Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009154/sj2231sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009154/sj2231Isup2.hkl |
CCDC reference: 643658
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).
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 |
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 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 |
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. |
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* |
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) |
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) |
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. |