Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111016246/sq3288sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111016246/sq3288Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111016246/sq3288IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111016246/sq3288IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111016246/sq3288IVsup5.hkl |
CCDC references: 833393; 833394; 833395; 833396
For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C28H24N4O3 | F(000) = 976 |
Mr = 464.51 | Dx = 1.302 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 2175 reflections |
a = 12.479 (4) Å | θ = 2.2–22.3° |
b = 11.452 (4) Å | µ = 0.09 mm−1 |
c = 16.776 (6) Å | T = 298 K |
β = 98.766 (6)° | Block, colourless |
V = 2369.4 (14) Å3 | 0.30 × 0.22 × 0.17 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2887 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.5°, θmin = 1.9° |
φ and ω scans | h = −15→15 |
12163 measured reflections | k = −13→13 |
4420 independent reflections | l = −15→20 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.0818P] where P = (Fo2 + 2Fc2)/3 |
4420 reflections | (Δ/σ)max = 0.001 |
318 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken intoaccount individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.3160 (2) | 0.9444 (2) | 0.28664 (16) | 0.0826 (8) | |
H1 | −0.3704 | 0.9862 | 0.3061 | 0.099* | |
C2 | −0.30154 (19) | 0.9626 (2) | 0.20766 (14) | 0.0701 (7) | |
H2 | −0.3450 | 1.0157 | 0.1756 | 0.084* | |
C3 | −0.22251 (17) | 0.90163 (18) | 0.17674 (13) | 0.0545 (5) | |
C4 | −0.1615 (2) | 0.8250 (2) | 0.22736 (13) | 0.0686 (7) | |
H4 | −0.1070 | 0.7815 | 0.2094 | 0.082* | |
C5 | −0.1822 (2) | 0.8133 (2) | 0.30522 (15) | 0.0821 (8) | |
H5 | −0.1400 | 0.7605 | 0.3385 | 0.099* | |
C6 | −0.20440 (18) | 0.92246 (19) | 0.09206 (12) | 0.0613 (6) | |
H6A | −0.2714 | 0.9106 | 0.0553 | 0.074* | |
H6B | −0.1804 | 1.0021 | 0.0861 | 0.074* | |
C7 | −0.09109 (17) | 0.84932 (18) | 0.00127 (12) | 0.0518 (5) | |
C8 | −0.12648 (19) | 0.93317 (19) | −0.05595 (13) | 0.0662 (6) | |
H8 | −0.1762 | 0.9894 | −0.0454 | 0.079* | |
C9 | −0.0877 (2) | 0.9333 (2) | −0.12897 (13) | 0.0683 (7) | |
H9 | −0.1126 | 0.9900 | −0.1671 | 0.082* | |
C10 | −0.01387 (18) | 0.8525 (2) | −0.14688 (12) | 0.0586 (6) | |
C11 | 0.02082 (16) | 0.76905 (18) | −0.08905 (12) | 0.0530 (5) | |
H11 | 0.0707 | 0.7133 | −0.1001 | 0.064* | |
C12 | −0.01635 (15) | 0.76563 (16) | −0.01498 (11) | 0.0467 (5) | |
C13 | 0.0280 (2) | 0.8536 (2) | −0.22700 (13) | 0.0774 (7) | |
H13A | 0.1057 | 0.8583 | −0.2177 | 0.116* | |
H13B | −0.0012 | 0.9200 | −0.2580 | 0.116* | |
H13C | 0.0059 | 0.7833 | −0.2561 | 0.116* | |
C14 | 0.02523 (15) | 0.67632 (16) | 0.04350 (12) | 0.0453 (5) | |
C15 | 0.12522 (15) | 0.53008 (16) | 0.08591 (11) | 0.0442 (5) | |
C16 | 0.20873 (15) | 0.44270 (16) | 0.07948 (12) | 0.0467 (5) | |
C17 | 0.25498 (17) | 0.43820 (17) | 0.00910 (13) | 0.0566 (6) | |
H17 | 0.2293 | 0.4885 | −0.0330 | 0.068* | |
C18 | 0.33780 (19) | 0.3617 (2) | −0.00037 (14) | 0.0643 (6) | |
C19 | 0.3735 (2) | 0.2886 (2) | 0.06317 (15) | 0.0715 (7) | |
H19 | 0.4294 | 0.2367 | 0.0584 | 0.086* | |
C20 | 0.32960 (19) | 0.2895 (2) | 0.13363 (14) | 0.0670 (6) | |
H20 | 0.3549 | 0.2378 | 0.1750 | 0.080* | |
C21 | 0.24763 (17) | 0.36757 (17) | 0.14278 (12) | 0.0526 (5) | |
C22 | 0.3868 (2) | 0.3605 (3) | −0.07722 (16) | 0.0979 (9) | |
H22A | 0.4442 | 0.4169 | −0.0735 | 0.147* | |
H22B | 0.3321 | 0.3795 | −0.1220 | 0.147* | |
H22C | 0.4154 | 0.2842 | −0.0851 | 0.147* | |
C23 | 0.23533 (17) | 0.29890 (18) | 0.27457 (12) | 0.0581 (6) | |
H23A | 0.3135 | 0.3030 | 0.2894 | 0.070* | |
H23B | 0.2161 | 0.2196 | 0.2578 | 0.070* | |
C24 | 0.18154 (16) | 0.33104 (17) | 0.34535 (12) | 0.0498 (5) | |
C25 | 0.1988 (2) | 0.2626 (2) | 0.41242 (14) | 0.0753 (7) | |
H25 | 0.2401 | 0.1950 | 0.4122 | 0.090* | |
C26 | 0.1563 (2) | 0.2920 (3) | 0.47990 (15) | 0.0827 (8) | |
H26 | 0.1714 | 0.2438 | 0.5248 | 0.099* | |
C27 | 0.07663 (19) | 0.4495 (2) | 0.41858 (15) | 0.0678 (6) | |
H27 | 0.0324 | 0.5147 | 0.4195 | 0.081* | |
C28 | 0.11751 (17) | 0.42766 (18) | 0.34910 (13) | 0.0571 (6) | |
H28 | 0.1022 | 0.4774 | 0.3050 | 0.069* | |
N1 | 0.08002 (14) | 0.56504 (14) | 0.14578 (10) | 0.0580 (5) | |
N2 | 0.01484 (14) | 0.66075 (15) | 0.11814 (10) | 0.0597 (5) | |
N3 | −0.2575 (2) | 0.8714 (2) | 0.33620 (13) | 0.0840 (6) | |
N4 | 0.09524 (16) | 0.38440 (19) | 0.48528 (12) | 0.0731 (6) | |
O1 | 0.09262 (10) | 0.59513 (11) | 0.01848 (7) | 0.0469 (3) | |
O2 | −0.12424 (12) | 0.84302 (13) | 0.07424 (8) | 0.0635 (4) | |
O3 | 0.20095 (12) | 0.37715 (13) | 0.21061 (8) | 0.0644 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0843 (19) | 0.093 (2) | 0.0783 (19) | 0.0130 (16) | 0.0363 (15) | −0.0085 (16) |
C2 | 0.0675 (16) | 0.0768 (16) | 0.0679 (16) | 0.0147 (13) | 0.0169 (12) | −0.0010 (13) |
C3 | 0.0570 (13) | 0.0580 (13) | 0.0497 (13) | 0.0019 (11) | 0.0115 (10) | 0.0005 (11) |
C4 | 0.0791 (17) | 0.0769 (16) | 0.0524 (14) | 0.0217 (13) | 0.0188 (12) | 0.0084 (13) |
C5 | 0.105 (2) | 0.0886 (18) | 0.0560 (16) | 0.0251 (16) | 0.0235 (14) | 0.0105 (14) |
C6 | 0.0651 (14) | 0.0659 (14) | 0.0542 (14) | 0.0192 (12) | 0.0127 (11) | 0.0066 (11) |
C7 | 0.0574 (13) | 0.0590 (12) | 0.0394 (12) | 0.0032 (10) | 0.0085 (9) | 0.0075 (10) |
C8 | 0.0744 (16) | 0.0708 (15) | 0.0542 (14) | 0.0163 (12) | 0.0125 (12) | 0.0120 (12) |
C9 | 0.0838 (17) | 0.0695 (15) | 0.0516 (14) | 0.0068 (13) | 0.0109 (12) | 0.0207 (12) |
C10 | 0.0667 (15) | 0.0683 (14) | 0.0419 (12) | −0.0091 (12) | 0.0118 (10) | 0.0091 (11) |
C11 | 0.0544 (13) | 0.0600 (13) | 0.0460 (12) | −0.0032 (10) | 0.0125 (10) | 0.0043 (11) |
C12 | 0.0492 (12) | 0.0521 (11) | 0.0392 (11) | −0.0034 (10) | 0.0075 (9) | 0.0035 (10) |
C13 | 0.0887 (18) | 0.0934 (18) | 0.0531 (15) | −0.0100 (15) | 0.0198 (13) | 0.0128 (13) |
C14 | 0.0453 (11) | 0.0496 (11) | 0.0431 (12) | −0.0006 (9) | 0.0130 (9) | −0.0015 (10) |
C15 | 0.0469 (11) | 0.0453 (10) | 0.0416 (11) | −0.0042 (9) | 0.0108 (9) | 0.0043 (9) |
C16 | 0.0497 (12) | 0.0431 (10) | 0.0491 (12) | −0.0045 (9) | 0.0135 (9) | −0.0024 (9) |
C17 | 0.0679 (14) | 0.0529 (12) | 0.0518 (13) | 0.0007 (11) | 0.0180 (11) | 0.0011 (10) |
C18 | 0.0743 (16) | 0.0625 (14) | 0.0621 (15) | 0.0096 (12) | 0.0299 (12) | −0.0020 (12) |
C19 | 0.0789 (17) | 0.0676 (15) | 0.0743 (17) | 0.0213 (13) | 0.0320 (14) | 0.0013 (13) |
C20 | 0.0759 (16) | 0.0646 (14) | 0.0640 (15) | 0.0199 (12) | 0.0217 (12) | 0.0095 (12) |
C21 | 0.0577 (13) | 0.0528 (12) | 0.0501 (13) | 0.0054 (10) | 0.0179 (10) | −0.0004 (10) |
C22 | 0.120 (2) | 0.107 (2) | 0.0793 (19) | 0.0331 (18) | 0.0557 (17) | 0.0084 (16) |
C23 | 0.0622 (14) | 0.0557 (12) | 0.0579 (14) | 0.0120 (11) | 0.0136 (11) | 0.0074 (11) |
C24 | 0.0475 (12) | 0.0515 (12) | 0.0501 (13) | 0.0010 (10) | 0.0062 (9) | 0.0010 (10) |
C25 | 0.0842 (18) | 0.0834 (17) | 0.0609 (16) | 0.0345 (14) | 0.0194 (13) | 0.0227 (14) |
C26 | 0.092 (2) | 0.102 (2) | 0.0571 (16) | 0.0235 (16) | 0.0209 (14) | 0.0216 (15) |
C27 | 0.0714 (16) | 0.0603 (14) | 0.0740 (17) | 0.0076 (12) | 0.0187 (13) | −0.0071 (13) |
C28 | 0.0663 (14) | 0.0504 (12) | 0.0554 (14) | 0.0072 (11) | 0.0115 (11) | 0.0047 (11) |
