Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199006072/na0090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00901sup2.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00902sup3.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00903sup4.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00904sup5.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00905sup6.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00906sup7.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00907sup8.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199006072/na00908sup9.fcf |
CCDC references: 141634; 141635; 141636; 141637; 141638; 141639; 141640; 141641
Data collection: CAD-4-PC Software (Enraf-Nonius, 1992) for (1), (3), (4), (7), (8); MSC/AFC Diffractometer Control (Molecular Structure Corporation 1988) for (2); KappaCCD (Nonius, 1998) for (5), (6). Cell refinement: SET4 & CELDIM in CAD-4-PC Software (Enraf-Nonius, 1992) for (1), (3), (4), (7), (8); MSC/AFC Diffractometer Control (Molecular Structure Corporation 1988) for (2); DENZO (Nonius, 1998) for (5), (6). Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for (1), (2), (3), (4), (7), (8); DENZO (Nonius, 1998) for (5), (6). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).
C16H38N42+·2(C12H9O2−) | F(000) = 356 |
Mr = 656.89 | ? #Insert any comments here. |
Triclinic, P1 | Dx = 1.199 Mg m−3 |
a = 8.6323 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.943 (3) Å | Cell parameters from 25 reflections |
c = 12.582 (2) Å | θ = 7.9–18.6° |
α = 98.783 (17)° | µ = 0.08 mm−1 |
β = 102.785 (15)° | T = 294 K |
γ = 115.746 (11)° | Needle, colourless |
V = 909.8 (4) Å3 | 0.39 × 0.19 × 0.17 mm |
Z = 1 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: X-ray tube | θmax = 25.5°, θmin = 2.4° |
Graphite monochromator | h = −10→9 |
θ/2θ scans | k = 0→12 |
3375 measured reflections | l = −15→15 |
3375 independent reflections | 3 standard reflections every 120 min |
2146 reflections with I > 2σ(I) | intensity decay: no decay, variation .2% |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0684P)2 + 0.0289P] where P = (Fo2 + 2Fc2)/3 |
3375 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 7.1857 (0.0045) x + 1.8968 (0.0086) y + 9.1043 (0.0078) z = 2.3388 (0.0024) * -0.0112 (0.0014) C11 * 0.0157 (0.0014) C12 * -0.0073 (0.0015) C13 * -0.0060 (0.0017) C14 * 0.0105 (0.0017) C15 * -0.0017 (0.0016) C16 0.0566 (0.0027) O1 - 0.0943 (0.0031) C21 0.6055 (0.0037) C22 0.5166 (0.0048) C23 - 0.2727 (0.0055) C24 - 0.9960 (0.0051) C25 - 0.9025 (0.0041) C26 1.4083 (0.0035) O2 Rms deviation of fitted atoms = 0.0098 - 7.3580 (0.0047) x - 0.9579 (0.0091) y + 3.3320 (0.0117) z = 0.9877 (0.0031) Angle to previous plane (with approximate e.s.d.) = 39.6 (1) * 0.0103 (0.0015) C21 * -0.0092 (0.0014) C22 * -0.0004 (0.0016) C23 * 0.0090 (0.0018) C24 * -0.0076 (0.0018) C25 * -0.0021 (0.0017) C26 - 0.0157 (0.0030) O2 0.0686 (0.0033) C11 - 0.6685 (0.0039) C12 - 0.6244 (0.0052) C13 0.1451 (0.0057) C14 0.8972 (0.0053) C15 0.8449 (0.0042) C16 - 1.3971 (0.0036) O1 Rms deviation of fitted atoms = 0.0075 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.14207 (18) | 0.37187 (15) | 0.29777 (11) | 0.0556 (4) | |
O2 | 0.0255 (2) | 0.16877 (17) | 0.39653 (12) | 0.0624 (4) | |
C11 | −0.0941 (3) | 0.1455 (2) | 0.15110 (16) | 0.0475 (5) | |
C12 | 0.0069 (3) | 0.3086 (2) | 0.19977 (16) | 0.0468 (5) | |
C13 | −0.0374 (3) | 0.4035 (3) | 0.14253 (18) | 0.0586 (6) | |
C14 | −0.1790 (3) | 0.3434 (3) | 0.0434 (2) | 0.0680 (6) | |
C15 | −0.2817 (3) | 0.1857 (3) | −0.00297 (19) | 0.0730 (7) | |
C16 | −0.2378 (3) | 0.0891 (3) | 0.05043 (18) | 0.0655 (6) | |
C21 | −0.0495 (3) | 0.0348 (2) | 0.20023 (17) | 0.0501 (5) | |
C22 | 0.0041 (3) | 0.0482 (2) | 0.31663 (18) | 0.0510 (5) | |
C23 | 0.0350 (3) | −0.0651 (3) | 0.3548 (2) | 0.0617 (6) | |
C24 | 0.0159 (3) | −0.1912 (3) | 0.2793 (3) | 0.0754 (7) | |
C25 | −0.0316 (4) | −0.2053 (3) | 0.1653 (3) | 0.0825 (8) | |
C26 | −0.0644 (3) | −0.0942 (2) | 0.1266 (2) | 0.0712 (7) | |
N1 | 0.4893 (2) | 0.53683 (19) | 0.34399 (12) | 0.0486 (4) | |
C2 | 0.5633 (3) | 0.7076 (2) | 0.38016 (18) | 0.0643 (6) | |
C3 | 0.4745 (3) | 0.7500 (3) | 0.45983 (18) | 0.0630 (6) | |
N4 | 0.5138 (2) | 0.70499 (18) | 0.56377 (13) | 0.0489 (4) | |
C5 | 0.4190 (3) | 0.7275 (2) | 0.64475 (17) | 0.0524 (5) | |
C51 | 0.2156 (3) | 0.6176 (3) | 0.58954 (19) | 0.0642 (6) | |
C52 | 0.4538 (4) | 0.8961 (3) | 0.6791 (2) | 0.0860 (8) | |
C6 | 0.4952 (3) | 0.6904 (3) | 0.75197 (17) | 0.0619 (6) | |
C7 | 0.4456 (3) | 0.5223 (3) | 0.74363 (16) | 0.0606 (6) | |
C71 | 0.5275 (4) | 0.5047 (4) | 0.85817 (19) | 0.0989 (10) | |
H2 | 0.0636 | 0.2479 | 0.3757 | 0.094* | |
H13 | 0.0318 | 0.5110 | 0.1728 | 0.070* | |
H14 | −0.2054 | 0.4097 | 0.0076 | 0.082* | |
H15 | −0.3797 | 0.1438 | −0.0695 | 0.088* | |
H16 | −0.3073 | −0.0179 | 0.0177 | 0.079* | |
H23 | 0.0689 | −0.0554 | 0.4323 | 0.074* | |
H24 | 0.0353 | −0.2669 | 0.3057 | 0.091* | |
H25 | −0.0418 | −0.2892 | 0.1141 | 0.099* | |
H26 | −0.0974 | −0.1055 | 0.0489 | 0.085* | |
H1A | 0.3673 | 0.4914 | 0.3164 | 0.058* | |
H1E | 0.5175 | 0.5061 | 0.4058 | 0.058* | |
H2A | 0.5419 | 0.7440 | 0.3140 | 0.077* | |
H2B | 0.6934 | 0.7581 | 0.4179 | 0.077* | |
H3A | 0.5186 | 0.8613 | 0.4790 | 0.076* | |
H3B | 0.3441 | 0.6977 | 0.4225 | 0.076* | |
H4A | 0.6343 | 0.7601 | 0.6001 | 0.059* | |
H51A | 0.1671 | 0.6555 | 0.5324 | 0.096* | |
H51B | 0.1565 | 0.6123 | 0.6463 | 0.096* | |
H51C | 0.1951 | 0.5156 | 0.5552 | 0.096* | |
H52A | 0.5823 | 0.9661 | 0.7105 | 0.129* | |
H52B | 0.3968 | 0.9069 | 0.7348 | 0.129* | |
H52C | 0.4041 | 0.9205 | 0.6133 | 0.129* | |
H6A | 0.6267 | 0.7513 | 0.7765 | 0.074* | |
H6B | 0.4555 | 0.7262 | 0.8114 | 0.074* | |
H7 | 0.3130 | 0.4597 | 0.7203 | 0.073* | |
H71A | 0.4878 | 0.3965 | 0.8517 | 0.148* | |
H71B | 0.4885 | 0.5457 | 0.9146 | 0.148* | |
H71C | 0.6577 | 0.5609 | 0.8800 | 0.148* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0492 (8) | 0.0496 (8) | 0.0527 (9) | 0.0164 (7) | 0.0093 (7) | 0.0079 (7) |
O2 | 0.0810 (11) | 0.0666 (10) | 0.0502 (8) | 0.0423 (9) | 0.0253 (8) | 0.0182 (7) |
C11 | 0.0463 (11) | 0.0481 (11) | 0.0441 (11) | 0.0187 (9) | 0.0189 (9) | 0.0094 (9) |
C12 | 0.0455 (12) | 0.0495 (11) | 0.0474 (11) | 0.0233 (10) | 0.0189 (10) | 0.0128 (9) |
C13 | 0.0655 (15) | 0.0545 (13) | 0.0614 (14) | 0.0323 (12) | 0.0239 (12) | 0.0167 (11) |
C14 | 0.0755 (17) | 0.0828 (18) | 0.0601 (14) | 0.0471 (15) | 0.0227 (13) | 0.0303 (13) |
C15 | 0.0668 (16) | 0.0893 (19) | 0.0503 (14) | 0.0341 (15) | 0.0062 (12) | 0.0175 (13) |
C16 | 0.0651 (15) | 0.0580 (13) | 0.0512 (13) | 0.0177 (12) | 0.0124 (11) | 0.0041 (11) |
C21 | 0.0513 (12) | 0.0426 (11) | 0.0538 (12) | 0.0180 (10) | 0.0236 (10) | 0.0124 (9) |
C22 | 0.0484 (12) | 0.0484 (12) | 0.0604 (13) | 0.0223 (10) | 0.0264 (10) | 0.0172 (10) |
C23 | 0.0602 (14) | 0.0617 (14) | 0.0735 (15) | 0.0303 (12) | 0.0313 (12) | 0.0301 (12) |
C24 | 0.0838 (18) | 0.0582 (15) | 0.105 (2) | 0.0389 (14) | 0.0474 (16) | 0.0389 (14) |
C25 | 0.110 (2) | 0.0485 (14) | 0.096 (2) | 0.0396 (15) | 0.0471 (17) | 0.0167 (13) |
C26 | 0.0951 (19) | 0.0480 (13) | 0.0668 (15) | 0.0284 (13) | 0.0350 (14) | 0.0133 (11) |
N1 | 0.0471 (10) | 0.0648 (11) | 0.0354 (8) | 0.0252 (9) | 0.0163 (7) | 0.0203 (8) |
C2 | 0.0734 (16) | 0.0605 (14) | 0.0560 (13) | 0.0235 (12) | 0.0266 (12) | 0.0281 (11) |
C3 | 0.0800 (16) | 0.0553 (13) | 0.0607 (14) | 0.0366 (12) | 0.0223 (12) | 0.0242 (11) |
N4 | 0.0424 (9) | 0.0566 (10) | 0.0428 (9) | 0.0215 (8) | 0.0123 (7) | 0.0107 (8) |
C5 | 0.0463 (12) | 0.0545 (12) | 0.0505 (12) | 0.0235 (10) | 0.0150 (9) | 0.0032 (9) |
C51 | 0.0498 (14) | 0.0736 (15) | 0.0691 (15) | 0.0314 (12) | 0.0193 (11) | 0.0156 (12) |
C52 | 0.093 (2) | 0.0620 (15) | 0.0955 (19) | 0.0339 (15) | 0.0390 (16) | 0.0002 (14) |
C6 | 0.0541 (13) | 0.0799 (16) | 0.0435 (12) | 0.0294 (12) | 0.0190 (10) | 0.0009 (11) |
C7 | 0.0574 (13) | 0.0921 (17) | 0.0412 (11) | 0.0371 (13) | 0.0259 (10) | 0.0253 (11) |
C71 | 0.122 (2) | 0.163 (3) | 0.0433 (14) | 0.086 (2) | 0.0367 (15) | 0.0451 (16) |
O1—C12 | 1.329 (2) | C24—C25 | 1.369 (4) |
O2—C22 | 1.357 (2) | C25—C26 | 1.383 (3) |
C11—C16 | 1.394 (3) | N1—C2 | 1.480 (3) |
C11—C12 | 1.414 (3) | N1—C7i | 1.497 (2) |
C11—C21 | 1.487 (3) | C2—C3 | 1.504 (3) |
C12—C13 | 1.398 (3) | C3—N4 | 1.463 (2) |
C13—C14 | 1.368 (3) | N4—C5 | 1.488 (2) |
C14—C15 | 1.367 (3) | C5—C51 | 1.523 (3) |
C15—C16 | 1.384 (3) | C5—C6 | 1.536 (3) |
C21—C26 | 1.400 (3) | C5—C52 | 1.540 (3) |
C21—C22 | 1.401 (3) | C6—C7 | 1.514 (3) |
C22—C23 | 1.393 (3) | C7—N1i | 1.497 (2) |
C23—C24 | 1.374 (3) | C7—C71 | 1.530 (3) |
C16—C11—C12 | 117.2 (2) | C25—C24—C23 | 119.9 (2) |
C16—C11—C21 | 119.67 (19) | C24—C25—C26 | 119.7 (2) |
C12—C11—C21 | 123.08 (18) | C25—C26—C21 | 122.3 (2) |
O1—C12—C13 | 120.12 (18) | C2—N1—C7i | 115.86 (16) |
O1—C12—C11 | 121.16 (18) | N1—C2—C3 | 110.43 (17) |
C13—C12—C11 | 118.72 (18) | N4—C3—C2 | 110.83 (18) |
C14—C13—C12 | 122.1 (2) | C3—N4—C5 | 115.82 (16) |
C13—C14—C15 | 119.9 (2) | N4—C5—C51 | 108.78 (16) |
C14—C15—C16 | 119.2 (2) | N4—C5—C6 | 106.95 (16) |
C15—C16—C11 | 122.8 (2) | C51—C5—C6 | 111.20 (18) |
C26—C21—C22 | 116.7 (2) | N4—C5—C52 | 112.33 (18) |
C26—C21—C11 | 118.81 (19) | C51—C5—C52 | 109.28 (19) |
C22—C21—C11 | 124.53 (18) | C6—C5—C52 | 108.31 (18) |
O2—C22—C23 | 117.1 (2) | C7—C6—C5 | 117.79 (17) |
O2—C22—C21 | 122.25 (19) | N1i—C7—C6 | 109.98 (16) |
C23—C22—C21 | 120.6 (2) | N1i—C7—C71 | 109.72 (19) |
C24—C23—C22 | 120.7 (2) | C6—C7—C71 | 111.2 (2) |
C16—C11—C12—O1 | 177.59 (18) | O2—C22—C23—C24 | 179.9 (2) |
C21—C11—C12—O1 | −4.5 (3) | C21—C22—C23—C24 | 0.9 (3) |
C16—C11—C12—C13 | −2.7 (3) | C22—C23—C24—C25 | 0.8 (4) |
C21—C11—C12—C13 | 175.21 (18) | C23—C24—C25—C26 | −1.5 (4) |
O1—C12—C13—C14 | −177.85 (19) | C24—C25—C26—C21 | 0.5 (4) |
C11—C12—C13—C14 | 2.4 (3) | C22—C21—C26—C25 | 1.2 (3) |
C12—C13—C14—C15 | −0.4 (4) | C11—C21—C26—C25 | −177.7 (2) |
C13—C14—C15—C16 | −1.3 (4) | C7i—N1—C2—C3 | 174.80 (17) |
C14—C15—C16—C11 | 0.9 (4) | N1—C2—C3—N4 | 62.7 (2) |
C12—C11—C16—C15 | 1.1 (3) | C2—C3—N4—C5 | −174.49 (17) |
C21—C11—C16—C15 | −176.9 (2) | C3—N4—C5—C51 | 65.9 (2) |
C16—C11—C21—C26 | 37.6 (3) | C3—N4—C5—C6 | −173.95 (16) |
C12—C11—C21—C26 | −140.2 (2) | C3—N4—C5—C52 | −55.2 (2) |
C16—C11—C21—C22 | −141.2 (2) | N4—C5—C6—C7 | −70.1 (2) |
C12—C11—C21—C22 | 41.0 (3) | C51—C5—C6—C7 | 48.5 (2) |
C26—C21—C22—O2 | 179.21 (19) | C52—C5—C6—C7 | 168.59 (19) |
C11—C21—C22—O2 | −2.0 (3) | C5—C6—C7—N1i | 59.9 (2) |
C26—C21—C22—C23 | −1.9 (3) | C5—C6—C7—C71 | −178.34 (18) |
C11—C21—C22—C23 | 176.93 (19) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.90 | 1.72 | 2.584 (3) | 160 |
N1—H1E···N4i | 0.90 | 2.10 | 2.818 (3) | 136 |
O2—H2···O1 | 0.82 | 1.70 | 2.488 (2) | 162 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C16H38N42+·2(C12H9O2S−)·2(CH4O) | ? #Insert any comments here. |
Mr = 785.11 | Dx = 1.202 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.659 (5) Å | Cell parameters from 7 reflections |
