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In the title compound, 2C
14H
14NO
+·I
3−·I
−, the cations are almost planar and exist in
E configurations. The dihedral angles between the pyridinium and benzene rings in the two unique cations are 2.6 (2) and 2.8 (2)°. O—H
I hydrogen bonds and weak C—H
I interactions are observed in the crystal structure. The cations are arranged in a zigzag fashion along the
c axis and are packed in an antiparallel manner into sheets parallel to the
bc plane. These sheets are interconnected
via O—H
I hydrogen bonds and weak C—H
I interactions to form a three-dimensional network.
Supporting information
CCDC reference: 643658
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.037
- wR factor = 0.079
- Data-to-parameter ratio = 36.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT410_ALERT_2_A Short Intra H...H Contact H1AB .. H7AB .. 1.75 Ang.
| Author Response: This is due to the disorder in the structure.
|
PLAT410_ALERT_2_A Short Intra H...H Contact H10A .. H8AB .. 1.63 Ang.
| Author Response: This is due to the disorder in the structure.
|
PLAT410_ALERT_2_A Short Intra H...H Contact H13B .. H8BB .. 1.58 Ang.
| Author Response: This is due to the disorder in the structure.
|
PLAT410_ALERT_2_A Short Intra H...H Contact H5BA .. H7BB .. 1.73 Ang.
| Author Response: This is due to the disorder in the structure.
|
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.14
PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C9A - C13A ... 1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1B - C6B ... 1.39 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C7BA .. C7BA .. 3.19 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 26
4 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
1 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
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Bis[4-(4-hydroxystyryl)-1-methylpyridinium] triiodide iodide
top
Crystal data top
2C14H14NO+·I3−·I− | F(000) = 1752 |
Mr = 932.12 | Dx = 2.054 Mg m−3 |
Monoclinic, P21/c | Melting point = 514–516 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.2337 (4) Å | Cell parameters from 11575 reflections |
b = 10.5627 (3) Å | θ = 1.7–35.0° |
c = 23.4193 (6) Å | µ = 4.16 mm−1 |
β = 121.106 (1)° | T = 100 K |