N1 | 0.0671 (12) | 0.0599 (11) | 0.0507 (11) | 0.0181 (9) | 0.0208 (9) | 0.0126 (9) |
N2 | 0.0675 (12) | 0.0649 (11) | 0.0502 (11) | 0.0211 (9) | 0.0200 (9) | 0.0147 (9) |
N3 | 0.1013 (17) | 0.0946 (16) | 0.0621 (14) | 0.0101 (14) | 0.0320 (13) | 0.0005 (13) |
N4 | 0.0758 (14) | 0.0852 (14) | 0.0617 (13) | 0.0023 (12) | 0.0209 (10) | −0.0071 (12) |
O1 | 0.0517 (8) | 0.0484 (7) | 0.0417 (8) | −0.0012 (6) | 0.0105 (6) | 0.0011 (6) |
O2 | 0.0758 (10) | 0.0721 (10) | 0.0461 (9) | 0.0274 (8) | 0.0205 (8) | 0.0134 (7) |
O3 | 0.0786 (10) | 0.0680 (9) | 0.0507 (9) | 0.0267 (8) | 0.0233 (8) | 0.0155 (7) |
C1—N3 | 1.319 (3) | C15—O1 | 1.364 (2) |
C1—C2 | 1.380 (3) | C15—C16 | 1.461 (3) |
C1—H1 | 0.9300 | C16—C17 | 1.392 (3) |
C2—C3 | 1.373 (3) | C16—C21 | 1.395 (3) |
C2—H2 | 0.9300 | C17—C18 | 1.383 (3) |
C3—C4 | 1.369 (3) | C17—H17 | 0.9300 |
C3—C6 | 1.491 (3) | C18—C19 | 1.374 (3) |
C4—C5 | 1.376 (3) | C18—C22 | 1.509 (3) |
C4—H4 | 0.9300 | C19—C20 | 1.376 (3) |
C5—N3 | 1.320 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.384 (3) |
C6—O2 | 1.417 (2) | C20—H20 | 0.9300 |
C6—H6A | 0.9700 | C21—O3 | 1.360 (2) |
C6—H6B | 0.9700 | C22—H22A | 0.9600 |
C7—O2 | 1.353 (2) | C22—H22B | 0.9600 |
C7—C8 | 1.382 (3) | C22—H22C | 0.9600 |
C7—C12 | 1.393 (3) | C23—O3 | 1.413 (2) |
C8—C9 | 1.384 (3) | C23—C24 | 1.496 (3) |
C8—H8 | 0.9300 | C23—H23A | 0.9700 |
C9—C10 | 1.371 (3) | C23—H23B | 0.9700 |
C9—H9 | 0.9300 | C24—C25 | 1.361 (3) |
C10—C11 | 1.384 (3) | C24—C28 | 1.372 (3) |
C10—C13 | 1.514 (3) | C25—C26 | 1.364 (3) |
C11—C12 | 1.392 (3) | C25—H25 | 0.9300 |
C11—H11 | 0.9300 | C26—N4 | 1.315 (3) |
C12—C14 | 1.457 (3) | C26—H26 | 0.9300 |
C13—H13A | 0.9600 | C27—N4 | 1.335 (3) |
C13—H13B | 0.9600 | C27—C28 | 1.365 (3) |
C13—H13C | 0.9600 | C27—H27 | 0.9300 |
C14—N2 | 1.291 (2) | C28—H28 | 0.9300 |
C14—O1 | 1.362 (2) | N1—N2 | 1.401 (2) |
C15—N1 | 1.288 (2) | ||
N3—C1—C2 | 124.0 (2) | C17—C16—C15 | 118.74 (18) |
N3—C1—H1 | 118.0 | C21—C16—C15 | 122.38 (17) |
C2—C1—H1 | 118.0 | C18—C17—C16 | 122.3 (2) |
C3—C2—C1 | 119.5 (2) | C18—C17—H17 | 118.8 |
C3—C2—H2 | 120.2 | C16—C17—H17 | 118.8 |
C1—C2—H2 | 120.2 | C19—C18—C17 | 117.1 (2) |
C4—C3—C2 | 117.1 (2) | C19—C18—C22 | 122.1 (2) |
C4—C3—C6 | 122.87 (19) | C17—C18—C22 | 120.8 (2) |
C2—C3—C6 | 120.0 (2) | C18—C19—C20 | 122.5 (2) |
C3—C4—C5 | 119.0 (2) | C18—C19—H19 | 118.8 |
C3—C4—H4 | 120.5 | C20—C19—H19 | 118.8 |
C5—C4—H4 | 120.5 | C19—C20—C21 | 119.8 (2) |
N3—C5—C4 | 124.9 (2) | C19—C20—H20 | 120.1 |
N3—C5—H5 | 117.5 | C21—C20—H20 | 120.1 |
C4—C5—H5 | 117.5 | O3—C21—C20 | 124.3 (2) |
O2—C6—C3 | 108.21 (16) | O3—C21—C16 | 116.33 (17) |
O2—C6—H6A | 110.1 | C20—C21—C16 | 119.40 (19) |
C3—C6—H6A | 110.1 | C18—C22—H22A | 109.5 |
O2—C6—H6B | 110.1 | C18—C22—H22B | 109.5 |
C3—C6—H6B | 110.1 | H22A—C22—H22B | 109.5 |
H6A—C6—H6B | 108.4 | C18—C22—H22C | 109.5 |
O2—C7—C8 | 123.81 (19) | H22A—C22—H22C | 109.5 |
O2—C7—C12 | 116.53 (17) | H22B—C22—H22C | 109.5 |
C8—C7—C12 | 119.66 (19) | O3—C23—C24 | 108.99 (16) |
C7—C8—C9 | 119.9 (2) | O3—C23—H23A | 109.9 |
C7—C8—H8 | 120.1 | C24—C23—H23A | 109.9 |
C9—C8—H8 | 120.1 | O3—C23—H23B | 109.9 |
C10—C9—C8 | 122.0 (2) | C24—C23—H23B | 109.9 |
C10—C9—H9 | 119.0 | H23A—C23—H23B | 108.3 |
C8—C9—H9 | 119.0 | C25—C24—C28 | 116.5 (2) |
C9—C10—C11 | 117.48 (19) | C25—C24—C23 | 118.72 (19) |
C9—C10—C13 | 121.5 (2) | C28—C24—C23 | 124.72 (19) |
C11—C10—C13 | 121.0 (2) | C24—C25—C26 | 120.7 (2) |
C10—C11—C12 | 122.3 (2) | C24—C25—H25 | 119.6 |
C10—C11—H11 | 118.9 | C26—C25—H25 | 119.6 |
C12—C11—H11 | 118.9 | N4—C26—C25 | 124.0 (2) |
C11—C12—C7 | 118.65 (18) | N4—C26—H26 | 118.0 |
C11—C12—C14 | 119.21 (18) | C25—C26—H26 | 118.0 |
C7—C12—C14 | 122.12 (17) | N4—C27—C28 | 125.0 (2) |
C10—C13—H13A | 109.5 | N4—C27—H27 | 117.5 |
C10—C13—H13B | 109.5 | C28—C27—H27 | 117.5 |
H13A—C13—H13B | 109.5 | C27—C28—C24 | 118.9 (2) |
C10—C13—H13C | 109.5 | C27—C28—H28 | 120.6 |
H13A—C13—H13C | 109.5 | C24—C28—H28 | 120.6 |
H13B—C13—H13C | 109.5 | C15—N1—N2 | 106.64 (15) |
N2—C14—O1 | 111.26 (17) | C14—N2—N1 | 106.85 (15) |
N2—C14—C12 | 132.22 (17) | C1—N3—C5 | 115.5 (2) |
O1—C14—C12 | 116.43 (16) | C26—N4—C27 | 114.8 (2) |
N1—C15—O1 | 111.48 (16) | C14—O1—C15 | 103.74 (14) |
N1—C15—C16 | 132.27 (18) | C7—O2—C6 | 118.66 (15) |
O1—C15—C16 | 116.04 (16) | C21—O3—C23 | 117.71 (15) |
C17—C16—C21 | 118.79 (18) | ||
N3—C1—C2—C3 | 0.5 (4) | C18—C19—C20—C21 | −1.2 (4) |
C1—C2—C3—C4 | −0.1 (3) | C19—C20—C21—O3 | −178.4 (2) |
C1—C2—C3—C6 | −178.6 (2) | C19—C20—C21—C16 | 1.5 (3) |
C2—C3—C4—C5 | 0.0 (4) | C17—C16—C21—O3 | 178.82 (18) |
C6—C3—C4—C5 | 178.5 (2) | C15—C16—C21—O3 | 2.1 (3) |
C3—C4—C5—N3 | −0.3 (4) | C17—C16—C21—C20 | −1.0 (3) |
C4—C3—C6—O2 | 5.6 (3) | C15—C16—C21—C20 | −177.7 (2) |
C2—C3—C6—O2 | −176.0 (2) | O3—C23—C24—C25 | 176.45 (19) |
O2—C7—C8—C9 | 179.7 (2) | O3—C23—C24—C28 | −5.6 (3) |
C12—C7—C8—C9 | 0.2 (3) | C28—C24—C25—C26 | −1.7 (3) |
C7—C8—C9—C10 | −0.4 (4) | C23—C24—C25—C26 | 176.4 (2) |
C8—C9—C10—C11 | 0.4 (3) | C24—C25—C26—N4 | 1.4 (4) |
C8—C9—C10—C13 | −180.0 (2) | N4—C27—C28—C24 | 1.1 (4) |
C9—C10—C11—C12 | −0.2 (3) | C25—C24—C28—C27 | 0.6 (3) |
C13—C10—C11—C12 | −179.84 (19) | C23—C24—C28—C27 | −177.4 (2) |
C10—C11—C12—C7 | 0.0 (3) | O1—C15—N1—N2 | −1.3 (2) |
C10—C11—C12—C14 | −178.96 (18) | C16—C15—N1—N2 | 173.02 (19) |
O2—C7—C12—C11 | −179.52 (17) | O1—C14—N2—N1 | 1.0 (2) |
C8—C7—C12—C11 | 0.0 (3) | C12—C14—N2—N1 | −175.38 (19) |
O2—C7—C12—C14 | −0.6 (3) | C15—N1—N2—C14 | 0.2 (2) |
C8—C7—C12—C14 | 178.96 (19) | C2—C1—N3—C5 | −0.8 (4) |
C11—C12—C14—N2 | 171.1 (2) | C4—C5—N3—C1 | 0.6 (4) |
C7—C12—C14—N2 | −7.8 (3) | C25—C26—N4—C27 | 0.2 (4) |
C11—C12—C14—O1 | −5.1 (3) | C28—C27—N4—C26 | −1.4 (4) |
C7—C12—C14—O1 | 175.98 (17) | N2—C14—O1—C15 | −1.7 (2) |
N1—C15—C16—C17 | −168.9 (2) | C12—C14—O1—C15 | 175.28 (15) |
O1—C15—C16—C17 | 5.2 (3) | N1—C15—O1—C14 | 1.9 (2) |
N1—C15—C16—C21 | 7.8 (3) | C16—C15—O1—C14 | −173.48 (15) |
O1—C15—C16—C21 | −178.09 (17) | C8—C7—O2—C6 | 3.7 (3) |
C21—C16—C17—C18 | 0.2 (3) | C12—C7—O2—C6 | −176.79 (18) |
C15—C16—C17—C18 | 177.06 (19) | C3—C6—O2—C7 | −177.19 (17) |
C16—C17—C18—C19 | 0.1 (3) | C20—C21—O3—C23 | −2.8 (3) |
C16—C17—C18—C22 | −179.2 (2) | C16—C21—O3—C23 | 177.37 (17) |
C17—C18—C19—C20 | 0.4 (4) | C24—C23—O3—C21 | 175.04 (17) |
C22—C18—C19—C20 | 179.7 (2) |
[Hg2Cl2(C28H24N4O3)]·CH4O | Z = 2 |
Mr = 768.04 | F(000) = 752 |
Triclinic, P1 | Dx = 1.759 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8422 (18) Å | Cell parameters from 3677 reflections |
b = 12.927 (3) Å | θ = 2.4–24.5° |
c = 13.066 (3) Å | µ = 5.53 mm−1 |
α = 95.232 (3)° | T = 298 K |
β = 97.758 (3)° | Block, colourless |
γ = 99.318 (3)° | 0.16 × 0.14 × 0.08 mm |
V = 1450.5 (5) Å3 |
Bruker SMART CCD area-detector diffractometer | 5294 independent reflections |
Radiation source: fine-focus sealed tube | 4319 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 25.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→10 |
Tmin = 0.472, Tmax = 0.666 | k = −9→15 |
7519 measured reflections | l = −15→15 |
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) = 0.129 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0724P)2] where P = (Fo2 + 2Fc2)/3 |
5294 reflections | (Δ/σ)max = 0.002 |
363 parameters | Δρmax = 1.71 e Å−3 |