b = 17.892 (5) Å | θ = 7.3–11.7° |
c = 11.679 (5) Å | µ = 0.17 mm−1 |
β = 103.107 (5)° | T = 294 K |
V = 2169.3 (15) Å3 | Plate, colourless |
Z = 2 | 0.45 × 0.40 × 0.35 mm |
F(000) = 848 |
Rigaku AFC7S diffractometer | Rint = 0.005 |
Radiation source: X-ray tube | θmax = 25.0°, θmin = 2.6° |
Graphite monochromator | h = 0→12 |
θ/2θ scans | k = −3→21 |
3947 measured reflections | l = −13→13 |
3802 independent reflections | 3 standard reflections every 120 min |
2602 reflections with I > 2σ(I) | intensity decay: no decay, variation 1.3% |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0386P)2 + 0.5476P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3802 reflections | Δρmax = 0.18 e Å−3 |
250 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0079 (8) |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 2.2021 (0.0115) x + 6.9120 (0.0250) y + 9.6780 (0.0097) z = 9.7313 (0.0203) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 - 6.3950 (0.0077) x + 14.1678 (0.0115) y + 0.2916 (0.0102) z = 12.0716 (0.0103) Angle to previous plane (with approximate e.s.d.) = 85.4 (1) * -0.0030 (0.0015) C11 * 0.0012 (0.0016) C12 * 0.0025 (0.0016) C13 * -0.0044 (0.0014) C14 * 0.0026 (0.0014) C15 * 0.0010 (0.0014) C16 - 0.0157 (0.0028) S1 0.0036 (0.0029) O14 Rms deviation of fitted atoms = 0.0027 2.2021 (0.0115) x + 6.9120 (0.0250) y + 9.6780 (0.0097) z = 9.7313 (0.0203) Angle to previous plane (with approximate e.s.d.) = 85.4 (1) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 6.5928 (0.0071) x + 11.1414 (0.0120) y - 7.0894 (0.0084) z = 8.4897 (0.0106) Angle to previous plane (with approximate e.s.d.) = 86.4 (1) * 0.0014 (0.0014) C21 * -0.0076 (0.0013) C22 * 0.0068 (0.0013) C23 * 0.0001 (0.0013) C24 * -0.0062 (0.0014) C25 * 0.0055 (0.0015) C26 - 0.0041 (0.0026) S1 - 0.0283 (0.0026) O24 Rms deviation of fitted atoms = 0.0054 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.12477 (6) | 0.90037 (3) | 0.33408 (6) | 0.0688 (2) | |
O14 | −0.24497 (14) | 0.73052 (9) | 0.54380 (13) | 0.0622 (4) | |
O24 | 0.55531 (14) | 0.68254 (8) | 0.39553 (13) | 0.0563 (4) | |
C11 | 0.01274 (18) | 0.84943 (12) | 0.39596 (19) | 0.0508 (5) | |
C12 | 0.0198 (2) | 0.85044 (13) | 0.5154 (2) | 0.0615 (6) | |
C13 | −0.0662 (2) | 0.81075 (13) | 0.56357 (19) | 0.0605 (6) | |
C14 | −0.16215 (18) | 0.76840 (11) | 0.49264 (18) | 0.0478 (5) | |
C15 | −0.17021 (19) | 0.76773 (11) | 0.37249 (18) | 0.0511 (5) | |
C16 | −0.08357 (19) | 0.80770 (12) | 0.32518 (18) | 0.0500 (5) | |
C21 | 0.25397 (19) | 0.83529 (12) | 0.35116 (18) | 0.0497 (5) | |
C22 | 0.2565 (2) | 0.78005 (12) | 0.26799 (18) | 0.0530 (6) | |
C23 | 0.3571 (2) | 0.73005 (12) | 0.28090 (17) | 0.0500 (5) | |
C24 | 0.45981 (19) | 0.73180 (11) | 0.38014 (18) | 0.0452 (5) | |
C25 | 0.4554 (2) | 0.78700 (12) | 0.46368 (18) | 0.0516 (5) | |
C26 | 0.3553 (2) | 0.83788 (12) | 0.44890 (19) | 0.0541 (5) | |
N1 | 0.44606 (14) | 0.46172 (8) | 0.32989 (13) | 0.0405 (4) | |
C2 | 0.5232 (2) | 0.39167 (11) | 0.35142 (18) | 0.0519 (5) | |
C3 | 0.65844 (19) | 0.40705 (12) | 0.41881 (18) | 0.0538 (5) | |
N4 | 0.65965 (14) | 0.43751 (8) | 0.53556 (13) | 0.0404 (4) | |
C5 | 0.78775 (17) | 0.46309 (11) | 0.60467 (17) | 0.0453 (5) | |
C51 | 0.8915 (2) | 0.40230 (13) | 0.6151 (2) | 0.0670 (7) | |
C52 | 0.8286 (2) | 0.53278 (13) | 0.54649 (19) | 0.0597 (6) | |
C6 | 0.77066 (18) | 0.48131 (12) | 0.72884 (17) | 0.0485 (5) | |
C7 | 0.68709 (18) | 0.54758 (11) | 0.74550 (16) | 0.0452 (5) | |
C71 | 0.6799 (2) | 0.55608 (14) | 0.87367 (17) | 0.0630 (6) | |
O1 | 0.56065 (16) | 0.57851 (9) | 0.24233 (15) | 0.0684 (5) | |
C1 | 0.6700 (3) | 0.57961 (15) | 0.1946 (2) | 0.0768 (7) | |
H14 | −0.3061 | 0.7156 | 0.4930 | 0.093* | |
H12 | 0.0837 | 0.8784 | 0.5642 | 0.074* | |
H13 | −0.0598 | 0.8123 | 0.6443 | 0.073* | |
H15 | −0.2346 | 0.7401 | 0.3234 | 0.061* | |
H16 | −0.0900 | 0.8066 | 0.2444 | 0.060* | |
H22 | 0.1888 | 0.7768 | 0.2021 | 0.064* | |
H23 | 0.3568 | 0.6945 | 0.2228 | 0.060* | |
H25 | 0.5215 | 0.7896 | 0.5310 | 0.062* | |
H26 | 0.3562 | 0.8744 | 0.5057 | 0.065* | |
H1A | 0.4888 | 0.4951 | 0.2954 | 0.049* | |
H1E | 0.4398 | 0.4808 | 0.3996 | 0.049* | |
H2A | 0.5255 | 0.3686 | 0.2768 | 0.062* | |
H2B | 0.4824 | 0.3569 | 0.3954 | 0.062* | |
H3A | 0.7079 | 0.3611 | 0.4271 | 0.065* | |
H3B | 0.6988 | 0.4424 | 0.3754 | 0.065* | |
H4A | 0.6296 | 0.4023 | 0.5774 | 0.048* | |
H51A | 0.8638 | 0.3581 | 0.6489 | 0.101* | |
H51B | 0.9705 | 0.4199 | 0.6645 | 0.101* | |
H51C | 0.9049 | 0.3909 | 0.5385 | 0.101* | |
H52A | 0.8533 | 0.5188 | 0.4753 | 0.090* | |
H52B | 0.9004 | 0.5560 | 0.5992 | 0.090* | |
H52C | 0.7580 | 0.5673 | 0.5285 | 0.090* | |
H6A | 0.7354 | 0.4373 | 0.7584 | 0.058* | |
H6B | 0.8557 | 0.4894 | 0.7786 | 0.058* | |
H7 | 0.7250 | 0.5931 | 0.7211 | 0.054* | |
H71A | 0.6304 | 0.5997 | 0.8821 | 0.094* | |
H71B | 0.7653 | 0.5611 | 0.9219 | 0.094* | |
H71C | 0.6394 | 0.5127 | 0.8978 | 0.094* | |
H1 | 0.5662 | 0.6119 | 0.2914 | 0.103* | |
H1C | 0.6633 | 0.5407 | 0.1368 | 0.115* | 0.50 |
H1D | 0.7456 | 0.5716 | 0.2560 | 0.115* | 0.50 |
H1F | 0.6760 | 0.6272 | 0.1582 | 0.115* | 0.50 |
H1G | 0.7266 | 0.6190 | 0.2305 | 0.115* | 0.50 |
H1H | 0.6444 | 0.5881 | 0.1114 | 0.115* | 0.50 |
H1I | 0.7139 | 0.5325 | 0.2091 | 0.115* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0514 (3) | 0.0586 (4) | 0.0958 (5) | 0.0039 (3) | 0.0152 (3) | 0.0266 (3) |
O14 | 0.0525 (9) | 0.0726 (11) | 0.0595 (10) | −0.0044 (8) | 0.0082 (7) | 0.0114 (8) |
O24 | 0.0524 (8) | 0.0484 (8) | 0.0699 (10) | −0.0014 (7) | 0.0181 (7) | −0.0075 (7) |
C11 | 0.0391 (11) | 0.0479 (12) | 0.0623 (14) | 0.0042 (9) | 0.0052 (9) | 0.0056 (10) |
C12 | 0.0510 (13) | 0.0663 (15) | 0.0587 (15) | −0.0096 (11) | −0.0055 (11) | −0.0019 (12) |
C13 | 0.0553 (13) | 0.0748 (16) | 0.0450 (13) | −0.0028 (12) | −0.0019 (10) | 0.0012 (11) |
C14 | 0.0407 (11) | 0.0480 (12) | 0.0527 (13) | 0.0085 (9) | 0.0061 (9) | 0.0062 (10) |
C15 | 0.0468 (12) | 0.0491 (12) | 0.0533 (13) | −0.0029 (10) | 0.0030 (10) | −0.0074 (10) |
C16 | 0.0493 (12) | 0.0534 (12) | 0.0473 (12) | 0.0062 (10) | 0.0108 (10) | −0.0017 (10) |
C21 | 0.0428 (11) | 0.0493 (12) | 0.0575 (13) | −0.0055 (9) | 0.0124 (10) | 0.0104 (10) |
C22 | 0.0477 (12) | 0.0586 (14) | 0.0497 (13) | −0.0176 (11) | 0.0049 (10) | 0.0115 (11) |
C23 | 0.0563 (13) | 0.0487 (12) | 0.0469 (12) | −0.0168 (10) | 0.0155 (10) | −0.0046 (10) |
C24 | 0.0458 (11) | 0.0414 (11) | 0.0513 (12) | −0.0110 (9) | 0.0170 (9) | 0.0010 (9) |
C25 | 0.0489 (12) | 0.0522 (13) | 0.0498 (12) | −0.0022 (10) | 0.0029 (9) | −0.0056 (10) |
C26 | 0.0542 (13) | 0.0514 (13) | 0.0565 (13) | −0.0016 (10) | 0.0120 (10) | −0.0077 (10) |
N1 | 0.0445 (9) | 0.0407 (9) | 0.0374 (8) | −0.0044 (7) | 0.0118 (7) | −0.0065 (7) |
C2 | 0.0646 (13) | 0.0431 (12) | 0.0469 (12) | 0.0056 (10) | 0.0101 (10) | −0.0109 (9) |
C3 | 0.0535 (12) | 0.0599 (14) | 0.0491 (12) | 0.0138 (11) | 0.0136 (10) | −0.0089 (10) |
N4 | 0.0425 (9) | 0.0402 (9) | 0.0405 (9) | −0.0008 (7) | 0.0139 (7) | −0.0015 (7) |
C5 | 0.0376 (10) | 0.0485 (12) | 0.0502 (12) | 0.0002 (9) | 0.0109 (9) | 0.0071 (10) |
C51 | 0.0481 (12) | 0.0763 (17) | 0.0767 (16) | 0.0154 (12) | 0.0142 (11) | 0.0099 (13) |
C52 | 0.0573 (13) | 0.0626 (14) | 0.0625 (14) | −0.0121 (11) | 0.0207 (11) | 0.0062 (11) |
C6 | 0.0412 (11) | 0.0560 (13) | 0.0442 (12) | −0.0062 (9) | 0.0007 (9) | 0.0073 (10) |
C7 | 0.0459 (11) | 0.0483 (12) | 0.0394 (11) | −0.0117 (9) | 0.0054 (9) | −0.0044 (9) |
C71 | 0.0716 (15) | 0.0703 (15) | 0.0433 (12) | −0.0129 (13) | 0.0054 (11) | −0.0113 (11) |
O1 | 0.0786 (11) | 0.0532 (10) | 0.0833 (12) | −0.0147 (8) | 0.0393 (9) | −0.0145 (8) |
C1 | 0.0883 (19) | 0.0754 (17) | 0.0778 (18) | 0.0093 (15) | 0.0420 (15) | 0.0088 (14) |
S1—C21 | 1.780 (2) | C24—C25 | 1.397 (3) |
S1—C11 | 1.781 (2) | C25—C26 | 1.383 (3) |
O14—C14 | 1.355 (2) | N1—C2 | 1.489 (2) |
O24—C24 | 1.328 (2) | N1—C7i | 1.500 (2) |
C11—C12 | 1.380 (3) | C2—C3 | 1.503 (3) |
C11—C16 | 1.382 (3) | C3—N4 | 1.466 (2) |
C12—C13 | 1.376 (3) | N4—C5 | 1.492 (2) |
C13—C14 | 1.386 (3) | C5—C52 | 1.530 (3) |
C14—C15 | 1.386 (3) | C5—C51 | 1.536 (3) |
C15—C16 | 1.379 (3) | C5—C6 | 1.537 (3) |
C21—C26 | 1.383 (3) | C6—C7 | 1.522 (3) |
C21—C22 | 1.390 (3) | C7—N1i | 1.500 (2) |
C22—C23 | 1.378 (3) | C7—C71 | 1.524 (3) |
C23—C24 | 1.403 (3) | O1—C1 | 1.402 (3) |
C21—S1—C11 | 101.11 (10) | C25—C24—C23 | 116.71 (19) |
C12—C11—C16 | 118.3 (2) | C26—C25—C24 | 121.7 (2) |
C12—C11—S1 | 121.06 (17) | C21—C26—C25 | 121.1 (2) |
C16—C11—S1 | 120.62 (17) | C2—N1—C7i | 114.75 (15) |
C13—C12—C11 | 121.2 (2) | N1—C2—C3 | 111.21 (16) |
C12—C13—C14 | 120.5 (2) | N4—C3—C2 | 111.12 (16) |
O14—C14—C15 | 123.03 (19) | C3—N4—C5 | 115.55 (15) |
O14—C14—C13 | 118.4 (2) | N4—C5—C52 | 109.13 (16) |
C15—C14—C13 | 118.5 (2) | N4—C5—C51 | 112.32 (17) |
C16—C15—C14 | 120.52 (19) | C52—C5—C51 | 109.88 (17) |
C15—C16—C11 | 121.0 (2) | N4—C5—C6 | 106.61 (14) |
C26—C21—C22 | 117.7 (2) | C52—C5—C6 | 110.66 (17) |
C26—C21—S1 | 120.69 (17) | C51—C5—C6 | 108.20 (17) |
C22—C21—S1 | 121.60 (16) | C7—C6—C5 | 118.94 (16) |
C23—C22—C21 | 121.5 (2) | N1i—C7—C6 | 109.98 (15) |
C22—C23—C24 | 121.2 (2) | N1i—C7—C71 | 109.62 (16) |
O24—C24—C25 | 121.41 (18) | C6—C7—C71 | 111.40 (17) |
O24—C24—C23 | 121.87 (18) | ||
C21—S1—C11—C12 | 85.4 (2) | C22—C23—C24—C25 | −0.7 (3) |
C21—S1—C11—C16 | −94.51 (18) | O24—C24—C25—C26 | −179.14 (19) |
C16—C11—C12—C13 | 0.3 (3) | C23—C24—C25—C26 | −0.6 (3) |
S1—C11—C12—C13 | −179.59 (18) | C22—C21—C26—C25 | −0.3 (3) |
C11—C12—C13—C14 | 0.2 (4) | S1—C21—C26—C25 | 179.22 (16) |
C12—C13—C14—O14 | −179.7 (2) | C24—C25—C26—C21 | 1.1 (3) |
C12—C13—C14—C15 | −0.7 (3) | C7i—N1—C2—C3 | 175.20 (16) |
O14—C14—C15—C16 | 179.66 (18) | N1—C2—C3—N4 | 62.7 (2) |
C13—C14—C15—C16 | 0.7 (3) | C2—C3—N4—C5 | −173.18 (16) |
C14—C15—C16—C11 | −0.2 (3) | C3—N4—C5—C52 | 68.8 (2) |
C12—C11—C16—C15 | −0.3 (3) | C3—N4—C5—C51 | −53.3 (2) |
S1—C11—C16—C15 | 179.60 (16) | C3—N4—C5—C6 | −171.64 (16) |
C11—S1—C21—C26 | −93.67 (18) | N4—C5—C6—C7 | −67.5 (2) |
C11—S1—C21—C22 | 85.87 (18) | C52—C5—C6—C7 | 51.0 (2) |
C26—C21—C22—C23 | −0.9 (3) | C51—C5—C6—C7 | 171.46 (17) |
S1—C21—C22—C23 | 179.51 (15) | C5—C6—C7—N1i | 57.3 (2) |
C21—C22—C23—C24 | 1.5 (3) | C5—C6—C7—C71 | 179.08 (17) |
C22—C23—C24—O24 | 177.86 (17) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.90 | 1.85 | 2.733 (3) | 168 |
N1—H1E···N4i | 0.90 | 2.05 | 2.792 (2) | 139 |
O1—H1···O24 | 0.82 | 1.78 | 2.591 (3) | 172 |
O14—H14···O24ii | 0.82 | 1.75 | 2.568 (2) | 174 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z. |
C16H38N42+·2(C12H9O4S−)·2(CH4O) | ? #Insert any comments here. |
Mr = 849.09 | Dx = 1.275 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7736 (10) Å | Cell parameters from 25 reflections |
b = 18.1167 (18) Å | θ = 8.4–13.4° |
c = 11.5532 (14) Å | µ = 0.18 mm−1 |
β = 101.136 (9)° | T = 294 K |
V = 2212.5 (4) Å3 | Plate, colourless |
Z = 2 | 0.42 × 0.33 × 0.12 mm |
