Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011961/ob6371sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011961/ob6371Isup2.hkl |
CCDC reference: 245272
Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.
C27H34N64+·4ClO4−·H2O | Z = 2 |
Mr = 858.42 | F(000) = 888 |
Triclinic, P1 | Dx = 1.577 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6648 (6) Å | Cell parameters from 8505 reflections |
b = 12.3882 (6) Å | θ = 2.4–27.9° |
c = 12.5333 (6) Å | µ = 0.41 mm−1 |
α = 92.168 (1)° | T = 173 K |
β = 91.050 (1)° | Plate, colourless |
γ = 92.252 (1)° | 0.50 × 0.40 × 0.25 mm |
V = 1808.09 (15) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 8519 independent reflections |
Radiation source: fine-focus sealed tube | 7487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.9°, θmin = 1.6° |
φ and ω scans | h = −15→13 |
Absorption correction: multi-scan (SADABS; Scheldrick, 1996) | k = −16→15 |
Tmin = 0.821, Tmax = 0.904 | l = −16→16 |
13190 measured reflections |
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)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.183 | w = 1/[σ2(Fo2) + (0.0956P)2 + 2.858P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
8519 reflections | Δρmax = 1.25 e Å−3 |
512 parameters | Δρmin = −1.19 e Å−3 |
0 restraints | Extinction correction: SHELXTL-NT, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (10) |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.4974 (0.0104) x - 9.0912 (0.0099) y + 3.8244 (0.0144) z = 3.9411 (0.0113) * -0.0021 (0.0019) N6 * -0.0068 (0.0018) C23 * 0.0095 (0.0020) C24 * -0.0034 (0.0021) C25 * -0.0054 (0.0021) C26 * 0.0083 (0.0021) C27 Rms deviation of fitted atoms = 0.0065 2.0958 (0.0146) x - 8.0267 (0.0125) y + 9.6089 (0.0106) z = 3.2947 (0.0080) Angle to previous plane (with approximate e.s.d.) = 38.14 (0.12) * 0.0090 (0.0020) N5 * 0.0018 (0.0019) C17 * -0.0101 (0.0021) C18 * 0.0077 (0.0024) C19 * 0.0028 (0.0025) C20 * -0.0112 (0.0023) C21 Rms deviation of fitted atoms = 0.0080 4.3281 (0.0123) x - 6.5188 (0.0124) y - 9.5383 (0.0095) z = 1.0154 (0.0100) Angle to previous plane (with approximate e.s.d.) = 79.47 (0.08) * -0.0021 (0.0018) N4 * 0.0023 (0.0018) C11 * 0.0013 (0.0020) C12 * -0.0050 (0.0021) C13 * 0.0052 (0.0021) C14 * -0.0017 (0.0020) C15 Rms deviation of fitted atoms = 0.0033 3.0708 (0.0158) x - 4.8544 (0.0164) y - 10.9697 (0.0084) z = 0.2415 (0.0054) Angle to previous plane (with approximate e.s.d.) = 11.62 (0.17) * 0.0012 (0.0019) N3 * 0.0095 (0.0021) C5 * -0.0108 (0.0027) C6 * 0.0017 (0.0028) C7 * 0.0089 (0.0025) C8 * -0.0105 (0.0021) C9 Rms deviation of fitted atoms = 0.0082 |
