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The asymmetric unit of the title compound, (C12H9N2)[BiI4(C12H8N2)]·C12H8N2, comprises a 1,10-phenanthrolinium cation and a tetra­iodo­(1,10-phenanthroline)bis­muthate(III) anion, together with a neutral 1,10-phenanthroline mol­ecule. The BiIII ion adopts a distorted octa­hedral coordination geometry, binding to the two N atoms of a chelating 1,10-phenanthroline ligand and four iodide ions. N—H...N and C—H...I hydrogen bonding between the 1,10-phenanthroline mol­ecule, the 1,10-phenanthrolinium cation and the BiIII complex cation stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014991/sj2049sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014991/sj2049Isup2.hkl
Contains datablock I

CCDC reference: 608606

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.018 Å
  • R factor = 0.042
  • wR factor = 0.104
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.53 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Bi1 - I1 .. 7.95 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Bi1 - I3 .. 9.64 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Bi1 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 18 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. I3 .. 3.16 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. I2 .. 3.19 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H35 .. I1 .. 3.25 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 0.534 Tmax scaled 0.121 Tmin scaled 0.104
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,10-Phenanthrolinium tetraiodo(1,10-phenanthroline-κ2N,N')bismuthate(III) 1,10-phenanthroline top
Crystal data top
(C12H9N2)[BiI4(C12H8N2)]·C12H8N2F(000) = 2312
Mr = 1258.20Dx = 2.257 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4041 reflections
a = 14.732 (3) Åθ = 2.3–23.2°
b = 17.414 (4) ŵ = 8.13 mm1
c = 15.424 (3) ÅT = 298 K
β = 110.629 (3)°Block, orange
V = 3703.1 (13) Å30.30 × 0.28 × 0.26 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
6517 independent reflections
Radiation source: fine-focus sealed tube4042 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1710
Tmin = 0.194, Tmax = 0.226k = 1920
19288 measured reflectionsl = 1718
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0264P)2 + 15.5137P]
where P = (Fo2 + 2Fc2)/3
6517 reflections(Δ/σ)max < 0.001
424 parametersΔρmax = 1.84 e Å3
0 restraintsΔρmin = 2.01 e Å3
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
