




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808033138/hy2157sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808033138/hy2157Isup2.hkl |
CCDC reference: 709531
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.012 Å
- R factor = 0.085
- wR factor = 0.185
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.158 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O11
Alert level C Value of measurement temperature given = 293.000 Value of melting point given = 0.000 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd1 -- O12 .. 9.85 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O12 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cd1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C45 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1N ... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_4_G Check the Absolute Configuration of N1 ..... R PLAT793_ALERT_4_G Check the Absolute Configuration of N2 ..... S PLAT793_ALERT_4_G Check the Absolute Configuration of N3 ..... S PLAT793_ALERT_4_G Check the Absolute Configuration of N4 ..... R
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 14 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of Cd(OH)2 (0.146 g, 1 mmol), benzene-1,3-dicarboxylic acid (0.162 g, 1 mmol) and 3,4:9,10:17,18:23,24-tetrabenzo-1,12,15,26-tetraaza-5,8,19,22- tetraoxacyclooctacosane (0.596 g, 1 mmol) in EtOH (10 ml) was placed in a 20 ml Teflon-lined reactor and heated at 393 K for 3 d. After the reactor was gradually cooled to room temperature at a rate of 10 K h-1, colorless crystals were obtained.
H atoms bound to C atoms were positioned geometrically and refined as riding, with C—H = 0.93 (CH) and 0.97 Å (CH2) and with Uiso(H) = 1.2Ueq(C). H atoms bound to N and O atoms were located in a difference Fourier map and refined with restraints of N—H = 0.84 (2) and O—H = 0.86 (2) Å and with Uiso(H) = 1.2Ueq(N) or Uiso(H) = 1.5Ueq(O).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
[Cd(C8H4O4)(C36H44N4O4)]·C8H6O4 | F(000) = 2152 |
Mr = 1039.39 | Dx = 1.464 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 10582 reflections |
a = 12.912 (3) Å | θ = 3.1–27.5° |
b = 23.330 (5) Å | µ = 0.53 mm−1 |
c = 16.086 (3) Å | T = 293 K |
β = 103.37 (3)° | Block, colourless |
V = 4714.4 (18) Å3 | 0.34 × 0.29 × 0.21 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 10582 independent reflections |