V = 3014.73 (15) Å3 | Needle, orange |
Z = 4 | 0.53 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 13215 independent reflections |
Radiation source: fine-focus sealed tube | 11575 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.0°, θmin = 1.7° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −17→17 |
Tmin = 0.218, Tmax = 0.633 | l = −37→37 |
127631 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0179P)2 + 10.6762P] where P = (Fo2 + 2Fc2)/3 |
13215 reflections | (Δ/σ)max = 0.002 |
361 parameters | Δρmax = 1.87 e Å−3 |
12 restraints | Δρmin = −1.45 e Å−3 |
Special details top
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature
attachment. |
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 | Uiso*/Ueq | Occ. (<1) |
I1 | 0.121137 (15) | 0.322709 (17) | 0.122663 (9) | 0.02261 (4) | |
I2 | 0.329067 (15) | 0.327530 (17) | 0.122046 (9) | 0.02451 (4) | |
I3 | −0.084039 (15) | 0.312324 (18) | 0.123346 (9) | 0.02532 (4) | |
I4 | 0.632169 (16) | 0.29844 (2) | 0.128485 (9) | 0.02832 (4) | |
O1A | 0.6295 (2) | 0.9284 (2) | 0.70974 (11) | 0.0330 (5) | |
H1AA | 0.6030 | 0.9974 | 0.6933 | 0.049* | |
N1A | 0.1894 (2) | 0.2146 (2) | 0.34098 (12) | 0.0237 (4) | |
C1A | 0.4320 (3) | 0.7599 (4) | 0.55756 (17) | 0.0397 (9) | |
H1AB | 0.3724 | 0.7758 | 0.5151 | 0.048* | |
C2A | 0.4846 (3) | 0.8614 (4) | 0.60103 (15) | 0.0314 (6) | |
H2AA | 0.4609 | 0.9441 | 0.5879 | 0.038* | |
C3A | 0.5732 (2) | 0.8353 (3) | 0.66460 (14) | 0.0262 (5) | |
C4A | 0.6072 (3) | 0.7102 (3) | 0.68415 (18) | 0.0323 (6) | |
H4AA | 0.6653 | 0.6930 | 0.7270 | 0.039* | |
C5A | 0.5547 (4) | 0.6131 (4) | 0.6400 (2) | 0.0413 (8) | |
H5AA | 0.5786 | 0.5304 | 0.6532 | 0.050* | |
C6A | 0.4671 (3) | 0.6351 (4) | 0.57645 (19) | 0.0417 (9) | |
C7AA | 0.4233 (3) | 0.5168 (3) | 0.53615 (18) | 0.0219 (6) | 0.70 |
H7AA | 0.4558 | 0.4390 | 0.5539 | 0.026* | 0.70 |
C8AA | 0.3362 (3) | 0.5246 (3) | 0.47388 (18) | 0.0218 (6) | 0.70 |
H8AA | 0.3035 | 0.6025 | 0.4563 | 0.026* | 0.70 |
C7AB | 0.3813 (6) | 0.5742 (8) | 0.5130 (3) | 0.0281 (19) | 0.30 |
H7AB | 0.3278 | 0.6255 | 0.4798 | 0.034* | 0.30 |
C8AB | 0.3778 (6) | 0.4492 (8) | 0.5015 (3) | 0.032 (2) | 0.30 |
H8AB | 0.4254 | 0.3926 | 0.5341 | 0.039* | 0.30 |
C9A | 0.2921 (3) | 0.4070 (4) | 0.4330 (2) | 0.0477 (11) | |