xyzUiso*/Ueq
Bi10.66762 (3)0.13483 (2)0.33335 (3)0.03893 (13)
I10.84747 (6)0.02976 (4)0.41790 (5)0.0488 (2)
I20.47649 (6)0.19492 (4)0.20779 (6)0.0578 (2)
I30.77691 (6)0.28625 (4)0.34843 (6)0.0601 (3)
I40.61898 (8)0.13910 (8)0.50620 (7)0.1062 (4)
N10.6909 (6)0.0976 (5)0.1840 (6)0.040 (2)
N20.5842 (6)0.0112 (4)0.2611 (6)0.037 (2)
N30.2033 (8)0.1149 (6)0.1822 (7)0.065 (3)
N40.0769 (7)0.2349 (6)0.1138 (6)0.056 (3)
H40.11830.22160.08870.068*
N50.0876 (7)0.3529 (5)0.4609 (6)0.056 (3)
N60.2133 (7)0.2342 (5)0.5148 (6)0.049 (2)
C10.7426 (9)0.1390 (7)0.1475 (7)0.056 (3)
H10.76980.18450.17680.067*
C20.7584 (10)0.1188 (8)0.0687 (8)0.067 (4)
H20.79640.14980.04600.081*
C30.7192 (10)0.0541 (8)0.0236 (8)0.064 (4)
H30.73080.03990.02970.077*
C40.6606 (9)0.0077 (7)0.0574 (8)0.055 (3)
C50.6499 (7)0.0331 (6)0.1401 (7)0.037 (3)
C60.5901 (7)0.0113 (5)0.1801 (7)0.037 (3)
C70.5410 (8)0.0760 (6)0.1313 (9)0.049 (3)
C80.4844 (9)0.1152 (6)0.1720 (10)0.061 (4)
H80.45010.15830.14250.073*
C90.4774 (9)0.0921 (7)0.2542 (10)0.063 (4)
H90.43970.11910.28120.076*
C100.5287 (9)0.0268 (6)0.2963 (9)0.055 (3)
H100.52330.00960.35140.066*
C110.6094 (10)0.0597 (7)0.0127 (8)0.062 (4)
H110.61550.07630.04230.074*
C120.5537 (9)0.0985 (7)0.0483 (9)0.062 (4)
H120.52180.14210.01760.075*
C130.2603 (10)0.0561 (9)0.2156 (10)0.082 (5)
H130.30520.04350.18800.098*
C140.2584 (10)0.0109 (8)0.2898 (9)0.072 (4)
H140.30040.03050.31030.087*
C150.1944 (9)0.0286 (7)0.3309 (8)0.059 (3)
H150.19230.00060.38070.070*
C160.1306 (8)0.0910 (6)0.2991 (7)0.045 (3)
C170.1392 (8)0.1315 (6)0.2242 (7)0.040 (3)
C180.0741 (8)0.1951 (6)0.1877 (7)0.041 (3)
C190.0063 (8)0.2163 (6)0.2283 (8)0.044 (3)
C200.0532 (9)0.2789 (7)0.1912 (8)0.055 (3)
H200.09750.29540.21780.066*
C210.0467 (9)0.3158 (7)0.1170 (8)0.059 (3)
H210.08740.35720.09150.071*
C220.0201 (10)0.2922 (8)0.0789 (8)0.068 (4)
H220.02450.31780.02750.081*
C230.0613 (8)0.1122 (6)0.3379 (7)0.046 (3)
H230.05630.08390.38720.055*
C240.0026 (8)0.1721 (6)0.3058 (7)0.047 (3)
H240.04150.18560.33410.056*
C250.0281 (10)0.4107 (8)0.4368 (9)0.072 (4)
H250.01220.42010.47040.086*
C260.0218 (12)0.4597 (8)0.3626 (10)0.089 (5)
H260.02060.50130.34840.107*
C270.0781 (12)0.4453 (7)0.3123 (10)0.079 (5)
H270.07430.47630.26200.094*
C280.1433 (9)0.3827 (6)0.3368 (8)0.049 (3)
C290.1474 (8)0.3384 (6)0.4134 (8)0.044 (3)
C300.2135 (8)0.2749 (6)0.4411 (7)0.039 (3)
C310.2710 (8)0.2588 (6)0.3890 (8)0.043 (3)
C320.3360 (9)0.1978 (8)0.4194 (9)0.062 (4)
H320.37720.18470.38780.074*