Radiation source: 18 kW rotation anode | 4951 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.158 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→15 |
Tmin = 0.842, Tmax = 0.913 | k = −30→30 |
43452 measured reflections | l = −20→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)] = 0.085 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0557P)2 + 6.3548P] where P = (Fo2 + 2Fc2)/3 |
10582 reflections | (Δ/σ)max = 0.001 |
640 parameters | Δρmax = 0.68 e Å−3 |
9 restraints | Δρmin = −0.71 e Å−3 |
[Cd(C8H4O4)(C36H44N4O4)]·C8H6O4 | V = 4714.4 (18) Å3 |
Mr = 1039.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.912 (3) Å | µ = 0.53 mm−1 |
b = 23.330 (5) Å | T = 293 K |
c = 16.086 (3) Å | 0.34 × 0.29 × 0.21 mm |
β = 103.37 (3)° |
Rigaku R-AXIS RAPID diffractometer | 10582 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4951 reflections with I > 2σ(I) |
Tmin = 0.842, Tmax = 0.913 | Rint = 0.158 |
43452 measured reflections |
R[F2 > 2σ(F2)] = 0.085 | 9 restraints |
wR(F2) = 0.185 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.68 e Å−3 |
10582 reflections | Δρmin = −0.71 e Å−3 |
640 parameters |
Refinement. The crystal quality is not fine and weakly diffracting, so that the value of R(int) is greater than 0.15. |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.82429 (4) | 0.70844 (2) | 0.68005 (3) | 0.04757 (17) | |
C1 | 0.7605 (6) | 0.6571 (3) | 0.9444 (4) | 0.060 (2) | |
C2 | 0.6668 (8) | 0.6673 (4) | 0.9702 (6) | 0.090 (3) | |
H2 | 0.6228 | 0.6975 | 0.9463 | 0.108* | |
C3 | 0.6387 (9) | 0.6330 (7) | 1.0308 (7) | 0.126 (5) | |
H3 | 0.5769 | 0.6406 | 1.0492 | 0.151* | |
C4 | 0.7012 (12) | 0.5884 (6) | 1.0634 (6) | 0.122 (5) | |
H4 | 0.6794 | 0.5639 | 1.1016 | 0.147* | |
C5 | 0.7954 (11) | 0.5784 (5) | 1.0419 (6) | 0.109 (4) | |
H5 | 0.8402 | 0.5490 | 1.0675 | 0.131* | |
C6 | 0.8223 (8) | 0.6133 (4) | 0.9807 (5) | 0.074 (2) | |
C7 | 1.0047 (8) | 0.5921 (5) | 1.0100 (6) | 0.116 (4) | |
H7A | 0.9959 | 0.5561 | 1.0378 | 0.140* | |
H7B | 1.0177 | 0.6217 | 1.0535 | 0.140* | |
C8 | 1.1002 (8) | 0.5876 (5) | 0.9714 (7) | 0.116 (4) | |
H8A | 1.1646 | 0.5853 | 1.0165 | 0.140* | |
H8B | 1.0951 | 0.5532 | 0.9370 | 0.140* | |
C9 | 1.1934 (7) | 0.6434 (4) | 0.8896 (6) | 0.088 (3) | |
C10 | 1.2900 (8) | 0.6155 (5) | 0.9199 (6) | 0.115 (4) | |
H10 | 1.2977 | 0.5887 | 0.9636 | 0.138* | |