C10A | 0.3249 (3) | 0.2810 (5) | 0.44930 (17) | 0.0458 (11) | |
H10A | 0.3822 | 0.2608 | 0.4919 | 0.055* | |
C11A | 0.2727 (3) | 0.1851 (4) | 0.40227 (16) | 0.0333 (7) | |
H11A | 0.2953 | 0.1015 | 0.4132 | 0.040* | |
C12A | 0.1571 (3) | 0.3365 (3) | 0.32474 (18) | 0.0313 (6) | |
H12A | 0.0995 | 0.3548 | 0.2819 | 0.038* | |
C13A | 0.2057 (4) | 0.4327 (4) | 0.3687 (2) | 0.0439 (9) | |
H13A | 0.1814 | 0.5154 | 0.3561 | 0.053* | |
C14A | 0.1344 (3) | 0.1165 (3) | 0.28959 (17) | 0.0323 (6) | |
H14A | 0.1656 | 0.0353 | 0.3081 | 0.048* | |
H14B | 0.1442 | 0.1344 | 0.2528 | 0.048* | |
H14C | 0.0575 | 0.1158 | 0.2743 | 0.048* | |
O1B | −0.1438 (2) | 0.1437 (2) | 0.26606 (12) | 0.0303 (4) | |
H1BA | −0.1912 | 0.1807 | 0.2328 | 0.045* | |
N1B | 0.33268 (19) | 0.7713 (2) | 0.67738 (12) | 0.0219 (4) | |
C1B | −0.0564 (3) | 0.4397 (3) | 0.36074 (16) | 0.0295 (6) | |
H1BB | −0.0751 | 0.5251 | 0.3545 | 0.035* | |
C2B | −0.1141 (2) | 0.3568 (3) | 0.30860 (14) | 0.0234 (5) | |
H2BA | −0.1707 | 0.3868 | 0.2679 | 0.028* | |
C3B | −0.0884 (2) | 0.2285 (3) | 0.31627 (14) | 0.0226 (5) | |
C4B | −0.0035 (3) | 0.1847 (3) | 0.37771 (16) | 0.0291 (6) | |
H4BA | 0.0146 | 0.0992 | 0.3838 | 0.035* | |
C5B | 0.0541 (3) | 0.2707 (4) | 0.43008 (15) | 0.0345 (7) | |
H5BA | 0.1107 | 0.2412 | 0.4710 | 0.041* | |
C6B | 0.0287 (3) | 0.3996 (3) | 0.42229 (15) | 0.0326 (7) | |
C7BA | 0.0815 (3) | 0.5022 (3) | 0.47232 (15) | 0.0220 (6) | 0.80 |
H7BA | 0.0526 | 0.5835 | 0.4606 | 0.026* | 0.80 |
C8BA | 0.1689 (3) | 0.4837 (3) | 0.53354 (16) | 0.0222 (5) | 0.80 |
H8BA | 0.1976 | 0.4026 | 0.5465 | 0.027* | 0.80 |
C7BB | 0.1178 (6) | 0.4377 (9) | 0.4899 (3) | 0.0152 (19) | 0.20 |
H7BB | 0.1674 | 0.3765 | 0.5177 | 0.018* | 0.20 |
C8BB | 0.1299 (8) | 0.5567 (9) | 0.5127 (3) | 0.0222 (5) | 0.20 |
H8BB | 0.0809 | 0.6189 | 0.4856 | 0.027* | 0.20 |
C9B | 0.2204 (3) | 0.5905 (3) | 0.58086 (19) | 0.0386 (8) | |
C10B | 0.3095 (3) | 0.5581 (3) | 0.6436 (2) | 0.0377 (7) | |
H10B | 0.3317 | 0.4741 | 0.6536 | 0.045* | |
C11B | 0.3626 (3) | 0.6486 (3) | 0.68925 (19) | 0.0318 (6) | |
H11B | 0.4222 | 0.6260 | 0.7306 | 0.038* | |
C12B | 0.2466 (2) | 0.8079 (3) | 0.61860 (14) | 0.0256 (5) | |
H12B | 0.2257 | 0.8926 | 0.6112 | 0.031* | |
C13B | 0.1892 (3) | 0.7188 (4) | 0.56906 (15) | 0.0348 (7) | |