C330.3383 (9)0.1579 (7)0.4961 (9)0.062 (3)
H330.38160.11730.51740.074*
C340.2768 (9)0.1772 (7)0.5423 (8)0.061 (4)
H340.27990.14930.59460.073*
C350.2037 (10)0.3629 (8)0.2847 (9)0.064 (4)
H350.20010.39150.23270.077*
C360.2642 (9)0.3045 (8)0.3100 (8)0.058 (3)
H360.30330.29280.27580.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.0396 (3)0.0432 (2)0.0369 (2)0.0028 (2)0.01699 (19)0.0039 (2)
I10.0482 (5)0.0543 (5)0.0459 (4)0.0083 (4)0.0192 (4)0.0009 (4)
I20.0532 (5)0.0503 (5)0.0597 (5)0.0127 (4)0.0073 (4)0.0057 (4)
I30.0594 (6)0.0546 (5)0.0785 (6)0.0074 (4)0.0395 (5)0.0202 (4)
I40.0935 (8)0.1831 (12)0.0602 (6)0.0536 (8)0.0497 (6)0.0260 (7)
N10.042 (6)0.047 (6)0.032 (5)0.003 (5)0.012 (4)0.005 (4)
N20.039 (6)0.027 (5)0.047 (6)0.003 (4)0.018 (5)0.014 (4)
N30.060 (7)0.092 (8)0.052 (6)0.030 (6)0.031 (6)0.016 (6)
N40.056 (7)0.081 (7)0.038 (6)0.026 (6)0.024 (5)0.020 (5)
N50.057 (7)0.060 (7)0.053 (6)0.013 (5)0.022 (6)0.005 (5)
N60.048 (6)0.059 (6)0.040 (6)0.003 (5)0.014 (5)0.014 (5)
C10.070 (9)0.072 (9)0.028 (6)0.020 (7)0.020 (6)0.001 (6)
C20.074 (10)0.095 (11)0.046 (8)0.011 (8)0.037 (7)0.001 (8)
C30.076 (10)0.086 (10)0.034 (7)0.018 (8)0.025 (7)0.007 (7)
C40.050 (8)0.074 (9)0.039 (7)0.016 (7)0.012 (6)0.004 (7)
C50.035 (7)0.034 (6)0.041 (6)0.014 (5)0.012 (5)0.004 (5)
C60.032 (6)0.027 (6)0.042 (7)0.005 (5)0.002 (5)0.001 (5)
C70.040 (7)0.028 (6)0.066 (8)0.011 (5)0.004 (6)0.003 (6)
C80.053 (9)0.027 (6)0.085 (10)0.008 (6)0.003 (8)0.008 (7)
C90.056 (9)0.049 (8)0.095 (11)0.003 (6)0.039 (8)0.020 (8)
C100.067 (9)0.030 (6)0.071 (9)0.014 (6)0.027 (7)0.022 (6)
C110.068 (10)0.068 (9)0.038 (7)0.007 (7)0.005 (7)0.013 (7)
C120.052 (9)0.040 (7)0.078 (10)0.004 (6)0.001 (8)0.024 (7)
C130.076 (11)0.108 (12)0.079 (11)0.035 (9)0.050 (9)0.005 (9)
C140.068 (10)0.088 (10)0.064 (9)0.028 (8)0.026 (8)0.004 (8)
C150.062 (9)0.062 (8)0.050 (8)0.003 (7)0.017 (7)0.016 (6)
C160.038 (7)0.058 (8)0.040 (7)0.006 (6)0.015 (6)0.005 (6)
C170.042 (7)0.049 (7)0.030 (6)0.007 (6)0.015 (5)0.004 (5)
C180.037 (7)0.043 (7)0.039 (7)0.002 (5)0.008 (6)0.002 (5)
C190.040 (7)0.052 (7)0.047 (7)0.015 (6)0.023 (6)0.004 (6)
C200.053 (8)0.060 (8)0.061 (8)0.007 (7)0.030 (7)0.006 (7)
C210.062 (9)0.055 (8)0.061 (9)0.012 (7)0.024 (7)0.011 (7)
C220.072 (10)0.092 (11)0.045 (8)0.017 (8)0.027 (7)0.024 (7)
C230.049 (8)0.051 (7)0.037 (7)0.004 (6)0.016 (6)0.005 (5)
C240.047 (8)0.056 (7)0.048 (7)0.004 (6)0.030 (6)0.001 (6)
C250.088 (11)0.071 (9)0.054 (9)0.034 (8)0.022 (8)0.000 (7)