0 restraints | Δρmin = −2.51 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.6190 (3) | 0.48310 (19) | 1.27556 (18) | 0.0765 (6) | |
Cl2 | 0.2212 (3) | 0.3264 (2) | 1.4246 (2) | 0.0840 (7) | |
C1 | 0.8050 (9) | 0.3897 (6) | 0.5070 (6) | 0.0550 (19) | |
H1 | 0.8302 | 0.4151 | 0.4460 | 0.066* | |
C2 | 0.9242 (9) | 0.3840 (6) | 0.5850 (6) | 0.0514 (17) | |
H2 | 1.0269 | 0.4051 | 0.5764 | 0.062* | |
C3 | 0.8890 (8) | 0.3467 (5) | 0.6758 (5) | 0.0401 (15) | |
C4 | 0.7354 (9) | 0.3175 (6) | 0.6840 (6) | 0.0509 (18) | |
H4 | 0.7072 | 0.2919 | 0.7442 | 0.061* | |
C5 | 0.6227 (9) | 0.3262 (6) | 0.6028 (6) | 0.0552 (19) | |
H5 | 0.5191 | 0.3070 | 0.6103 | 0.066* | |
C6 | 1.0139 (8) | 0.3402 (5) | 0.7644 (5) | 0.0463 (16) | |
H6A | 1.1147 | 0.3619 | 0.7439 | 0.056* | |
H6B | 1.0050 | 0.3884 | 0.8238 | 0.056* | |
C7 | 1.0527 (7) | 0.1606 (5) | 0.7323 (5) | 0.0394 (14) | |
C8 | 1.1368 (8) | 0.1814 (6) | 0.6529 (5) | 0.0506 (17) | |
H8 | 1.1638 | 0.2507 | 0.6387 | 0.061* | |
C9 | 1.1815 (8) | 0.1002 (7) | 0.5940 (6) | 0.0561 (19) | |
H9 | 1.2381 | 0.1157 | 0.5406 | 0.067* | |
C10 | 1.1435 (8) | −0.0032 (6) | 0.6132 (5) | 0.0500 (18) | |
C11 | 1.0616 (7) | −0.0231 (5) | 0.6934 (5) | 0.0432 (15) | |
H11 | 1.0362 | −0.0924 | 0.7079 | 0.052* | |
C12 | 1.0149 (7) | 0.0571 (5) | 0.7543 (5) | 0.0382 (14) | |
C13 | 1.1914 (10) | −0.0912 (8) | 0.5480 (6) | 0.071 (3) | |
H13A | 1.1975 | −0.0720 | 0.4792 | 0.106* | |
H13B | 1.1162 | −0.1545 | 0.5442 | 0.106* | |
H13C | 1.2909 | −0.1031 | 0.5790 | 0.106* | |
C14 | 0.9278 (7) | 0.0299 (5) | 0.8381 (5) | 0.0366 (14) | |
C15 | 0.8112 (7) | −0.0738 (5) | 0.9317 (5) | 0.0361 (14) | |
C16 | 0.7548 (7) | −0.1765 (4) | 0.9635 (5) | 0.0354 (14) | |
C17 | 0.7914 (8) | −0.2667 (5) | 0.9125 (5) | 0.0474 (16) | |
H17 | 0.8507 | −0.2592 | 0.8592 | 0.057* | |
C18 | 0.7429 (10) | −0.3665 (6) | 0.9384 (6) | 0.0558 (19) | |
C19 | 0.6591 (9) | −0.3760 (5) | 1.0198 (6) | 0.0521 (18) | |
H19 | 0.6293 | −0.4423 | 1.0405 | 0.063* | |
C20 | 0.6187 (9) | −0.2886 (5) | 1.0710 (6) | 0.0508 (17) | |
H20 | 0.5592 | −0.2968 | 1.1241 | 0.061* | |
C21 | 0.6670 (8) | −0.1880 (5) | 1.0431 (5) | 0.0418 (15) | |
C22 | 0.7850 (12) | −0.4623 (6) | 0.8817 (7) | 0.076 (3) | |
H22A | 0.7820 | −0.4535 | 0.8094 | 0.114* | |
H22B | 0.7122 | −0.5239 | 0.8891 | 0.114* | |
H22C | 0.8875 | −0.4704 | 0.9108 | 0.114* | |
C23 | 0.5339 (8) | −0.1077 (5) | 1.1671 (5) | 0.0463 (16) | |
H23A | 0.5789 | −0.1440 | 1.2222 | 0.056* | |
H23B | 0.4329 | −0.1484 | 1.1375 | 0.056* | |
C24 | 0.5170 (7) | 0.0000 (5) | 1.2102 (5) | 0.0412 (15) | |
C25 | 0.5910 (8) | 0.0889 (5) | 1.1761 (5) | 0.0472 (16) | |
H25 | 0.6532 | 0.0836 | 1.1245 | 0.057* | |
C26 | 0.5719 (8) | 0.1866 (6) | 1.2196 (5) | 0.0467 (16) | |
H26 | 0.6233 | 0.2467 | 1.1965 | 0.056* | |
C27 | 0.4098 (8) | 0.1113 (6) | 1.3247 (5) | 0.0486 (17) | |
H27 | 0.3455 | 0.1179 | 1.3748 | 0.058* | |
C28 | 0.4257 (8) | 0.0122 (6) | 1.2861 (5) | 0.0464 (16) | |
H28 | 0.3749 | −0.0467 | 1.3112 | 0.056* | |
C29 | 0.7942 (12) | 0.3096 (8) | 1.0448 (7) | 0.079 (3) | |
H29A | 0.8915 | 0.3236 | 1.0906 | 0.118* | |
H29B | 0.7332 | 0.2456 | 1.0591 | 0.118* | |
H29C | 0.7395 | 0.3671 | 1.0554 | 0.118* | |
Hg1 | 0.46076 (3) | 0.37308 (2) | 1.36711 (2) | 0.05369 (14) | |
N1 | 0.8781 (6) | 0.0882 (4) | 0.9074 (4) | 0.0395 (12) | |
N2 | 0.8021 (6) | 0.0210 (4) | 0.9694 (4) | 0.0413 (12) | |
N3 | 0.4828 (6) | 0.1989 (5) | 1.2933 (4) | 0.0456 (13) | |
N4 | 0.6559 (7) | 0.3609 (5) | 0.5146 (4) | 0.0479 (14) | |
O1 | 0.8918 (5) | −0.0737 (3) | 0.8499 (3) | 0.0389 (10) | |
O2 | 0.6302 (6) | −0.0988 (4) | 1.0899 (4) | 0.0494 (11) | |
O3 | 1.0028 (5) | 0.2354 (3) | 0.7935 (3) | 0.0443 (10) | |
O4 | 0.8205 (10) | 0.2989 (5) | 0.9445 (5) | 0.088 (2) | |
H4A | 0.8378 | 0.2394 | 0.9294 | 0.133* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0793 (15) | 0.0688 (15) | 0.0822 (14) | −0.0019 (11) | 0.0176 (11) | 0.0313 (11) |
Cl2 | 0.0803 (15) | 0.0824 (18) | 0.1061 (17) | 0.0273 (13) | 0.0504 (14) | 0.0229 (14) |
C1 | 0.066 (5) | 0.048 (5) | 0.057 (4) | 0.012 (4) | 0.016 (4) | 0.025 (3) |
C2 | 0.051 (4) | 0.039 (4) | 0.070 (5) | 0.007 (3) | 0.019 (4) | 0.019 (3) |
C3 | 0.051 (4) | 0.023 (3) | 0.051 (4) | 0.012 (3) | 0.017 (3) | 0.008 (3) |
C4 | 0.054 (4) | 0.050 (5) | 0.051 (4) | 0.004 (3) | 0.015 (3) | 0.016 (3) |
C5 | 0.049 (4) | 0.057 (5) | 0.060 (4) | 0.004 (4) | 0.017 (4) | 0.009 (4) |
C6 | 0.051 (4) | 0.034 (4) | 0.059 (4) | 0.011 (3) | 0.014 (3) | 0.012 (3) |
C7 | 0.037 (3) | 0.039 (4) | 0.044 (3) | 0.015 (3) | 0.000 (3) | 0.006 (3) |
C8 | 0.051 (4) | 0.051 (5) | 0.056 (4) | 0.019 (3) | 0.015 (3) | 0.015 (3) |
C9 | 0.045 (4) | 0.080 (6) | 0.051 (4) | 0.026 (4) | 0.012 (3) | 0.016 (4) |
C10 | 0.045 (4) | 0.058 (5) | 0.049 (4) | 0.024 (3) | −0.002 (3) | 0.000 (3) |
C11 | 0.045 (4) | 0.033 (4) | 0.051 (4) | 0.013 (3) | 0.001 (3) | 0.005 (3) |
C12 | 0.037 (3) | 0.037 (4) | 0.040 (3) | 0.013 (3) | −0.004 (3) | 0.005 (3) |
C13 | 0.069 (5) | 0.094 (7) | 0.055 (4) | 0.044 (5) | 0.006 (4) | −0.012 (4) |
C14 | 0.037 (3) | 0.026 (3) | 0.045 (3) | 0.010 (3) | −0.003 (3) | 0.001 (3) |
C15 | 0.041 (3) | 0.025 (3) | 0.044 (3) | 0.011 (3) | −0.001 (3) | 0.008 (3) |
C16 | 0.043 (3) | 0.017 (3) | 0.045 (3) | 0.010 (2) | −0.003 (3) | 0.002 (2) |
C17 | 0.057 (4) | 0.030 (4) | 0.056 (4) | 0.018 (3) | −0.001 (3) | 0.006 (3) |
C18 | 0.068 (5) | 0.031 (4) | 0.068 (5) | 0.021 (3) | −0.002 (4) | 0.003 (3) |
C19 | 0.056 (4) | 0.025 (4) | 0.073 (5) | 0.003 (3) | −0.002 (4) | 0.012 (3) |
C20 | 0.053 (4) | 0.032 (4) | 0.066 (4) | 0.004 (3) | 0.004 (3) | 0.011 (3) |
C21 | 0.044 (4) | 0.028 (3) | 0.051 (4) | 0.010 (3) | −0.006 (3) | 0.006 (3) |
C22 | 0.105 (7) | 0.032 (4) | 0.097 (6) | 0.033 (5) | 0.017 (6) | 0.002 (4) |
C23 | 0.049 (4) | 0.040 (4) | 0.048 (4) | 0.002 (3) | 0.007 (3) | 0.009 (3) |
C24 | 0.043 (4) | 0.038 (4) | 0.043 (3) | 0.012 (3) | −0.001 (3) | 0.007 (3) |
C25 | 0.057 (4) | 0.039 (4) | 0.049 (4) | 0.012 (3) | 0.017 (3) | 0.004 (3) |
C26 | 0.058 (4) | 0.034 (4) | 0.052 (4) | 0.010 (3) | 0.018 (3) | 0.009 (3) |
C27 | 0.045 (4) | 0.054 (5) | 0.049 (4) | 0.010 (3) | 0.012 (3) | 0.006 (3) |
C28 | 0.043 (4) | 0.043 (4) | 0.051 (4) | 0.001 (3) | 0.005 (3) | 0.009 (3) |
C29 | 0.089 (6) | 0.087 (7) | 0.075 (6) | 0.039 (5) | 0.028 (5) | 0.018 (5) |
Hg1 | 0.0624 (2) | 0.0448 (2) | 0.0596 (2) | 0.01581 (14) | 0.01790 (14) | 0.01235 (13) |
N1 | 0.046 (3) | 0.027 (3) | 0.047 (3) | 0.010 (2) | 0.006 (2) | 0.006 (2) |
N2 | 0.052 (3) | 0.026 (3) | 0.047 (3) | 0.010 (2) | 0.006 (2) | 0.006 (2) |
N3 | 0.048 (3) | 0.045 (4) | 0.047 (3) | 0.014 (3) | 0.011 (3) | 0.008 (3) |
N4 | 0.055 (4) | 0.035 (3) | 0.056 (3) | 0.011 (3) | 0.011 (3) | 0.008 (3) |
O1 | 0.047 (3) | 0.026 (2) | 0.045 (2) | 0.0134 (19) | 0.0023 (19) | 0.0038 (18) |
O2 | 0.064 (3) | 0.028 (3) | 0.059 (3) | 0.010 (2) | 0.019 (2) | 0.006 (2) |
O3 | 0.055 (3) | 0.032 (3) | 0.052 (2) | 0.015 (2) | 0.014 (2) | 0.012 (2) |
O4 | 0.151 (6) | 0.059 (4) | 0.084 (4) | 0.059 (4) | 0.059 (4) | 0.026 (3) |
Cl1—Hg1 | 2.352 (2) | C16—C17 | 1.395 (9) |
Cl2—Hg1 | 2.348 (2) | C17—C18 | 1.379 (10) |
C1—N4 | 1.330 (9) | C17—H17 | 0.9300 |
C1—C2 | 1.380 (10) | C18—C19 | 1.380 (11) |
C1—H1 | 0.9300 | C18—C22 | 1.509 (10) |