H13B | 0.1301 | 0.7437 | 0.5280 | 0.042* | |
C14B | 0.3958 (3) | 0.8655 (3) | 0.72972 (15) | 0.0313 (6) | |
H14D | 0.3649 | 0.9480 | 0.7140 | 0.047* | |
H14E | 0.4707 | 0.8649 | 0.7406 | 0.047* | |
H14F | 0.3929 | 0.8450 | 0.7687 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02419 (7) | 0.01945 (7) | 0.02222 (7) | −0.00301 (6) | 0.01059 (6) | −0.00377 (6) |
I2 | 0.02313 (8) | 0.02278 (8) | 0.02732 (8) | −0.00479 (6) | 0.01281 (6) | −0.00523 (6) |
I3 | 0.02476 (8) | 0.02567 (8) | 0.02669 (8) | −0.00330 (6) | 0.01412 (7) | −0.00567 (6) |
I4 | 0.02720 (8) | 0.03347 (10) | 0.02115 (7) | −0.00368 (7) | 0.01025 (6) | −0.00301 (7) |
O1A | 0.0359 (12) | 0.0355 (12) | 0.0244 (10) | −0.0083 (10) | 0.0134 (9) | −0.0057 (9) |
N1A | 0.0226 (10) | 0.0270 (11) | 0.0235 (10) | 0.0002 (8) | 0.0134 (8) | −0.0001 (8) |
C1A | 0.0268 (14) | 0.070 (3) | 0.0244 (13) | −0.0117 (15) | 0.0145 (12) | −0.0126 (15) |
C2A | 0.0241 (12) | 0.0447 (18) | 0.0249 (13) | 0.0016 (12) | 0.0122 (11) | −0.0039 (12) |
C3A | 0.0234 (12) | 0.0337 (14) | 0.0237 (12) | −0.0042 (10) | 0.0138 (10) | −0.0051 (10) |
C4A | 0.0344 (15) | 0.0359 (16) | 0.0351 (15) | −0.0020 (12) | 0.0240 (13) | 0.0030 (13) |
C5A | 0.054 (2) | 0.0376 (18) | 0.056 (2) | −0.0118 (16) | 0.045 (2) | −0.0099 (16) |
C6A | 0.049 (2) | 0.052 (2) | 0.0464 (19) | −0.0251 (17) | 0.0398 (18) | −0.0228 (17) |
C7AA | 0.0202 (15) | 0.0240 (17) | 0.0217 (15) | 0.0045 (13) | 0.0110 (13) | 0.0053 (14) |
C8AA | 0.0198 (15) | 0.0251 (17) | 0.0223 (15) | 0.0029 (13) | 0.0122 (13) | 0.0031 (13) |
C7AB | 0.028 (4) | 0.034 (5) | 0.031 (5) | −0.007 (4) | 0.022 (4) | −0.005 (4) |
C8AB | 0.028 (5) | 0.040 (6) | 0.037 (5) | −0.001 (4) | 0.023 (4) | 0.000 (4) |
C9A | 0.045 (2) | 0.064 (3) | 0.056 (2) | −0.0269 (19) | 0.0419 (19) | −0.033 (2) |
C10A | 0.0226 (13) | 0.094 (3) | 0.0229 (13) | −0.0112 (17) | 0.0129 (11) | −0.0092 (17) |
C11A | 0.0249 (13) | 0.052 (2) | 0.0251 (13) | 0.0059 (13) | 0.0148 (11) | 0.0054 (13) |
C12A | 0.0335 (15) | 0.0261 (14) | 0.0427 (17) | 0.0012 (11) | 0.0256 (14) | 0.0020 (12) |
C13A | 0.052 (2) | 0.0335 (17) | 0.071 (3) | −0.0127 (15) | 0.049 (2) | −0.0170 (17) |
C14A | 0.0347 (15) | 0.0316 (15) | 0.0310 (14) | −0.0071 (12) | 0.0173 (12) | −0.0084 (12) |