C11 | 1.3740 (9) | 0.6284 (6) | 0.8837 (9) | 0.125 (5) | |
H11 | 1.4389 | 0.6099 | 0.9030 | 0.150* | |
C12 | 1.3626 (8) | 0.6679 (5) | 0.8201 (9) | 0.118 (4) | |
H12 | 1.4198 | 0.6770 | 0.7964 | 0.142* | |
C13 | 1.2657 (7) | 0.6944 (4) | 0.7910 (6) | 0.090 (3) | |
H13 | 1.2587 | 0.7213 | 0.7474 | 0.108* | |
C14 | 1.1804 (6) | 0.6827 (3) | 0.8234 (5) | 0.068 (2) | |
C15 | 1.0722 (5) | 0.7088 (3) | 0.7890 (4) | 0.0609 (18) | |
H15A | 1.0460 | 0.7242 | 0.8363 | 0.073* | |
H15B | 1.0793 | 0.7405 | 0.7516 | 0.073* | |
C16 | 1.0233 (7) | 0.6366 (4) | 0.6768 (5) | 0.112 (4) | |
H16A | 0.9934 | 0.5984 | 0.6763 | 0.134* | |
H16B | 1.1002 | 0.6326 | 0.6917 | 0.134* | |
C17 | 0.9913 (7) | 0.6604 (5) | 0.5876 (5) | 0.109 (4) | |
H17A | 1.0314 | 0.6952 | 0.5845 | 0.131* | |
H17B | 1.0097 | 0.6329 | 0.5480 | 0.131* | |
C18 | 0.8618 (6) | 0.7140 (3) | 0.4908 (4) | 0.0618 (19) | |
H18A | 0.9104 | 0.7459 | 0.5070 | 0.074* | |
H18B | 0.7899 | 0.7289 | 0.4809 | 0.074* | |
C19 | 0.8784 (6) | 0.6886 (3) | 0.4090 (4) | 0.060 (2) | |
C20 | 0.9703 (7) | 0.6970 (4) | 0.3810 (5) | 0.078 (2) | |
H20 | 1.0252 | 0.7175 | 0.4161 | 0.094* | |
C21 | 0.9863 (8) | 0.6769 (4) | 0.3043 (6) | 0.088 (3) | |
H21 | 1.0501 | 0.6830 | 0.2882 | 0.106* | |
C22 | 0.9040 (9) | 0.6474 (4) | 0.2527 (5) | 0.089 (3) | |
H22 | 0.9115 | 0.6337 | 0.2001 | 0.107* | |
C23 | 0.8087 (8) | 0.6377 (4) | 0.2782 (5) | 0.079 (3) | |
H23 | 0.7531 | 0.6180 | 0.2426 | 0.095* | |
C24 | 0.7984 (6) | 0.6576 (3) | 0.3560 (4) | 0.061 (2) | |
C25 | 0.6174 (6) | 0.6254 (3) | 0.3339 (5) | 0.069 (2) | |
H25A | 0.6326 | 0.5885 | 0.3115 | 0.083* | |
H25B | 0.5930 | 0.6513 | 0.2862 | 0.083* | |
C26 | 0.5341 (6) | 0.6190 (3) | 0.3835 (5) | 0.071 (2) | |
H26A | 0.4684 | 0.6056 | 0.3463 | 0.085* | |
H26B | 0.5567 | 0.5910 | 0.4286 | 0.085* | |
C27 | 0.4366 (6) | 0.6752 (3) | 0.4613 (5) | 0.062 (2) | |
C28 | 0.3364 (6) | 0.6499 (3) | 0.4314 (5) | 0.071 (2) | |
H28 | 0.3222 | 0.6279 | 0.3819 | 0.086* | |
C29 | 0.2600 (6) | 0.6585 (4) | 0.4766 (7) | 0.088 (3) | |
H29 | 0.1943 | 0.6406 | 0.4583 | 0.105* | |
C30 | 0.2770 (7) | 0.6917 (4) | 0.5464 (7) | 0.095 (3) | |
H30 | 0.2229 | 0.6979 | 0.5747 | 0.115* | |
C31 | 0.3760 (7) | 0.7167 (4) | 0.5760 (5) | 0.080 (3) | |
H31 | 0.3876 | 0.7399 | 0.6242 | 0.096* | |
C32 | 0.4574 (6) | 0.7078 (3) | 0.5354 (4) | 0.0611 (19) | |
C33 | 0.5690 (5) | 0.7290 (3) | 0.5729 (4) | 0.061 (2) | |