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 | ||
N1 | 0.40662 (19) | 0.20289 (17) | 0.02173 (16) | 0.0225 (4) | |
N2 | 0.37651 (19) | 0.21089 (18) | 0.42106 (16) | 0.0237 (4) | |
N3 | 0.2165 (2) | 0.27265 (19) | −0.08218 (18) | 0.0275 (5) | |
N4 | 0.6085 (2) | 0.31537 (19) | −0.04565 (18) | 0.0277 (5) | |
N5 | 0.1549 (2) | 0.1608 (2) | 0.4444 (2) | 0.0311 (5) | |
N6 | 0.5972 (2) | 0.2981 (2) | 0.56764 (18) | 0.0286 (5) | |
C1 | 0.3905 (2) | 0.2653 (2) | 0.12303 (19) | 0.0233 (5) | |
C2 | 0.3988 (3) | 0.2012 (2) | 0.2244 (2) | 0.0334 (6) | |
C3 | 0.3783 (2) | 0.2731 (2) | 0.32284 (19) | 0.0246 (5) | |
C4 | 0.3130 (2) | 0.1234 (2) | −0.0026 (2) | 0.0282 (5) | |
C5 | 0.2069 (2) | 0.1743 (2) | −0.0421 (2) | 0.0295 (5) | |
C6 | 0.1004 (3) | 0.1214 (3) | −0.0467 (3) | 0.0457 (8) | |
C7 | 0.0090 (3) | 0.1693 (3) | −0.0946 (3) | 0.0529 (9) | |
C8 | 0.0233 (3) | 0.2705 (3) | −0.1360 (3) | 0.0426 (7) | |
C9 | 0.1287 (3) | 0.3223 (3) | −0.1276 (2) | 0.0347 (6) | |
C10 | 0.5167 (2) | 0.1504 (2) | 0.0177 (2) | 0.0256 (5) | |
C11 | 0.6172 (2) | 0.2300 (2) | 0.01619 (19) | 0.0247 (5) | |
C12 | 0.7192 (2) | 0.2174 (2) | 0.0712 (2) | 0.0314 (6) | |
C13 | 0.8090 (3) | 0.2923 (3) | 0.0614 (3) | 0.0375 (6) | |
C14 | 0.7972 (3) | 0.3787 (3) | −0.0041 (3) | 0.0372 (6) | |
C15 | 0.6941 (3) | 0.3891 (2) | −0.0573 (2) | 0.0329 (6) | |
C16 | 0.3213 (2) | 0.2702 (2) | 0.5074 (2) | 0.0273 (5) | |
C17 | 0.1938 (2) | 0.2452 (2) | 0.5057 (2) | 0.0268 (5) | |
C18 | 0.1168 (3) | 0.3006 (3) | 0.5675 (2) | 0.0352 (6) | |
C19 | 0.0023 (3) | 0.2654 (3) | 0.5649 (3) | 0.0440 (8) | |
C20 | −0.0343 (3) | 0.1777 (3) | 0.4991 (3) | 0.0471 (8) | |
C21 | 0.0438 (3) | 0.1263 (3) | 0.4376 (3) | 0.0431 (7) | |
C22 | 0.4858 (2) | 0.1646 (2) | 0.4520 (2) | 0.0259 (5) | |
C23 | 0.5839 (2) | 0.2468 (2) | 0.4706 (2) | 0.0255 (5) | |
C24 | 0.6603 (2) | 0.2752 (2) | 0.3928 (2) | 0.0314 (6) | |
C25 | 0.7452 (3) | 0.3553 (3) | 0.4135 (2) | 0.0368 (6) | |
C26 | 0.7547 (3) | 0.4057 (3) | 0.5140 (3) | 0.0359 (6) | |
C27 | 0.6794 (2) | 0.3745 (3) | 0.5909 (2) | 0.0340 (6) | |
H3N | 0.283 (3) | 0.307 (3) | −0.083 (3) | 0.040 (10)* | |
H4N | 0.544 (4) | 0.323 (3) | −0.081 (3) | 0.041 (10)* | |
H5N | 0.203 (4) | 0.129 (3) | 0.416 (3) | 0.039 (10)* | |
H6N | 0.550 (3) | 0.272 (3) | 0.617 (3) | 0.037 (9)* | |
