3—C4—C5	−10 (2)	C7—C6—N2—H3	−167.4
C8—C3—C4—C5	178.1 (12)	C5—N1—Sb1—I3	43.6 (10)
C3—C4—C5—N1	6 (3)	C5'—N1—Sb1—I3	90 (2)
C4—C3—C4'—C5'	60 (3)	C1—N1—Sb1—I3	−151.2 (8)
C2'—C3—C4'—C5'	7 (5)	C1'—N1—Sb1—I3	−71 (2)
C2—C3—C4'—C5'	−57 (4)	C5—N1—Sb1—I1	137.4 (10)
C8—C3—C4'—C5'	175 (3)	C5'—N1—Sb1—I1	−176 (2)
C3—C4'—C5'—N1	16 (6)	C1—N1—Sb1—I1	−57.3 (8)
N2—C6—C7—C8	−0.3 (12)	C1'—N1—Sb1—I1	23 (2)
C6—C7—C8—C9	0.1 (11)	C5—N1—Sb1—I2	−131.6 (10)
C6—C7—C8—C3	−180.0 (7)	C5'—N1—Sb1—I2	−85 (2)
C4'—C3—C8—C7	146 (2)	C1—N1—Sb1—I2	33.6 (8)
C4—C3—C8—C7	−159.8 (11)	C1'—N1—Sb1—I2	114 (2)
C2'—C3—C8—C7	−46.4 (19)	C5—N1—Sb1—I2ⁱ	−42.7 (10)
C2—C3—C8—C7	29.3 (12)	C5'—N1—Sb1—I2ⁱ	4 (2)
C4'—C3—C8—C9	−34 (2)	C1—N1—Sb1—I2ⁱ	122.5 (8)
C4—C3—C8—C9	20.2 (15)	C1'—N1—Sb1—I2ⁱ	−157 (2)
C2'—C3—C8—C9	133.5 (18)	N1—Sb1—I2—Sb1ⁱ	87.99 (16)
C2—C3—C8—C9	−150.7 (9)	I1—Sb1—I2—Sb1ⁱ	172.98 (2)
C7—C8—C9—C10	0.1 (12)	I4—Sb1—I2—Sb1ⁱ	−92.77 (2)
C3—C8—C9—C10	−179.9 (8)	I2ⁱ—Sb1—I2—Sb1ⁱ	0.0
C8—C9—C10—N2	0.1 (14)	N3—C11—C12—C13	0.5 (14)
C4—C5—N1—C5'	68 (2)	C11—C12—C13—C14	−1.6 (13)
C4—C5—N1—C1	1 (2)	C11—C12—C13—C13ⁱⁱ	178.7 (10)
C4—C5—N1—C1'	−57.9 (19)	C12—C13—C14—C15	1.7 (15)
C4—C5—N1—Sb1	166.4 (11)	C13ⁱⁱ—C13—C14—C15	−178.5 (11)
C4'—C5'—N1—C5	−89 (4)	C13—C14—C15—N3	−0.8 (18)
C4'—C5'—N1—C1	37 (4)	C14—C15—N3—C11	−0.3 (16)
C4'—C5'—N1—C1'	−30 (5)	C12—C11—N3—C15	0.5 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.88	1.87	2.71 (2)	160

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