H33A | 0.5943 | 0.7499 | 0.5293 | 0.073* | |
H33B | 0.5674 | 0.7554 | 0.6191 | 0.073* | |
C34 | 0.6087 (6) | 0.6435 (3) | 0.6662 (4) | 0.064 (2) | |
H34A | 0.6400 | 0.6059 | 0.6645 | 0.077* | |
H34B | 0.5319 | 0.6394 | 0.6492 | 0.077* | |
C35 | 0.6395 (5) | 0.6666 (3) | 0.7562 (4) | 0.0595 (19) | |
H35A | 0.6105 | 0.7049 | 0.7574 | 0.071* | |
H35B | 0.6090 | 0.6425 | 0.7934 | 0.071* | |
C36 | 0.7893 (6) | 0.6938 (3) | 0.8745 (4) | 0.060 (2) | |
H36A | 0.7562 | 0.7311 | 0.8744 | 0.072* | |
H36B | 0.8658 | 0.6995 | 0.8878 | 0.072* | |
C38 | 0.7114 (7) | 0.5151 (4) | 0.5534 (5) | 0.071 (2) | |
C39 | 0.7151 (6) | 0.4983 (3) | 0.4656 (5) | 0.0593 (19) | |
C40 | 0.6242 (6) | 0.4738 (3) | 0.4124 (5) | 0.072 (2) | |
H40 | 0.5629 | 0.4677 | 0.4322 | 0.086* | |
C41 | 0.6280 (8) | 0.4590 (4) | 0.3298 (5) | 0.086 (3) | |
H41 | 0.5688 | 0.4422 | 0.2941 | 0.104* | |
C42 | 0.7189 (8) | 0.4687 (3) | 0.2990 (6) | 0.081 (2) | |
H42 | 0.7195 | 0.4590 | 0.2430 | 0.097* | |
C43 | 0.8081 (6) | 0.4928 (3) | 0.3516 (5) | 0.067 (2) | |
C44 | 0.8058 (6) | 0.5070 (3) | 0.4330 (5) | 0.065 (2) | |
H44 | 0.8662 | 0.5230 | 0.4683 | 0.078* | |
C45 | 0.9072 (7) | 0.5032 (4) | 0.3212 (7) | 0.078 (2) | |
C46 | 0.6529 (6) | 1.0083 (3) | 0.7105 (5) | 0.066 (2) | |
C47 | 0.7441 (6) | 0.9768 (3) | 0.6899 (4) | 0.0484 (16) | |
C48 | 0.7501 (6) | 0.9177 (3) | 0.6919 (4) | 0.0528 (17) | |
H48 | 0.6959 | 0.8967 | 0.7069 | 0.063* | |
C49 | 0.8341 (6) | 0.8891 (3) | 0.6723 (4) | 0.058 (2) | |
C50 | 0.9124 (6) | 0.9191 (3) | 0.6491 (4) | 0.063 (2) | |
H50 | 0.9692 | 0.8996 | 0.6357 | 0.075* | |
C51 | 0.9097 (7) | 0.9778 (3) | 0.6448 (5) | 0.073 (2) | |
H51 | 0.9634 | 0.9981 | 0.6281 | 0.088* | |
C52 | 0.8253 (6) | 1.0064 (3) | 0.6661 (4) | 0.067 (2) | |
H52 | 0.8233 | 1.0462 | 0.6642 | 0.080* | |
C53 | 0.8379 (8) | 0.8241 (3) | 0.6773 (5) | 0.065 (2) | |
O1 | 0.5169 (4) | 0.6717 (2) | 0.4188 (3) | 0.0736 (15) | |
O2 | 0.7106 (4) | 0.6477 (2) | 0.3893 (3) | 0.0721 (15) | |
O3 | 0.9132 (6) | 0.6043 (3) | 0.9519 (4) | 0.114 (2) | |
O4 | 1.1044 (6) | 0.6339 (3) | 0.9226 (4) | 0.117 (2) | |
O6 | 0.9880 (5) | 0.5205 (3) | 0.3692 (5) | 0.108 (2) | |
O7 | 0.6451 (5) | 0.4982 (3) | 0.5886 (4) | 0.105 (2) | |
O9 | 0.6665 (4) | 1.0564 (2) | 0.7453 (3) | 0.0647 (13) | |
O10 | 0.5626 (5) | 0.9828 (3) | 0.6893 (4) | 0.100 (2) | |
O11 | 0.7628 (5) | 0.7989 (2) | 0.6994 (4) | 0.0899 (19) | |