H1A | 0.3141 | 0.2974 | 0.1201 | 0.028* | |
H1B | 0.4488 | 0.3256 | 0.1282 | 0.028* | |
H2A | 0.3411 | 0.1403 | 0.2205 | 0.040* | |
H2B | 0.4758 | 0.1708 | 0.2300 | 0.040* | |
H3A | 0.4398 | 0.3305 | 0.3297 | 0.030* | |
H3B | 0.3042 | 0.3083 | 0.3141 | 0.030* | |
H4A | 0.2950 | 0.0838 | 0.0625 | 0.034* | |
H4B | 0.3382 | 0.0704 | −0.0576 | 0.034* | |
H6 | 0.0902 | 0.0524 | −0.0169 | 0.055* | |
H7 | −0.0641 | 0.1325 | −0.0991 | 0.063* | |
H8 | −0.0391 | 0.3035 | −0.1698 | 0.051* | |
H9 | 0.1400 | 0.3929 | −0.1538 | 0.042* | |
H10A | 0.5177 | 0.1023 | −0.0471 | 0.031* | |
H10B | 0.5246 | 0.1051 | 0.0806 | 0.031* | |
H12 | 0.7276 | 0.1576 | 0.1155 | 0.038* | |
H13 | 0.8790 | 0.2845 | 0.0997 | 0.045* | |
H14 | 0.8589 | 0.4298 | −0.0122 | 0.045* | |
H15 | 0.6837 | 0.4484 | −0.1020 | 0.040* | |
H16A | 0.3360 | 0.3487 | 0.4999 | 0.033* | |
H16B | 0.3546 | 0.2503 | 0.5768 | 0.033* | |
H18 | 0.1418 | 0.3618 | 0.6110 | 0.042* | |
H19 | −0.0512 | 0.3015 | 0.6084 | 0.053* | |
H20 | −0.1127 | 0.1537 | 0.4968 | 0.057* | |
H21 | 0.0204 | 0.0671 | 0.3908 | 0.052* | |
H22A | 0.5072 | 0.1119 | 0.3952 | 0.031* | |
H22B | 0.4744 | 0.1247 | 0.5181 | 0.031* | |
H24 | 0.6547 | 0.2396 | 0.3243 | 0.038* | |
H25 | 0.7965 | 0.3755 | 0.3590 | 0.044* | |
H26 | 0.8123 | 0.4608 | 0.5294 | 0.043* | |
H27 | 0.6855 | 0.4070 | 0.6607 | 0.041* | |
O1 | 0.4856 (2) | 0.21659 (18) | 0.74620 (16) | 0.0314 (4) | |
H101 | 0.520 (4) | 0.165 (4) | 0.750 (4) | 0.057 (13)* | |
H102 | 0.422 (4) | 0.204 (3) | 0.748 (3) | 0.039 (11)* | |
Cl1 | 0.40441 (5) | 0.47317 (5) | 0.79135 (5) | 0.02524 (16) | |
Cl2 | 0.26320 (6) | 0.01407 (5) | 0.69972 (5) | 0.03152 (17) | |
Cl3 | 0.25709 (6) | 0.91307 (6) | 0.26587 (6) | 0.03417 (18) | |
Cl4 | 0.06659 (6) | 0.43105 (7) | 0.23417 (6) | 0.0398 (2) | |
O11 | 0.40262 (18) | 0.42509 (16) | 0.89601 (16) | 0.0326 (4) | |
O12 | 0.3695 (2) | 0.58222 (16) | 0.80275 (17) | 0.0358 (5) | |
O21 | 0.2543 (2) | 0.12858 (18) | 0.72360 (18) | 0.0390 (5) | |
O14 | 0.3273 (2) | 0.41089 (19) | 0.72085 (18) | 0.0421 (5) | |
O13 | 0.5195 (2) | 0.47124 (19) | 0.7529 (2) | 0.0438 (5) | |
O23 | 0.3638 (2) | −0.0223 (2) | 0.75433 (19) | 0.0448 (6) | |
O22 | 0.2762 (3) | −0.0046 (3) | 0.5877 (2) | 0.0670 (9) | |
O24 | 0.1657 (3) | −0.0449 (3) | 0.7391 (3) | 0.0698 (9) | |
O31 | 0.2141 (3) | 0.8049 (2) | 0.2723 (4) | 0.0904 (13) | |
O34 | 0.3340 (7) | 0.9377 (3) | 0.3485 (4) | 0.157 (3) | |
O33 | 0.3170 (6) | 0.9211 (3) | 0.1752 (3) | 0.153 (3) | |