C2—C3 | 1.375 (9) | C19—C20 | 1.381 (10) |
C2—H2 | 0.9300 | C19—H19 | 0.9300 |
C3—C4 | 1.371 (10) | C20—C21 | 1.399 (9) |
C3—C6 | 1.506 (10) | C20—H20 | 0.9300 |
C4—C5 | 1.379 (11) | C21—O2 | 1.363 (8) |
C4—H4 | 0.9300 | C22—H22A | 0.9600 |
C5—N4 | 1.327 (9) | C22—H22B | 0.9600 |
C5—H5 | 0.9300 | C22—H22C | 0.9600 |
C6—O3 | 1.432 (8) | C23—O2 | 1.406 (8) |
C6—H6A | 0.9700 | C23—C24 | 1.492 (9) |
C6—H6B | 0.9700 | C23—H23A | 0.9700 |
C7—O3 | 1.365 (7) | C23—H23B | 0.9700 |
C7—C8 | 1.376 (9) | C24—C25 | 1.370 (10) |
C7—C12 | 1.391 (9) | C24—C28 | 1.374 (9) |
C8—C9 | 1.386 (10) | C25—C26 | 1.383 (10) |
C8—H8 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.379 (11) | C26—N3 | 1.338 (8) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.373 (10) | C27—N3 | 1.337 (9) |
C10—C13 | 1.509 (10) | C27—C28 | 1.369 (10) |
C11—C12 | 1.398 (9) | C27—H27 | 0.9300 |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
C12—C14 | 1.459 (9) | C29—O4 | 1.360 (10) |
C13—H13A | 0.9600 | C29—H29A | 0.9600 |
C13—H13B | 0.9600 | C29—H29B | 0.9600 |
C13—H13C | 0.9600 | C29—H29C | 0.9600 |
C14—N1 | 1.292 (8) | Hg1—N3 | 2.416 (6) |
C14—O1 | 1.354 (7) | Hg1—N4i | 2.441 (6) |
C15—N2 | 1.297 (8) | N1—N2 | 1.395 (7) |
C15—O1 | 1.362 (7) | N4—Hg1ii | 2.441 (6) |
C15—C16 | 1.459 (8) | O4—H4A | 0.8200 |
C16—C21 | 1.383 (9) | ||
N4—C1—C2 | 123.4 (7) | C18—C19—H19 | 119.5 |
N4—C1—H1 | 118.3 | C20—C19—H19 | 119.5 |
C2—C1—H1 | 118.3 | C19—C20—C21 | 120.2 (7) |
C3—C2—C1 | 119.1 (7) | C19—C20—H20 | 119.9 |
C3—C2—H2 | 120.5 | C21—C20—H20 | 119.9 |
C1—C2—H2 | 120.5 | O2—C21—C16 | 117.2 (6) |
C4—C3—C2 | 117.6 (6) | O2—C21—C20 | 123.1 (7) |
C4—C3—C6 | 120.9 (6) | C16—C21—C20 | 119.7 (6) |
C2—C3—C6 | 121.5 (6) | C18—C22—H22A | 109.5 |
C3—C4—C5 | 119.9 (7) | C18—C22—H22B | 109.5 |
C3—C4—H4 | 120.0 | H22A—C22—H22B | 109.5 |
C5—C4—H4 | 120.0 | C18—C22—H22C | 109.5 |
N4—C5—C4 | 122.7 (7) | H22A—C22—H22C | 109.5 |
N4—C5—H5 | 118.6 | H22B—C22—H22C | 109.5 |
C4—C5—H5 | 118.6 | O2—C23—C24 | 109.1 (5) |
O3—C6—C3 | 111.5 (5) | O2—C23—H23A | 109.9 |
O3—C6—H6A | 109.3 | C24—C23—H23A | 109.9 |
C3—C6—H6A | 109.3 | O2—C23—H23B | 109.9 |
O3—C6—H6B | 109.3 | C24—C23—H23B | 109.9 |
C3—C6—H6B | 109.3 | H23A—C23—H23B | 108.3 |
H6A—C6—H6B | 108.0 | C25—C24—C28 | 118.2 (6) |
O3—C7—C8 | 124.5 (6) | C25—C24—C23 | 121.6 (6) |
O3—C7—C12 | 116.1 (6) | C28—C24—C23 | 120.3 (6) |
C8—C7—C12 | 119.4 (6) | C24—C25—C26 | 118.9 (6) |
C7—C8—C9 | 120.6 (7) | C24—C25—H25 | 120.5 |
C7—C8—H8 | 119.7 | C26—C25—H25 | 120.5 |
C9—C8—H8 | 119.7 | N3—C26—C25 | 123.1 (7) |
C10—C9—C8 | 121.1 (7) | N3—C26—H26 | 118.5 |
C10—C9—H9 | 119.4 | C25—C26—H26 | 118.5 |
C8—C9—H9 | 119.4 | N3—C27—C28 | 122.7 (6) |
C11—C10—C9 | 117.9 (7) | N3—C27—H27 | 118.7 |
C11—C10—C13 | 121.4 (7) | C28—C27—H27 | 118.7 |
C9—C10—C13 | 120.7 (7) | C27—C28—C24 | 119.9 (7) |
C10—C11—C12 | 122.3 (7) | C27—C28—H28 | 120.0 |
C10—C11—H11 | 118.8 | C24—C28—H28 | 120.0 |
C12—C11—H11 | 118.8 | O4—C29—H29A | 109.5 |
C7—C12—C11 | 118.7 (6) | O4—C29—H29B | 109.5 |
C7—C12—C14 | 122.1 (6) | H29A—C29—H29B | 109.5 |
C11—C12—C14 | 119.2 (6) | O4—C29—H29C | 109.5 |
C10—C13—H13A | 109.5 | H29A—C29—H29C | 109.5 |
C10—C13—H13B | 109.5 | H29B—C29—H29C | 109.5 |
H13A—C13—H13B | 109.5 | Cl2—Hg1—Cl1 | 149.21 (10) |
C10—C13—H13C | 109.5 | Cl2—Hg1—N3 | 97.36 (15) |
H13A—C13—H13C | 109.5 | Cl1—Hg1—N3 | 102.37 (15) |
H13B—C13—H13C | 109.5 | Cl2—Hg1—N4i | 105.22 (16) |
N1—C14—O1 | 111.4 (6) | Cl1—Hg1—N4i | 98.30 (16) |
N1—C14—C12 | 131.5 (6) | N3—Hg1—N4i | 89.80 (19) |
O1—C14—C12 | 117.2 (5) | C14—N1—N2 | 107.5 (5) |
N2—C15—O1 | 112.1 (5) | C14—N1—H4A | 137.5 |
N2—C15—C16 | 131.3 (6) | N2—N1—H4A | 113.1 |
O1—C15—C16 | 116.6 (5) | C15—N2—N1 | 105.6 (5) |
C21—C16—C17 | 118.5 (6) | C27—N3—C26 | 117.2 (6) |
C21—C16—C15 | 122.5 (6) | C27—N3—Hg1 | 122.1 (4) |
C17—C16—C15 | 119.0 (6) | C26—N3—Hg1 | 120.7 (5) |
C18—C17—C16 | 122.4 (7) | C5—N4—C1 | 117.2 (6) |
C18—C17—H17 | 118.8 | C5—N4—Hg1ii | 123.9 (5) |
C16—C17—H17 | 118.8 | C1—N4—Hg1ii | 118.9 (5) |
C17—C18—C19 | 118.1 (7) | C14—O1—C15 | 103.5 (5) |
C17—C18—C22 | 121.0 (8) | C21—O2—C23 | 119.0 (5) |
C19—C18—C22 | 120.8 (7) | C7—O3—C6 | 119.0 (5) |
C18—C19—C20 | 121.0 (7) | C29—O4—H4A | 109.5 |
N4—C1—C2—C3 | 0.1 (11) | C19—C20—C21—C16 | 0.4 (10) |
C1—C2—C3—C4 | −0.4 (10) | O2—C23—C24—C25 | −1.2 (8) |
C1—C2—C3—C6 | −179.0 (6) | O2—C23—C24—C28 | 178.9 (6) |
C2—C3—C4—C5 | 0.0 (11) | C28—C24—C25—C26 | 0.4 (10) |
C6—C3—C4—C5 | 178.6 (7) | C23—C24—C25—C26 | −179.5 (6) |
C3—C4—C5—N4 | 0.9 (12) | C24—C25—C26—N3 | −0.6 (11) |
C4—C3—C6—O3 | 57.3 (8) | N3—C27—C28—C24 | −1.6 (10) |
C2—C3—C6—O3 | −124.2 (7) | C25—C24—C28—C27 | 0.6 (10) |
O3—C7—C8—C9 | −179.4 (6) | C23—C24—C28—C27 | −179.5 (6) |
C12—C7—C8—C9 | 1.1 (10) | O1—C14—N1—N2 | −0.8 (6) |
C7—C8—C9—C10 | −0.1 (11) | C12—C14—N1—N2 | −179.6 (6) |
C8—C9—C10—C11 | −0.8 (10) | O1—C14—N1—H4A | −163.2 |
C8—C9—C10—C13 | 179.4 (6) | C12—C14—N1—H4A | 18.0 |
C9—C10—C11—C12 | 0.8 (10) | O1—C15—N2—N1 | 1.5 (6) |
C13—C10—C11—C12 | −179.4 (6) | C16—C15—N2—N1 | 179.5 (6) |
O3—C7—C12—C11 | 179.4 (5) | C14—N1—N2—C15 | −0.4 (6) |
C8—C7—C12—C11 | −1.1 (9) | H4A—N1—N2—C15 | 166.8 |
O3—C7—C12—C14 | −0.3 (8) | C28—C27—N3—C26 | 1.3 (10) |
C8—C7—C12—C14 | 179.2 (6) | C28—C27—N3—Hg1 | −177.6 (5) |
C10—C11—C12—C7 | 0.2 (9) | C25—C26—N3—C27 | −0.2 (10) |
C10—C11—C12—C14 | 179.9 (6) | C25—C26—N3—Hg1 | 178.7 (5) |
C7—C12—C14—N1 | −4.0 (10) | Cl2—Hg1—N3—C27 | −24.2 (5) |
C11—C12—C14—N1 | 176.3 (6) | Cl1—Hg1—N3—C27 | 179.6 (5) |
C7—C12—C14—O1 | 177.3 (5) | N4i—Hg1—N3—C27 | 81.1 (5) |
C11—C12—C14—O1 | −2.4 (8) | Cl2—Hg1—N3—C26 | 156.9 (5) |
N2—C15—C16—C21 | 4.2 (10) | Cl1—Hg1—N3—C26 | 0.7 (5) |
O1—C15—C16—C21 | −177.8 (5) | N4i—Hg1—N3—C26 | −97.8 (5) |
N2—C15—C16—C17 | −175.3 (6) | C4—C5—N4—C1 | −1.2 (11) |
O1—C15—C16—C17 | 2.7 (8) | C4—C5—N4—Hg1ii | 178.3 (6) |
C21—C16—C17—C18 | 0.2 (10) | C2—C1—N4—C5 | 0.8 (11) |
C15—C16—C17—C18 | 179.8 (6) | C2—C1—N4—Hg1ii | −178.7 (6) |
C16—C17—C18—C19 | −2.0 (11) | N1—C14—O1—C15 | 1.6 (6) |
C16—C17—C18—C22 | −179.8 (7) | C12—C14—O1—C15 | −179.4 (5) |
C17—C18—C19—C20 | 2.9 (11) | N2—C15—O1—C14 | −1.9 (6) |
C22—C18—C19—C20 | −179.2 (7) | C16—C15—O1—C14 | 179.8 (5) |
C18—C19—C20—C21 | −2.2 (11) | C16—C21—O2—C23 | 176.5 (6) |
C17—C16—C21—O2 | −178.6 (5) | C20—C21—O2—C23 | −2.7 (9) |
C15—C16—C21—O2 | 1.9 (9) | C24—C23—O2—C21 | 177.1 (5) |
C17—C16—C21—C20 | 0.6 (9) | C8—C7—O3—C6 | 11.1 (9) |
C15—C16—C21—C20 | −178.9 (6) | C12—C7—O3—C6 | −169.4 (5) |
C19—C20—C21—O2 | 179.5 (6) | C3—C6—O3—C7 | 76.3 (7) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···N1 | 0.82 | 2.05 | 2.862 (8) | 174 |
O4—H4A···O3 | 0.82 | 2.45 | 2.856 (7) | 112 |
[Hg2Br2(C28H24N4O3)]·CH4O | Z = 2 |
Mr = 856.96 | F(000) = 824 |
Triclinic, P1 | Dx = 1.974 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8247 (12) Å | Cell parameters from 4801 reflections |
b = 12.9673 (18) Å | θ = 2.4–28.1° |
c = 13.0197 (18) Å | µ = 8.15 mm−1 |
α = 95.747 (2)° | T = 123 K |
β = 99.101 (2)° | Block, colourless |
γ = 98.902 (2)° | 0.40 × 0.28 × 0.10 mm |
V = 1441.5 (3) Å3 |
Bruker SMART CCD area-detector diffractometer | 5274 independent reflections |
Radiation source: fine-focus sealed tube | 4754 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 25.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→10 |