O12 | 0.9136 (5) | 0.7986 (2) | 0.6586 (4) | 0.0844 (17) | |
N1 | 0.6446 (5) | 0.6817 (3) | 0.6058 (4) | 0.0567 (16) | |
H1N | 0.654 (6) | 0.660 (3) | 0.566 (3) | 0.068* | |
N2 | 0.7561 (4) | 0.6687 (2) | 0.7885 (3) | 0.0499 (14) | |
H2N | 0.776 (5) | 0.6348 (12) | 0.789 (4) | 0.060* | |
N3 | 0.8784 (5) | 0.6731 (3) | 0.5614 (4) | 0.0558 (15) | |
H3N | 0.843 (5) | 0.6439 (19) | 0.547 (4) | 0.067* | |
N4 | 0.9934 (5) | 0.6679 (3) | 0.7413 (4) | 0.0573 (16) | |
H4N | 0.981 (6) | 0.649 (3) | 0.783 (3) | 0.069* | |
O5 | 0.8952 (6) | 0.4924 (3) | 0.2400 (5) | 0.108 (2) | |
H5O | 0.953 (5) | 0.503 (5) | 0.228 (7) | 0.162* | |
O8 | 0.7893 (5) | 0.5506 (3) | 0.5885 (3) | 0.0796 (16) | |
H8O | 0.795 (7) | 0.549 (4) | 0.6431 (17) | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0465 (3) | 0.0453 (3) | 0.0494 (3) | 0.0013 (3) | 0.0079 (2) | 0.0025 (3) |
C1 | 0.066 (5) | 0.064 (5) | 0.046 (4) | −0.005 (4) | 0.005 (4) | −0.009 (4) |
C2 | 0.081 (7) | 0.116 (8) | 0.074 (6) | 0.007 (6) | 0.017 (5) | 0.011 (6) |
C3 | 0.091 (8) | 0.215 (15) | 0.070 (7) | −0.046 (9) | 0.015 (6) | 0.017 (8) |
C4 | 0.150 (12) | 0.157 (13) | 0.057 (6) | −0.067 (10) | 0.017 (8) | 0.009 (7) |
C5 | 0.169 (12) | 0.087 (8) | 0.061 (6) | 0.002 (8) | 0.002 (7) | 0.015 (5) |
C6 | 0.103 (7) | 0.067 (6) | 0.045 (4) | 0.013 (5) | 0.004 (5) | 0.004 (4) |
C7 | 0.119 (9) | 0.145 (10) | 0.079 (6) | 0.001 (8) | 0.009 (7) | 0.043 (7) |
C8 | 0.128 (10) | 0.103 (9) | 0.108 (8) | 0.035 (7) | 0.008 (7) | 0.030 (7) |
C9 | 0.063 (6) | 0.114 (8) | 0.075 (6) | 0.021 (5) | −0.007 (5) | −0.012 (6) |
C10 | 0.087 (7) | 0.150 (10) | 0.082 (6) | 0.051 (7) | −0.033 (6) | −0.036 (6) |
C11 | 0.057 (6) | 0.150 (12) | 0.145 (11) | 0.031 (8) | −0.020 (7) | −0.052 (9) |
C12 | 0.060 (7) | 0.126 (10) | 0.164 (12) | −0.006 (7) | 0.015 (8) | −0.066 (9) |
C13 | 0.057 (5) | 0.084 (7) | 0.122 (8) | −0.018 (5) | 0.007 (5) | −0.029 (5) |
C14 | 0.050 (4) | 0.072 (5) | 0.072 (5) | 0.000 (4) | −0.006 (4) | −0.017 (5) |
C15 | 0.057 (4) | 0.056 (4) | 0.065 (4) | 0.000 (4) | 0.005 (4) | −0.009 (4) |
C16 | 0.082 (7) | 0.139 (9) | 0.098 (7) | 0.050 (6) | −0.015 (6) | −0.042 (7) |
C17 | 0.079 (6) | 0.175 (11) | 0.076 (6) | 0.056 (7) | 0.024 (5) | 0.019 (6) |
C18 | 0.074 (5) | 0.049 (4) | 0.059 (4) | −0.010 (4) | 0.009 (4) | −0.001 (4) |
C19 | 0.066 (5) | 0.062 (5) | 0.053 (4) | −0.004 (4) | 0.016 (4) | 0.007 (3) |