O1B | 0.0363 (11) | 0.0227 (10) | 0.0297 (10) | −0.0029 (8) | 0.0154 (9) | −0.0063 (8) |
N1B | 0.0214 (9) | 0.0215 (10) | 0.0226 (10) | −0.0032 (8) | 0.0112 (8) | 0.0008 (8) |
C1B | 0.0353 (15) | 0.0265 (13) | 0.0342 (14) | −0.0088 (11) | 0.0232 (13) | −0.0099 (11) |
C2B | 0.0256 (12) | 0.0213 (11) | 0.0249 (11) | −0.0014 (9) | 0.0141 (10) | −0.0009 (9) |
C3B | 0.0228 (11) | 0.0238 (12) | 0.0227 (11) | −0.0018 (9) | 0.0129 (9) | −0.0016 (9) |
C4B | 0.0253 (12) | 0.0332 (15) | 0.0302 (13) | 0.0060 (11) | 0.0154 (11) | 0.0092 (11) |
C5B | 0.0208 (12) | 0.061 (2) | 0.0204 (12) | −0.0013 (13) | 0.0096 (10) | 0.0059 (13) |
C6B | 0.0288 (13) | 0.0499 (19) | 0.0234 (12) | −0.0153 (13) | 0.0165 (11) | −0.0110 (12) |
C7BA | 0.0217 (13) | 0.0220 (15) | 0.0236 (14) | 0.0032 (12) | 0.0126 (12) | 0.0048 (12) |
C8BA | 0.0241 (14) | 0.0197 (13) | 0.0242 (14) | 0.0010 (10) | 0.0135 (12) | 0.0016 (10) |
C7BB | 0.010 (4) | 0.022 (5) | 0.011 (4) | 0.001 (4) | 0.003 (3) | 0.005 (4) |
C8BB | 0.0241 (14) | 0.0197 (13) | 0.0242 (14) | 0.0010 (10) | 0.0135 (12) | 0.0016 (10) |
C9B | 0.0440 (18) | 0.0428 (19) | 0.0479 (19) | −0.0234 (15) | 0.0373 (17) | −0.0227 (16) |
C10B | 0.0424 (18) | 0.0267 (15) | 0.059 (2) | −0.0043 (13) | 0.0368 (18) | −0.0066 (14) |
C11B | 0.0312 (14) | 0.0250 (13) | 0.0464 (18) | 0.0021 (11) | 0.0251 (14) | 0.0059 (12) |
C12B | 0.0265 (12) | 0.0283 (13) | 0.0199 (11) | −0.0028 (10) | 0.0104 (10) | 0.0023 (9) |
C13B | 0.0258 (13) | 0.056 (2) | 0.0218 (12) | −0.0149 (14) | 0.0121 (11) | −0.0056 (13) |
C14B | 0.0333 (15) | 0.0358 (16) | 0.0219 (12) | −0.0123 (12) | 0.0122 (11) | −0.0045 (11) |
Geometric parameters (Å, º) top
I1—I3 | 2.9308 (3) | C14A—H14C | 0.9600 |
I1—I2 | 2.9675 (3) | O1B—C3B | 1.360 (3) |
O1A—C3A | 1.361 (4) | O1B—H1BA | 0.8200 |
O1A—H1AA | 0.8200 | N1B—C12B | 1.343 (4) |
N1A—C11A | 1.343 (4) | N1B—C11B | 1.348 (4) |
N1A—C12A | 1.354 (4) | N1B—C14B | 1.470 (4) |
N1A—C14A | 1.470 (4) | C1B—C2B | 1.377 (4) |
C1A—C6A | 1.398 (6) | C1B—C6B | 1.386 (5) |
C1A—C2A | 1.399 (5) | C1B—H1BB | 0.9300 |
C1A—H1AB | 0.9300 | C2B—C3B | 1.390 (4) |
C2A—C3A | 1.394 (4) | C2B—H2BA | 0.9300 |
C2A—H2AA | 0.9300 | C3B—C4B | 1.395 (4) |
C3A—C4A | 1.401 (5) | C4B—C5B | 1.401 (5) |
C4A—C5A | 1.371 (5) | C4B—H4BA | 0.9300 |