Tmin = 0.139, Tmax = 0.496 | k = −15→15 |
7538 measured reflections | l = −15→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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0848P)2] where P = (Fo2 + 2Fc2)/3 |
5274 reflections | (Δ/σ)max = 0.001 |
363 parameters | Δρmax = 2.73 e Å−3 |
0 restraints | Δρmin = −3.43 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.61390 (9) | 0.48874 (6) | 1.27101 (5) | 0.03088 (19) | |
Br2 | 0.19318 (9) | 0.32231 (6) | 1.41557 (6) | 0.03231 (19) | |
C1 | 0.7988 (8) | 0.3911 (5) | 0.5109 (5) | 0.0251 (15) | |
H1 | 0.8237 | 0.4191 | 0.4498 | 0.030* | |
C2 | 0.9202 (8) | 0.3855 (5) | 0.5910 (5) | 0.0236 (14) | |
H2 | 1.0254 | 0.4089 | 0.5847 | 0.028* | |
C3 | 0.8845 (8) | 0.3451 (5) | 0.6802 (5) | 0.0182 (13) | |
C4 | 0.7297 (8) | 0.3125 (5) | 0.6856 (5) | 0.0257 (15) | |
H4 | 0.7020 | 0.2843 | 0.7460 | 0.031* | |
C5 | 0.6145 (8) | 0.3211 (5) | 0.6023 (5) | 0.0263 (15) | |
H5 | 0.5083 | 0.2993 | 0.6071 | 0.032* | |
C6 | 1.0121 (8) | 0.3385 (5) | 0.7714 (5) | 0.0217 (14) | |
H6A | 1.1153 | 0.3602 | 0.7519 | 0.026* | |
H6B | 1.0036 | 0.3875 | 0.8328 | 0.026* | |
C7 | 1.0503 (7) | 0.1601 (5) | 0.7363 (5) | 0.0187 (13) | |
C8 | 1.1326 (8) | 0.1814 (5) | 0.6571 (5) | 0.0214 (13) | |
H8 | 1.1594 | 0.2519 | 0.6435 | 0.026* | |
C9 | 1.1770 (8) | 0.0997 (6) | 0.5968 (5) | 0.0238 (14) | |
H9 | 1.2334 | 0.1158 | 0.5424 | 0.029* | |
C10 | 1.1410 (8) | −0.0035 (5) | 0.6143 (5) | 0.0236 (14) | |
C11 | 1.0602 (8) | −0.0249 (5) | 0.6948 (5) | 0.0222 (14) | |
H11 | 1.0353 | −0.0956 | 0.7084 | 0.027* | |
C12 | 1.0141 (7) | 0.0555 (5) | 0.7568 (5) | 0.0174 (13) | |
C13 | 1.1906 (9) | −0.0914 (6) | 0.5480 (5) | 0.0310 (16) | |
H13A | 1.1759 | −0.0784 | 0.4745 | 0.046* | |
H13B | 1.1272 | −0.1589 | 0.5540 | 0.046* | |
H13C | 1.3008 | −0.0935 | 0.5728 | 0.046* | |
C14 | 0.9285 (7) | 0.0294 (5) | 0.8402 (5) | 0.0154 (12) | |
C15 | 0.8123 (7) | −0.0756 (5) | 0.9320 (5) | 0.0171 (12) | |
C16 | 0.7549 (7) | −0.1783 (5) | 0.9633 (5) | 0.0168 (13) | |
C17 | 0.7998 (8) | −0.2679 (5) | 0.9122 (5) | 0.0207 (13) | |
H17 | 0.8615 | −0.2598 | 0.8591 | 0.025* | |
C18 | 0.7538 (8) | −0.3678 (5) | 0.9398 (5) | 0.0232 (14) | |
C19 | 0.6653 (8) | −0.3766 (5) | 1.0173 (5) | 0.0245 (15) | |
H19 | 0.6350 | −0.4443 | 1.0371 | 0.029* | |
C20 | 0.6183 (8) | −0.2910 (5) | 1.0677 (5) | 0.0240 (14) | |
H20 | 0.5549 | −0.3003 | 1.1198 | 0.029* | |
C21 | 0.6657 (7) | −0.1901 (5) | 1.0408 (5) | 0.0190 (13) | |
C22 | 0.8045 (10) | −0.4619 (5) | 0.8859 (6) | 0.0332 (17) | |
H22A | 0.8021 | −0.4543 | 0.8115 | 0.050* | |
H22B | 0.7337 | −0.5261 | 0.8923 | 0.050* | |
H22C | 0.9108 | −0.4664 | 0.9188 | 0.050* | |
C23 | 0.5319 (7) | −0.1107 (5) | 1.1651 (5) | 0.0188 (13) | |
H23A | 0.5827 | −0.1463 | 1.2215 | 0.023* | |
H23B | 0.4281 | −0.1532 | 1.1356 | 0.023* | |
C24 | 0.5150 (7) | −0.0023 (5) | 1.2083 (5) | 0.0194 (13) | |
C25 | 0.5905 (8) | 0.0879 (5) | 1.1772 (5) | 0.0216 (13) | |
H25 | 0.6549 | 0.0832 | 1.1256 | 0.026* | |
C26 | 0.5710 (8) | 0.1842 (5) | 1.2219 (5) | 0.0236 (14) | |
H26 | 0.6238 | 0.2458 | 1.2005 | 0.028* | |
C27 | 0.4076 (8) | 0.1086 (5) | 1.3251 (5) | 0.0213 (13) | |
H27 | 0.3429 | 0.1154 | 1.3763 | 0.026* | |
C28 | 0.4232 (8) | 0.0091 (5) | 1.2846 (5) | 0.0220 (14) | |
H28 | 0.3715 | −0.0512 | 1.3088 | 0.026* | |
C29 | 0.7860 (10) | 0.3041 (6) | 1.0472 (6) | 0.0371 (19) | |
H29A | 0.8834 | 0.3188 | 1.0983 | 0.056* | |
H29B | 0.7245 | 0.2373 | 1.0571 | 0.056* | |
H29C | 0.7263 | 0.3609 | 1.0576 | 0.056* | |
Hg1 | 0.45331 (3) | 0.368829 (18) | 1.365854 (17) | 0.02196 (12) | |
N1 | 0.8778 (6) | 0.0868 (4) | 0.9089 (4) | 0.0182 (11) | |
N2 | 0.8016 (6) | 0.0181 (4) | 0.9699 (4) | 0.0185 (11) | |
N3 | 0.4796 (6) | 0.1952 (4) | 1.2951 (4) | 0.0191 (11) | |
N4 | 0.6492 (6) | 0.3594 (4) | 0.5151 (4) | 0.0215 (11) | |
O1 | 0.8910 (5) | −0.0755 (3) | 0.8503 (3) | 0.0184 (9) | |
O2 | 0.6245 (6) | −0.1009 (3) | 1.0854 (3) | 0.0229 (10) | |
O3 | 0.9998 (5) | 0.2333 (3) | 0.7987 (3) | 0.0196 (9) | |
O4 | 0.8198 (7) | 0.2975 (4) | 0.9458 (4) | 0.0361 (13) | |
H4A | 0.8495 | 0.2401 | 0.9314 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0337 (4) | 0.0293 (4) | 0.0294 (4) | −0.0007 (3) | 0.0060 (3) | 0.0117 (3) |
Br2 | 0.0322 (4) | 0.0297 (4) | 0.0397 (4) | 0.0073 (3) | 0.0180 (3) | 0.0049 (3) |
C1 | 0.031 (4) | 0.020 (3) | 0.028 (3) | 0.009 (3) | 0.009 (3) | 0.006 (3) |
C2 | 0.028 (4) | 0.019 (3) | 0.025 (3) | 0.000 (3) | 0.008 (3) | 0.007 (3) |
C3 | 0.028 (4) | 0.009 (3) | 0.020 (3) | 0.007 (2) | 0.008 (3) | 0.002 (2) |
C4 | 0.028 (4) | 0.028 (4) | 0.022 (3) | 0.005 (3) | 0.006 (3) | 0.007 (3) |
C5 | 0.024 (4) | 0.029 (4) | 0.027 (4) | 0.006 (3) | 0.004 (3) | 0.006 (3) |
C6 | 0.027 (4) | 0.014 (3) | 0.026 (3) | 0.005 (3) | 0.004 (3) | 0.007 (2) |
C7 | 0.017 (3) | 0.022 (3) | 0.017 (3) | 0.008 (3) | −0.001 (2) | 0.001 (2) |
C8 | 0.021 (3) | 0.019 (3) | 0.023 (3) | 0.003 (3) | 0.001 (3) | 0.003 (2) |
C9 | 0.020 (3) | 0.037 (4) | 0.019 (3) | 0.014 (3) | 0.006 (3) | 0.007 (3) |
C10 | 0.020 (3) | 0.028 (4) | 0.020 (3) | 0.009 (3) | −0.005 (3) | −0.003 (3) |
C11 | 0.026 (4) | 0.020 (3) | 0.020 (3) | 0.011 (3) | −0.003 (3) | 0.001 (2) |
C12 | 0.017 (3) | 0.019 (3) | 0.015 (3) | 0.005 (2) | −0.004 (2) | 0.003 (2) |
C13 | 0.031 (4) | 0.036 (4) | 0.027 (4) | 0.014 (3) | 0.003 (3) | −0.004 (3) |
C14 | 0.014 (3) | 0.011 (3) | 0.020 (3) | 0.003 (2) | −0.002 (2) | 0.004 (2) |
C15 | 0.012 (3) | 0.019 (3) | 0.018 (3) | 0.001 (2) | −0.002 (2) | 0.000 (2) |
C16 | 0.017 (3) | 0.011 (3) | 0.020 (3) | 0.001 (2) | −0.005 (2) | 0.004 (2) |
C17 | 0.026 (4) | 0.017 (3) | 0.017 (3) | 0.008 (3) | −0.005 (3) | 0.002 (2) |
C18 | 0.029 (4) | 0.017 (3) | 0.021 (3) | 0.009 (3) | −0.008 (3) | −0.002 (2) |
C19 | 0.029 (4) | 0.012 (3) | 0.029 (3) | 0.002 (3) | −0.004 (3) | 0.006 (3) |
C20 | 0.025 (4) | 0.020 (3) | 0.024 (3) | −0.002 (3) | −0.001 (3) | 0.006 (3) |
C21 | 0.017 (3) | 0.016 (3) | 0.020 (3) | −0.001 (2) | −0.006 (2) | −0.001 (2) |
C22 | 0.051 (5) | 0.016 (3) | 0.034 (4) | 0.014 (3) | 0.004 (3) | 0.004 (3) |
C23 | 0.020 (3) | 0.017 (3) | 0.020 (3) | 0.002 (2) | 0.003 (2) | 0.004 (2) |
C24 | 0.020 (3) | 0.020 (3) | 0.016 (3) | 0.005 (3) | −0.005 (2) | 0.003 (2) |
C25 | 0.023 (4) | 0.022 (3) | 0.022 (3) | 0.006 (3) | 0.007 (3) | 0.002 (2) |
C26 | 0.027 (4) | 0.017 (3) | 0.026 (3) | 0.004 (3) | 0.004 (3) | 0.004 (3) |
C27 | 0.023 (3) | 0.022 (3) | 0.018 (3) | 0.003 (3) | 0.000 (2) | 0.003 (2) |
C28 | 0.023 (4) | 0.021 (3) | 0.020 (3) | 0.001 (3) | 0.001 (3) | 0.003 (2) |
C29 | 0.054 (5) | 0.037 (4) | 0.028 (4) | 0.021 (4) | 0.015 (4) | 0.008 (3) |
Hg1 | 0.02546 (18) | 0.01910 (17) | 0.02258 (17) | 0.00511 (11) | 0.00594 (11) | 0.00398 (10) |
N1 | 0.023 (3) | 0.011 (2) | 0.019 (3) | 0.003 (2) | 0.002 (2) | 0.0013 (19) |
N2 | 0.023 (3) | 0.013 (3) | 0.018 (3) | 0.004 (2) | −0.001 (2) | 0.0051 (19) |
N3 | 0.021 (3) | 0.021 (3) | 0.016 (3) | 0.009 (2) | 0.003 (2) | 0.002 (2) |
N4 | 0.022 (3) | 0.019 (3) | 0.024 (3) | 0.003 (2) | 0.002 (2) | 0.005 (2) |
O1 | 0.026 (3) | 0.011 (2) | 0.019 (2) | 0.0057 (18) | 0.0009 (18) | 0.0035 (16) |
O2 | 0.033 (3) | 0.012 (2) | 0.025 (2) | 0.0036 (19) | 0.0079 (19) | 0.0006 (17) |