F(000) = 912 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.010 |
Radiation source: X-ray tube | θmax = 25.4°, θmin = 2.1° |
Graphite monochromator | h = −13→12 |
θ/2θ scans | k = 0→21 |
4294 measured reflections | l = 0→13 |
4091 independent reflections | 3 standard reflections every 120 min |
2056 reflections with I > 2σ(I) | intensity decay: no decay, variation .5% |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0464P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
4091 reflections | Δρmax = 0.19 e Å−3 |
266 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0022 (6) |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 10.5555 (0.0029) x + 1.6199 (0.0352) y + 4.2169 (0.0141) z = 1.5960 (0.0300) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12 Rms deviation of fitted atoms = 0.0000 - 6.4110 (0.0092) x + 14.2835 (0.0122) y - 0.4393 (0.0133) z = 11.8572 (0.0117) Angle to previous plane (with approximate e.s.d.) = 51.3 (1) * -0.0013 (0.0019) C11 * -0.0015 (0.0020) C12 * 0.0058 (0.0020) C13 * -0.0075 (0.0019) C14 * 0.0048 (0.0020) C15 * -0.0004 (0.0019) C16 - 0.0506 (0.0036) S1 0.0074 (0.0037) O14 Rms deviation of fitted atoms = 0.0044 - 10.5555 (0.0029) x + 1.6199 (0.0352) y + 4.2169 (0.0141) z = 1.5960 (0.0300) Angle to previous plane (with approximate e.s.d.) = 51.3 (1) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12 Rms deviation of fitted atoms = 0.0000 6.3894 (0.0089) x + 11.4828 (0.0144) y - 6.9518 (0.0097) z = 8.6481 (0.0129) Angle to previous plane (with approximate e.s.d.) = 52.2 (1) * 0.0058 (0.0018) C21 * -0.0077 (0.0018) C22 * 0.0037 (0.0018) C23 * 0.0022 (0.0018) C24 * -0.0041 (0.0019) C25 * 0.0001 (0.0019) C26 - 0.0130 (0.0034) S1 - 0.0034 (0.0035) O24 Rms deviation of fitted atoms = 0.0046 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.12553 (6) | 0.89368 (4) | 0.34940 (7) | 0.0536 (2) | |
O11 | 0.16511 (18) | 0.95631 (11) | 0.4244 (2) | 0.0697 (6) | |
O12 | 0.07782 (18) | 0.90481 (12) | 0.22571 (18) | 0.0744 (7) | |
O14 | −0.25498 (17) | 0.73319 (12) | 0.55205 (18) | 0.0585 (6) | |
O24 | 0.55381 (16) | 0.68715 (10) | 0.40051 (17) | 0.0529 (5) | |
C11 | 0.0089 (2) | 0.84660 (15) | 0.4081 (2) | 0.0430 (7) | |
C12 | 0.0087 (2) | 0.85016 (16) | 0.5273 (2) | 0.0541 (8) | |
C13 | −0.0800 (2) | 0.81227 (17) | 0.5732 (3) | 0.0536 (8) | |
C14 | −0.1693 (2) | 0.76907 (15) | 0.5021 (3) | 0.0436 (7) | |
C15 | −0.1696 (2) | 0.76611 (15) | 0.3826 (3) | 0.0511 (8) | |
C16 | −0.0804 (2) | 0.80436 (15) | 0.3360 (3) | 0.0500 (7) | |
C21 | 0.2533 (2) | 0.83232 (15) | 0.3628 (2) | 0.0439 (7) | |
C22 | 0.2566 (2) | 0.77856 (16) | 0.2790 (2) | 0.0475 (7) | |
C23 | 0.3575 (2) | 0.73059 (15) | 0.2908 (2) | 0.0465 (7) | |
C24 | 0.4580 (2) | 0.73362 (15) | 0.3884 (2) | 0.0418 (7) | |
C25 | 0.4507 (2) | 0.78793 (15) | 0.4723 (2) | 0.0480 (7) | |
C26 | 0.3513 (2) | 0.83619 (15) | 0.4601 (2) | 0.0478 (7) | |
N1 | 0.44820 (18) | 0.45871 (11) | 0.33281 (17) | 0.0393 (5) | |
C2 | 0.5272 (2) | 0.39114 (15) | 0.3512 (2) | 0.0478 (7) | |
C3 | 0.6582 (2) | 0.40787 (15) | 0.4161 (2) | 0.0480 (7) | |
N4 | 0.65792 (17) | 0.43864 (11) | 0.53316 (17) | 0.0385 (5) | |
C5 | 0.7825 (2) | 0.46690 (15) | 0.5974 (2) | 0.0431 (7) | |
C51 | 0.8873 (2) | 0.40913 (17) | 0.6078 (3) | 0.0637 (9) | |
C52 | 0.8187 (3) | 0.53498 (16) | 0.5328 (3) | 0.0591 (8) | |
C6 | 0.7658 (2) | 0.48685 (15) | 0.7233 (2) | 0.0452 (7) | |
C7 | 0.6822 (2) | 0.55211 (15) | 0.7397 (2) | 0.0445 (7) | |
C71 | 0.6739 (3) | 0.56244 (17) | 0.8682 (2) | 0.0611 (8) | |
O1 | 0.55273 (19) | 0.58024 (11) | 0.2460 (2) | 0.0651 (6) | |
C1 | 0.6612 (3) | 0.58121 (18) | 0.1940 (3) | 0.0766 (10) | |
H14 | −0.3122 | 0.7177 | 0.5004 | 0.088* | |
H12 | 0.0691 | 0.8784 | 0.5764 | 0.065* | |
H13 | −0.0803 | 0.8156 | 0.6535 | 0.064* | |
H15 | −0.2304 | 0.7381 | 0.3334 | 0.061* | |
H16 | −0.0804 | 0.8017 | 0.2556 | 0.060* | |
H22 | 0.1906 | 0.7747 | 0.2143 | 0.057* | |
H23 | 0.3591 | 0.6953 | 0.2327 | 0.056* | |
H25 | 0.5151 | 0.7915 | 0.5384 | 0.058* | |
H26 | 0.3494 | 0.8719 | 0.5175 | 0.057* | |
H1A | 0.4886 | 0.4929 | 0.2973 | 0.047* | |
H1E | 0.4409 | 0.4767 | 0.4038 | 0.047* | |
H2A | 0.5314 | 0.3694 | 0.2753 | 0.057* | |
H2B | 0.4884 | 0.3554 | 0.3957 | 0.057* | |
H3A | 0.7081 | 0.3629 | 0.4242 | 0.058* | |
H3B | 0.6976 | 0.4428 | 0.3707 | 0.058* | |
H4A | 0.6310 | 0.4035 | 0.5776 | 0.046* | |
H51A | 0.8643 | 0.3665 | 0.6482 | 0.096* | |
H51B | 0.9647 | 0.4294 | 0.6512 | 0.096* | |
H51C | 0.8987 | 0.3952 | 0.5303 | 0.096* | |
H52A | 0.7526 | 0.5712 | 0.5264 | 0.089* | |
H52B | 0.8300 | 0.5211 | 0.4554 | 0.089* | |
H52C | 0.8961 | 0.5554 | 0.5762 | 0.089* | |
H6A | 0.7323 | 0.4437 | 0.7564 | 0.054* | |
H6B | 0.8492 | 0.4961 | 0.7702 | 0.054* | |
H7 | 0.7187 | 0.5968 | 0.7122 | 0.053* | |
H71A | 0.6205 | 0.6039 | 0.8756 | 0.092* | |
H71B | 0.7570 | 0.5711 | 0.9138 | 0.092* | |
H71C | 0.6390 | 0.5188 | 0.8965 | 0.092* | |
H1 | 0.5562 | 0.6146 | 0.2927 | 0.098* | |
H1P | 0.6652 | 0.6273 | 0.1540 | 0.115* | |
H1Q | 0.6565 | 0.5414 | 0.1385 | 0.115* | |
H1R | 0.7355 | 0.5756 | 0.2543 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0417 (4) | 0.0549 (5) | 0.0651 (5) | 0.0014 (4) | 0.0125 (4) | 0.0151 (5) |
O11 | 0.0586 (13) | 0.0428 (12) | 0.1096 (18) | −0.0072 (10) | 0.0212 (12) | −0.0038 (13) |
O12 | 0.0545 (12) | 0.1019 (18) | 0.0669 (15) | 0.0117 (12) | 0.0120 (11) | 0.0400 (13) |
O14 | 0.0468 (12) | 0.0661 (14) | 0.0639 (14) | −0.0070 (10) | 0.0137 (10) | 0.0121 (12) |
O24 | 0.0470 (11) | 0.0442 (11) | 0.0693 (14) | 0.0017 (10) | 0.0159 (10) | −0.0059 (10) |
C11 | 0.0358 (14) | 0.0457 (17) | 0.0475 (18) | −0.0007 (13) | 0.0080 (13) | 0.0013 (14) |
C12 | 0.0425 (16) | 0.066 (2) | 0.051 (2) | −0.0096 (15) | 0.0012 (14) | −0.0031 (16) |
C13 | 0.0474 (17) | 0.073 (2) | 0.0397 (17) | −0.0038 (16) | 0.0053 (14) | 0.0030 (16) |
C14 | 0.0352 (15) | 0.0465 (18) | 0.0497 (19) | 0.0038 (13) | 0.0094 (14) | 0.0055 (15) |
C15 | 0.0447 (16) | 0.0507 (18) | 0.058 (2) | −0.0069 (14) | 0.0092 (14) | −0.0109 (16) |
C16 | 0.0490 (16) | 0.0570 (19) | 0.0464 (18) | −0.0013 (15) | 0.0151 (14) | −0.0065 (16) |
C21 | 0.0369 (14) | 0.0482 (17) | 0.0471 (18) | −0.0049 (13) | 0.0095 (13) | 0.0045 (15) |
C22 | 0.0442 (16) | 0.0549 (19) | 0.0422 (17) | −0.0112 (14) | 0.0050 (13) | 0.0065 (16) |
C23 | 0.0544 (17) | 0.0437 (17) | 0.0435 (18) | −0.0109 (14) | 0.0147 (15) | −0.0040 (14) |
C24 | 0.0408 (15) | 0.0387 (16) | 0.0484 (18) | −0.0080 (13) | 0.0143 (14) | 0.0018 (14) |
C25 | 0.0383 (15) | 0.0535 (19) | 0.0489 (18) | −0.0039 (14) | 0.0004 (13) | −0.0054 (15) |
C26 | 0.0469 (16) | 0.0503 (18) | 0.0471 (18) | 0.0001 (14) | 0.0109 (14) | −0.0072 (15) |
N1 | 0.0423 (12) | 0.0420 (13) | 0.0342 (12) | −0.0043 (10) | 0.0090 (10) | −0.0067 (11) |
C2 | 0.0549 (17) | 0.0403 (16) | 0.0479 (17) | 0.0043 (14) | 0.0094 (14) | −0.0084 (14) |
C3 | 0.0463 (16) | 0.0526 (18) | 0.0453 (17) | 0.0089 (14) | 0.0093 (13) | −0.0094 (14) |
N4 | 0.0389 (12) | 0.0405 (13) | 0.0379 (12) | −0.0043 (10) | 0.0119 (10) | −0.0024 (11) |
C5 | 0.0352 (14) | 0.0462 (17) | 0.0479 (17) | −0.0013 (13) | 0.0084 (12) | 0.0034 (14) |
C51 | 0.0408 (16) | 0.082 (2) | 0.069 (2) | 0.0125 (16) | 0.0116 (15) | 0.0064 (18) |
C52 | 0.0552 (18) | 0.068 (2) | 0.0537 (19) | −0.0193 (16) | 0.0099 (15) | 0.0037 (17) |
C6 | 0.0393 (15) | 0.0519 (18) | 0.0413 (16) | −0.0054 (13) | −0.0004 (12) | 0.0040 (14) |
C7 | 0.0475 (16) | 0.0437 (16) | 0.0382 (16) | −0.0109 (14) | −0.0016 (13) | −0.0036 (14) |
C71 | 0.072 (2) | 0.068 (2) | 0.0407 (18) | −0.0038 (17) | 0.0042 (15) | −0.0094 (17) |
O1 | 0.0729 (14) | 0.0505 (14) | 0.0814 (17) | −0.0097 (11) | 0.0388 (13) | −0.0123 (11) |
C1 | 0.091 (2) | 0.080 (3) | 0.070 (2) | 0.019 (2) | 0.043 (2) | 0.0108 (19) |
S1—O12 | 1.436 (2) | C23—C24 | 1.406 (4) |
S1—O11 | 1.441 (2) | C24—C25 | 1.394 (4) |
S1—C21 | 1.753 (3) | C25—C26 | 1.369 (4) |
S1—C11 | 1.759 (3) | N1—C2 | 1.483 (3) |
O14—C14 | 1.347 (3) | N1—C7i | 1.503 (3) |
O24—C24 | 1.318 (3) | C2—C3 | 1.496 (3) |
C11—C16 | 1.377 (4) | C3—N4 | 1.463 (3) |
C11—C12 | 1.379 (4) | N4—C5 | 1.493 (3) |
C12—C13 | 1.364 (4) | C5—C51 | 1.527 (4) |
C13—C14 | 1.381 (4) | C5—C52 | 1.530 (4) |
C14—C15 | 1.380 (4) | C5—C6 | 1.543 (4) |
C15—C16 | 1.376 (4) | C6—C7 | 1.520 (4) |
C21—C22 | 1.378 (4) | C7—N1i | 1.503 (3) |
C21—C26 | 1.387 (4) | C7—C71 | 1.516 (3) |
C22—C23 | 1.377 (4) | O1—C1 | 1.413 (3) |
O12—S1—O11 | 119.68 (14) | C22—C23—C24 | 121.7 (3) |
O12—S1—C21 | 107.50 (13) | O24—C24—C25 | 121.7 (2) |
O11—S1—C21 | 108.07 (13) | O24—C24—C23 | 121.7 (3) |
O12—S1—C11 | 107.86 (13) | C25—C24—C23 | 116.5 (2) |
O11—S1—C11 | 107.46 (13) | C26—C25—C24 | 121.8 (3) |
C21—S1—C11 | 105.41 (13) | C25—C26—C21 | 120.6 (3) |
C16—C11—C12 | 119.6 (2) | C2—N1—C7i | 114.91 (19) |
C16—C11—S1 | 120.2 (2) | N1—C2—C3 | 111.4 (2) |
C12—C11—S1 | 120.1 (2) | N4—C3—C2 | 111.7 (2) |
C13—C12—C11 | 120.1 (3) | C3—N4—C5 | 115.30 (19) |
C12—C13—C14 | 120.9 (3) | N4—C5—C51 | 112.6 (2) |
O14—C14—C15 | 122.7 (3) | N4—C5—C52 | 108.9 (2) |
O14—C14—C13 | 118.3 (3) | C51—C5—C52 | 109.7 (2) |
C15—C14—C13 | 118.9 (3) | N4—C5—C6 | 106.92 (19) |
C16—C15—C14 | 120.3 (3) | C51—C5—C6 | 107.8 (2) |
C15—C16—C11 | 120.1 (3) | C52—C5—C6 | 111.0 (2) |
C22—C21—C26 | 119.1 (3) | C7—C6—C5 | 118.7 (2) |
C22—C21—S1 | 120.9 (2) | N1i—C7—C71 | 109.7 (2) |
C26—C21—S1 | 120.1 (2) | N1i—C7—C6 | 110.0 (2) |
C23—C22—C21 | 120.2 (3) | C71—C7—C6 | 111.5 (2) |
O12—S1—C11—C16 | 23.8 (3) | C26—C21—C22—C23 | −1.5 (4) |
O11—S1—C11—C16 | 154.1 (2) | S1—C21—C22—C23 | −179.8 (2) |
C21—S1—C11—C16 | −90.8 (2) | C21—C22—C23—C24 | 1.3 (4) |
O12—S1—C11—C12 | −158.0 (2) | C22—C23—C24—O24 | 179.2 (2) |
O11—S1—C11—C12 | −27.8 (3) | C22—C23—C24—C25 | −0.3 (4) |
C21—S1—C11—C12 | 87.3 (3) | O24—C24—C25—C26 | −179.9 (2) |
C16—C11—C12—C13 | −0.3 (4) | C23—C24—C25—C26 | −0.4 (4) |
S1—C11—C12—C13 | −178.5 (2) | C24—C25—C26—C21 | 0.2 (4) |
C11—C12—C13—C14 | 1.0 (4) | C22—C21—C26—C25 | 0.7 (4) |
C12—C13—C14—O14 | −179.7 (3) | S1—C21—C26—C25 | 179.1 (2) |
C12—C13—C14—C15 | −1.6 (4) | C7i—N1—C2—C3 | 175.7 (2) |
O14—C14—C15—C16 | 179.5 (2) | N1—C2—C3—N4 | 60.9 (3) |
C13—C14—C15—C16 | 1.5 (4) | C2—C3—N4—C5 | −171.7 (2) |
C14—C15—C16—C11 | −0.8 (4) | C3—N4—C5—C51 | −54.4 (3) |
C12—C11—C16—C15 | 0.2 (4) | C3—N4—C5—C52 | 67.5 (3) |
S1—C11—C16—C15 | 178.4 (2) | C3—N4—C5—C6 | −172.6 (2) |
O12—S1—C21—C22 | −31.1 (3) | N4—C5—C6—C7 | −68.4 (3) |
O11—S1—C21—C22 | −161.6 (2) | C51—C5—C6—C7 | 170.3 (2) |
C11—S1—C21—C22 | 83.7 (2) | C52—C5—C6—C7 | 50.2 (3) |
O12—S1—C21—C26 | 150.5 (2) | C5—C6—C7—N1i | 56.7 (3) |
O11—S1—C21—C26 | 20.0 (3) | C5—C6—C7—C71 | 178.6 (2) |
C11—S1—C21—C26 | −94.6 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.90 | 1.87 | 2.749 (3) | 166 |
N1—H1E···N4i | 0.90 | 2.08 | 2.801 (3) | 137 |
O1—H1···O24 | 0.82 | 1.81 | 2.632 (3) | 175 |
O14—H14···O24ii | 0.82 | 1.75 | 2.571 (3) | 174 |
C2—H2B···O24i | 0.97 | 2.60 | 3.460 (3) | 148 |
C16—H16···O12 | 0.93 | 2.60 | 2.946 (3) | 103 |
C26—H26···O11 | 0.93 | 2.57 | 2.934 (3) | 104 |