O42 | −0.0387 (5) | 0.4733 (5) | 0.2552 (6) | 0.151 (3) | |
O43 | 0.0608 (6) | 0.4127 (6) | 0.1248 (4) | 0.172 (3) | |
O32 | 0.1726 (3) | 0.9901 (3) | 0.2667 (6) | 0.149 (3) | |
O41 | 0.1612 (5) | 0.4995 (7) | 0.2472 (4) | 0.173 (3) | |
O44 | 0.0727 (6) | 0.3407 (7) | 0.2879 (8) | 0.225 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0272 (10) | 0.0212 (10) | 0.0189 (9) | −0.0002 (8) | −0.0003 (8) | −0.0004 (7) |
N2 | 0.0265 (10) | 0.0276 (11) | 0.0173 (9) | 0.0020 (8) | 0.0007 (8) | 0.0013 (8) |
N3 | 0.0268 (11) | 0.0305 (12) | 0.0251 (11) | −0.0001 (9) | −0.0002 (8) | 0.0008 (8) |
N4 | 0.0279 (11) | 0.0289 (11) | 0.0262 (11) | −0.0009 (9) | −0.0001 (9) | 0.0033 (8) |
N5 | 0.0301 (12) | 0.0297 (12) | 0.0335 (12) | −0.0006 (10) | −0.0014 (10) | 0.0029 (9) |
N6 | 0.0241 (10) | 0.0376 (13) | 0.0241 (11) | 0.0003 (9) | 0.0010 (8) | 0.0005 (9) |
C1 | 0.0287 (12) | 0.0224 (11) | 0.0189 (11) | 0.0009 (9) | 0.0001 (9) | −0.0001 (8) |
C2 | 0.0532 (17) | 0.0296 (13) | 0.0181 (12) | 0.0094 (12) | 0.0018 (11) | 0.0019 (10) |
C3 | 0.0287 (12) | 0.0246 (12) | 0.0209 (11) | 0.0043 (9) | −0.0003 (9) | 0.0015 (9) |
C4 | 0.0340 (14) | 0.0240 (12) | 0.0260 (12) | −0.0045 (10) | −0.0047 (10) | 0.0027 (9) |
C5 | 0.0314 (13) | 0.0327 (14) | 0.0243 (12) | −0.0017 (11) | 0.0011 (10) | 0.0020 (10) |
C6 | 0.0356 (16) | 0.0456 (19) | 0.056 (2) | −0.0089 (14) | 0.0027 (14) | 0.0125 (15) |
C7 | 0.0290 (16) | 0.063 (2) | 0.067 (2) | −0.0072 (15) | −0.0011 (15) | 0.0106 (18) |
C8 | 0.0284 (14) | 0.059 (2) | 0.0412 (17) | 0.0078 (14) | −0.0005 (12) | 0.0042 (14) |
C9 | 0.0341 (14) | 0.0391 (16) | 0.0315 (14) | 0.0085 (12) | 0.0031 (11) | 0.0034 (11) |
C10 | 0.0312 (13) | 0.0222 (11) | 0.0236 (12) | 0.0022 (10) | 0.0011 (9) | 0.0002 (9) |
C11 | 0.0274 (12) | 0.0251 (12) | 0.0218 (11) | 0.0029 (9) | 0.0024 (9) | −0.0011 (9) |
C12 | 0.0329 (14) | 0.0317 (14) | 0.0297 (13) | 0.0074 (11) | −0.0035 (11) | −0.0018 (10) |
C13 | 0.0289 (14) | 0.0432 (17) | 0.0396 (16) | 0.0039 (12) | −0.0046 (11) | −0.0078 (13) |
C14 | 0.0296 (14) | 0.0391 (16) | 0.0418 (16) | −0.0053 (12) | 0.0062 (12) | −0.0076 (12) |
C15 | 0.0360 (14) | 0.0320 (14) | 0.0307 (14) | −0.0035 (11) | 0.0038 (11) | 0.0031 (11) |
C16 | 0.0255 (12) | 0.0355 (14) | 0.0204 (11) | −0.0016 (10) | 0.0011 (9) | −0.0025 (10) |
C17 | 0.0259 (12) | 0.0323 (13) | 0.0224 (12) | 0.0013 (10) | −0.0018 (9) | 0.0061 (10) |
C18 | 0.0304 (14) | 0.0467 (17) | 0.0287 (14) | 0.0061 (12) | −0.0018 (11) | 0.0010 (12) |