C260.108 (14)0.076 (11)0.070 (11)0.041 (9)0.013 (10)0.006 (9)
C270.114 (14)0.043 (8)0.059 (9)0.005 (8)0.006 (9)0.013 (7)
C280.053 (8)0.043 (7)0.051 (7)0.008 (6)0.018 (6)0.014 (6)
C290.040 (7)0.046 (7)0.041 (7)0.010 (6)0.008 (6)0.004 (5)
C300.040 (7)0.045 (7)0.032 (6)0.015 (5)0.011 (5)0.002 (5)
C310.048 (8)0.038 (7)0.042 (7)0.009 (6)0.014 (6)0.008 (5)
C320.057 (9)0.079 (10)0.056 (8)0.000 (7)0.026 (7)0.006 (7)
C330.052 (9)0.067 (9)0.060 (9)0.009 (7)0.012 (7)0.005 (7)
C340.054 (9)0.069 (9)0.047 (8)0.001 (7)0.003 (7)0.027 (7)
C350.073 (10)0.064 (9)0.051 (8)0.026 (8)0.018 (7)0.012 (7)
C360.057 (9)0.082 (10)0.043 (7)0.022 (8)0.027 (7)0.004 (7)
Geometric parameters (Å, º) top
Bi1—N12.530 (8)C13—H130.9300
Bi1—N22.534 (8)C14—C151.343 (16)
Bi1—I22.9886 (10)C14—H140.9300
Bi1—I42.9953 (11)C15—C161.408 (15)
Bi1—I33.0554 (10)C15—H150.9300
Bi1—I13.1039 (9)C16—C171.396 (14)
N1—C11.312 (13)C16—C231.402 (14)
N1—C51.340 (12)C17—C181.443 (14)
N2—C101.309 (13)C18—C191.403 (14)
N2—C61.342 (12)C19—C201.390 (15)
N3—C131.311 (15)C19—C241.439 (14)
N3—C171.351 (13)C20—C211.345 (15)
N4—C221.291 (14)C20—H200.9300
N4—C181.347 (13)C21—C221.376 (16)
N4—H40.8600C21—H210.9300
N5—C251.301 (14)C22—H220.9300
N5—C291.354 (13)C23—C241.335 (14)
N6—C341.328 (14)C23—H230.9300
N6—C301.340 (12)C24—H240.9300
C1—C21.362 (15)C25—C261.405 (18)
C1—H10.9300C25—H250.9300
C2—C31.343 (16)C26—C271.343 (19)
C2—H20.9300C26—H260.9300
C3—C41.409 (17)C27—C281.414 (17)
C3—H30.9300C27—H270.9300
C4—C51.410 (14)C28—C291.394 (14)
C4—C111.433 (16)C28—C351.435 (17)
C5—C61.463 (14)C29—C301.435 (15)
C6—C71.405 (14)C30—C311.386 (14)
C7—C81.388 (16)C31—C321.396 (16)
C7—C121.413 (16)C31—C361.428 (15)
C8—C91.368 (16)C32—C331.363 (16)
C8—H80.9300C32—H320.9300
C9—C101.392 (16)C33—C341.376 (16)
C9—H90.9300C33—H330.9300
C10—H100.9300C34—H340.9300
C11—C121.323 (16)C35—C361.318 (16)
C11—H110.9300C35—H350.9300
C12—H120.9300C36—H360.9300
C13—C141.398 (17)
N1—Bi1—N265.3 (3)C13—C14—H14120.7
N1—Bi1—I284.19 (19)C14—C15—C16120.4 (12)
N2—Bi1—I279.17 (18)C14—C15—H15119.8
N1—Bi1—I4165.5 (2)C16—C15—H15119.8
N2—Bi1—I4100.44 (19)C17—C16—C23120.8 (11)
I2—Bi1—I495.85 (3)C17—C16—C15115.7 (10)
N1—Bi1—I393.1 (2)C23—C16—C15123.5 (11)
N2—Bi1—I3158.06 (19)N3—C17—C16124.8 (10)
I2—Bi1—I395.63 (3)N3—C17—C18117.2 (10)
I4—Bi1—I3101.29 (3)C16—C17—C18118.0 (10)
N1—Bi1—I182.07 (19)N4—C18—C19118.8 (10)
N2—Bi1—I183.92 (18)N4—C18—C17120.8 (10)
I2—Bi1—I1161.55 (3)C19—C18—C17120.5 (10)
I4—Bi1—I194.43 (3)C20—C19—C18117.9 (10)