C52—H52C···O12iii | 0.96 | 2.46 | 3.398 (4) | 167 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x+1, −y+3/2, z+1/2. |
C16H38N42+·2(C7H5O3−)·2(CH4O) | F(000) = 340 |
Mr = 624.81 | ? #Insert any comments here. |
Triclinic, P1 | Dx = 1.215 Mg m−3 |
a = 8.0814 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1981 (12) Å | Cell parameters from 25 reflections |
c = 10.7800 (16) Å | θ = 8.7–17.4° |
α = 79.789 (10)° | µ = 0.09 mm−1 |
β = 80.728 (10)° | T = 294 K |
γ = 80.28 (1)° | Block, colourless |
V = 853.89 (19) Å3 | 0.42 × 0.29 × 0.21 mm |
Z = 1 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: X-ray tube | θmax = 25.4°, θmin = 2.1° |
Graphite monochromator | h = −9→9 |
θ/2θ scans | k = 0→12 |
3169 measured reflections | l = −12→13 |
3169 independent reflections | 3 standard reflections every 120 min |
1794 reflections with I > 2σ(I) | intensity decay: no decay, variation 1.0% |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
3169 reflections | Δρmax = 0.17 e Å−3 |
206 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (4) |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 0.4190 (0.0052) x + 8.5094 (0.0045) y - 4.1027 (0.0083) z = 0.7116 (0.0023) * -0.0038 (0.0018) C11 * 0.0001 (0.0016) C12 * -0.0013 (0.0015) C13 * 0.0031 (0.0017) C14 * -0.0004 (0.0016) C15 * -0.0008 (0.0017) C16 * 0.0031 (0.0013) C1 0.0698 (0.0028) O1 - 0.0319 (0.0030) O2 - 0.0187 (0.0031) O3 Rms deviation of fitted atoms = 0.0023 - 0.3482 (0.0096) x + 8.2795 (0.0063) y - 4.5396 (0.0102) z = 0.6108 (0.0065) Angle to previous plane (with approximate e.s.d.) = 2.7 (1) * -0.0071 (0.0018) C1 * 0.0020 (0.0005) C11 * 0.0026 (0.0007) O1 * 0.0026 (0.0007) O2 Rms deviation of fitted atoms = 0.0041 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.47787 (18) | 0.26972 (16) | 0.32017 (15) | 0.0462 (4) | |
O2 | 0.63698 (19) | 0.18684 (19) | 0.15680 (17) | 0.0612 (5) | |
O3 | −0.11098 (18) | 0.20664 (17) | 0.27105 (16) | 0.0510 (5) | |
C1 | 0.4970 (3) | 0.2153 (2) | 0.2215 (2) | 0.0393 (6) | |
C11 | 0.3430 (2) | 0.18478 (19) | 0.1757 (2) | 0.0311 (5) | |
C12 | 0.1828 (2) | 0.2100 (2) | 0.2434 (2) | 0.0351 (5) | |
C13 | 0.0424 (2) | 0.1816 (2) | 0.1993 (2) | 0.0347 (5) | |
C14 | 0.0622 (3) | 0.1292 (2) | 0.0874 (2) | 0.0395 (6) | |
C15 | 0.2219 (3) | 0.1042 (2) | 0.0201 (2) | 0.0443 (6) | |
C16 | 0.3614 (3) | 0.1321 (2) | 0.0638 (2) | 0.0378 (5) | |
N1 | 0.6562 (2) | 0.48140 (17) | 0.32951 (15) | 0.0352 (4) | |
C2 | 0.8148 (3) | 0.4710 (2) | 0.3854 (2) | 0.0396 (5) | |
C3 | 0.8140 (3) | 0.3725 (2) | 0.5072 (2) | 0.0435 (6) | |
N4 | 0.6864 (2) | 0.42249 (17) | 0.60766 (16) | 0.0360 (4) | |
C5 | 0.6756 (3) | 0.3322 (2) | 0.7330 (2) | 0.0421 (6) | |
C51 | 0.6327 (3) | 0.1976 (2) | 0.7142 (3) | 0.0623 (8) | |
C52 | 0.8402 (3) | 0.3113 (3) | 0.7913 (3) | 0.0723 (9) | |
C6 | 0.5360 (3) | 0.4017 (2) | 0.8239 (2) | 0.0422 (6) | |
C7 | 0.3546 (3) | 0.4242 (2) | 0.7943 (2) | 0.0396 (5) | |
C71 | 0.2298 (3) | 0.4802 (3) | 0.9007 (2) | 0.0558 (7) | |
O4 | 0.2704 (3) | 0.22339 (19) | 0.54747 (19) | 0.0720 (6) | |
C41 | 0.2467 (5) | 0.0892 (3) | 0.5848 (3) | 0.1010 (12) | |
H3 | −0.1862 | 0.1979 | 0.2317 | 0.077* | |
H12 | 0.1693 | 0.2459 | 0.3185 | 0.042* | |
H14 | −0.0316 | 0.1107 | 0.0574 | 0.047* | |
H15 | 0.2353 | 0.0684 | −0.0550 | 0.053* | |
H16 | 0.4684 | 0.1154 | 0.0178 | 0.045* | |
H1E | 0.5684 | 0.5085 | 0.3865 | 0.042* | |
H1A | 0.6442 | 0.3987 | 0.3170 | 0.042* | |
H2A | 0.8275 | 0.5589 | 0.4021 | 0.048* | |
H2B | 0.9108 | 0.4421 | 0.3249 | 0.048* | |
H3A | 0.7901 | 0.2870 | 0.4923 | 0.052* | |
H3B | 0.9251 | 0.3577 | 0.5347 | 0.052* | |
H4A | 0.7090 | 0.5025 | 0.6194 | 0.043* | |
H51A | 0.5398 | 0.2132 | 0.6655 | 0.093* | |
H51B | 0.6016 | 0.1458 | 0.7956 | 0.093* | |
H51C | 0.7297 | 0.1490 | 0.6697 | 0.093* | |
H52A | 0.9307 | 0.2682 | 0.7364 | 0.108* | |
H52B | 0.8270 | 0.2557 | 0.8730 | 0.108* | |
H52C | 0.8665 | 0.3970 | 0.8011 | 0.108* | |
H6A | 0.5378 | 0.3489 | 0.9080 | 0.051* | |
H6B | 0.5659 | 0.4887 | 0.8284 | 0.051* | |
H7 | 0.3250 | 0.3377 | 0.7844 | 0.048* | |
H71A | 0.2598 | 0.5635 | 0.9136 | 0.084* | |
H71B | 0.2337 | 0.4166 | 0.9778 | 0.084* | |
H71C | 0.1174 | 0.4957 | 0.8778 | 0.084* | |
H4 | 0.3396 | 0.2301 | 0.4829 | 0.108* | |
H41A | 0.3545 | 0.0327 | 0.5786 | 0.151* | |
H41B | 0.1770 | 0.0656 | 0.5303 | 0.151* | |
H41C | 0.1921 | 0.0768 | 0.6711 | 0.151* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0362 (9) | 0.0569 (10) | 0.0531 (11) | −0.0154 (7) | −0.0104 (8) | −0.0164 (9) |
O2 | 0.0249 (9) | 0.0955 (14) | 0.0706 (13) | −0.0115 (8) | −0.0062 (8) | −0.0302 (10) |
O3 | 0.0263 (8) | 0.0711 (12) | 0.0627 (11) | −0.0086 (8) | −0.0046 (8) | −0.0288 (9) |
C1 | 0.0284 (13) | 0.0390 (13) | 0.0520 (16) | −0.0068 (10) | −0.0113 (11) | −0.0041 (11) |
C11 | 0.0256 (11) | 0.0287 (11) | 0.0395 (13) | −0.0045 (8) | −0.0091 (9) | −0.0020 (9) |
C12 | 0.0292 (11) | 0.0397 (13) | 0.0394 (13) | −0.0055 (9) | −0.0084 (10) | −0.0102 (10) |
C13 | 0.0225 (11) | 0.0368 (12) | 0.0458 (14) | −0.0028 (9) | −0.0080 (10) | −0.0077 (10) |
C14 | 0.0326 (13) | 0.0447 (14) | 0.0477 (15) | −0.0094 (10) | −0.0136 (11) | −0.0136 (11) |
C15 | 0.0432 (14) | 0.0513 (15) | 0.0428 (14) | −0.0104 (11) | −0.0032 (11) | −0.0184 (11) |
C16 | 0.0302 (12) | 0.0407 (13) | 0.0431 (14) | −0.0069 (9) | −0.0017 (10) | −0.0097 (11) |
N1 | 0.0352 (10) | 0.0400 (10) | 0.0314 (10) | −0.0076 (8) | −0.0043 (8) | −0.0068 (8) |
C2 | 0.0327 (12) | 0.0505 (14) | 0.0383 (13) | −0.0092 (10) | −0.0050 (10) | −0.0109 (11) |
C3 | 0.0369 (13) | 0.0547 (15) | 0.0376 (14) | 0.0018 (11) | −0.0092 (10) | −0.0077 (11) |
N4 | 0.0402 (10) | 0.0381 (11) | 0.0302 (10) | −0.0052 (8) | −0.0068 (8) | −0.0058 (8) |
C5 | 0.0438 (13) | 0.0458 (14) | 0.0357 (13) | −0.0040 (11) | −0.0112 (11) | −0.0004 (11) |
C51 | 0.0751 (19) | 0.0445 (16) | 0.0588 (18) | −0.0035 (13) | 0.0026 (15) | −0.0007 (13) |
C52 | 0.0541 (17) | 0.109 (3) | 0.0469 (17) | 0.0013 (16) | −0.0197 (14) | 0.0063 (16) |
C6 | 0.0519 (15) | 0.0468 (14) | 0.0280 (12) | −0.0097 (11) | −0.0115 (11) | 0.0020 (10) |
C7 | 0.0461 (13) | 0.0395 (13) | 0.0323 (13) | −0.0094 (10) | −0.0036 (10) | −0.0011 (10) |
C71 | 0.0574 (16) | 0.0660 (17) | 0.0369 (14) | −0.0035 (13) | 0.0032 (12) | −0.0028 (12) |
O4 | 0.0839 (15) | 0.0652 (13) | 0.0659 (14) | −0.0070 (10) | −0.0030 (11) | −0.0179 (10) |
C41 | 0.124 (3) | 0.074 (2) | 0.098 (3) | −0.016 (2) | −0.002 (2) | −0.004 (2) |
O1—C1 | 1.261 (3) | N1—C7i | 1.506 (3) |
O2—C1 | 1.248 (3) | C2—C3 | 1.505 (3) |
O3—C13 | 1.361 (2) | C3—N4 | 1.468 (3) |
C1—C11 | 1.508 (3) | N4—C5 | 1.493 (3) |
C11—C16 | 1.382 (3) | C5—C51 | 1.526 (3) |
C11—C12 | 1.387 (3) | C5—C52 | 1.529 (3) |
C12—C13 | 1.389 (3) | C5—C6 | 1.535 (3) |
C13—C14 | 1.379 (3) | C6—C7 | 1.522 (3) |
C14—C15 | 1.381 (3) | C7—N1i | 1.506 (3) |
C15—C16 | 1.379 (3) | C7—C71 | 1.525 (3) |
N1—C2 | 1.482 (2) | O4—C41 | 1.392 (3) |
O2—C1—O1 | 123.9 (2) | N1—C2—C3 | 111.30 (17) |
O2—C1—C11 | 117.1 (2) | N4—C3—C2 | 111.17 (18) |
O1—C1—C11 | 119.00 (19) | C3—N4—C5 | 115.45 (16) |
C16—C11—C12 | 119.40 (18) | N4—C5—C51 | 108.61 (18) |
C16—C11—C1 | 119.50 (18) | N4—C5—C52 | 111.95 (19) |
C12—C11—C1 | 121.09 (19) | C51—C5—C52 | 110.5 (2) |
C11—C12—C13 | 120.2 (2) | N4—C5—C6 | 107.40 (17) |
O3—C13—C14 | 122.77 (18) | C51—C5—C6 | 111.06 (18) |
O3—C13—C12 | 117.34 (19) | C52—C5—C6 | 107.30 (19) |
C14—C13—C12 | 119.89 (19) | C7—C6—C5 | 118.41 (18) |
C13—C14—C15 | 119.9 (2) | N1i—C7—C6 | 108.95 (17) |
C16—C15—C14 | 120.3 (2) | N1i—C7—C71 | 110.52 (18) |
C15—C16—C11 | 120.3 (2) | C6—C7—C71 | 111.69 (19) |
C2—N1—C7i | 115.56 (16) | ||
O2—C1—C11—C16 | −2.2 (3) | C1—C11—C16—C15 | −179.7 (2) |
O1—C1—C11—C16 | 176.4 (2) | C7i—N1—C2—C3 | −178.95 (18) |
O2—C1—C11—C12 | 178.4 (2) | N1—C2—C3—N4 | −67.5 (2) |
O1—C1—C11—C12 | −3.0 (3) | C2—C3—N4—C5 | −179.80 (17) |
C16—C11—C12—C13 | 0.4 (3) | C3—N4—C5—C51 | −59.7 (2) |
C1—C11—C12—C13 | 179.76 (19) | C3—N4—C5—C52 | 62.6 (3) |
C11—C12—C13—O3 | 178.98 (19) | C3—N4—C5—C6 | −179.86 (17) |
C11—C12—C13—C14 | −0.5 (3) | N4—C5—C6—C7 | 64.5 (2) |
O3—C13—C14—C15 | −179.0 (2) | C51—C5—C6—C7 | −54.2 (3) |
C12—C13—C14—C15 | 0.5 (3) | C52—C5—C6—C7 | −175.0 (2) |
C13—C14—C15—C16 | −0.4 (3) | C5—C6—C7—N1i | −63.8 (2) |
C14—C15—C16—C11 | 0.3 (3) | C5—C6—C7—C71 | 173.87 (19) |
C12—C11—C16—C15 | −0.3 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.90 | 2.03 | 2.815 (2) | 145 |
N1—H1A···O3ii | 0.90 | 2.59 | 3.202 (2) | 126 |
N1—H1E···N4i | 0.90 | 2.06 | 2.793 (2) | 138 |
O3—H3···O2iii | 0.82 | 1.78 | 2.596 (2) | 175 |
O4—H4···O1 | 0.82 | 1.94 | 2.752 (3) | 171 |
C2—H2A···O4i | 0.97 | 2.36 | 3.260 (3) | 155 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z. |
C16H38N42+·2(C7H5O3−)·CH4O | F(000) = 644 |
Mr = 592.77 | #all measured reflections were used in the cell-dimension refinement |
Triclinic, P1 | Dx = 1.216 Mg m−3 |
a = 9.4481 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8905 (6) Å | Cell parameters from 18522 reflections |
c = 18.0942 (12) Å | θ = 4.2–26.4° |
α = 88.704 (5)° | µ = 0.09 mm−1 |
β = 78.675 (4)° | T = 100 K |
γ = 77.525 (4)° | Block, colourless |
V = 1618.43 (19) Å3 | 0.35 × 0.20 × 0.20 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 2949 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.091 |
Graphite monochromator | θmax = 26.4°, θmin = 4.2° |
ω scans | h = 0→11 |
18522 measured reflections | k = −11→12 |
6587 independent reflections | l = −22→22 |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0462P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.84 | (Δ/σ)max = 0.001 |
6587 reflections | Δρmax = 0.24 e Å−3 |
394 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0048 (11) |
Experimental. All measured reflections were used in the refinement to determine the cell data. Measurements made at the start and end of the data collection showed that there was no measurable crystal decay at 100 K. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N11 | 0.0581 (2) | 1.14634 (18) | 0.05413 (12) | 0.0282 (5) | |
C12 | −0.0809 (3) | 1.2146 (2) | 0.10162 (15) | 0.0323 (7) | |
C13 | −0.1717 (3) | 1.1116 (2) | 0.13351 (14) | 0.0314 (7) | |
N14 | −0.1966 (2) | 1.02788 (18) | 0.07178 (11) | 0.0273 (5) | |
C15 | −0.2930 (3) | 0.9248 (2) | 0.09334 (15) | 0.0300 (6) | |
C151 | −0.4463 (3) | 1.0006 (3) | 0.13263 (16) | 0.0389 (7) | |
C152 | −0.2226 (5) | 0.8143 (4) | 0.1439 (2) | 0.0301 (13) | 0.584 (5) |
C16 | −0.3022 (3) | 0.8537 (2) | 0.02107 (15) | 0.0323 (7) | |
C17 | −0.1611 (3) | 0.7632 (2) | −0.02441 (16) | 0.0337 (7) | |
C171 | −0.2027 (3) | 0.6843 (3) | −0.08635 (17) | 0.0464 (8) | |
C172 | −0.0866 (7) | 0.6546 (6) | 0.0335 (4) | 0.050 (2) | 0.416 (5) |
N21 | 0.5580 (2) | 0.35942 (19) | 0.57514 (12) | 0.0305 (5) | |
C22 | 0.7120 (3) | 0.3734 (2) | 0.57168 (15) | 0.0296 (6) | |
C23 | 0.7908 (3) | 0.3797 (2) | 0.49110 (15) | 0.0317 (7) | |
N24 | 0.7259 (2) | 0.51046 (18) | 0.45557 (11) | 0.0269 (5) | |
C25 | 0.7840 (3) | 0.5265 (2) | 0.37250 (14) | 0.0288 (6) | |