C19 | 0.0286 (15) | 0.062 (2) | 0.0427 (17) | 0.0100 (14) | 0.0026 (12) | 0.0078 (15) |
C20 | 0.0267 (14) | 0.055 (2) | 0.061 (2) | −0.0028 (14) | −0.0026 (14) | 0.0151 (17) |
C21 | 0.0357 (16) | 0.0374 (16) | 0.055 (2) | −0.0079 (13) | −0.0098 (14) | 0.0047 (14) |
C22 | 0.0282 (12) | 0.0269 (12) | 0.0228 (11) | 0.0029 (10) | −0.0012 (9) | 0.0031 (9) |
C23 | 0.0266 (12) | 0.0275 (12) | 0.0228 (12) | 0.0071 (10) | −0.0012 (9) | 0.0033 (9) |
C24 | 0.0329 (14) | 0.0379 (15) | 0.0240 (12) | 0.0039 (11) | 0.0034 (10) | 0.0035 (10) |
C25 | 0.0314 (14) | 0.0461 (17) | 0.0337 (15) | 0.0008 (12) | 0.0048 (11) | 0.0123 (12) |
C26 | 0.0286 (14) | 0.0366 (15) | 0.0425 (16) | −0.0019 (11) | −0.0024 (11) | 0.0054 (12) |
C27 | 0.0286 (13) | 0.0405 (16) | 0.0323 (14) | 0.0009 (11) | −0.0031 (11) | −0.0053 (11) |
O1 | 0.0314 (11) | 0.0313 (11) | 0.0317 (10) | 0.0021 (9) | 0.0015 (8) | 0.0030 (8) |
Cl1 | 0.0301 (3) | 0.0202 (3) | 0.0253 (3) | 0.0010 (2) | 0.0011 (2) | −0.0005 (2) |
Cl2 | 0.0335 (3) | 0.0291 (3) | 0.0319 (3) | 0.0009 (3) | −0.0035 (2) | 0.0015 (2) |
Cl3 | 0.0302 (3) | 0.0284 (3) | 0.0435 (4) | −0.0001 (3) | 0.0065 (3) | −0.0059 (3) |
Cl4 | 0.0318 (4) | 0.0434 (4) | 0.0441 (4) | −0.0049 (3) | −0.0069 (3) | 0.0090 (3) |
O11 | 0.0381 (11) | 0.0305 (10) | 0.0293 (10) | −0.0007 (8) | −0.0021 (8) | 0.0073 (8) |
O13 | 0.0386 (12) | 0.0386 (12) | 0.0553 (14) | 0.0047 (9) | 0.0174 (10) | 0.0054 (10) |
O12 | 0.0505 (13) | 0.0233 (10) | 0.0342 (10) | 0.0104 (9) | 0.0007 (9) | −0.0001 (8) |
O14 | 0.0498 (13) | 0.0410 (12) | 0.0339 (11) | −0.0050 (10) | −0.0074 (9) | −0.0093 (9) |
O21 | 0.0418 (12) | 0.0300 (11) | 0.0459 (12) | 0.0075 (9) | 0.0039 (9) | 0.0028 (9) |
O22 | 0.110 (3) | 0.0619 (18) | 0.0301 (13) | 0.0273 (18) | −0.0094 (14) | −0.0031 (11) |
O23 | 0.0500 (14) | 0.0407 (12) | 0.0445 (13) | 0.0157 (10) | −0.0098 (10) | 0.0026 (10) |
O24 | 0.0445 (15) | 0.0543 (17) | 0.110 (3) | −0.0133 (13) | 0.0057 (16) | 0.0136 (17) |
O31 | 0.0486 (17) | 0.0366 (15) | 0.185 (4) | −0.0123 (13) | 0.000 (2) | 0.002 (2) |
O32 | 0.0435 (19) | 0.048 (2) | 0.357 (9) | 0.0187 (16) | 0.024 (3) | −0.020 (3) |
O33 | 0.324 (8) | 0.056 (2) | 0.090 (3) | 0.067 (3) | 0.132 (4) | 0.031 (2) |
O34 | 0.292 (8) | 0.054 (2) | 0.118 (4) | −0.023 (3) | −0.130 (5) | −0.004 (2) |
O41 | 0.139 (4) | 0.287 (8) | 0.078 (3) | −0.164 (5) | −0.005 (3) | −0.011 (4) |
O42 | 0.111 (4) | 0.115 (4) | 0.239 (7) | 0.062 (3) | 0.086 (4) | 0.075 (4) |