O3 | 0.024 (2) | 0.013 (2) | 0.025 (2) | 0.0066 (18) | 0.0055 (18) | 0.0050 (17) |
O4 | 0.062 (4) | 0.025 (3) | 0.032 (3) | 0.021 (3) | 0.024 (3) | 0.010 (2) |
Br1—Hg1 | 2.4914 (7) | C16—C17 | 1.422 (8) |
Br2—Hg1 | 2.4844 (8) | C17—C18 | 1.396 (9) |
C1—N4 | 1.332 (9) | C17—H17 | 0.9500 |
C1—C2 | 1.388 (10) | C18—C19 | 1.374 (10) |
C1—H1 | 0.9500 | C18—C22 | 1.510 (9) |
C2—C3 | 1.381 (9) | C19—C20 | 1.385 (9) |
C2—H2 | 0.9500 | C19—H19 | 0.9500 |
C3—C4 | 1.382 (10) | C20—C21 | 1.406 (9) |
C3—C6 | 1.520 (9) | C20—H20 | 0.9500 |
C4—C5 | 1.390 (10) | C21—O2 | 1.367 (7) |
C4—H4 | 0.9500 | C22—H22A | 0.9800 |
C5—N4 | 1.343 (9) | C22—H22B | 0.9800 |
C5—H5 | 0.9500 | C22—H22C | 0.9800 |
C6—O3 | 1.436 (7) | C23—O2 | 1.423 (7) |
C6—H6A | 0.9900 | C23—C24 | 1.499 (8) |
C6—H6B | 0.9900 | C23—H23A | 0.9900 |
C7—O3 | 1.359 (7) | C23—H23B | 0.9900 |
C7—C8 | 1.378 (9) | C24—C25 | 1.384 (9) |
C7—C12 | 1.407 (9) | C24—C28 | 1.388 (9) |
C8—C9 | 1.396 (9) | C25—C26 | 1.371 (9) |
C8—H8 | 0.9500 | C25—H25 | 0.9500 |
C9—C10 | 1.378 (10) | C26—N3 | 1.352 (8) |
C9—H9 | 0.9500 | C26—H26 | 0.9500 |
C10—C11 | 1.385 (10) | C27—N3 | 1.328 (9) |
C10—C13 | 1.521 (9) | C27—C28 | 1.380 (9) |
C11—C12 | 1.403 (8) | C27—H27 | 0.9500 |
C11—H11 | 0.9500 | C28—H28 | 0.9500 |
C12—C14 | 1.456 (9) | C29—O4 | 1.397 (8) |
C13—H13A | 0.9800 | C29—H29A | 0.9800 |
C13—H13B | 0.9800 | C29—H29B | 0.9800 |
C13—H13C | 0.9800 | C29—H29C | 0.9800 |
C14—N1 | 1.284 (8) | Hg1—N3 | 2.405 (5) |
C14—O1 | 1.374 (7) | Hg1—N4i | 2.415 (5) |
C15—N2 | 1.288 (8) | N1—N2 | 1.415 (7) |
C15—O1 | 1.359 (8) | N4—Hg1ii | 2.415 (5) |
C15—C16 | 1.470 (9) | O4—H4A | 0.8400 |
C16—C21 | 1.381 (9) | ||
N4—C1—C2 | 123.5 (6) | C18—C19—H19 | 118.6 |
N4—C1—H1 | 118.2 | C20—C19—H19 | 118.6 |
C2—C1—H1 | 118.2 | C19—C20—C21 | 119.1 (7) |
C3—C2—C1 | 118.5 (7) | C19—C20—H20 | 120.4 |
C3—C2—H2 | 120.8 | C21—C20—H20 | 120.4 |
C1—C2—H2 | 120.8 | O2—C21—C16 | 116.7 (6) |
C2—C3—C4 | 118.4 (6) | O2—C21—C20 | 123.6 (6) |
C2—C3—C6 | 121.0 (6) | C16—C21—C20 | 119.7 (6) |
C4—C3—C6 | 120.6 (6) | C18—C22—H22A | 109.5 |
C3—C4—C5 | 119.8 (6) | C18—C22—H22B | 109.5 |
C3—C4—H4 | 120.1 | H22A—C22—H22B | 109.5 |
C5—C4—H4 | 120.1 | C18—C22—H22C | 109.5 |
N4—C5—C4 | 121.8 (7) | H22A—C22—H22C | 109.5 |
N4—C5—H5 | 119.1 | H22B—C22—H22C | 109.5 |
C4—C5—H5 | 119.1 | O2—C23—C24 | 108.0 (5) |
O3—C6—C3 | 110.8 (5) | O2—C23—H23A | 110.1 |
O3—C6—H6A | 109.5 | C24—C23—H23A | 110.1 |
C3—C6—H6A | 109.5 | O2—C23—H23B | 110.1 |
O3—C6—H6B | 109.5 | C24—C23—H23B | 110.1 |
C3—C6—H6B | 109.5 | H23A—C23—H23B | 108.4 |
H6A—C6—H6B | 108.1 | C25—C24—C28 | 118.1 (6) |
O3—C7—C8 | 125.1 (6) | C25—C24—C23 | 122.8 (6) |
O3—C7—C12 | 115.8 (6) | C28—C24—C23 | 119.1 (6) |
C8—C7—C12 | 119.1 (6) | C26—C25—C24 | 119.1 (6) |
C7—C8—C9 | 120.3 (6) | C26—C25—H25 | 120.4 |
C7—C8—H8 | 119.8 | C24—C25—H25 | 120.4 |
C9—C8—H8 | 119.8 | N3—C26—C25 | 122.7 (6) |
C10—C9—C8 | 121.7 (6) | N3—C26—H26 | 118.6 |
C10—C9—H9 | 119.2 | C25—C26—H26 | 118.6 |
C8—C9—H9 | 119.2 | N3—C27—C28 | 122.4 (6) |
C9—C10—C11 | 118.2 (6) | N3—C27—H27 | 118.8 |
C9—C10—C13 | 120.9 (6) | C28—C27—H27 | 118.8 |
C11—C10—C13 | 120.9 (6) | C27—C28—C24 | 119.5 (6) |
C10—C11—C12 | 121.5 (6) | C27—C28—H28 | 120.2 |
C10—C11—H11 | 119.3 | C24—C28—H28 | 120.2 |
C12—C11—H11 | 119.3 | O4—C29—H29A | 109.5 |
C11—C12—C7 | 119.3 (6) | O4—C29—H29B | 109.5 |
C11—C12—C14 | 119.7 (6) | H29A—C29—H29B | 109.5 |
C7—C12—C14 | 121.0 (6) | O4—C29—H29C | 109.5 |
C10—C13—H13A | 109.5 | H29A—C29—H29C | 109.5 |
C10—C13—H13B | 109.5 | H29B—C29—H29C | 109.5 |
H13A—C13—H13B | 109.5 | N3—Hg1—N4i | 89.01 (17) |
C10—C13—H13C | 109.5 | N3—Hg1—Br2 | 97.87 (14) |
H13A—C13—H13C | 109.5 | N4i—Hg1—Br2 | 108.12 (13) |
H13B—C13—H13C | 109.5 | N3—Hg1—Br1 | 104.29 (13) |
N1—C14—O1 | 111.0 (5) | N4i—Hg1—Br1 | 99.03 (13) |
N1—C14—C12 | 132.2 (6) | Br2—Hg1—Br1 | 145.07 (3) |
O1—C14—C12 | 116.8 (5) | C14—N1—N2 | 107.2 (5) |
N2—C15—O1 | 112.1 (5) | C14—N1—H4A | 135.7 |
N2—C15—C16 | 130.6 (6) | N2—N1—H4A | 116.0 |
O1—C15—C16 | 117.3 (5) | C15—N2—N1 | 106.0 (5) |
C21—C16—C17 | 119.8 (6) | C27—N3—C26 | 118.1 (5) |
C21—C16—C15 | 123.3 (6) | C27—N3—Hg1 | 122.5 (4) |
C17—C16—C15 | 116.9 (6) | C26—N3—Hg1 | 119.4 (4) |
C18—C17—C16 | 120.3 (6) | C1—N4—C5 | 118.0 (6) |
C18—C17—H17 | 119.8 | C1—N4—Hg1ii | 119.2 (4) |
C16—C17—H17 | 119.8 | C5—N4—Hg1ii | 122.8 (5) |
C19—C18—C17 | 118.3 (6) | C15—O1—C14 | 103.7 (5) |
C19—C18—C22 | 122.1 (6) | C21—O2—C23 | 118.0 (5) |
C17—C18—C22 | 119.6 (7) | C7—O3—C6 | 118.1 (5) |
C18—C19—C20 | 122.7 (6) | C29—O4—H4A | 109.5 |
N4—C1—C2—C3 | −0.2 (10) | C19—C20—C21—C16 | 1.5 (9) |
C1—C2—C3—C4 | −0.2 (9) | O2—C23—C24—C25 | −4.5 (8) |
C1—C2—C3—C6 | −179.0 (6) | O2—C23—C24—C28 | 177.2 (5) |
C2—C3—C4—C5 | −0.1 (9) | C28—C24—C25—C26 | −0.5 (9) |
C6—C3—C4—C5 | 178.7 (6) | C23—C24—C25—C26 | −178.9 (6) |
C3—C4—C5—N4 | 0.8 (10) | C24—C25—C26—N3 | −0.5 (10) |
C2—C3—C6—O3 | −126.2 (6) | N3—C27—C28—C24 | −1.2 (9) |
C4—C3—C6—O3 | 55.0 (8) | C25—C24—C28—C27 | 1.3 (9) |
O3—C7—C8—C9 | −179.1 (6) | C23—C24—C28—C27 | 179.7 (6) |
C12—C7—C8—C9 | 1.1 (9) | O1—C14—N1—N2 | 0.2 (6) |
C7—C8—C9—C10 | −0.2 (10) | C12—C14—N1—N2 | 179.7 (6) |
C8—C9—C10—C11 | −0.7 (10) | O1—C14—N1—H4A | −166.9 |
C8—C9—C10—C13 | −179.8 (6) | C12—C14—N1—H4A | 12.6 |
C9—C10—C11—C12 | 0.7 (9) | O1—C15—N2—N1 | 0.4 (6) |
C13—C10—C11—C12 | 179.8 (6) | C16—C15—N2—N1 | −179.9 (6) |
C10—C11—C12—C7 | 0.3 (9) | C14—N1—N2—C15 | −0.4 (6) |
C10—C11—C12—C14 | 179.6 (6) | H4A—N1—N2—C15 | 169.7 |
O3—C7—C12—C11 | 179.1 (5) | C28—C27—N3—C26 | 0.2 (9) |
C8—C7—C12—C11 | −1.2 (9) | C28—C27—N3—Hg1 | −179.8 (5) |
O3—C7—C12—C14 | −0.3 (8) | C25—C26—N3—C27 | 0.6 (9) |
C8—C7—C12—C14 | 179.5 (5) | C25—C26—N3—Hg1 | −179.3 (5) |
C11—C12—C14—N1 | 177.6 (6) | N4i—Hg1—N3—C27 | 82.2 (5) |
C7—C12—C14—N1 | −3.1 (10) | Br2—Hg1—N3—C27 | −26.0 (5) |
C11—C12—C14—O1 | −2.9 (8) | Br1—Hg1—N3—C27 | −178.7 (4) |
C7—C12—C14—O1 | 176.4 (5) | N4i—Hg1—N3—C26 | −97.8 (5) |
N2—C15—C16—C21 | 4.2 (10) | Br2—Hg1—N3—C26 | 154.0 (4) |
O1—C15—C16—C21 | −176.2 (5) | Br1—Hg1—N3—C26 | 1.3 (5) |
N2—C15—C16—C17 | −173.6 (6) | C2—C1—N4—C5 | 0.8 (9) |
O1—C15—C16—C17 | 6.1 (8) | C2—C1—N4—Hg1ii | −177.7 (5) |
C21—C16—C17—C18 | 0.2 (9) | C4—C5—N4—C1 | −1.1 (10) |
C15—C16—C17—C18 | 178.1 (5) | C4—C5—N4—Hg1ii | 177.4 (5) |
C16—C17—C18—C19 | −0.3 (9) | N2—C15—O1—C14 | −0.3 (6) |
C16—C17—C18—C22 | −179.1 (6) | C16—C15—O1—C14 | 179.9 (5) |
C17—C18—C19—C20 | 0.9 (10) | N1—C14—O1—C15 | 0.1 (6) |
C22—C18—C19—C20 | 179.8 (6) | C12—C14—O1—C15 | −179.5 (5) |
C18—C19—C20—C21 | −1.5 (10) | C16—C21—O2—C23 | 179.7 (5) |
C17—C16—C21—O2 | −179.0 (5) | C20—C21—O2—C23 | 1.6 (8) |
C15—C16—C21—O2 | 3.3 (9) | C24—C23—O2—C21 | 174.8 (5) |
C17—C16—C21—C20 | −0.8 (9) | C8—C7—O3—C6 | 9.6 (9) |
C15—C16—C21—C20 | −178.5 (5) | C12—C7—O3—C6 | −170.6 (5) |
C19—C20—C21—O2 | 179.5 (6) | C3—C6—O3—C7 | 76.8 (7) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···N1 | 0.84 | 2.04 | 2.865 (7) | 167 |
O4—H4A···O3 | 0.84 | 2.34 | 2.818 (6) | 116 |
[Hg2I2(C28H24N4O3)]·CH4O | Z = 2 |
Mr = 950.94 | F(000) = 896 |
Triclinic, P1 | Dx = 2.070 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.046 (3) Å | Cell parameters from 2168 reflections |
b = 13.153 (4) Å | θ = 2.4–22.1° |
c = 13.213 (4) Å | µ = 7.11 mm−1 |