C251 | 0.9407 (3) | 0.5502 (3) | 0.36330 (16) | 0.0384 (7) | |
C252 | 0.7816 (3) | 0.3989 (2) | 0.32830 (15) | 0.0409 (7) | |
C26 | 0.6832 (3) | 0.6570 (2) | 0.34857 (15) | 0.0326 (7) | |
C27 | 0.5235 (3) | 0.6509 (2) | 0.34705 (15) | 0.0316 (7) | |
C271 | 0.4531 (3) | 0.7739 (3) | 0.30435 (16) | 0.0429 (8) | |
O31 | 0.32303 (19) | 0.79367 (16) | 0.02026 (10) | 0.0366 (5) | |
O32 | 0.13097 (19) | 0.84985 (15) | 0.11570 (10) | 0.0322 (5) | |
O34 | 0.51690 (18) | 0.31050 (16) | 0.23799 (10) | 0.0323 (4) | |
C31 | 0.3188 (3) | 0.6491 (2) | 0.12526 (14) | 0.0247 (6) | |
C32 | 0.4594 (3) | 0.5722 (2) | 0.09665 (15) | 0.0286 (6) | |
C33 | 0.5239 (3) | 0.4601 (2) | 0.13438 (15) | 0.0302 (6) | |
C34 | 0.4475 (3) | 0.4208 (2) | 0.20190 (14) | 0.0252 (6) | |
C35 | 0.3058 (3) | 0.4930 (2) | 0.23037 (14) | 0.0286 (6) | |
C36 | 0.2424 (3) | 0.6055 (2) | 0.19213 (14) | 0.0284 (6) | |
C37 | 0.2528 (3) | 0.7722 (2) | 0.08461 (15) | 0.0287 (6) | |
O41 | 0.36644 (19) | 0.28621 (16) | 0.37491 (10) | 0.0328 (4) | |
O42 | 0.19257 (18) | 0.28052 (16) | 0.47672 (10) | 0.0352 (5) | |
O44 | 0.00216 (18) | −0.11098 (16) | 0.25975 (10) | 0.0332 (5) | |
C41 | 0.1857 (3) | 0.1533 (2) | 0.36872 (15) | 0.0273 (6) | |
C42 | 0.2264 (3) | 0.1330 (2) | 0.29082 (15) | 0.0301 (6) | |
C43 | 0.1656 (3) | 0.0463 (2) | 0.25408 (15) | 0.0315 (7) | |
C44 | 0.0645 (3) | −0.0235 (2) | 0.29374 (15) | 0.0267 (6) | |
C45 | 0.0227 (3) | −0.0061 (2) | 0.37097 (15) | 0.0317 (7) | |
C46 | 0.0836 (3) | 0.0838 (2) | 0.40718 (15) | 0.0304 (6) | |
C47 | 0.2520 (3) | 0.2466 (2) | 0.40966 (16) | 0.0287 (6) | |
O1 | 0.5917 (2) | 0.16624 (17) | 0.44604 (12) | 0.0456 (5) | |
C1 | 0.6208 (3) | 0.0293 (3) | 0.4182 (2) | 0.0585 (10) | |
H11A | 0.1045 | 1.0792 | 0.0809 | 0.034* | |
H12A | −0.1366 | 1.2814 | 0.0722 | 0.039* | |
H12B | −0.0607 | 1.2643 | 0.1426 | 0.039* | |
H13A | −0.1209 | 1.0508 | 0.1673 | 0.038* | |
H13B | −0.2661 | 1.1602 | 0.1622 | 0.038* | |
H14E | −0.1078 | 0.9816 | 0.0470 | 0.033* | |
H14A | −0.2366 | 1.0868 | 0.0391 | 0.033* | |
H15A | −0.4873 | 1.0691 | 0.0997 | 0.058* | |
H15B | −0.4393 | 1.0450 | 0.1780 | 0.058* | |
H15C | −0.5091 | 0.9356 | 0.1449 | 0.058* | |
H15D | −0.1264 | 0.7682 | 0.1177 | 0.045* | 0.584 (5) |
H15E | −0.2837 | 0.7479 | 0.1565 | 0.045* | 0.584 (5) |
H15F | −0.2138 | 0.8576 | 0.1893 | 0.045* | 0.584 (5) |
H16A | −0.3407 | 0.9251 | −0.0119 | 0.039* | |
H16B | −0.3746 | 0.7964 | 0.0341 | 0.039* | |
H17A | −0.1149 | 0.6268 | −0.1151 | 0.070* | |
H17B | −0.2496 | 0.7493 | −0.1190 | 0.070* | |
H17C | −0.2693 | 0.6275 | −0.0636 | 0.070* | |
H17D | 0.0026 | 0.5964 | 0.0065 | 0.075* | 0.416 (5) |
H17E | −0.1546 | 0.5985 | 0.0553 | 0.075* | 0.416 (5) |
H17F | −0.0638 | 0.7051 | 0.0727 | 0.075* | 0.416 (5) |
H21A | 0.5591 | 0.2833 | 0.5485 | 0.037* | |
H22A | 0.7644 | 0.2950 | 0.5959 | 0.036* | |
H22B | 0.7116 | 0.4570 | 0.5988 | 0.036* | |
H23A | 0.8948 | 0.3753 | 0.4897 | 0.038* | |
H23B | 0.7826 | 0.3007 | 0.4627 | 0.038* | |
H24A | 0.7405 | 0.5822 | 0.4807 | 0.032* | |
H24E | 0.6276 | 0.5174 | 0.4623 | 0.032* | |
H25A | 0.9392 | 0.6316 | 0.3916 | 0.058* | |
H25B | 0.9792 | 0.5623 | 0.3110 | 0.058* | |
H25C | 1.0024 | 0.4716 | 0.3816 | 0.058* | |
H25D | 0.6820 | 0.3861 | 0.3352 | 0.061* | |
H25E | 0.8427 | 0.3192 | 0.3460 | 0.061* | |
H25F | 0.8186 | 0.4106 | 0.2758 | 0.061* | |
H26A | 0.6810 | 0.7325 | 0.3824 | 0.039* | |
H26B | 0.7289 | 0.6805 | 0.2985 | 0.039* | |
H27 | 0.5257 | 0.5663 | 0.3193 | 0.038* | |
H27A | 0.3530 | 0.7691 | 0.3035 | 0.064* | |
H27B | 0.5082 | 0.7713 | 0.2536 | 0.064* | |
H27C | 0.4537 | 0.8585 | 0.3291 | 0.064* | |
H34 | 0.4658 | 0.3028 | 0.2794 | 0.048* | |
H32 | 0.5115 | 0.5967 | 0.0510 | 0.034* | |
H33 | 0.6189 | 0.4107 | 0.1144 | 0.036* | |
H35 | 0.2529 | 0.4661 | 0.2751 | 0.034* | |
H36 | 0.1465 | 0.6532 | 0.2116 | 0.034* | |
H44 | 0.0478 | −0.1281 | 0.2164 | 0.050* | |
H42 | 0.2954 | 0.1786 | 0.2633 | 0.036* | |
H43 | 0.1931 | 0.0347 | 0.2020 | 0.038* | |
H45 | −0.0448 | −0.0533 | 0.3984 | 0.038* | |
H46 | 0.0541 | 0.0971 | 0.4591 | 0.036* | |
H1 | 0.5252 | 0.2139 | 0.4278 | 0.068* | |
H1A | 0.6820 | −0.0304 | 0.4475 | 0.088* | |
H1B | 0.6711 | 0.0250 | 0.3665 | 0.088* | |
H1C | 0.5294 | −0.0001 | 0.4217 | 0.088* | |
H15 | −0.2496 | 0.8560 | 0.1270 | 0.036* | 0.416 (5) |
H17 | −0.1154 | 0.6960 | 0.0093 | 0.040* | 0.584 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0255 (12) | 0.0263 (11) | 0.0328 (14) | −0.0053 (9) | −0.0061 (11) | −0.0016 (10) |
C12 | 0.0285 (15) | 0.0329 (14) | 0.0342 (18) | −0.0049 (12) | −0.0044 (13) | −0.0064 (13) |
C13 | 0.0312 (16) | 0.0324 (14) | 0.0284 (16) | −0.0023 (11) | −0.0048 (13) | −0.0042 (12) |
N14 | 0.0248 (12) | 0.0303 (11) | 0.0254 (13) | −0.0038 (9) | −0.0041 (10) | 0.0007 (10) |
C15 | 0.0252 (15) | 0.0324 (14) | 0.0333 (17) | −0.0083 (11) | −0.0062 (13) | 0.0067 (13) |
C151 | 0.0303 (16) | 0.0460 (16) | 0.0394 (19) | −0.0123 (13) | −0.0010 (14) | 0.0059 (14) |
C152 | 0.033 (3) | 0.039 (3) | 0.023 (3) | −0.017 (2) | −0.007 (2) | 0.003 (2) |
C16 | 0.0288 (15) | 0.0349 (14) | 0.0367 (18) | −0.0127 (11) | −0.0083 (14) | 0.0009 (13) |
C17 | 0.0296 (16) | 0.0324 (14) | 0.0408 (19) | −0.0110 (12) | −0.0053 (14) | −0.0037 (13) |
C171 | 0.0424 (18) | 0.0471 (17) | 0.054 (2) | −0.0208 (14) | −0.0059 (16) | −0.0112 (16) |
C172 | 0.043 (5) | 0.046 (4) | 0.059 (6) | −0.008 (3) | −0.007 (4) | 0.005 (4) |
N21 | 0.0298 (13) | 0.0329 (12) | 0.0300 (14) | −0.0093 (9) | −0.0061 (11) | 0.0005 (10) |
C22 | 0.0281 (15) | 0.0289 (13) | 0.0331 (17) | −0.0053 (11) | −0.0104 (14) | 0.0044 (12) |
C23 | 0.0284 (15) | 0.0285 (14) | 0.0368 (18) | −0.0033 (11) | −0.0063 (14) | 0.0018 (13) |
N24 | 0.0244 (12) | 0.0264 (11) | 0.0309 (14) | −0.0072 (9) | −0.0054 (11) | −0.0033 (10) |
C25 | 0.0311 (16) | 0.0312 (14) | 0.0240 (16) | −0.0102 (11) | −0.0014 (13) | −0.0018 (12) |
C251 | 0.0300 (16) | 0.0464 (16) | 0.0360 (19) | −0.0065 (12) | −0.0013 (14) | 0.0026 (14) |
C252 | 0.0492 (18) | 0.0369 (15) | 0.0356 (18) | −0.0064 (13) | −0.0084 (15) | −0.0057 (13) |
C26 | 0.0374 (17) | 0.0358 (14) | 0.0251 (16) | −0.0111 (12) | −0.0040 (14) | 0.0020 (12) |
C27 | 0.0345 (16) | 0.0340 (15) | 0.0276 (17) | −0.0094 (12) | −0.0078 (14) | 0.0059 (13) |
C271 | 0.0388 (18) | 0.0498 (17) | 0.042 (2) | −0.0106 (13) | −0.0122 (16) | 0.0167 (15) |
O31 | 0.0376 (11) | 0.0419 (11) | 0.0276 (12) | −0.0070 (8) | −0.0030 (10) | 0.0080 (9) |
O32 | 0.0345 (11) | 0.0306 (9) | 0.0289 (11) | −0.0013 (8) | −0.0069 (9) | 0.0018 (8) |
O34 | 0.0294 (10) | 0.0329 (9) | 0.0315 (12) | −0.0040 (8) | −0.0021 (9) | 0.0042 (9) |
C31 | 0.0292 (15) | 0.0231 (13) | 0.0231 (15) | −0.0078 (11) | −0.0055 (13) | −0.0013 (11) |
C32 | 0.0288 (15) | 0.0315 (14) | 0.0256 (16) | −0.0110 (11) | −0.0001 (13) | −0.0008 (12) |
C33 | 0.0253 (15) | 0.0298 (14) | 0.0325 (18) | −0.0043 (11) | −0.0002 (14) | 0.0010 (13) |
C34 | 0.0275 (15) | 0.0206 (13) | 0.0279 (16) | −0.0042 (11) | −0.0076 (13) | −0.0013 (12) |
C35 | 0.0289 (15) | 0.0339 (14) | 0.0224 (16) | −0.0090 (12) | −0.0010 (13) | 0.0023 (12) |
C36 | 0.0243 (15) | 0.0299 (14) | 0.0286 (17) | −0.0011 (11) | −0.0044 (13) | −0.0022 (13) |
C37 | 0.0319 (16) | 0.0312 (14) | 0.0261 (17) | −0.0103 (12) | −0.0093 (14) | 0.0004 (13) |
O41 | 0.0341 (11) | 0.0356 (10) | 0.0306 (12) | −0.0115 (8) | −0.0068 (10) | 0.0035 (8) |
O42 | 0.0379 (11) | 0.0407 (11) | 0.0270 (12) | −0.0120 (8) | −0.0014 (10) | −0.0078 (9) |
O44 | 0.0371 (11) | 0.0356 (10) | 0.0274 (12) | −0.0115 (8) | −0.0034 (9) | −0.0030 (9) |
C41 | 0.0267 (15) | 0.0258 (13) | 0.0283 (16) | −0.0031 (11) | −0.0057 (13) | 0.0006 (12) |
C42 | 0.0306 (15) | 0.0329 (14) | 0.0265 (16) | −0.0081 (11) | −0.0038 (13) | 0.0022 (12) |
C43 | 0.0347 (16) | 0.0363 (15) | 0.0233 (16) | −0.0079 (12) | −0.0052 (14) | 0.0005 (13) |
C44 | 0.0251 (15) | 0.0272 (13) | 0.0277 (17) | −0.0040 (11) | −0.0065 (13) | 0.0000 (12) |
C45 | 0.0308 (15) | 0.0338 (15) | 0.0310 (17) | −0.0118 (12) | −0.0018 (14) | 0.0001 (13) |
C46 | 0.0345 (16) | 0.0324 (14) | 0.0225 (16) | −0.0036 (12) | −0.0054 (13) | 0.0006 (12) |
C47 | 0.0289 (16) | 0.0248 (14) | 0.0311 (18) | −0.0012 (11) | −0.0083 (14) | 0.0039 (13) |
O1 | 0.0483 (14) | 0.0393 (11) | 0.0524 (14) | −0.0072 (9) | −0.0192 (11) | −0.0063 (10) |
C1 | 0.052 (2) | 0.0422 (17) | 0.079 (3) | −0.0040 (14) | −0.0126 (19) | −0.0084 (17) |
N11—C12 | 1.456 (3) | C27—C271 | 1.526 (3) |
N11—C17i | 1.479 (3) | O31—C37 | 1.260 (3) |
C12—C13 | 1.504 (3) | O32—C37 | 1.270 (3) |
C13—N14 | 1.489 (3) | O34—C34 | 1.369 (3) |
N14—C15 | 1.505 (3) | C31—C32 | 1.387 (3) |
C15—C151 | 1.522 (3) | C31—C36 | 1.392 (3) |
C15—C16 | 1.525 (3) | C31—C37 | 1.491 (3) |
C15—C152 | 1.535 (5) | C32—C33 | 1.380 (3) |
C16—C17 | 1.531 (3) | C33—C34 | 1.385 (3) |
C17—N11i | 1.479 (3) | C34—C35 | 1.379 (3) |
C17—C171 | 1.537 (3) | C35—C36 | 1.384 (3) |
C17—C172 | 1.631 (7) | O41—C47 | 1.274 (3) |
N21—C27ii | 1.479 (3) | O42—C47 | 1.253 (3) |
N21—C22 | 1.480 (3) | O44—C44 | 1.364 (3) |
C22—C23 | 1.508 (3) | C41—C46 | 1.374 (3) |
C23—N24 | 1.495 (3) | C41—C42 | 1.393 (3) |
N24—C25 | 1.513 (3) | C41—C47 | 1.502 (3) |
C25—C252 | 1.516 (3) | C42—C43 | 1.377 (3) |
C25—C251 | 1.525 (3) | C43—C44 | 1.377 (3) |
C25—C26 | 1.538 (3) | C44—C45 | 1.380 (3) |
C26—C27 | 1.529 (3) | C45—C46 | 1.395 (3) |
C27—N21ii | 1.479 (3) | O1—C1 | 1.407 (3) |
C12—N11—C17i | 115.79 (18) | N21ii—C27—C26 | 109.6 (2) |
N11—C12—C13 | 111.26 (19) | C271—C27—C26 | 110.0 (2) |
N14—C13—C12 | 110.4 (2) | C32—C31—C36 | 117.4 (2) |
C13—N14—C15 | 117.6 (2) | C32—C31—C37 | 120.6 (2) |
N14—C15—C151 | 109.23 (18) | C36—C31—C37 | 122.0 (2) |
N14—C15—C16 | 107.6 (2) | C33—C32—C31 | 121.5 (3) |
C151—C15—C16 | 110.1 (2) | C32—C33—C34 | 120.1 (2) |
N14—C15—C152 | 110.0 (2) | O34—C34—C35 | 122.4 (2) |
C151—C15—C152 | 111.4 (3) | O34—C34—C33 | 118.1 (2) |
C16—C15—C152 | 108.3 (2) | C35—C34—C33 | 119.5 (2) |
C15—C16—C17 | 118.5 (2) | C34—C35—C36 | 119.8 (3) |
N11i—C17—C16 | 108.15 (18) | C35—C36—C31 | 121.6 (2) |
N11i—C17—C171 | 113.4 (2) | O31—C37—O32 | 123.3 (2) |
C16—C17—C171 | 108.7 (2) | O31—C37—C31 | 117.2 (2) |
N11i—C17—C172 | 108.6 (3) | O32—C37—C31 | 119.5 (2) |
C16—C17—C172 | 107.5 (3) | C46—C41—C42 | 117.7 (2) |
C171—C17—C172 | 110.2 (3) | C46—C41—C47 | 120.9 (2) |
C27ii—N21—C22 | 113.2 (2) | C42—C41—C47 | 121.4 (2) |
N21—C22—C23 | 110.9 (2) | C43—C42—C41 | 120.7 (3) |
N24—C23—C22 | 110.77 (19) | C44—C43—C42 | 120.6 (2) |
C23—N24—C25 | 117.16 (18) | O44—C44—C43 | 122.6 (2) |
N24—C25—C252 | 110.4 (2) | O44—C44—C45 | 117.5 (2) |
N24—C25—C251 | 108.0 (2) | C43—C44—C45 | 119.9 (2) |
C252—C25—C251 | 111.1 (2) | C44—C45—C46 | 118.7 (2) |
N24—C25—C26 | 106.02 (18) | C41—C46—C45 | 122.2 (2) |
C252—C25—C26 | 111.8 (2) | O42—C47—O41 | 123.2 (2) |
C251—C25—C26 | 109.2 (2) | O42—C47—C41 | 118.2 (2) |
C27—C26—C25 | 117.8 (2) | O41—C47—C41 | 118.6 (2) |
N21ii—C27—C271 | 113.9 (2) | ||
C17i—N11—C12—C13 | −175.6 (2) | C32—C33—C34—O34 | −178.9 (2) |
N11—C12—C13—N14 | −55.6 (3) | C32—C33—C34—C35 | 1.2 (3) |