O43 | 0.193 (6) | 0.235 (7) | 0.073 (3) | −0.150 (6) | 0.001 (3) | −0.018 (4) |
O44 | 0.166 (6) | 0.212 (7) | 0.323 (10) | 0.084 (6) | 0.081 (6) | 0.224 (8) |
N1—C4 | 1.461 (3) | C12—C13 | 1.382 (4) |
N1—C10 | 1.463 (3) | C12—H12 | 0.9500 |
N1—C1 | 1.480 (3) | C16—H16A | 0.9900 |
N2—C16 | 1.459 (3) | C16—H16B | 0.9900 |
N2—C22 | 1.469 (3) | C27—C26 | 1.372 (4) |
N2—C3 | 1.477 (3) | C27—H27 | 0.9500 |
N4—C15 | 1.341 (4) | C26—C25 | 1.386 (5) |
N4—C11 | 1.341 (3) | C26—H26 | 0.9500 |
N4—H4N | 0.87 (4) | C9—C8 | 1.365 (5) |
C1—C2 | 1.526 (3) | C9—H9 | 0.9500 |
C1—H1A | 0.9900 | C14—C13 | 1.382 (5) |
C1—H1B | 0.9900 | C14—H14 | 0.9500 |
C3—C2 | 1.522 (4) | C18—C19 | 1.387 (4) |
C3—H3A | 0.9900 | C18—H18 | 0.9500 |
C3—H3B | 0.9900 | C13—H13 | 0.9500 |
N6—C27 | 1.341 (4) | C19—C20 | 1.389 (6) |
N6—C23 | 1.354 (3) | C19—H19 | 0.9500 |
N6—H6N | 0.90 (4) | C8—C7 | 1.381 (5) |
N5—C17 | 1.334 (4) | C8—H8 | 0.9500 |
N5—C21 | 1.348 (4) | C21—C20 | 1.365 (5) |
N5—H5N | 0.78 (4) | C21—H21 | 0.9500 |
N3—C5 | 1.336 (4) | C6—C7 | 1.379 (5) |
N3—C9 | 1.344 (4) | C6—H6 | 0.9500 |
N3—H3N | 0.88 (4) | C25—H25 | 0.9500 |
C4—C5 | 1.496 (4) | C20—H20 | 0.9500 |
C4—H4A | 0.9900 | C7—H7 | 0.9500 |
C4—H4B | 0.9900 | Cl1—O12 | 1.429 (2) |
C22—C23 | 1.510 (4) | Cl1—O14 | 1.431 (2) |
C22—H22A | 0.9900 | Cl1—O13 | 1.435 (2) |
C22—H22B | 0.9900 | Cl1—O11 | 1.461 (2) |
C10—C11 | 1.502 (4) | Cl2—O22 | 1.426 (3) |
C10—H10A | 0.9900 | Cl2—O24 | 1.433 (3) |
C10—H10B | 0.9900 | Cl2—O23 | 1.444 (2) |
C5—C6 | 1.381 (4) | Cl2—O21 | 1.447 (2) |
C17—C18 | 1.382 (4) | Cl3—O33 | 1.349 (3) |
C17—C16 | 1.507 (4) | Cl3—O34 | 1.376 (4) |
C24—C23 | 1.379 (4) | Cl3—O32 | 1.398 (3) |
C24—C25 | 1.389 (4) | Cl3—O31 | 1.418 (3) |
C24—H24 | 0.9500 | Cl4—O44 | 1.332 (5) |
C11—C12 | 1.381 (4) | Cl4—O41 | 1.369 (4) |
C2—H2A | 0.9900 | Cl4—O42 | 1.379 (4) |
C2—H2B | 0.9900 | Cl4—O43 | 1.381 (5) |
C15—C14 | 1.377 (4) | O1—H102 | 0.76 (4) |
C15—H15 | 0.9500 | O1—H101 | 0.77 (5) |
C4—N1—C10 | 109.9 (2) | C11—C12—H12 | 120.2 |
C4—N1—C1 | 112.7 (2) | C13—C12—H12 | 120.2 |
C10—N1—C1 | 113.11 (19) | N2—C16—C17 | 110.9 (2) |
C16—N2—C22 | 114.3 (2) | N2—C16—H16A | 109.5 |
C16—N2—C3 | 111.0 (2) | C17—C16—H16A | 109.5 |
C22—N2—C3 | 115.6 (2) | N2—C16—H16B | 109.5 |
C15—N4—C11 | 123.3 (3) | C17—C16—H16B | 109.5 |
C15—N4—H4N | 118 (3) | H16A—C16—H16B | 108.0 |
C11—N4—H4N | 119 (3) | N6—C27—C26 | 120.1 (3) |
N1—C1—C2 | 115.6 (2) | N6—C27—H27 | 119.9 |