I3—Bi1—I197.34 (3)C20—C19—C24123.9 (10)
C1—N1—C5118.1 (9)C18—C19—C24118.2 (11)
C1—N1—Bi1122.4 (7)C21—C20—C19120.1 (11)
C5—N1—Bi1119.6 (7)C21—C20—H20119.9
C10—N2—C6119.5 (10)C19—C20—H20119.9
C10—N2—Bi1121.6 (8)C20—C21—C22119.8 (12)
C6—N2—Bi1118.5 (6)C20—C21—H21120.1
C13—N3—C17116.0 (10)C22—C21—H21120.1
C22—N4—C18122.8 (10)N4—C22—C21120.6 (11)
C22—N4—H4118.6N4—C22—H22119.7
C18—N4—H4118.6C21—C22—H22119.7
C25—N5—C29119.5 (11)C24—C23—C16121.4 (10)
C34—N6—C30117.0 (10)C24—C23—H23119.3
N1—C1—C2123.2 (12)C16—C23—H23119.3
N1—C1—H1118.4C23—C24—C19121.1 (10)
C2—C1—H1118.4C23—C24—H24119.5
C3—C2—C1120.1 (12)C19—C24—H24119.5
C3—C2—H2120.0N5—C25—C26123.1 (13)
C1—C2—H2120.0N5—C25—H25118.4
C2—C3—C4119.8 (11)C26—C25—H25118.4
C2—C3—H3120.1C27—C26—C25118.7 (13)
C4—C3—H3120.1C27—C26—H26120.6
C3—C4—C5115.7 (11)C25—C26—H26120.6
C3—C4—C11125.3 (11)C26—C27—C28119.3 (13)
C5—C4—C11119.0 (12)C26—C27—H27120.4
N1—C5—C4123.1 (10)C28—C27—H27120.4
N1—C5—C6117.5 (9)C29—C28—C27118.4 (12)
C4—C5—C6119.5 (10)C29—C28—C35119.4 (11)
N2—C6—C7122.9 (10)C27—C28—C35122.2 (12)
N2—C6—C5119.0 (9)N5—C29—C28120.9 (11)
C7—C6—C5118.1 (10)N5—C29—C30119.0 (10)
C8—C7—C6115.4 (11)C28—C29—C30120.1 (11)
C8—C7—C12124.5 (12)N6—C30—C31124.7 (11)
C6—C7—C12120.0 (12)N6—C30—C29117.1 (10)
C9—C8—C7121.9 (12)C31—C30—C29118.2 (10)
C9—C8—H8119.1C30—C31—C32116.5 (11)
C7—C8—H8119.1C30—C31—C36120.6 (11)
C8—C9—C10117.8 (12)C32—C31—C36122.9 (11)
C8—C9—H9121.1C33—C32—C31119.0 (12)
C10—C9—H9121.1C33—C32—H32120.5
N2—C10—C9122.4 (12)C31—C32—H32120.5
N2—C10—H10118.8C32—C33—C34120.3 (12)
C9—C10—H10118.8C32—C33—H33119.8
C12—C11—C4121.1 (12)C34—C33—H33119.8
C12—C11—H11119.4N6—C34—C33122.4 (11)
C4—C11—H11119.4N6—C34—H34118.8
C11—C12—C7122.3 (12)C33—C34—H34118.8
C11—C12—H12118.9C36—C35—C28120.6 (12)
C7—C12—H12118.9C36—C35—H35119.7
N3—C13—C14124.5 (12)C28—C35—H35119.7
N3—C13—H13117.7C35—C36—C31121.2 (12)
C14—C13—H13117.7C35—C36—H36119.4
C15—C14—C13118.5 (13)C31—C36—H36119.4
C15—C14—H14120.7
N2—Bi1—N1—C1179.7 (9)C14—C15—C16—C170.1 (17)
I2—Bi1—N1—C199.6 (9)C14—C15—C16—C23179.3 (12)
I4—Bi1—N1—C1169.5 (7)C13—N3—C17—C160.2 (18)
I3—Bi1—N1—C14.3 (9)C13—N3—C17—C18178.8 (11)
I1—Bi1—N1—C192.7 (9)C23—C16—C17—N3179.6 (11)
N2—Bi1—N1—C50.1 (7)C15—C16—C17—N30.2 (17)
I2—Bi1—N1—C580.8 (7)C23—C16—C17—C180.6 (15)
I4—Bi1—N1—C510.0 (13)C15—C16—C17—C18178.8 (10)
I3—Bi1—N1—C5176.2 (7)C22—N4—C18—C190.4 (17)
I1—Bi1—N1—C586.8 (7)C22—N4—C18—C17179.9 (11)
N1—Bi1—N2—C10175.9 (9)N3—C17—C18—N41.1 (15)