C12—C13—N14—C15 | −176.63 (19) | O34—C34—C35—C36 | 178.7 (2) |
C13—N14—C15—C151 | 60.0 (3) | C33—C34—C35—C36 | −1.4 (3) |
C13—N14—C15—C16 | 179.62 (18) | C34—C35—C36—C31 | −0.4 (3) |
C13—N14—C15—C152 | −62.5 (3) | C32—C31—C36—C35 | 2.3 (3) |
N14—C15—C16—C17 | 65.1 (3) | C37—C31—C36—C35 | −178.5 (2) |
C151—C15—C16—C17 | −175.9 (2) | C32—C31—C37—O31 | 7.4 (3) |
C152—C15—C16—C17 | −53.9 (3) | C36—C31—C37—O31 | −171.8 (2) |
C15—C16—C17—N11i | −65.9 (3) | C32—C31—C37—O32 | −172.4 (2) |
C15—C16—C17—C171 | 170.6 (2) | C36—C31—C37—O32 | 8.5 (3) |
C15—C16—C17—C172 | 51.2 (4) | C46—C41—C42—C43 | 0.1 (3) |
C27ii—N21—C22—C23 | 178.51 (19) | C47—C41—C42—C43 | 179.5 (2) |
N21—C22—C23—N24 | 67.4 (2) | C41—C42—C43—C44 | −0.7 (3) |
C22—C23—N24—C25 | −174.68 (19) | C42—C43—C44—O44 | −179.6 (2) |
C23—N24—C25—C252 | 50.2 (3) | C42—C43—C44—C45 | 0.4 (4) |
C23—N24—C25—C251 | −71.5 (2) | O44—C44—C45—C46 | −179.44 (19) |
C23—N24—C25—C26 | 171.52 (18) | C43—C44—C45—C46 | 0.6 (3) |
N24—C25—C26—C27 | −68.9 (3) | C42—C41—C46—C45 | 0.9 (4) |
C252—C25—C26—C27 | 51.5 (3) | C47—C41—C46—C45 | −178.5 (2) |
C251—C25—C26—C27 | 174.9 (2) | C44—C45—C46—C41 | −1.3 (4) |
C25—C26—C27—N21ii | 67.9 (3) | C46—C41—C47—O42 | −13.4 (3) |
C25—C26—C27—C271 | −166.2 (2) | C42—C41—C47—O42 | 167.2 (2) |
C36—C31—C32—C33 | −2.5 (3) | C46—C41—C47—O41 | 165.9 (2) |
C37—C31—C32—C33 | 178.3 (2) | C42—C41—C47—O41 | −13.5 (3) |
C31—C32—C33—C34 | 0.8 (3) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O41 | 0.82 | 1.94 | 2.740 (3) | 167 |
N11—H11A···O32 | 0.90 | 2.31 | 3.098 (2) | 145 |
N14—H14A···O31i | 0.90 | 1.76 | 2.656 (3) | 177 |
N14—H14E···N11 | 0.90 | 2.51 | 2.857 (3) | 103 |
N14—H14E···N11i | 0.90 | 2.16 | 2.811 (3) | 128 |
N21—H21A···O1 | 0.90 | 2.14 | 2.976 (3) | 154 |
N24—H24A···O42ii | 0.90 | 1.86 | 2.746 (2) | 169 |
N24—H24E···N21 | 0.90 | 2.61 | 2.993 (3) | 107 |
N24—H24E···N21ii | 0.90 | 2.13 | 2.867 (3) | 139 |
O34—H34···O41 | 0.82 | 1.82 | 2.637 (3) | 175 |
O44—H44···O32iii | 0.82 | 1.83 | 2.650 (3) | 173 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z. |
C16H40N44+·4(C6H6O3P−)·2(H2O) | #all measured reflections were used in the cell-dimension refinement |
Mr = 952.86 | Dx = 1.344 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7391 (2) Å | Cell parameters from 22140 reflections |
b = 26.1558 (7) Å | θ = 4.1–26.4° |
c = 10.7871 (2) Å | µ = 0.23 mm−1 |
β = 107.267 (13)° | T = 100 K |
V = 2354.57 (9) Å3 | Block, colourless |
Z = 2 | 0.30 × 0.25 × 0.15 mm |
F(000) = 1016 |
Nonius KappaCCD diffractometer | 3777 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.065 |
Graphite monochromator | θmax = 26.4°, θmin = 4.1° |
ω scans | h = −10→10 |
22140 measured reflections | k = −32→32 |
4796 independent reflections | l = −13→12 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.036P)2 + 1.8098P] where P = (Fo2 + 2Fc2)/3 |
4796 reflections | (Δ/σ)max = 0.001 |
293 parameters | Δρmax = 0.30 e Å−3 |
2 restraints | Δρmin = −0.50 e Å−3 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.22188 (19) | 0.45794 (6) | 0.39406 (15) | 0.0168 (4) | |
C2 | 0.2388 (2) | 0.46753 (8) | 0.26172 (18) | 0.0192 (4) | |
C3 | 0.3886 (2) | 0.49741 (8) | 0.26343 (19) | 0.0186 (4) | |
N4 | 0.36879 (18) | 0.55320 (6) | 0.28357 (16) | 0.0161 (3) | |
C5 | 0.5034 (2) | 0.58926 (8) | 0.27940 (19) | 0.0187 (4) | |
C51 | 0.4413 (3) | 0.64264 (8) | 0.2964 (2) | 0.0242 (5) | |
C52 | 0.5293 (3) | 0.58504 (9) | 0.1455 (2) | 0.0254 (5) | |
C6 | 0.6615 (2) | 0.57577 (8) | 0.38366 (18) | 0.0184 (4) | |
C7 | 0.6654 (2) | 0.58190 (8) | 0.52680 (19) | 0.0174 (4) | |
C71 | 0.7214 (3) | 0.63440 (8) | 0.5836 (2) | 0.0220 (4) | |
P1 | 0.17496 (6) | 0.58371 (2) | 0.56751 (5) | 0.01579 (13) | |
O11 | 0.03695 (16) | 0.61071 (6) | 0.46200 (13) | 0.0212 (3) | |
O12 | 0.27633 (15) | 0.55078 (5) | 0.50622 (13) | 0.0176 (3) | |
O13 | 0.10300 (16) | 0.55628 (6) | 0.65931 (13) | 0.0200 (3) | |
C11 | 0.3037 (2) | 0.63435 (8) | 0.65256 (19) | 0.0176 (4) | |
C12 | 0.3067 (2) | 0.68168 (8) | 0.5937 (2) | 0.0225 (4) | |
C13 | 0.4092 (3) | 0.72019 (9) | 0.6575 (2) | 0.0284 (5) | |
C14 | 0.5116 (3) | 0.71150 (9) | 0.7808 (2) | 0.0307 (5) | |
C15 | 0.5113 (3) | 0.66464 (9) | 0.8408 (2) | 0.0276 (5) | |
C16 | 0.4071 (2) | 0.62632 (8) | 0.7779 (2) | 0.0221 (4) | |
P2 | −0.00716 (6) | 0.60642 (2) | 0.09060 (5) | 0.01818 (13) | |
O21 | −0.17523 (16) | 0.58084 (6) | 0.02509 (14) | 0.0232 (3) | |
O22 | 0.12444 (16) | 0.57146 (6) | 0.07621 (13) | 0.0214 (3) | |
O23 | 0.0103 (2) | 0.62282 (6) | 0.22699 (14) | 0.0297 (4) | |
C21 | −0.0122 (2) | 0.66266 (8) | −0.00639 (19) | 0.0191 (4) | |
C22 | 0.0615 (3) | 0.66309 (9) | −0.1044 (2) | 0.0261 (5) | |
C23 | 0.0650 (3) | 0.70769 (9) | −0.1743 (2) | 0.0303 (5) | |
C24 | −0.0030 (3) | 0.75197 (9) | −0.1455 (2) | 0.0280 (5) | |
C25 | −0.0777 (3) | 0.75181 (9) | −0.0495 (2) | 0.0280 (5) | |
C26 | −0.0834 (3) | 0.70746 (8) | 0.0195 (2) | 0.0236 (5) | |
O1 | −0.20958 (19) | 0.48739 (6) | 0.09896 (14) | 0.0248 (3) | |
H1A | 0.1183 | 0.4478 | 0.3849 | 0.020* | |
H1B | 0.2387 | 0.4882 | 0.4395 | 0.020* | |
H2A | 0.1437 | 0.4866 | 0.2095 | 0.023* | |
H2B | 0.2408 | 0.4343 | 0.2184 | 0.023* | |
H3A | 0.4806 | 0.4843 | 0.3339 | 0.022* | |
H3B | 0.4124 | 0.4922 | 0.1801 | 0.022* | |
H4A | 0.3511 | 0.5571 | 0.3630 | 0.019* | |
H4B | 0.2774 | 0.5639 | 0.2216 | 0.019* | |
H51A | 0.3468 | 0.6503 | 0.2230 | 0.036* | |
H51B | 0.5251 | 0.6680 | 0.2997 | 0.036* | |
H51C | 0.4122 | 0.6439 | 0.3773 | 0.036* | |
H52A | 0.5684 | 0.5507 | 0.1347 | 0.038* | |
H52B | 0.6084 | 0.6105 | 0.1381 | 0.038* | |
H52C | 0.4277 | 0.5912 | 0.0781 | 0.038* | |
H6A | 0.7474 | 0.5974 | 0.3689 | 0.022* | |
H6B | 0.6882 | 0.5398 | 0.3702 | 0.022* | |
H7 | 0.5554 | 0.5755 | 0.5338 | 0.021* | |
H71A | 0.7203 | 0.6356 | 0.6742 | 0.033* | |
H71B | 0.6494 | 0.6607 | 0.5334 | 0.033* | |
H71C | 0.8305 | 0.6406 | 0.5798 | 0.033* | |
H11 | 0.0545 | 0.6086 | 0.3897 | 0.032* | |
H12 | 0.2374 | 0.6876 | 0.5087 | 0.027* | |
H13 | 0.4092 | 0.7524 | 0.6167 | 0.034* | |
H14 | 0.5823 | 0.7377 | 0.8245 | 0.037* | |
H15 | 0.5825 | 0.6587 | 0.9251 | 0.033* | |
H16 | 0.4060 | 0.5945 | 0.8200 | 0.026* | |
H21 | −0.1752 | 0.5509 | 0.0532 | 0.035* | |
H22 | 0.1097 | 0.6328 | −0.1239 | 0.031* | |
H23 | 0.1143 | 0.7076 | −0.2418 | 0.036* | |
H24 | 0.0016 | 0.7826 | −0.1918 | 0.034* | |
H25 | −0.1255 | 0.7823 | −0.0304 | 0.034* | |
H26 | −0.1362 | 0.7076 | 0.0848 | 0.028* | |
H1C | −0.172 (3) | 0.4660 (11) | 0.049 (3) | 0.056 (6)* | |
H1D | −0.174 (4) | 0.4737 (11) | 0.180 (2) | 0.056 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0144 (8) | 0.0171 (9) | 0.0193 (8) | −0.0002 (7) | 0.0059 (7) | 0.0008 (6) |
C2 | 0.0195 (10) | 0.0214 (11) | 0.0164 (9) | 0.0011 (8) | 0.0050 (8) | 0.0015 (8) |
C3 | 0.0196 (10) | 0.0189 (11) | 0.0186 (10) | 0.0024 (8) | 0.0080 (8) | 0.0014 (8) |
N4 | 0.0129 (8) | 0.0190 (9) | 0.0169 (8) | 0.0006 (7) | 0.0053 (6) | 0.0022 (7) |
C5 | 0.0167 (9) | 0.0203 (11) | 0.0193 (10) | −0.0014 (8) | 0.0057 (8) | 0.0039 (8) |
C51 | 0.0203 (10) | 0.0219 (11) | 0.0283 (11) | 0.0009 (9) | 0.0040 (9) | 0.0052 (9) |
C52 | 0.0214 (10) | 0.0351 (13) | 0.0217 (11) | −0.0016 (9) | 0.0096 (9) | 0.0068 (9) |
C6 | 0.0141 (9) | 0.0221 (11) | 0.0197 (10) | 0.0009 (8) | 0.0062 (8) | 0.0017 (8) |
C7 | 0.0141 (9) | 0.0185 (10) | 0.0195 (10) | 0.0009 (8) | 0.0047 (8) | 0.0022 (8) |
C71 | 0.0230 (11) | 0.0187 (11) | 0.0249 (11) | −0.0010 (8) | 0.0083 (9) | 0.0011 (8) |
P1 | 0.0134 (2) | 0.0193 (3) | 0.0151 (2) | 0.0001 (2) | 0.00502 (19) | 0.00021 (19) |
O11 | 0.0161 (7) | 0.0328 (9) | 0.0150 (7) | 0.0046 (6) | 0.0053 (6) | 0.0021 (6) |
O12 | 0.0165 (7) | 0.0186 (7) | 0.0194 (7) | 0.0003 (6) | 0.0080 (5) | −0.0007 (5) |
O13 | 0.0171 (7) | 0.0265 (8) | 0.0174 (7) | −0.0013 (6) | 0.0069 (5) | 0.0020 (6) |
C11 | 0.0150 (9) | 0.0208 (11) | 0.0185 (10) | 0.0010 (8) | 0.0074 (8) | −0.0021 (8) |
C12 | 0.0225 (10) | 0.0217 (11) | 0.0236 (11) | 0.0025 (9) | 0.0073 (9) | 0.0022 (8) |
C13 | 0.0289 (12) | 0.0202 (12) | 0.0362 (13) | −0.0019 (9) | 0.0097 (10) | 0.0005 (9) |
C14 | 0.0285 (12) | 0.0240 (12) | 0.0367 (13) | −0.0062 (10) | 0.0055 (10) | −0.0061 (10) |
C15 | 0.0238 (11) | 0.0311 (13) | 0.0242 (11) | −0.0031 (9) | 0.0015 (9) | −0.0027 (9) |
C16 | 0.0225 (11) | 0.0226 (11) | 0.0211 (10) | −0.0001 (9) | 0.0064 (8) | 0.0011 (8) |
P2 | 0.0186 (3) | 0.0210 (3) | 0.0147 (3) | 0.0024 (2) | 0.0045 (2) | 0.0014 (2) |
O21 | 0.0189 (7) | 0.0244 (8) | 0.0264 (8) | 0.0011 (6) | 0.0067 (6) | 0.0066 (6) |
O22 | 0.0185 (7) | 0.0238 (8) | 0.0208 (7) | 0.0048 (6) | 0.0044 (6) | 0.0022 (6) |
O23 | 0.0434 (10) | 0.0301 (9) | 0.0161 (7) | 0.0058 (7) | 0.0098 (7) | 0.0012 (6) |
C21 | 0.0172 (10) | 0.0218 (11) | 0.0164 (9) | −0.0005 (8) | 0.0021 (8) | 0.0005 (8) |
C22 | 0.0312 (12) | 0.0257 (12) | 0.0242 (11) | 0.0036 (10) | 0.0125 (9) | 0.0018 (9) |
C23 | 0.0389 (13) | 0.0298 (13) | 0.0261 (12) | −0.0004 (10) | 0.0156 (10) | 0.0039 (9) |
C24 | 0.0333 (13) | 0.0238 (12) | 0.0216 (11) | −0.0050 (10) | 0.0001 (9) | 0.0037 (9) |
C25 | 0.0315 (12) | 0.0197 (12) | 0.0293 (12) | 0.0026 (9) | 0.0035 (10) | −0.0023 (9) |
C26 | 0.0262 (11) | 0.0237 (12) | 0.0203 (10) | 0.0020 (9) | 0.0062 (9) | −0.0023 (8) |
O1 | 0.0313 (8) | 0.0227 (8) | 0.0209 (8) | 0.0037 (7) | 0.0085 (6) | 0.0017 (6) |
N1—C2 | 1.499 (2) | C11—C12 | 1.395 (3) |
N1—C7i | 1.512 (2) | C11—C16 | 1.401 (3) |
C2—C3 | 1.520 (3) | C12—C13 | 1.388 (3) |
C3—N4 | 1.493 (3) | C13—C14 | 1.384 (3) |
N4—C5 | 1.519 (2) | C14—C15 | 1.386 (3) |
C5—C51 | 1.529 (3) | C15—C16 | 1.388 (3) |
C5—C52 | 1.530 (3) | P2—O23 | 1.4962 (15) |
C5—C6 | 1.541 (3) | P2—O22 | 1.5129 (15) |
C6—C7 | 1.543 (3) | P2—O21 | 1.5774 (15) |
C7—N1i | 1.512 (2) | P2—C21 | 1.798 (2) |
C7—C71 | 1.524 (3) | C21—C22 | 1.392 (3) |
P1—O13 | 1.5036 (14) | C21—C26 | 1.393 (3) |
P1—O12 | 1.5204 (14) | C22—C23 | 1.394 (3) |
P1—O11 | 1.5601 (14) | C23—C24 | 1.378 (3) |
P1—C11 | 1.803 (2) | C24—C25 | 1.379 (3) |
O11—H11 | 0.8400 | C25—C26 | 1.387 (3) |
C2—N1—C7i | 114.90 (15) | C12—C11—P1 | 120.90 (15) |
N1—C2—C3 | 113.74 (16) | C16—C11—P1 | 120.48 (16) |
N4—C3—C2 | 111.57 (16) | C13—C12—C11 | 120.99 (19) |
C3—N4—C5 | 118.57 (15) | C14—C13—C12 | 119.7 (2) |
N4—C5—C51 | 104.93 (16) | C13—C14—C15 | 120.2 (2) |
N4—C5—C52 | 108.40 (16) | C14—C15—C16 | 120.1 (2) |
C51—C5—C52 | 109.65 (17) | C15—C16—C11 | 120.3 (2) |
N4—C5—C6 | 111.76 (15) | O23—P2—O22 | 114.55 (9) |
C51—C5—C6 | 113.27 (17) | O23—P2—O21 | 111.82 (9) |
C52—C5—C6 | 108.70 (16) | O22—P2—O21 | 109.44 (8) |
C5—C6—C7 | 117.06 (16) | O23—P2—C21 | 108.38 (9) |
N1i—C7—C71 | 108.43 (16) | O22—P2—C21 | 108.84 (9) |
N1i—C7—C6 | 108.08 (15) | O21—P2—C21 | 103.15 (9) |
C71—C7—C6 | 113.90 (17) | C22—C21—C26 | 118.7 (2) |
O13—P1—O12 | 115.31 (8) | C22—C21—P2 | 120.77 (16) |
O13—P1—O11 | 108.22 (8) | C26—C21—P2 | 120.47 (16) |
O12—P1—O11 | 111.30 (8) | C21—C22—C23 | 120.4 (2) |
O13—P1—C11 | 109.60 (9) | C24—C23—C22 | 120.1 (2) |
O12—P1—C11 | 106.34 (8) | C23—C24—C25 | 119.9 (2) |
O11—P1—C11 | 105.63 (9) | C24—C25—C26 | 120.4 (2) |