C4A—H4AA | 0.9300 | C5B—C6B | 1.396 (6) |
C5A—C6A | 1.381 (6) | C5B—H5BA | 0.9300 |
C5A—H5AA | 0.9300 | C6B—C7BA | 1.485 (3) |
C6A—C7AA | 1.494 (4) | C6B—C7BB | 1.485 (3) |
C6A—C7AB | 1.496 (4) | C7BA—C8BA | 1.341 (5) |
C7AA—C8AA | 1.343 (5) | C7BA—H7BA | 0.9300 |
C7AA—H7AA | 0.9300 | C8BA—C9B | 1.483 (3) |
C8AA—C9A | 1.494 (4) | C8BA—H8BA | 0.9300 |
C8AA—H8AA | 0.9300 | C7BB—C8BB | 1.342 (5) |
C7AB—C8AB | 1.343 (5) | C7BB—H7BB | 0.9300 |
C7AB—H7AB | 0.9300 | C8BB—C9B | 1.486 (3) |
C8AB—C9A | 1.496 (4) | C8BB—H8BB | 0.9300 |
C8AB—H8AB | 0.9300 | C9B—C10B | 1.400 (6) |
C9A—C13A | 1.393 (7) | C9B—C13B | 1.408 (6) |
C9A—C10A | 1.397 (7) | C10B—C11B | 1.339 (5) |
C10A—C11A | 1.395 (6) | C10B—H10B | 0.9300 |
C10A—H10A | 0.9300 | C11B—H11B | 0.9300 |
C11A—H11A | 0.9300 | C12B—C13B | 1.386 (4) |
C12A—C13A | 1.355 (5) | C12B—H12B | 0.9300 |
C12A—H12A | 0.9300 | C13B—H13B | 0.9300 |
C13A—H13A | 0.9300 | C14B—H14D | 0.9600 |
C14A—H14A | 0.9600 | C14B—H14E | 0.9600 |
C14A—H14B | 0.9600 | C14B—H14F | 0.9600 |
| | | |
I3—I1—I2 | 178.838 (8) | C3B—O1B—H1BA | 109.5 |
C3A—O1A—H1AA | 109.5 | C12B—N1B—C11B | 120.8 (3) |
C11A—N1A—C12A | 120.3 (3) | C12B—N1B—C14B | 120.1 (3) |
C11A—N1A—C14A | 121.0 (3) | C11B—N1B—C14B | 119.1 (3) |
C12A—N1A—C14A | 118.7 (3) | C2B—C1B—C6B | 121.9 (3) |
C6A—C1A—C2A | 121.5 (3) | C2B—C1B—H1BB | 119.1 |
C6A—C1A—H1AB | 119.2 | C6B—C1B—H1BB | 119.1 |
C2A—C1A—H1AB | 119.2 | C1B—C2B—C3B | 120.6 (3) |
C3A—C2A—C1A | 118.3 (4) | C1B—C2B—H2BA | 119.7 |
C3A—C2A—H2AA | 120.9 | C3B—C2B—H2BA | 119.7 |
C1A—C2A—H2AA | 120.9 | O1B—C3B—C2B | 122.3 (3) |
O1A—C3A—C2A | 122.1 (3) | O1B—C3B—C4B | 118.6 (3) |
O1A—C3A—C4A | 117.6 (3) | C2B—C3B—C4B | 119.1 (3) |
C2A—C3A—C4A | 120.3 (3) | C3B—C4B—C5B | 119.4 (3) |
C5A—C4A—C3A | 119.8 (3) | C3B—C4B—H4BA | 120.3 |
C5A—C4A—H4AA | 120.1 | C5B—C4B—H4BA | 120.3 |
C3A—C4A—H4AA | 120.1 | C6B—C5B—C4B | 121.5 (3) |
C4A—C5A—C6A | 121.6 (4) | C6B—C5B—H5BA | 119.3 |
C4A—C5A—H5AA | 119.2 | C4B—C5B—H5BA | 119.3 |
C6A—C5A—H5AA | 119.2 | C1B—C6B—C5B | 117.6 (3) |
C5A—C6A—C1A | 118.4 (3) | C1B—C6B—C7BA | 114.3 (3) |
C5A—C6A—C7AA | 113.0 (4) | C5B—C6B—C7BA | 128.1 (3) |
C1A—C6A—C7AA | 128.6 (4) | C1B—C6B—C7BB | 146.4 (5) |
C5A—C6A—C7AB | 144.9 (5) | C5B—C6B—C7BB | 96.0 (4) |
C1A—C6A—C7AB | 96.7 (5) | C8BA—C7BA—C6B | 123.3 (3) |