I2—Bi1—N2—C1087.3 (8)C16—C17—C18—N4178.0 (10)
I4—Bi1—N2—C106.7 (8)N3—C17—C18—C19179.3 (10)
I3—Bi1—N2—C10165.3 (6)C16—C17—C18—C191.6 (15)
I1—Bi1—N2—C10100.1 (8)N4—C18—C19—C201.6 (15)
N1—Bi1—N2—C62.2 (6)C17—C18—C19—C20178.8 (10)
I2—Bi1—N2—C686.3 (7)N4—C18—C19—C24178.6 (10)
I4—Bi1—N2—C6179.7 (6)C17—C18—C19—C241.1 (15)
I3—Bi1—N2—C68.3 (10)C18—C19—C20—C211.9 (17)
I1—Bi1—N2—C686.3 (7)C24—C19—C20—C21178.2 (11)
C5—N1—C1—C21.6 (17)C19—C20—C21—C221.2 (19)
Bi1—N1—C1—C2178.0 (9)C18—N4—C22—C210 (2)
N1—C1—C2—C31 (2)C20—C21—C22—N40 (2)
C1—C2—C3—C41 (2)C17—C16—C23—C241.0 (17)
C2—C3—C4—C51.8 (18)C15—C16—C23—C24179.6 (11)
C2—C3—C4—C11175.6 (12)C16—C23—C24—C191.6 (17)
C1—N1—C5—C40.6 (15)C20—C19—C24—C23179.6 (11)
Bi1—N1—C5—C4179.0 (8)C18—C19—C24—C230.6 (16)
C1—N1—C5—C6178.2 (10)C29—N5—C25—C260 (2)
Bi1—N1—C5—C62.2 (11)N5—C25—C26—C272 (2)
C3—C4—C5—N11.1 (16)C25—C26—C27—C281 (2)
C11—C4—C5—N1176.4 (10)C26—C27—C28—C291 (2)
C3—C4—C5—C6179.8 (10)C26—C27—C28—C35178.3 (13)
C11—C4—C5—C62.3 (15)C25—N5—C29—C282.7 (17)
C10—N2—C6—C71.8 (14)C25—N5—C29—C30179.4 (11)
Bi1—N2—C6—C7175.6 (7)C27—C28—C29—N52.9 (17)
C10—N2—C6—C5178.1 (9)C35—C28—C29—N5176.3 (10)
Bi1—N2—C6—C54.3 (11)C27—C28—C29—C30179.2 (10)
N1—C5—C6—N24.4 (13)C35—C28—C29—C301.6 (16)
C4—C5—C6—N2176.8 (9)C34—N6—C30—C314.0 (16)
N1—C5—C6—C7175.5 (9)C34—N6—C30—C29177.7 (10)
C4—C5—C6—C73.3 (14)N5—C29—C30—N61.4 (15)
N2—C6—C7—C80.8 (15)C28—C29—C30—N6179.4 (10)
C5—C6—C7—C8179.1 (9)N5—C29—C30—C31177.0 (10)
N2—C6—C7—C12177.3 (10)C28—C29—C30—C310.9 (15)
C5—C6—C7—C122.8 (14)N6—C30—C31—C323.2 (16)
C6—C7—C8—C90.2 (17)C29—C30—C31—C32178.4 (10)
C12—C7—C8—C9177.7 (11)N6—C30—C31—C36178.4 (10)
C7—C8—C9—C100.7 (18)C29—C30—C31—C360.0 (15)
C6—N2—C10—C92.3 (16)C30—C31—C32—C330.9 (17)
Bi1—N2—C10—C9175.8 (8)C36—C31—C32—C33179.2 (11)
C8—C9—C10—N21.7 (18)C31—C32—C33—C340.4 (19)
C3—C4—C11—C12178.0 (13)C30—N6—C34—C332.4 (18)
C5—C4—C11—C120.8 (18)C32—C33—C34—N60 (2)
C4—C11—C12—C70.3 (19)C29—C28—C35—C361.5 (18)
C8—C7—C12—C11179.3 (12)C27—C28—C35—C36179.4 (12)
C6—C7—C12—C111.4 (18)C28—C35—C36—C310.6 (19)
C17—N3—C13—C140 (2)C30—C31—C36—C350.1 (17)
N3—C13—C14—C150 (2)C32—C31—C36—C35178.2 (12)
C13—C14—C15—C160 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N6i0.862.232.970 (13)144
N4—H4···N5i0.862.272.861 (13)126
C2—H2···I3i0.933.163.873 (12)135
C11—H11···I2ii0.933.193.960 (12)141
C35—H35···I1iii0.933.254.137 (13)161
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1/2.
 

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