C12—C11—C16 | 118.58 (19) | C25—C26—C21 | 120.5 (2) |
C7i—N1—C2—C3 | −73.5 (2) | C12—C13—C14—C15 | −0.3 (4) |
N1—C2—C3—N4 | −78.4 (2) | C13—C14—C15—C16 | −0.6 (4) |
C2—C3—N4—C5 | −176.20 (15) | C14—C15—C16—C11 | 1.2 (3) |
C3—N4—C5—C51 | 177.24 (16) | C12—C11—C16—C15 | −0.8 (3) |
C3—N4—C5—C52 | 60.1 (2) | P1—C11—C16—C15 | 177.09 (16) |
C3—N4—C5—C6 | −59.6 (2) | O23—P2—C21—C22 | 142.68 (17) |
N4—C5—C6—C7 | −65.2 (2) | O22—P2—C21—C22 | 17.5 (2) |
C51—C5—C6—C7 | 53.1 (2) | O21—P2—C21—C22 | −98.64 (18) |
C52—C5—C6—C7 | 175.19 (17) | O23—P2—C21—C26 | −34.19 (19) |
C5—C6—C7—N1i | 148.43 (17) | O22—P2—C21—C26 | −159.35 (16) |
C5—C6—C7—C71 | −91.0 (2) | O21—P2—C21—C26 | 84.49 (18) |
O13—P1—C11—C12 | −139.96 (16) | C26—C21—C22—C23 | 0.6 (3) |
O12—P1—C11—C12 | 94.78 (17) | P2—C21—C22—C23 | −176.31 (17) |
O11—P1—C11—C12 | −23.58 (18) | C21—C22—C23—C24 | 0.8 (3) |
O13—P1—C11—C16 | 42.25 (18) | C22—C23—C24—C25 | −1.4 (3) |
O12—P1—C11—C16 | −83.02 (17) | C23—C24—C25—C26 | 0.7 (3) |
O11—P1—C11—C16 | 158.62 (16) | C24—C25—C26—C21 | 0.7 (3) |
C16—C11—C12—C13 | −0.2 (3) | C22—C21—C26—C25 | −1.4 (3) |
P1—C11—C12—C13 | −178.02 (16) | P2—C21—C26—C25 | 175.57 (16) |
C11—C12—C13—C14 | 0.7 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O13ii | 0.92 | 1.85 | 2.750 (2) | 164 |
N1—H1B···O12 | 0.92 | 1.78 | 2.692 (2) | 171 |
O1—H1C···O22iii | 0.90 | 1.81 | 2.707 (2) | 169 |
O1—H1D···O13ii | 0.91 | 1.83 | 2.744 (2) | 178 |
N4—H4A···O12 | 0.92 | 1.85 | 2.753 (2) | 164 |
N4—H4B···O22 | 0.92 | 1.74 | 2.637 (2) | 163 |
O11—H11···O23 | 0.84 | 1.72 | 2.496 (2) | 152 |
O21—H21···O1 | 0.84 | 1.78 | 2.616 (2) | 171 |
C2—H2B···O21iii | 0.99 | 2.55 | 3.234 (2) | 126 |
C3—H3A···O12i | 0.99 | 2.48 | 3.467 (2) | 174 |
C6—H6A···O11iv | 0.99 | 2.45 | 3.266 (2) | 139 |
C7—H7···O12 | 1.00 | 2.45 | 3.439 (2) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) x+1, y, z. |
C16H38N42+·2(C7H5O4−) | ? #Insert any comments here. |
Mr = 592.72 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9162 (13) Å | Cell parameters from 25 reflections |
b = 11.8903 (10) Å | θ = 9.6–19.4° |
c = 14.5229 (18) Å | µ = 0.09 mm−1 |
β = 100.419 (7)° | T = 294 K |
V = 1514.3 (3) Å3 | Plate, colourless |
Z = 2 | 0.41 × 0.41 × 0.29 mm |
F(000) = 640 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.009 |
Radiation source: X-ray tube | θmax = 27.4°, θmin = 2.2° |
Graphite monochromator | h = −11→11 |
θ/2θ scans | k = 0→15 |
3595 measured reflections | l = 0→18 |
3470 independent reflections | 3 standard reflections every 120 min |
2576 reflections with I > 2σ(I) | intensity decay: no decay, variation 0.2% |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.2636P] where P = (Fo2 + 2Fc2)/3 |
3470 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.17725 (12) | 0.61562 (9) | 0.10997 (7) | 0.0393 (3) | |
O2 | 0.33606 (12) | 0.56332 (10) | 0.23823 (8) | 0.0509 (3) | |
O3 | −0.19034 (14) | 0.28535 (11) | 0.05391 (7) | 0.0518 (3) | |
O5 | 0.02568 (15) | 0.27834 (11) | 0.37796 (7) | 0.0540 (3) | |
C1 | 0.21763 (15) | 0.55155 (12) | 0.17928 (9) | 0.0319 (3) | |
C11 | 0.11094 (14) | 0.45609 (12) | 0.19206 (9) | 0.0301 (3) | |
C12 | 0.00825 (16) | 0.41599 (13) | 0.11550 (10) | 0.0355 (3) | |
C13 | −0.08879 (16) | 0.32853 (13) | 0.12695 (10) | 0.0351 (3) | |
C14 | −0.08607 (16) | 0.28071 (13) | 0.21394 (10) | 0.0361 (3) | |
C15 | 0.01691 (17) | 0.32110 (13) | 0.29050 (9) | 0.0350 (3) | |
C16 | 0.11514 (16) | 0.40886 (12) | 0.27973 (10) | 0.0331 (3) | |
N1 | 0.49503 (13) | 0.33192 (9) | 0.50291 (8) | 0.0286 (2) | |
C2 | 0.50602 (17) | 0.30885 (12) | 0.40487 (10) | 0.0340 (3) | |
C3 | 0.62426 (17) | 0.38170 (12) | 0.37278 (11) | 0.0371 (3) | |
C5 | 0.70088 (15) | 0.58758 (12) | 0.35190 (9) | 0.0307 (3) | |
N4 | 0.58177 (12) | 0.50317 (9) | 0.37138 (7) | 0.0270 (2) | |
C51 | 0.84959 (17) | 0.56789 (14) | 0.42040 (12) | 0.0453 (4) | |
C52 | 0.72246 (19) | 0.57140 (14) | 0.25080 (10) | 0.0421 (4) | |
C6 | 0.63498 (17) | 0.70457 (12) | 0.36406 (10) | 0.0342 (3) | |
C7 | 0.61803 (16) | 0.74121 (12) | 0.46240 (10) | 0.0344 (3) | |
C71 | 0.5768 (2) | 0.86617 (14) | 0.46170 (15) | 0.0602 (5) | |
H3 | −0.1907 | 0.3242 | 0.0072 | 0.078* | |
H5 | −0.0354 | 0.2265 | 0.3766 | 0.081* | |
H12 | 0.0049 | 0.4480 | 0.0567 | 0.043* | |
H14 | −0.1522 | 0.2223 | 0.2213 | 0.043* | |
H16 | 0.1834 | 0.4358 | 0.3311 | 0.040* | |
H1A | 0.5872 | 0.3216 | 0.5391 | 0.034* | |
H2A | 0.4077 | 0.3223 | 0.3653 | 0.041* | |
H2B | 0.5321 | 0.2304 | 0.3985 | 0.041* | |
H3A | 0.7214 | 0.3711 | 0.4143 | 0.045* | |
H3B | 0.6363 | 0.3588 | 0.3104 | 0.045* | |
H4E | 0.5572 | 0.5203 | 0.4272 | 0.032* | |
H4A | 0.4972 | 0.5127 | 0.3277 | 0.032* | |
H51A | 0.8947 | 0.4985 | 0.4053 | 0.068* | |
H51B | 0.8291 | 0.5640 | 0.4830 | 0.068* | |
H51C | 0.9186 | 0.6288 | 0.4160 | 0.068* | |
H52A | 0.7933 | 0.6263 | 0.2359 | 0.063* | |
H52B | 0.6262 | 0.5804 | 0.2095 | 0.063* | |
H52C | 0.7614 | 0.4973 | 0.2435 | 0.063* | |
H6A | 0.6991 | 0.7593 | 0.3403 | 0.041* | |
H6B | 0.5351 | 0.7085 | 0.3245 | 0.041* | |
H7 | 0.7168 | 0.7312 | 0.5039 | 0.041* | |
H71A | 0.4823 | 0.8784 | 0.4194 | 0.090* | |
H71B | 0.6560 | 0.9094 | 0.4417 | 0.090* | |
H71C | 0.5662 | 0.8891 | 0.5236 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0463 (6) | 0.0389 (6) | 0.0317 (5) | −0.0030 (5) | 0.0045 (4) | 0.0029 (5) |
O2 | 0.0372 (6) | 0.0537 (7) | 0.0542 (7) | −0.0089 (5) | −0.0120 (5) | 0.0059 (6) |
O3 | 0.0547 (7) | 0.0661 (8) | 0.0296 (6) | −0.0297 (6) | −0.0052 (5) | 0.0034 (5) |
O5 | 0.0667 (8) | 0.0619 (8) | 0.0296 (6) | −0.0247 (6) | −0.0017 (5) | 0.0074 (5) |
C1 | 0.0310 (7) | 0.0331 (7) | 0.0311 (7) | 0.0010 (6) | 0.0046 (5) | −0.0057 (6) |
C11 | 0.0274 (6) | 0.0311 (7) | 0.0314 (7) | 0.0031 (5) | 0.0043 (5) | −0.0025 (6) |
C12 | 0.0369 (7) | 0.0412 (8) | 0.0271 (7) | −0.0037 (6) | 0.0022 (6) | 0.0025 (6) |
C13 | 0.0345 (7) | 0.0408 (8) | 0.0281 (7) | −0.0044 (6) | 0.0007 (5) | −0.0035 (6) |
C14 | 0.0382 (8) | 0.0379 (8) | 0.0317 (7) | −0.0062 (6) | 0.0049 (6) | −0.0003 (6) |
C15 | 0.0385 (8) | 0.0397 (8) | 0.0263 (7) | 0.0013 (6) | 0.0045 (6) | 0.0010 (6) |
C16 | 0.0318 (7) | 0.0374 (8) | 0.0281 (7) | 0.0006 (6) | −0.0004 (5) | −0.0026 (6) |
N1 | 0.0295 (5) | 0.0251 (6) | 0.0308 (6) | −0.0003 (4) | 0.0042 (4) | 0.0016 (5) |
C2 | 0.0430 (8) | 0.0251 (7) | 0.0338 (7) | 0.0024 (6) | 0.0068 (6) | −0.0028 (6) |
C3 | 0.0453 (8) | 0.0289 (7) | 0.0400 (8) | 0.0073 (6) | 0.0157 (7) | 0.0023 (6) |
C5 | 0.0297 (7) | 0.0319 (7) | 0.0305 (7) | −0.0028 (5) | 0.0058 (5) | 0.0015 (6) |
N4 | 0.0301 (5) | 0.0265 (6) | 0.0242 (5) | 0.0026 (4) | 0.0044 (4) | 0.0023 (4) |
C51 | 0.0333 (8) | 0.0504 (10) | 0.0486 (9) | 0.0008 (7) | −0.0026 (7) | −0.0048 (8) |
C52 | 0.0489 (9) | 0.0454 (9) | 0.0349 (8) | −0.0027 (7) | 0.0155 (7) | 0.0018 (7) |
C6 | 0.0375 (7) | 0.0294 (7) | 0.0362 (7) | −0.0042 (6) | 0.0078 (6) | 0.0050 (6) |
C7 | 0.0357 (7) | 0.0283 (7) | 0.0400 (8) | −0.0052 (6) | 0.0089 (6) | −0.0014 (6) |
C71 | 0.0916 (14) | 0.0278 (8) | 0.0711 (13) | −0.0066 (9) | 0.0414 (11) | 0.0002 (8) |
O1—C1 | 1.2618 (17) | N1—C2 | 1.4706 (18) |
O2—C1 | 1.2413 (16) | N1—C7i | 1.4865 (17) |
O3—C13 | 1.3643 (16) | C2—C3 | 1.502 (2) |
O5—C15 | 1.3572 (17) | C3—N4 | 1.4924 (17) |
C1—C11 | 1.5137 (19) | C5—N4 | 1.5244 (17) |
C11—C16 | 1.3860 (19) | C5—C51 | 1.5249 (19) |
C11—C12 | 1.3906 (19) | C5—C52 | 1.5270 (19) |
C12—C13 | 1.382 (2) | C5—C6 | 1.533 (2) |
C13—C14 | 1.382 (2) | C6—C7 | 1.527 (2) |
C14—C15 | 1.393 (2) | C7—N1i | 1.4865 (17) |
C15—C16 | 1.389 (2) | C7—C71 | 1.530 (2) |
O2—C1—O1 | 124.51 (14) | C2—N1—C7i | 112.77 (11) |
O2—C1—C11 | 118.36 (13) | N1—C2—C3 | 111.48 (12) |
O1—C1—C11 | 117.10 (12) | N4—C3—C2 | 111.81 (11) |
C16—C11—C12 | 120.01 (13) | N4—C5—C51 | 109.31 (11) |
C16—C11—C1 | 120.22 (12) | N4—C5—C52 | 107.98 (11) |
C12—C11—C1 | 119.77 (12) | C51—C5—C52 | 111.23 (12) |
C13—C12—C11 | 119.86 (13) | N4—C5—C6 | 106.36 (10) |
O3—C13—C14 | 117.10 (13) | C51—C5—C6 | 111.74 (12) |
O3—C13—C12 | 122.11 (13) | C52—C5—C6 | 110.05 (12) |
C14—C13—C12 | 120.79 (13) | C3—N4—C5 | 117.13 (10) |
C13—C14—C15 | 119.21 (13) | C7—C6—C5 | 118.15 (12) |
O5—C15—C16 | 117.12 (12) | N1i—C7—C6 | 109.76 (11) |
O5—C15—C14 | 122.41 (14) | N1i—C7—C71 | 113.16 (12) |
C16—C15—C14 | 120.47 (13) | C6—C7—C71 | 109.59 (13) |
C11—C16—C15 | 119.67 (12) | ||
O2—C1—C11—C16 | 21.9 (2) | O5—C15—C16—C11 | −179.79 (13) |
O1—C1—C11—C16 | −156.36 (13) | C14—C15—C16—C11 | −0.3 (2) |
O2—C1—C11—C12 | −158.22 (14) | C7i—N1—C2—C3 | −178.36 (11) |
O1—C1—C11—C12 | 23.50 (19) | N1—C2—C3—N4 | −65.04 (15) |
C16—C11—C12—C13 | −0.4 (2) | C2—C3—N4—C5 | 172.57 (11) |
C1—C11—C12—C13 | 179.72 (13) | C51—C5—N4—C3 | −53.74 (15) |
C11—C12—C13—O3 | −179.25 (14) | C52—C5—N4—C3 | 67.40 (15) |
C11—C12—C13—C14 | 0.5 (2) | C6—C5—N4—C3 | −174.52 (11) |
O3—C13—C14—C15 | 179.28 (14) | N4—C5—C6—C7 | 68.59 (15) |
C12—C13—C14—C15 | −0.5 (2) | C51—C5—C6—C7 | −50.61 (17) |
C13—C14—C15—O5 | 179.85 (14) | C52—C5—C6—C7 | −174.69 (12) |
C13—C14—C15—C16 | 0.4 (2) | C5—C6—C7—N1i | −64.77 (16) |
C12—C11—C16—C15 | 0.3 (2) | C5—C6—C7—C71 | 170.38 (13) |
C1—C11—C16—C15 | −179.83 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3ii | 0.90 | 2.33 | 3.100 (2) | 143 |
N4—H4A···O2 | 0.90 | 1.85 | 2.742 (2) | 168 |
N4—H4E···N1i | 0.90 | 2.12 | 2.846 (2) | 137 |
O3—H3···O1iii | 0.82 | 1.87 | 2.677 (2) | 168 |
O5—H5···O1iv | 0.82 | 1.86 | 2.676 (2) | 172 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+1/2, z+1/2; (iii) −x, −y+1, −z; (iv) −x, y−1/2, −z+1/2. |
C16H38N42+·C12H10O2·2(C12H9O2−) | ? #Insert any comments here. |
Mr = 843.09 | Dx = 1.227 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9634 (10) Å | Cell parameters from 25 reflections |
b = 18.8981 (19) Å | θ = 10.0–18.4° |
c = 12.2344 (11) Å | µ = 0.08 mm−1 |
β = 97.725 (7)° | T = 294 K |
V = 2282.7 (4) Å3 | Plate, colourless |
Z = 2 | 0.28 × 0.22 × 0.04 mm |
F(000) = 908 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: X-ray tube | θmax = 25.4°, θmin = 2.1° |
Graphite monochromator | h = −12→11 |
θ/2θ scans | k = 0→22 |
4427 measured reflections | l = 0→14 |
4232 independent reflections | 3 standard reflections every 120 min |
2138 reflections with I > 2σ(I) | intensity decay: no decay, variation .6% |
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)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max < 0.001 |
4232 reflections | Δρmax = 0.19 e Å−3 |