N1—C1—H1A | 108.4 | C26—C27—H27 | 119.9 |
C2—C1—H1A | 108.4 | C27—C26—C25 | 118.7 (3) |
N1—C1—H1B | 108.4 | C27—C26—H26 | 120.7 |
C2—C1—H1B | 108.4 | C25—C26—H26 | 120.7 |
H1A—C1—H1B | 107.4 | N3—C9—C8 | 119.4 (3) |
N2—C3—C2 | 111.8 (2) | N3—C9—H9 | 120.3 |
N2—C3—H3A | 109.3 | C8—C9—H9 | 120.3 |
C2—C3—H3A | 109.3 | C15—C14—C13 | 118.7 (3) |
N2—C3—H3B | 109.3 | C15—C14—H14 | 120.6 |
C2—C3—H3B | 109.3 | C13—C14—H14 | 120.6 |
H3A—C3—H3B | 107.9 | C17—C18—C19 | 118.9 (3) |
C27—N6—C23 | 123.5 (2) | C17—C18—H18 | 120.5 |
C27—N6—H6N | 122 (2) | C19—C18—H18 | 120.5 |
C23—N6—H6N | 114 (2) | C12—C13—C14 | 120.1 (3) |
C17—N5—C21 | 124.0 (3) | C12—C13—H13 | 119.9 |
C17—N5—H5N | 114 (3) | C14—C13—H13 | 119.9 |
C21—N5—H5N | 122 (3) | C18—C19—C20 | 120.3 (3) |
C5—N3—C9 | 123.7 (3) | C18—C19—H19 | 119.9 |
C5—N3—H3N | 120 (3) | C20—C19—H19 | 119.9 |
C9—N3—H3N | 116 (3) | C9—C8—C7 | 118.9 (3) |
N1—C4—C5 | 112.4 (2) | C9—C8—H8 | 120.6 |
N1—C4—H4A | 109.1 | C7—C8—H8 | 120.6 |
C5—C4—H4A | 109.1 | N5—C21—C20 | 119.0 (3) |
N1—C4—H4B | 109.1 | N5—C21—H21 | 120.5 |
C5—C4—H4B | 109.1 | C20—C21—H21 | 120.5 |
H4A—C4—H4B | 107.9 | C7—C6—C5 | 119.7 (3) |
N2—C22—C23 | 114.4 (2) | C7—C6—H6 | 120.1 |
N2—C22—H22A | 108.7 | C5—C6—H6 | 120.1 |
C23—C22—H22A | 108.7 | C26—C25—C24 | 119.6 (3) |
N2—C22—H22B | 108.7 | C26—C25—H25 | 120.2 |
C23—C22—H22B | 108.7 | C24—C25—H25 | 120.2 |
H22A—C22—H22B | 107.6 | C21—C20—C19 | 119.1 (3) |
N1—C10—C11 | 112.7 (2) | C21—C20—H20 | 120.4 |
N1—C10—H10A | 109.0 | C19—C20—H20 | 120.4 |
C11—C10—H10A | 109.0 | C6—C7—C8 | 120.2 (3) |
N1—C10—H10B | 109.0 | C6—C7—H7 | 119.9 |
C11—C10—H10B | 109.0 | C8—C7—H7 | 119.9 |
H10A—C10—H10B | 107.8 | O12—Cl1—O14 | 110.69 (14) |
N3—C5—C6 | 118.0 (3) | O12—Cl1—O13 | 109.99 (14) |
N3—C5—C4 | 118.7 (2) | O14—Cl1—O13 | 110.62 (15) |
C6—C5—C4 | 123.1 (3) | O12—Cl1—O11 | 108.75 (12) |
N5—C17—C18 | 118.7 (3) | O14—Cl1—O11 | 108.48 (14) |
N5—C17—C16 | 117.1 (2) | O13—Cl1—O11 | 108.25 (14) |
C18—C17—C16 | 124.1 (3) | O22—Cl2—O24 | 112.0 (2) |
C23—C24—C25 | 120.7 (3) | O22—Cl2—O23 | 108.57 (17) |
C23—C24—H24 | 119.6 | O24—Cl2—O23 | 107.53 (18) |
C25—C24—H24 | 119.6 | O22—Cl2—O21 | 109.80 (16) |
N4—C11—C12 | 118.5 (3) | O24—Cl2—O21 | 110.36 (17) |
N4—C11—C10 | 117.8 (2) | O23—Cl2—O21 | 108.43 (14) |
C12—C11—C10 | 123.6 (2) | O33—Cl3—O34 | 106.1 (5) |
N6—C23—C24 | 117.3 (3) | O33—Cl3—O32 | 108.8 (4) |
N6—C23—C22 | 119.1 (2) | O34—Cl3—O32 | 108.9 (4) |
C24—C23—C22 | 123.5 (2) | O33—Cl3—O31 | 108.5 (3) |