C8AA—C7AA—C6A | 119.0 (3) | C8BA—C7BA—H7BA | 118.4 |
C8AA—C7AA—H7AA | 120.5 | C6B—C7BA—H7BA | 118.4 |
C6A—C7AA—H7AA | 120.5 | C7BA—C8BA—C9B | 121.0 (3) |
C7AA—C8AA—C9A | 119.4 (4) | C7BA—C8BA—H8BA | 119.5 |
C7AA—C8AA—H8AA | 120.3 | C9B—C8BA—H8BA | 119.5 |
C9A—C8AA—H8AA | 120.3 | C8BB—C7BB—C6B | 122.8 (5) |
C8AB—C7AB—C6A | 123.2 (5) | C8BB—C7BB—H7BB | 118.6 |
C8AB—C7AB—H7AB | 118.4 | C6B—C7BB—H7BB | 118.6 |
C6A—C7AB—H7AB | 118.4 | C7BB—C8BB—C9B | 120.9 (5) |
C7AB—C8AB—C9A | 115.7 (4) | C7BB—C8BB—H8BB | 119.5 |
C7AB—C8AB—H8AB | 122.2 | C9B—C8BB—H8BB | 119.5 |
C9A—C8AB—H8AB | 122.2 | C10B—C9B—C13B | 117.7 (3) |
C13A—C9A—C10A | 117.7 (3) | C10B—C9B—C8BA | 115.3 (3) |
C13A—C9A—C8AA | 112.0 (4) | C13B—C9B—C8BA | 127.0 (4) |
C10A—C9A—C8AA | 130.3 (4) | C10B—C9B—C8BB | 151.7 (5) |
C13A—C9A—C8AB | 151.2 (5) | C13B—C9B—C8BB | 90.6 (5) |
C10A—C9A—C8AB | 91.1 (5) | C11B—C10B—C9B | 119.6 (3) |
C11A—C10A—C9A | 120.6 (3) | C11B—C10B—H10B | 120.2 |
C11A—C10A—H10A | 119.7 | C9B—C10B—H10B | 120.2 |
C9A—C10A—H10A | 119.7 | C10B—C11B—N1B | 122.3 (3) |
N1A—C11A—C10A | 119.5 (4) | C10B—C11B—H11B | 118.8 |
N1A—C11A—H11A | 120.3 | N1B—C11B—H11B | 118.8 |
C10A—C11A—H11A | 120.3 | N1B—C12B—C13B | 119.6 (3) |
N1A—C12A—C13A | 122.2 (4) | N1B—C12B—H12B | 120.2 |
N1A—C12A—H12A | 118.9 | C13B—C12B—H12B | 120.2 |
C13A—C12A—H12A | 118.9 | C12B—C13B—C9B | 120.0 (3) |
C12A—C13A—C9A | 119.7 (4) | C12B—C13B—H13B | 120.0 |
C12A—C13A—H13A | 120.2 | C9B—C13B—H13B | 120.0 |
C9A—C13A—H13A | 120.2 | N1B—C14B—H14D | 109.5 |
N1A—C14A—H14A | 109.5 | N1B—C14B—H14E | 109.5 |
N1A—C14A—H14B | 109.5 | H14D—C14B—H14E | 109.5 |
H14A—C14A—H14B | 109.5 | N1B—C14B—H14F | 109.5 |
N1A—C14A—H14C | 109.5 | H14D—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
H14B—C14A—H14C | 109.5 | | |
| | | |
C6A—C1A—C2A—C3A | −0.5 (5) | C6B—C1B—C2B—C3B | 0.0 (5) |
C1A—C2A—C3A—O1A | 179.4 (3) | C1B—C2B—C3B—O1B | 179.7 (3) |
C1A—C2A—C3A—C4A | −0.8 (5) | C1B—C2B—C3B—C4B | 0.3 (4) |
O1A—C3A—C4A—C5A | −178.6 (3) | O1B—C3B—C4B—C5B | −179.8 (3) |
C2A—C3A—C4A—C5A | 1.5 (5) | C2B—C3B—C4B—C5B | −0.3 (4) |
C3A—C4A—C5A—C6A | −1.0 (5) | C3B—C4B—C5B—C6B | 0.0 (5) |
C4A—C5A—C6A—C1A | −0.2 (5) | C2B—C1B—C6B—C5B | −0.3 (5) |
C4A—C5A—C6A—C7AA | 178.9 (3) | C2B—C1B—C6B—C7BA | 179.8 (3) |