286 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0055 (8) |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.2689 (0.0080) x - 2.7804 (0.0228) y + 8.2178 (0.0097) z = 4.8716 (0.0128) * -0.0018 (0.0018) C11 * 0.0040 (0.0018) C12 * -0.0026 (0.0019) C13 * -0.0010 (0.0020) C14 * 0.0031 (0.0023) C15 * -0.0018 (0.0022) C16 0.0258 (0.0038) O14 0.0161 (0.0048) C11_$1 (label _$1 refers to an atom at (2 - x, 1 - y, -z) 0.0103 (0.0053) C12_$1 0.0170 (0.0052) C13_$1 0.0153 (0.0052) C14_$1 0.0112 (0.0051) C15_$1 0.0161 (0.0057) C16_$1 Rms deviation of fitted atoms = 0.0026 6.2689 (0.0080) x - 2.7804 (0.0228) y + 8.2178 (0.0097) z = 4.8859 (0.0158) Angle to previous plane (with approximate e.s.d.) = 0.0 (2) * 0.0018 (0.0018) C11_$1 * -0.0040 (0.0019) C12_$1 * 0.0026 (0.0019) C13_$1 * 0.0010 (0.0020) C14_$1 * -0.0031 (0.0023) C15_$1 * 0.0018 (0.0022) C16_$1 - 0.0258 (0.0038) O14_$1 - 0.0072 (0.0024) Inv1 (Inv1 is a dummy atom at 0, 1/2,0) Rms deviation of fitted atoms = 0.0026 - 4.4506 (0.0088) x + 15.6967 (0.0110) y + 4.7660 (0.0115) z = 3.9473 (0.0054) Angle to previous plane (with approximate e.s.d.) = 81.4 (1) * 0.0155 (0.0016) C21 * -0.0118 (0.0017) C22 * -0.0028 (0.0017) C23 * 0.0138 (0.0018) C24 * -0.0100 (0.0019) C25 * -0.0046 (0.0019) C26 0.0725 (0.0036) O24 0.1354 (0.0037) C31 0.5005 (0.0062) C34 0.7095 (0.0071) O34 Rms deviation of fitted atoms = 0.0108 - 1.5384 (0.0093) x + 18.4407 (0.0046) y - 1.6236 (0.0127) z = 4.2357 (0.0020) Angle to previous plane (with approximate e.s.d.) = 34.1 (1) * 0.0028 (0.0017) C31 * 0.0006 (0.0017) C32 * -0.0027 (0.0018) C33 * 0.0013 (0.0018) C34 * 0.0022 (0.0018) C35 * -0.0042 (0.0018) C36 0.0020 (0.0035) O34 0.0658 (0.0038) C21 0.3644 (0.0060) C24 0.5523 (0.0070) O24 Rms deviation of fitted atoms = 0.0026 |
x | y | z | Uiso*/Ueq | ||
C11 | 0.9475 (2) | 0.49370 (13) | 0.03683 (19) | 0.0360 (6) | |
C12 | 0.8967 (3) | 0.42730 (14) | 0.0538 (2) | 0.0459 (7) | |
C13 | 0.8001 (3) | 0.41508 (14) | 0.1225 (2) | 0.0458 (7) | |
C14 | 0.7503 (3) | 0.46944 (14) | 0.1791 (2) | 0.0426 (6) | |
O14 | 0.65757 (19) | 0.45884 (9) | 0.24956 (17) | 0.0571 (6) | |
C15 | 0.7997 (3) | 0.53630 (15) | 0.1645 (3) | 0.0682 (10) | |
C16 | 0.8955 (3) | 0.54783 (15) | 0.0948 (3) | 0.0631 (9) | |
C21 | 0.2177 (2) | 0.26553 (12) | 0.1602 (2) | 0.0342 (6) | |
C22 | 0.2739 (2) | 0.24735 (12) | 0.2668 (2) | 0.0364 (6) | |
C23 | 0.4012 (2) | 0.27002 (12) | 0.31299 (19) | 0.0355 (6) | |
C24 | 0.4809 (2) | 0.31186 (13) | 0.2531 (2) | 0.0389 (6) | |
O24 | 0.60170 (16) | 0.33611 (9) | 0.29835 (14) | 0.0499 (5) | |
C25 | 0.4273 (3) | 0.32807 (15) | 0.1447 (2) | 0.0483 (7) | |
C26 | 0.2993 (2) | 0.30557 (14) | 0.1004 (2) | 0.0442 (7) | |
C31 | 0.0759 (2) | 0.24639 (12) | 0.1160 (2) | 0.0349 (6) | |
C32 | 0.0341 (2) | 0.23306 (13) | 0.0055 (2) | 0.0399 (6) | |
C33 | −0.0997 (2) | 0.21826 (13) | −0.0337 (2) | 0.0408 (7) | |
C34 | −0.1970 (2) | 0.21651 (12) | 0.0362 (2) | 0.0371 (6) | |
O34 | −0.32973 (16) | 0.20249 (11) | 0.00226 (14) | 0.0516 (5) | |
C35 | −0.1577 (2) | 0.22958 (13) | 0.1468 (2) | 0.0426 (7) | |
C36 | −0.0240 (2) | 0.24381 (14) | 0.1858 (2) | 0.0412 (6) | |
N1 | 0.49383 (19) | 0.54981 (11) | 0.34583 (16) | 0.0395 (5) | |
C2 | 0.5724 (3) | 0.61183 (14) | 0.3922 (2) | 0.0479 (7) | |
C3 | 0.6971 (3) | 0.58896 (15) | 0.4669 (2) | 0.0521 (8) | |
N4 | 0.66320 (19) | 0.55448 (11) | 0.56589 (17) | 0.0402 (5) | |
C5 | 0.7799 (2) | 0.52234 (14) | 0.6384 (2) | 0.0417 (6) | |
C51 | 0.8924 (3) | 0.57641 (15) | 0.6736 (3) | 0.0644 (9) | |
C52 | 0.8376 (3) | 0.46191 (15) | 0.5765 (3) | 0.0648 (9) | |
C6 | 0.7265 (3) | 0.49519 (15) | 0.7422 (2) | 0.0539 (8) | |
C7 | 0.6320 (3) | 0.43188 (15) | 0.7314 (2) | 0.0536 (8) | |
C71 | 0.5940 (4) | 0.4073 (2) | 0.8406 (3) | 0.0988 (14) | |
H12 | 0.9290 | 0.3890 | 0.0173 | 0.055* | |
H13 | 0.7685 | 0.3693 | 0.1305 | 0.055* | |
H14 | 0.6493 | 0.4163 | 0.2600 | 0.086* | |
H15 | 0.7682 | 0.5742 | 0.2022 | 0.082* | |
H16 | 0.9263 | 0.5937 | 0.0864 | 0.076* | |
H22 | 0.2241 | 0.2189 | 0.3087 | 0.044* | |
H23 | 0.4341 | 0.2572 | 0.3850 | 0.043* | |
H25 | 0.4786 | 0.3545 | 0.1013 | 0.058* | |
H26 | 0.2668 | 0.3177 | 0.0280 | 0.053* | |
H32 | 0.0976 | 0.2341 | −0.0437 | 0.048* | |
H33 | −0.1243 | 0.2094 | −0.1085 | 0.049* | |
H34 | −0.3400 | 0.1925 | −0.0636 | 0.077* | |
H35 | −0.2218 | 0.2288 | 0.1954 | 0.051* | |
H36 | 0.0002 | 0.2519 | 0.2608 | 0.049* | |
H1A | 0.5475 | 0.5228 | 0.3094 | 0.047* | |
H1E | 0.4700 | 0.5238 | 0.4018 | 0.047* | |
H2A | 0.5162 | 0.6407 | 0.4334 | 0.057* | |
H2B | 0.5985 | 0.6403 | 0.3326 | 0.057* | |
H3A | 0.7488 | 0.5566 | 0.4274 | 0.062* | |
H3B | 0.7533 | 0.6300 | 0.4876 | 0.062* | |
H4A | 0.6235 | 0.5865 | 0.6056 | 0.048* | |
H51A | 0.8560 | 0.6153 | 0.7107 | 0.097* | |
H51B | 0.9282 | 0.5936 | 0.6095 | 0.097* | |
H51C | 0.9635 | 0.5542 | 0.7225 | 0.097* | |
H52A | 0.8848 | 0.4809 | 0.5197 | 0.097* | |
H52B | 0.7651 | 0.4321 | 0.5438 | 0.097* | |
H52C | 0.8992 | 0.4347 | 0.6270 | 0.097* | |
H6A | 0.8040 | 0.4833 | 0.7959 | 0.065* | |
H6B | 0.6797 | 0.5340 | 0.7727 | 0.065* | |
H7 | 0.6778 | 0.3928 | 0.6989 | 0.064* | |
H71A | 0.5273 | 0.3705 | 0.8281 | 0.148* | |
H71B | 0.5576 | 0.4463 | 0.8773 | 0.148* | |
H71C | 0.6730 | 0.3894 | 0.8857 | 0.148* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0320 (14) | 0.0380 (15) | 0.0377 (15) | 0.0017 (11) | 0.0036 (11) | 0.0056 (12) |
C12 | 0.0467 (16) | 0.0431 (16) | 0.0509 (18) | −0.0031 (13) | 0.0180 (14) | −0.0067 (13) |
C13 | 0.0484 (16) | 0.0375 (15) | 0.0537 (18) | −0.0083 (13) | 0.0146 (14) | −0.0046 (13) |
C14 | 0.0406 (15) | 0.0461 (16) | 0.0433 (17) | −0.0021 (12) | 0.0134 (13) | 0.0015 (14) |
O14 | 0.0606 (12) | 0.0470 (12) | 0.0710 (14) | −0.0066 (10) | 0.0353 (11) | −0.0020 (11) |
C15 | 0.077 (2) | 0.0387 (18) | 0.101 (3) | 0.0021 (15) | 0.056 (2) | −0.0001 (17) |
C16 | 0.069 (2) | 0.0362 (16) | 0.093 (3) | 0.0024 (15) | 0.0436 (19) | 0.0098 (16) |
C21 | 0.0325 (13) | 0.0370 (14) | 0.0336 (14) | 0.0022 (11) | 0.0060 (11) | −0.0047 (12) |
C22 | 0.0375 (14) | 0.0376 (14) | 0.0355 (15) | −0.0017 (12) | 0.0099 (12) | −0.0001 (12) |
C23 | 0.0368 (14) | 0.0403 (15) | 0.0288 (14) | −0.0002 (11) | 0.0018 (11) | 0.0014 (11) |
C24 | 0.0350 (15) | 0.0437 (15) | 0.0377 (15) | −0.0022 (12) | 0.0038 (12) | 0.0020 (12) |
O24 | 0.0371 (10) | 0.0636 (13) | 0.0464 (11) | −0.0151 (9) | −0.0040 (9) | 0.0096 (9) |
C25 | 0.0432 (16) | 0.0636 (19) | 0.0383 (17) | −0.0134 (14) | 0.0058 (13) | 0.0101 (14) |
C26 | 0.0395 (15) | 0.0580 (17) | 0.0336 (15) | −0.0057 (13) | −0.0003 (13) | 0.0068 (13) |
C31 | 0.0347 (13) | 0.0350 (14) | 0.0355 (15) | 0.0027 (11) | 0.0062 (12) | −0.0043 (11) |
C32 | 0.0323 (14) | 0.0580 (18) | 0.0308 (15) | −0.0010 (12) | 0.0093 (12) | −0.0009 (12) |
C33 | 0.0359 (15) | 0.0524 (16) | 0.0332 (15) | −0.0023 (12) | 0.0009 (12) | −0.0015 (12) |
C34 | 0.0277 (14) | 0.0405 (15) | 0.0421 (16) | 0.0006 (11) | 0.0009 (12) | −0.0018 (12) |
O34 | 0.0322 (10) | 0.0787 (14) | 0.0435 (11) | −0.0051 (9) | 0.0035 (9) | −0.0070 (11) |
C35 | 0.0348 (14) | 0.0545 (17) | 0.0413 (16) | −0.0069 (12) | 0.0147 (12) | −0.0083 (13) |
C36 | 0.0387 (15) | 0.0534 (16) | 0.0319 (14) | −0.0034 (12) | 0.0061 (12) | −0.0122 (12) |
N1 | 0.0328 (11) | 0.0486 (13) | 0.0377 (13) | −0.0028 (10) | 0.0073 (10) | 0.0038 (10) |
C2 | 0.0479 (17) | 0.0475 (17) | 0.0485 (18) | −0.0089 (13) | 0.0072 (13) | 0.0031 (14) |
C3 | 0.0401 (16) | 0.0655 (19) | 0.0504 (18) | −0.0175 (14) | 0.0057 (14) | 0.0059 (15) |
N4 | 0.0357 (12) | 0.0475 (13) | 0.0378 (13) | −0.0017 (10) | 0.0064 (10) | 0.0002 (10) |
C5 | 0.0310 (14) | 0.0457 (16) | 0.0477 (17) | −0.0033 (12) | 0.0025 (12) | 0.0010 (13) |
C51 | 0.0509 (18) | 0.060 (2) | 0.076 (2) | −0.0136 (15) | −0.0120 (16) | 0.0105 (17) |
C52 | 0.0554 (19) | 0.057 (2) | 0.085 (2) | 0.0043 (15) | 0.0211 (17) | −0.0015 (18) |
C6 | 0.0401 (16) | 0.069 (2) | 0.0494 (18) | −0.0064 (14) | −0.0067 (13) | 0.0086 (15) |
C7 | 0.0364 (15) | 0.0644 (19) | 0.0567 (19) | −0.0037 (14) | −0.0060 (14) | 0.0223 (15) |
C71 | 0.081 (3) | 0.143 (4) | 0.066 (2) | −0.043 (2) | −0.016 (2) | 0.049 (2) |
C11—C12 | 1.379 (3) | C31—C36 | 1.397 (3) |
C11—C16 | 1.384 (4) | C32—C33 | 1.383 (3) |
C11—C11i | 1.489 (5) | C33—C34 | 1.377 (3) |
C12—C13 | 1.380 (3) | C34—O34 | 1.358 (3) |
C13—C14 | 1.369 (3) | C34—C35 | 1.379 (3) |
C14—O14 | 1.360 (3) | C35—C36 | 1.379 (3) |
C14—C15 | 1.376 (4) | N1—C2 | 1.479 (3) |
C15—C16 | 1.380 (4) | N1—C7ii | 1.505 (3) |
C21—C26 | 1.389 (3) | C2—C3 | 1.503 (3) |
C21—C22 | 1.391 (3) | C3—N4 | 1.455 (3) |
C21—C31 | 1.488 (3) | N4—C5 | 1.494 (3) |
C22—C23 | 1.386 (3) | C5—C52 | 1.525 (4) |
C23—C24 | 1.396 (3) | C5—C6 | 1.530 (4) |
C24—O24 | 1.337 (3) | C5—C51 | 1.535 (3) |
C24—C25 | 1.396 (3) | C6—C7 | 1.517 (3) |
C25—C26 | 1.383 (3) | C7—N1ii | 1.505 (3) |
C31—C32 | 1.383 (3) | C7—C71 | 1.510 (4) |
C12—C11—C16 | 115.2 (2) | C36—C31—C21 | 120.4 (2) |
C12—C11—C11i | 122.6 (3) | C33—C32—C31 | 121.7 (2) |
C16—C11—C11i | 122.2 (3) | C34—C33—C32 | 121.0 (2) |
C13—C12—C11 | 123.0 (2) | O34—C34—C33 | 123.6 (2) |
C14—C13—C12 | 120.8 (2) | O34—C34—C35 | 118.1 (2) |
O14—C14—C13 | 122.2 (2) | C33—C34—C35 | 118.3 (2) |
O14—C14—C15 | 120.2 (2) | C36—C35—C34 | 120.6 (2) |
C13—C14—C15 | 117.6 (2) | C35—C36—C31 | 122.0 (2) |
C14—C15—C16 | 121.0 (3) | C2—N1—C7ii | 114.3 (2) |
C15—C16—C11 | 122.5 (3) | N1—C2—C3 | 110.9 (2) |
C26—C21—C22 | 116.0 (2) | N4—C3—C2 | 111.7 (2) |
C26—C21—C31 | 122.4 (2) | C3—N4—C5 | 115.3 (2) |
C22—C21—C31 | 121.6 (2) | N4—C5—C52 | 108.9 (2) |
C23—C22—C21 | 122.4 (2) | N4—C5—C6 | 107.4 (2) |
C22—C23—C24 | 121.0 (2) | C52—C5—C6 | 111.0 (2) |
O24—C24—C23 | 121.4 (2) | N4—C5—C51 | 112.1 (2) |
O24—C24—C25 | 121.8 (2) | C52—C5—C51 | 109.1 (2) |
C23—C24—C25 | 116.8 (2) | C6—C5—C51 | 108.2 (2) |
C26—C25—C24 | 121.3 (2) | C7—C6—C5 | 118.2 (2) |
C25—C26—C21 | 122.4 (2) | N1ii—C7—C71 | 109.8 (2) |
C32—C31—C36 | 116.4 (2) | N1ii—C7—C6 | 109.2 (2) |
C32—C31—C21 | 123.1 (2) | C71—C7—C6 | 113.1 (3) |
C16—C11—C12—C13 | 0.6 (4) | C22—C21—C31—C36 | 33.0 (3) |
C11i—C11—C12—C13 | 179.5 (3) | C36—C31—C32—C33 | 0.3 (4) |
C11—C12—C13—C14 | −0.7 (4) | C21—C31—C32—C33 | −177.3 (2) |
C12—C13—C14—O14 | −178.3 (2) | C31—C32—C33—C34 | 0.3 (4) |
C12—C13—C14—C15 | 0.2 (4) | C32—C33—C34—O34 | 179.8 (2) |
O14—C14—C15—C16 | 178.9 (3) | C32—C33—C34—C35 | −0.3 (4) |
C13—C14—C15—C16 | 0.3 (5) | O34—C34—C35—C36 | 179.7 (2) |
C14—C15—C16—C11 | −0.4 (5) | C33—C34—C35—C36 | −0.2 (4) |
C12—C11—C16—C15 | 0.0 (4) | C34—C35—C36—C31 | 0.7 (4) |
C11i—C11—C16—C15 | −178.9 (3) | C32—C31—C36—C35 | −0.7 (4) |
C26—C21—C22—C23 | 2.6 (3) | C21—C31—C36—C35 | 176.9 (2) |
C31—C21—C22—C23 | −174.1 (2) | C7ii—N1—C2—C3 | −179.2 (2) |
C21—C22—C23—C24 | −1.0 (4) | N1—C2—C3—N4 | −67.1 (3) |
C22—C23—C24—O24 | 177.5 (2) | C2—C3—N4—C5 | 173.0 (2) |
C22—C23—C24—C25 | −1.4 (4) | C3—N4—C5—C52 | −64.9 (3) |
O24—C24—C25—C26 | −176.8 (2) | C3—N4—C5—C6 | 174.8 (2) |
C23—C24—C25—C26 | 2.1 (4) | C3—N4—C5—C51 | 56.0 (3) |
C24—C25—C26—C21 | −0.4 (4) | N4—C5—C6—C7 | 69.3 (3) |
C22—C21—C26—C25 | −1.9 (4) | C52—C5—C6—C7 | −49.7 (3) |
C31—C21—C26—C25 | 174.8 (2) | C51—C5—C6—C7 | −169.4 (2) |
C26—C21—C31—C32 | 33.9 (4) | C5—C6—C7—N1ii | −61.3 (3) |
C22—C21—C31—C32 | −149.6 (2) | C5—C6—C7—C71 | 176.1 (3) |
C26—C21—C31—C36 | −143.6 (3) |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O14 | 0.90 | 1.85 | 2.742 (3) | 172 |
N1—H1E···N4ii | 0.90 | 2.06 | 2.820 (3) | 141 |
O14—H14···O24 | 0.82 | 1.67 | 2.477 (2) | 166 |
O34—H34···O24iii | 0.82 | 1.79 | 2.601 (2) | 167 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x−1, −y+1/2, z−1/2. |