C3—C2—C1 | 110.8 (2) | O34—Cl3—O31 | 109.9 (3) |
C3—C2—H2A | 109.5 | O32—Cl3—O31 | 114.3 (2) |
C1—C2—H2A | 109.5 | O44—Cl4—O41 | 114.0 (5) |
C3—C2—H2B | 109.5 | O44—Cl4—O42 | 107.1 (4) |
C1—C2—H2B | 109.5 | O41—Cl4—O42 | 117.2 (5) |
H2A—C2—H2B | 108.1 | O44—Cl4—O43 | 113.3 (6) |
N4—C15—C14 | 119.7 (3) | O41—Cl4—O43 | 102.4 (3) |
N4—C15—H15 | 120.2 | O42—Cl4—O43 | 102.3 (5) |
C14—C15—H15 | 120.2 | H102—O1—H101 | 111 (5) |
C11—C12—C13 | 119.7 (3) | ||
C4—N1—C1—C2 | 68.0 (3) | N1—C1—C2—C3 | −178.8 (2) |
C10—N1—C1—C2 | −57.5 (3) | C11—N4—C15—C14 | 0.1 (4) |
C16—N2—C3—C2 | −161.5 (2) | N4—C11—C12—C13 | 0.0 (4) |
C22—N2—C3—C2 | 66.1 (3) | C10—C11—C12—C13 | 177.1 (3) |
C10—N1—C4—C5 | −157.3 (2) | C22—N2—C16—C17 | −138.2 (2) |
C1—N1—C4—C5 | 75.5 (3) | C3—N2—C16—C17 | 88.8 (3) |
C16—N2—C22—C23 | −72.1 (3) | N5—C17—C16—N2 | 13.3 (3) |
C3—N2—C22—C23 | 58.7 (3) | C18—C17—C16—N2 | −170.2 (3) |
C4—N1—C10—C11 | 166.5 (2) | C23—N6—C27—C26 | 1.0 (4) |
C1—N1—C10—C11 | −66.5 (3) | N6—C27—C26—C25 | −1.3 (5) |
C9—N3—C5—C6 | −0.8 (4) | C5—N3—C9—C8 | −1.1 (4) |
C9—N3—C5—C4 | 174.4 (3) | N4—C15—C14—C13 | −0.8 (4) |
N1—C4—C5—N3 | 20.6 (3) | N5—C17—C18—C19 | 1.0 (4) |
N1—C4—C5—C6 | −164.4 (3) | C16—C17—C18—C19 | −175.4 (3) |
C21—N5—C17—C18 | 0.9 (4) | C11—C12—C13—C14 | −0.7 (4) |
C21—N5—C17—C16 | 177.5 (3) | C15—C14—C13—C12 | 1.1 (5) |
C15—N4—C11—C12 | 0.3 (4) | C17—C18—C19—C20 | −1.6 (5) |
C15—N4—C11—C10 | −177.0 (2) | N3—C9—C8—C7 | 1.8 (5) |
N1—C10—C11—N4 | −42.1 (3) | C17—N5—C21—C20 | −2.1 (5) |
N1—C10—C11—C12 | 140.8 (2) | N3—C5—C6—C7 | 1.9 (5) |
C27—N6—C23—C24 | 0.5 (4) | C4—C5—C6—C7 | −173.1 (3) |
C27—N6—C23—C22 | −177.9 (3) | C27—C26—C25—C24 | 0.1 (5) |
C25—C24—C23—N6 | −1.6 (4) | C23—C24—C25—C26 | 1.3 (4) |
C25—C24—C23—C22 | 176.7 (3) | N5—C21—C20—C19 | 1.4 (5) |
N2—C22—C23—N6 | 85.1 (3) | C18—C19—C20—C21 | 0.4 (5) |
N2—C22—C23—C24 | −93.2 (3) | C5—C6—C7—C8 | −1.2 (6) |
N2—C3—C2—C1 | 175.3 (2) | C9—C8—C7—C6 | −0.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O11i | 0.88 (4) | 2.00 (4) | 2.845 (3) | 160 (4) |
N3—H3N···N1 | 0.88 (4) | 2.38 (4) | 2.737 (3) | 105 (3) |
N4—H4N···O1i | 0.87 (4) | 2.57 (4) | 3.137 (3) | 124 (3) |
N5—H5N···N2 | 0.78 (4) | 2.23 (4) | 2.659 (3) | 115 (4) |
N6—H6N···O1 | 0.90 (4) | 1.93 (4) | 2.810 (3) | 165 (3) |
O1—H102···O21 | 0.76 (4) | 2.14 (4) | 2.876 (3) | 163 (4) |
O1—H101···O33ii | 0.77 (5) | 2.41 (5) | 3.088 (7) | 147 (5) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1. |