C4A—C5A—C6A—C7AB | −176.0 (7) | C2B—C1B—C6B—C7BB | 174.6 (9) |
C2A—C1A—C6A—C5A | 1.0 (5) | C4B—C5B—C6B—C1B | 0.3 (5) |
C2A—C1A—C6A—C7AA | −178.0 (3) | C4B—C5B—C6B—C7BA | −179.9 (3) |
C2A—C1A—C6A—C7AB | 178.6 (5) | C4B—C5B—C6B—C7BB | −176.9 (5) |
C5A—C6A—C7AA—C8AA | 178.3 (3) | C1B—C6B—C7BA—C8BA | −176.4 (3) |
C1A—C6A—C7AA—C8AA | −2.6 (6) | C5B—C6B—C7BA—C8BA | 3.8 (5) |
C7AB—C6A—C7AA—C8AA | 3.8 (7) | C7BB—C6B—C7BA—C8BA | −1.7 (8) |
C6A—C7AA—C8AA—C9A | 179.6 (3) | C6B—C7BA—C8BA—C9B | 178.2 (3) |
C5A—C6A—C7AB—C8AB | −6.6 (14) | C1B—C6B—C7BB—C8BB | 8.4 (17) |
C1A—C6A—C7AB—C8AB | 177.1 (9) | C5B—C6B—C7BB—C8BB | −176.0 (11) |
C7AA—C6A—C7AB—C8AB | 2.2 (6) | C7BA—C6B—C7BB—C8BB | −0.4 (8) |
C6A—C7AB—C8AB—C9A | −174.8 (6) | C6B—C7BB—C8BB—C9B | −180.0 (8) |
C7AA—C8AA—C9A—C13A | −176.9 (3) | C7BA—C8BA—C9B—C10B | 178.6 (3) |
C7AA—C8AA—C9A—C10A | 2.3 (6) | C7BA—C8BA—C9B—C13B | −1.4 (5) |
C7AA—C8AA—C9A—C8AB | 3.8 (7) | C7BA—C8BA—C9B—C8BB | 0.5 (9) |
C7AB—C8AB—C9A—C13A | −0.2 (16) | C7BB—C8BB—C9B—C10B | −6 (2) |
C7AB—C8AB—C9A—C10A | 180.0 (8) | C7BB—C8BB—C9B—C13B | 176.2 (11) |
C7AB—C8AB—C9A—C8AA | 1.1 (5) | C7BB—C8BB—C9B—C8BA | −2.3 (7) |
C13A—C9A—C10A—C11A | 0.3 (5) | C13B—C9B—C10B—C11B | −1.2 (5) |
C8AA—C9A—C10A—C11A | −178.8 (3) | C8BA—C9B—C10B—C11B | 178.7 (3) |
C8AB—C9A—C10A—C11A | −179.8 (5) | C8BB—C9B—C10B—C11B | −179.0 (12) |
C12A—N1A—C11A—C10A | 0.7 (4) | C9B—C10B—C11B—N1B | 0.8 (5) |
C14A—N1A—C11A—C10A | 178.3 (3) | C12B—N1B—C11B—C10B | 0.5 (5) |
C9A—C10A—C11A—N1A | −0.6 (5) | C14B—N1B—C11B—C10B | −179.3 (3) |
C11A—N1A—C12A—C13A | −0.4 (5) | C11B—N1B—C12B—C13B | −1.3 (4) |
C14A—N1A—C12A—C13A | −178.1 (3) | C14B—N1B—C12B—C13B | 178.5 (3) |
N1A—C12A—C13A—C9A | 0.2 (5) | N1B—C12B—C13B—C9B | 0.8 (5) |
C10A—C9A—C13A—C12A | −0.1 (5) | C10B—C9B—C13B—C12B | 0.4 (5) |
C8AA—C9A—C13A—C12A | 179.2 (3) | C8BA—C9B—C13B—C12B | −179.5 (3) |
C8AB—C9A—C13A—C12A | −179.9 (9) | C8BB—C9B—C13B—C12B | 179.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1AA···I4i | 0.82 | 2.79 | 3.467 (2) | 141 |
O1B—H1BA···I4ii | 0.82 | 2.74 | 3.550 (3) | 172 |
C14B—H14F···I4iii | 0.96 | 3.02 | 3.943 (4) | 162 |
C8BA—H8BA···I2iv | 0.93 | 3.02 | 3.927 (3) | 165 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x, −y+1/2, z+1/2. |
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