α = 95.975 (4)° | T = 298 K |
β = 99.503 (4)° | Block, colourless |
γ = 97.271 (4)° | 0.21 × 0.10 × 0.04 mm |
V = 1525.4 (7) Å3 |
Bruker SMART CCD area-detector diffractometer | 5543 independent reflections |
Radiation source: fine-focus sealed tube | 4328 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 25.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→9 |
Tmin = 0.317, Tmax = 0.764 | k = −15→15 |
8032 measured reflections | l = −15→15 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0321P)2] where P = (Fo2 + 2Fc2)/3 |
5543 reflections | (Δ/σ)max = 0.001 |
363 parameters | Δρmax = 1.29 e Å−3 |
0 restraints | Δρmin = −1.03 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.61915 (7) | 0.49150 (5) | 1.26739 (4) | 0.0630 (2) | |
I2 | 0.18974 (7) | 0.32120 (5) | 1.41435 (5) | 0.0632 (2) | |
C1 | 0.7947 (10) | 0.3845 (6) | 0.5172 (6) | 0.051 (2) | |
H1 | 0.8208 | 0.4133 | 0.4601 | 0.061* | |
C2 | 0.9079 (9) | 0.3810 (6) | 0.5982 (6) | 0.047 (2) | |
H2 | 1.0067 | 0.4093 | 0.5961 | 0.056* | |
C3 | 0.8762 (9) | 0.3354 (5) | 0.6838 (5) | 0.0365 (17) | |
C4 | 0.7253 (10) | 0.2986 (7) | 0.6803 (6) | 0.054 (2) | |
H4 | 0.6966 | 0.2674 | 0.7354 | 0.064* | |
C5 | 0.6173 (10) | 0.3071 (7) | 0.5973 (7) | 0.057 (2) | |
H5 | 0.5168 | 0.2822 | 0.5985 | 0.068* | |
C6 | 0.9958 (9) | 0.3286 (5) | 0.7746 (6) | 0.0411 (18) | |
H6A | 1.0948 | 0.3502 | 0.7584 | 0.049* | |
H6B | 0.9829 | 0.3751 | 0.8334 | 0.049* | |
C7 | 1.0385 (8) | 0.1541 (6) | 0.7407 (5) | 0.0376 (17) | |
C8 | 1.1214 (9) | 0.1734 (6) | 0.6628 (6) | 0.048 (2) | |
H8 | 1.1465 | 0.2410 | 0.6497 | 0.058* | |
C9 | 1.1663 (9) | 0.0935 (7) | 0.6051 (6) | 0.048 (2) | |
H9 | 1.2195 | 0.1085 | 0.5526 | 0.058* | |
C10 | 1.1349 (9) | −0.0082 (6) | 0.6225 (6) | 0.0457 (19) | |
C11 | 1.0557 (8) | −0.0266 (6) | 0.6999 (6) | 0.0422 (18) | |
H11 | 1.0330 | −0.0946 | 0.7124 | 0.051* | |
C12 | 1.0066 (8) | 0.0514 (6) | 0.7619 (5) | 0.0346 (16) | |
C13 | 1.1848 (9) | −0.0928 (7) | 0.5577 (7) | 0.058 (2) | |
H13A | 1.2070 | −0.0685 | 0.4950 | 0.087* | |
H13B | 1.1056 | −0.1509 | 0.5411 | 0.087* | |
H13C | 1.2741 | −0.1132 | 0.5953 | 0.087* | |
C14 | 0.9234 (8) | 0.0248 (6) | 0.8431 (5) | 0.0365 (17) | |
C15 | 0.8129 (8) | −0.0765 (6) | 0.9323 (5) | 0.0373 (17) | |
C16 | 0.7627 (8) | −0.1785 (5) | 0.9614 (6) | 0.0367 (17) | |
C17 | 0.8060 (9) | −0.2658 (6) | 0.9131 (6) | 0.0404 (18) | |
H17 | 0.8660 | −0.2580 | 0.8629 | 0.048* | |
C18 | 0.7629 (10) | −0.3645 (6) | 0.9369 (6) | 0.051 (2) | |
C19 | 0.6741 (10) | −0.3730 (6) | 1.0119 (6) | 0.052 (2) | |
H19 | 0.6445 | −0.4379 | 1.0300 | 0.062* | |
C20 | 0.6276 (10) | −0.2873 (6) | 1.0611 (6) | 0.047 (2) | |
H20 | 0.5660 | −0.2959 | 1.1103 | 0.056* | |
C21 | 0.6720 (8) | −0.1892 (6) | 1.0376 (5) | 0.0382 (17) | |
C22 | 0.8147 (11) | −0.4571 (6) | 0.8852 (7) | 0.064 (3) | |
H22A | 0.8127 | −0.4502 | 0.8133 | 0.097* | |
H22B | 0.7486 | −0.5184 | 0.8913 | 0.097* | |
H22C | 0.9162 | −0.4620 | 0.9177 | 0.097* | |
C23 | 0.5409 (9) | −0.1098 (6) | 1.1592 (6) | 0.0452 (19) | |
H23A | 0.5893 | −0.1449 | 1.2137 | 0.054* | |
H23B | 0.4428 | −0.1498 | 1.1296 | 0.054* | |
C24 | 0.5211 (8) | −0.0040 (6) | 1.2025 (5) | 0.0379 (17) | |
C25 | 0.5888 (8) | 0.0846 (6) | 1.1707 (6) | 0.0420 (19) | |
H25 | 0.6470 | 0.0803 | 1.1191 | 0.050* | |
C26 | 0.5680 (9) | 0.1800 (6) | 1.2176 (6) | 0.050 (2) | |
H26 | 0.6147 | 0.2392 | 1.1964 | 0.059* | |
C27 | 0.4177 (9) | 0.1065 (7) | 1.3184 (6) | 0.048 (2) | |
H27 | 0.3562 | 0.1137 | 1.3679 | 0.057* | |
C28 | 0.4329 (9) | 0.0080 (6) | 1.2783 (6) | 0.045 (2) | |
H28 | 0.3849 | −0.0494 | 1.3017 | 0.054* | |
C29 | 0.7829 (13) | 0.3011 (9) | 1.0450 (8) | 0.085 (3) | |
H29A | 0.8807 | 0.3149 | 1.0892 | 0.127* | |
H29B | 0.7276 | 0.2389 | 1.0600 | 0.127* | |
H29C | 0.7281 | 0.3577 | 1.0570 | 0.127* | |
Hg1 | 0.46045 (4) | 0.36330 (2) | 1.36488 (2) | 0.04805 (13) | |
N1 | 0.8711 (7) | 0.0824 (5) | 0.9092 (4) | 0.0398 (15) | |
N2 | 0.7993 (7) | 0.0144 (4) | 0.9691 (5) | 0.0399 (15) | |
N3 | 0.4857 (8) | 0.1912 (5) | 1.2903 (5) | 0.0458 (16) | |
N4 | 0.6496 (7) | 0.3496 (5) | 0.5145 (5) | 0.0419 (15) | |
O1 | 0.8913 (5) | −0.0780 (4) | 0.8520 (4) | 0.0383 (12) | |
O2 | 0.6315 (6) | −0.1014 (4) | 1.0818 (4) | 0.0497 (14) | |
O3 | 0.9883 (6) | 0.2256 (4) | 0.8012 (4) | 0.0418 (12) | |
O4 | 0.8009 (10) | 0.2893 (5) | 0.9428 (5) | 0.083 (2) | |
H4A | 0.8363 | 0.2359 | 0.9303 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0726 (4) | 0.0573 (4) | 0.0576 (4) | −0.0073 (3) | 0.0144 (3) | 0.0171 (3) |
I2 | 0.0629 (4) | 0.0592 (4) | 0.0738 (4) | 0.0087 (3) | 0.0341 (3) | 0.0030 (3) |
C1 | 0.059 (6) | 0.053 (6) | 0.047 (5) | 0.012 (4) | 0.020 (4) | 0.016 (4) |
C2 | 0.049 (5) | 0.043 (5) | 0.053 (5) | 0.012 (4) | 0.013 (4) | 0.014 (4) |
C3 | 0.052 (5) | 0.025 (4) | 0.036 (4) | 0.012 (3) | 0.014 (4) | 0.007 (3) |
C4 | 0.051 (5) | 0.065 (6) | 0.049 (5) | 0.007 (4) | 0.011 (4) | 0.021 (4) |
C5 | 0.045 (5) | 0.066 (6) | 0.058 (6) | −0.001 (4) | 0.009 (4) | 0.014 (5) |
C6 | 0.052 (5) | 0.027 (4) | 0.046 (4) | 0.012 (3) | 0.010 (4) | 0.007 (3) |
C7 | 0.034 (4) | 0.042 (5) | 0.039 (4) | 0.015 (3) | 0.005 (3) | 0.006 (3) |
C8 | 0.044 (5) | 0.046 (5) | 0.060 (5) | 0.010 (4) | 0.019 (4) | 0.011 (4) |
C9 | 0.040 (5) | 0.064 (6) | 0.045 (5) | 0.017 (4) | 0.014 (4) | 0.011 (4) |
C10 | 0.040 (5) | 0.045 (5) | 0.049 (5) | 0.013 (4) | 0.001 (4) | −0.005 (4) |
C11 | 0.036 (4) | 0.040 (5) | 0.048 (5) | 0.011 (3) | 0.000 (4) | 0.001 (4) |
C12 | 0.033 (4) | 0.035 (4) | 0.034 (4) | 0.011 (3) | 0.000 (3) | 0.000 (3) |
C13 | 0.050 (5) | 0.062 (6) | 0.063 (6) | 0.021 (4) | 0.013 (4) | −0.009 (4) |
C14 | 0.043 (4) | 0.030 (4) | 0.035 (4) | 0.008 (3) | 0.001 (3) | 0.008 (3) |
C15 | 0.036 (4) | 0.035 (5) | 0.039 (4) | 0.006 (3) | 0.002 (3) | 0.007 (3) |
C16 | 0.032 (4) | 0.028 (4) | 0.046 (4) | 0.005 (3) | −0.002 (3) | 0.003 (3) |
C17 | 0.047 (5) | 0.035 (5) | 0.045 (4) | 0.020 (3) | 0.008 (4) | 0.011 (3) |
C18 | 0.062 (6) | 0.034 (5) | 0.055 (5) | 0.013 (4) | 0.000 (4) | 0.003 (4) |
C19 | 0.064 (6) | 0.033 (5) | 0.058 (5) | 0.006 (4) | 0.007 (4) | 0.012 (4) |
C20 | 0.061 (5) | 0.033 (5) | 0.045 (5) | 0.006 (4) | 0.007 (4) | 0.007 (4) |
C21 | 0.037 (4) | 0.039 (5) | 0.036 (4) | 0.008 (3) | 0.001 (3) | 0.000 (3) |
C22 | 0.082 (7) | 0.027 (5) | 0.084 (7) | 0.016 (4) | 0.012 (6) | −0.001 (4) |
C23 | 0.045 (5) | 0.044 (5) | 0.045 (5) | 0.005 (4) | 0.007 (4) | 0.003 (4) |
C24 | 0.046 (4) | 0.030 (4) | 0.037 (4) | 0.009 (3) | 0.003 (3) | 0.003 (3) |
C25 | 0.047 (5) | 0.035 (5) | 0.048 (5) | 0.010 (4) | 0.017 (4) | 0.004 (4) |
C26 | 0.060 (5) | 0.035 (5) | 0.060 (5) | 0.006 (4) | 0.029 (4) | 0.006 (4) |
C27 | 0.043 (5) | 0.053 (6) | 0.051 (5) | 0.007 (4) | 0.018 (4) | 0.004 (4) |
C28 | 0.049 (5) | 0.042 (5) | 0.043 (4) | 0.000 (4) | 0.010 (4) | 0.009 (4) |
C29 | 0.087 (8) | 0.087 (9) | 0.086 (8) | 0.013 (6) | 0.040 (7) | −0.001 (6) |
Hg1 | 0.0548 (2) | 0.0410 (2) | 0.0514 (2) | 0.00717 (15) | 0.01765 (15) | 0.00725 (14) |
N1 | 0.052 (4) | 0.028 (4) | 0.038 (3) | 0.006 (3) | 0.005 (3) | 0.001 (3) |
N2 | 0.056 (4) | 0.022 (3) | 0.046 (4) | 0.013 (3) | 0.014 (3) | 0.008 (3) |
N3 | 0.059 (4) | 0.034 (4) | 0.047 (4) | 0.007 (3) | 0.021 (3) | 0.002 (3) |
N4 | 0.046 (4) | 0.039 (4) | 0.042 (4) | 0.009 (3) | 0.011 (3) | 0.004 (3) |
O1 | 0.044 (3) | 0.026 (3) | 0.045 (3) | 0.008 (2) | 0.007 (2) | 0.003 (2) |
O2 | 0.064 (4) | 0.034 (3) | 0.058 (3) | 0.012 (3) | 0.026 (3) | 0.005 (3) |
O3 | 0.056 (3) | 0.031 (3) | 0.043 (3) | 0.011 (2) | 0.016 (3) | 0.010 (2) |
O4 | 0.136 (7) | 0.055 (5) | 0.080 (5) | 0.040 (4) | 0.061 (5) | 0.018 (3) |
I1—Hg1 | 2.6482 (7) | C16—C21 | 1.406 (10) |
I2—Hg1 | 2.6440 (9) | C17—C18 | 1.390 (10) |
C1—N4 | 1.328 (10) | C17—H17 | 0.9300 |
C1—C2 | 1.362 (11) | C18—C19 | 1.379 (11) |
C1—H1 | 0.9300 | C18—C22 | 1.500 (11) |
C2—C3 | 1.388 (10) | C19—C20 | 1.389 (11) |
C2—H2 | 0.9300 | C19—H19 | 0.9300 |
C3—C4 | 1.380 (11) | C20—C21 | 1.385 (10) |
C3—C6 | 1.495 (10) | C20—H20 | 0.9300 |
C4—C5 | 1.367 (12) | C21—O2 | 1.358 (9) |
C4—H4 | 0.9300 | C22—H22A | 0.9600 |
C5—N4 | 1.337 (10) | C22—H22B | 0.9600 |
C5—H5 | 0.9300 | C22—H22C | 0.9600 |
C6—O3 | 1.431 (8) | C23—O2 | 1.417 (8) |
C6—H6A | 0.9700 | C23—C24 | 1.492 (10) |
C6—H6B | 0.9700 | C23—H23A | 0.9700 |
C7—O3 | 1.343 (8) | C23—H23B | 0.9700 |
C7—C8 | 1.395 (10) | C24—C25 | 1.384 (10) |
C7—C12 | 1.411 (10) | C24—C28 | 1.388 (10) |
C8—C9 | 1.376 (11) | C25—C26 | 1.389 (10) |
C8—H8 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.384 (11) | C26—N3 | 1.317 (9) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.367 (10) | C27—N3 | 1.321 (10) |
C10—C13 | 1.493 (10) | C27—C28 | 1.380 (11) |
C11—C12 | 1.407 (10) | C27—H27 | 0.9300 |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
C12—C14 | 1.456 (9) | C29—O4 | 1.383 (10) |
C13—H13A | 0.9600 | C29—H29A | 0.9600 |
C13—H13B | 0.9600 | C29—H29B | 0.9600 |
C13—H13C | 0.9600 | C29—H29C | 0.9600 |
C14—N1 | 1.285 (9) | Hg1—N3 | 2.427 (6) |
C14—O1 | 1.368 (8) | Hg1—N4i | 2.429 (6) |
C15—N2 | 1.272 (9) | N1—N2 | 1.421 (8) |
C15—O1 | 1.370 (8) | N4—Hg1ii | 2.429 (6) |
C15—C16 | 1.472 (10) | O4—H4A | 0.8200 |
C16—C17 | 1.387 (10) | ||
N4—C1—C2 | 124.4 (7) | C18—C19—H19 | 119.1 |
N4—C1—H1 | 117.8 | C20—C19—H19 | 119.1 |
C2—C1—H1 | 117.8 | C21—C20—C19 | 120.6 (8) |
C1—C2—C3 | 120.2 (7) | C21—C20—H20 | 119.7 |
C1—C2—H2 | 119.9 | C19—C20—H20 | 119.7 |
C3—C2—H2 | 119.9 | O2—C21—C20 | 124.4 (7) |
C4—C3—C2 | 115.1 (7) | O2—C21—C16 | 117.0 (6) |
C4—C3—C6 | 122.2 (6) | C20—C21—C16 | 118.5 (7) |
C2—C3—C6 | 122.6 (7) | C18—C22—H22A | 109.5 |
C5—C4—C3 | 121.3 (7) | C18—C22—H22B | 109.5 |
C5—C4—H4 | 119.3 | H22A—C22—H22B | 109.5 |
C3—C4—H4 | 119.3 | C18—C22—H22C | 109.5 |
N4—C5—C4 | 123.0 (8) | H22A—C22—H22C | 109.5 |
N4—C5—H5 | 118.5 | H22B—C22—H22C | 109.5 |
C4—C5—H5 | 118.5 | O2—C23—C24 | 109.0 (6) |
O3—C6—C3 | 111.3 (6) | O2—C23—H23A | 109.9 |
O3—C6—H6A | 109.4 | C24—C23—H23A | 109.9 |
C3—C6—H6A | 109.4 | O2—C23—H23B | 109.9 |
O3—C6—H6B | 109.4 | C24—C23—H23B | 109.9 |
C3—C6—H6B | 109.4 | H23A—C23—H23B | 108.3 |
H6A—C6—H6B | 108.0 | C25—C24—C28 | 117.6 (7) |
O3—C7—C8 | 125.8 (7) | C25—C24—C23 | 122.5 (7) |
O3—C7—C12 | 115.5 (6) | C28—C24—C23 | 119.9 (7) |
C8—C7—C12 | 118.7 (7) | C24—C25—C26 | 118.7 (7) |
C9—C8—C7 | 120.7 (8) | C24—C25—H25 | 120.7 |
C9—C8—H8 | 119.7 | C26—C25—H25 | 120.7 |
C7—C8—H8 | 119.7 | N3—C26—C25 | 123.6 (7) |
C8—C9—C10 | 122.2 (7) | N3—C26—H26 | 118.2 |
C8—C9—H9 | 118.9 | C25—C26—H26 | 118.2 |
C10—C9—H9 | 118.9 | N3—C27—C28 | 123.5 (7) |
C11—C10—C9 | 116.9 (7) | N3—C27—H27 | 118.3 |
C11—C10—C13 | 122.6 (8) | C28—C27—H27 | 118.3 |
C9—C10—C13 | 120.5 (8) | C27—C28—C24 | 119.0 (7) |
C10—C11—C12 | 123.8 (7) | C27—C28—H28 | 120.5 |
C10—C11—H11 | 118.1 | C24—C28—H28 | 120.5 |
C12—C11—H11 | 118.1 | O4—C29—H29A | 109.5 |
C11—C12—C7 | 117.7 (7) | O4—C29—H29B | 109.5 |
C11—C12—C14 | 120.1 (7) | H29A—C29—H29B | 109.5 |
C7—C12—C14 | 122.2 (6) | O4—C29—H29C | 109.5 |
C10—C13—H13A | 109.5 | H29A—C29—H29C | 109.5 |
C10—C13—H13B | 109.5 | H29B—C29—H29C | 109.5 |
H13A—C13—H13B | 109.5 | N3—Hg1—N4i | 90.0 (2) |
C10—C13—H13C | 109.5 | N3—Hg1—I2 | 98.62 (15) |
H13A—C13—H13C | 109.5 | N4i—Hg1—I2 | 108.08 (14) |
H13B—C13—H13C | 109.5 | N3—Hg1—I1 | 105.39 (14) |
N1—C14—O1 | 112.5 (6) | N4i—Hg1—I1 | 100.77 (14) |
N1—C14—C12 | 130.7 (7) | I2—Hg1—I1 | 142.20 (3) |
O1—C14—C12 | 116.8 (6) | C14—N1—N2 | 106.0 (6) |
N2—C15—O1 | 113.0 (6) | C14—N1—H4A | 136.4 |
N2—C15—C16 | 131.9 (7) | N2—N1—H4A | 116.5 |
O1—C15—C16 | 115.2 (6) | C15—N2—N1 | 106.2 (6) |
C17—C16—C21 | 119.4 (7) | C26—N3—C27 | 117.6 (7) |
C17—C16—C15 | 119.4 (7) | C26—N3—Hg1 | 119.7 (5) |
C21—C16—C15 | 121.3 (7) | C27—N3—Hg1 | 122.6 (5) |
C16—C17—C18 | 122.4 (7) | C1—N4—C5 | 115.9 (7) |
C16—C17—H17 | 118.8 | C1—N4—Hg1ii | 120.4 (5) |
C18—C17—H17 | 118.8 | C5—N4—Hg1ii | 123.7 (5) |
C19—C18—C17 | 117.2 (8) | C14—O1—C15 | 102.3 (5) |
C19—C18—C22 | 121.7 (8) | C21—O2—C23 | 118.2 (6) |
C17—C18—C22 | 121.2 (8) | C7—O3—C6 | 118.6 (6) |
C18—C19—C20 | 121.9 (7) | C29—O4—H4A | 109.5 |
N4—C1—C2—C3 | 2.4 (13) | C15—C16—C21—C20 | 179.6 (7) |
C1—C2—C3—C4 | −1.8 (12) | O2—C23—C24—C25 | −2.1 (10) |
C1—C2—C3—C6 | 179.5 (7) | O2—C23—C24—C28 | 178.4 (7) |
C2—C3—C4—C5 | 0.2 (12) | C28—C24—C25—C26 | 1.4 (11) |
C6—C3—C4—C5 | 178.9 (8) | C23—C24—C25—C26 | −178.0 (7) |
C3—C4—C5—N4 | 1.0 (14) | C24—C25—C26—N3 | −0.7 (13) |
C4—C3—C6—O3 | 51.6 (10) | N3—C27—C28—C24 | −1.6 (13) |
C2—C3—C6—O3 | −129.8 (7) | C25—C24—C28—C27 | −0.4 (11) |
O3—C7—C8—C9 | −179.6 (7) | C23—C24—C28—C27 | 179.1 (7) |
C12—C7—C8—C9 | 2.4 (12) | O1—C14—N1—N2 | 0.8 (8) |
C7—C8—C9—C10 | −1.4 (13) | C12—C14—N1—N2 | 179.7 (7) |
C8—C9—C10—C11 | 0.4 (12) | O1—C14—N1—H4A | −166.5 |
C8—C9—C10—C13 | 179.7 (8) | C12—C14—N1—H4A | 12.4 |
C9—C10—C11—C12 | −0.4 (11) | O1—C15—N2—N1 | 1.0 (8) |
C13—C10—C11—C12 | −179.7 (7) | C16—C15—N2—N1 | 179.8 (7) |
C10—C11—C12—C7 | 1.5 (11) | C14—N1—N2—C15 | −1.1 (8) |
C10—C11—C12—C14 | −179.7 (7) | H4A—N1—N2—C15 | 169.1 |
O3—C7—C12—C11 | 179.4 (6) | C25—C26—N3—C27 | −1.2 (13) |
C8—C7—C12—C11 | −2.4 (10) | C25—C26—N3—Hg1 | 179.9 (6) |
O3—C7—C12—C14 | 0.6 (10) | C28—C27—N3—C26 | 2.4 (13) |
C8—C7—C12—C14 | 178.8 (7) | C28—C27—N3—Hg1 | −178.7 (6) |
C11—C12—C14—N1 | 178.4 (7) | N4i—Hg1—N3—C26 | −100.6 (7) |
C7—C12—C14—N1 | −2.8 (12) | I2—Hg1—N3—C26 | 151.1 (6) |
C11—C12—C14—O1 | −2.7 (10) | I1—Hg1—N3—C26 | 0.6 (7) |
C7—C12—C14—O1 | 176.0 (6) | N4i—Hg1—N3—C27 | 80.6 (7) |
N2—C15—C16—C17 | −174.0 (8) | I2—Hg1—N3—C27 | −27.7 (7) |
O1—C15—C16—C17 | 4.7 (10) | I1—Hg1—N3—C27 | −178.2 (6) |
N2—C15—C16—C21 | 5.8 (13) | C2—C1—N4—C5 | −1.2 (12) |
O1—C15—C16—C21 | −175.4 (6) | C2—C1—N4—Hg1ii | 179.3 (6) |
C21—C16—C17—C18 | 0.0 (11) | C4—C5—N4—C1 | −0.5 (13) |
C15—C16—C17—C18 | 179.9 (7) | C4—C5—N4—Hg1ii | 179.0 (7) |
C16—C17—C18—C19 | −0.1 (12) | N1—C14—O1—C15 | −0.2 (8) |
C16—C17—C18—C22 | −178.4 (8) | C12—C14—O1—C15 | −179.3 (6) |
C17—C18—C19—C20 | 0.7 (13) | N2—C15—O1—C14 | −0.5 (8) |
C22—C18—C19—C20 | 179.1 (8) | C16—C15—O1—C14 | −179.5 (6) |
C18—C19—C20—C21 | −1.3 (13) | C20—C21—O2—C23 | 1.7 (11) |
C19—C20—C21—O2 | 179.9 (7) | C16—C21—O2—C23 | −179.6 (6) |
C19—C20—C21—C16 | 1.2 (12) | C24—C23—O2—C21 | 175.4 (6) |
C17—C16—C21—O2 | −179.3 (7) | C8—C7—O3—C6 | 11.3 (11) |
C15—C16—C21—O2 | 0.8 (10) | C12—C7—O3—C6 | −170.6 (6) |
C17—C16—C21—C20 | −0.6 (11) | C3—C6—O3—C7 | 74.6 (8) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···N1 | 0.82 | 2.08 | 2.878 (9) | 164 |
O4—H4A···O3 | 0.82 | 2.36 | 2.855 (8) | 119 |