C20 | 0.085 (6) | 0.086 (7) | 0.065 (5) | −0.010 (5) | 0.019 (5) | 0.004 (4) |
C21 | 0.090 (7) | 0.096 (7) | 0.084 (6) | −0.007 (6) | 0.032 (6) | 0.012 (5) |
C22 | 0.125 (8) | 0.094 (7) | 0.059 (5) | −0.002 (6) | 0.041 (6) | −0.002 (5) |
C23 | 0.103 (7) | 0.085 (6) | 0.048 (4) | −0.014 (5) | 0.015 (5) | −0.013 (4) |
C24 | 0.068 (5) | 0.062 (5) | 0.054 (4) | −0.001 (4) | 0.013 (4) | 0.005 (4) |
C25 | 0.070 (5) | 0.062 (5) | 0.065 (5) | −0.007 (4) | −0.005 (4) | −0.013 (4) |
C26 | 0.072 (5) | 0.062 (5) | 0.078 (5) | −0.006 (4) | 0.015 (5) | −0.009 (4) |
C27 | 0.055 (5) | 0.064 (5) | 0.063 (5) | 0.001 (4) | 0.007 (4) | 0.013 (4) |
C28 | 0.064 (5) | 0.067 (6) | 0.076 (5) | −0.002 (4) | 0.001 (5) | 0.007 (4) |
C29 | 0.044 (5) | 0.091 (7) | 0.119 (8) | 0.011 (5) | 0.000 (5) | 0.023 (6) |
C30 | 0.060 (6) | 0.117 (9) | 0.111 (8) | 0.011 (5) | 0.022 (6) | −0.001 (6) |
C31 | 0.066 (5) | 0.105 (7) | 0.067 (5) | 0.024 (5) | 0.010 (4) | 0.004 (5) |
C32 | 0.062 (5) | 0.066 (5) | 0.051 (4) | 0.013 (4) | 0.003 (4) | 0.009 (4) |
C33 | 0.059 (4) | 0.057 (5) | 0.060 (4) | 0.004 (4) | 0.004 (4) | 0.001 (3) |
C34 | 0.059 (5) | 0.051 (5) | 0.074 (5) | −0.009 (4) | 0.002 (4) | 0.008 (4) |
C35 | 0.055 (4) | 0.061 (5) | 0.064 (5) | 0.007 (4) | 0.017 (4) | 0.008 (4) |
C36 | 0.063 (5) | 0.058 (5) | 0.057 (4) | −0.003 (4) | 0.006 (4) | −0.005 (3) |
C38 | 0.077 (6) | 0.071 (6) | 0.070 (5) | −0.010 (5) | 0.023 (5) | 0.003 (4) |
C39 | 0.060 (5) | 0.053 (5) | 0.071 (5) | −0.001 (4) | 0.026 (4) | 0.010 (4) |
C40 | 0.068 (5) | 0.070 (6) | 0.085 (6) | −0.017 (4) | 0.031 (5) | −0.008 (4) |
C41 | 0.093 (7) | 0.087 (7) | 0.076 (6) | −0.025 (5) | 0.015 (5) | −0.015 (5) |
C42 | 0.102 (7) | 0.065 (6) | 0.082 (6) | −0.009 (5) | 0.039 (6) | −0.007 (4) |
C43 | 0.078 (6) | 0.063 (5) | 0.069 (5) | −0.001 (4) | 0.032 (5) | −0.002 (4) |
C44 | 0.063 (5) | 0.052 (5) | 0.087 (6) | 0.003 (4) | 0.032 (4) | 0.006 (4) |
C45 | 0.085 (7) | 0.071 (6) | 0.094 (7) | 0.010 (5) | 0.054 (6) | 0.010 (5) |
C46 | 0.068 (5) | 0.056 (5) | 0.081 (5) | −0.006 (4) | 0.032 (4) | 0.003 (4) |
C47 | 0.060 (4) | 0.046 (4) | 0.044 (4) | 0.000 (3) | 0.021 (3) | −0.008 (3) |
C48 | 0.063 (5) | 0.050 (5) | 0.049 (4) | −0.009 (4) | 0.020 (4) | −0.003 (3) |
C49 | 0.073 (5) | 0.045 (4) | 0.047 (4) | −0.002 (4) | −0.005 (4) | −0.002 (3) |
C50 | 0.063 (5) | 0.061 (5) | 0.065 (5) | 0.013 (4) | 0.018 (4) | −0.010 (4) |
C51 | 0.085 (6) | 0.057 (6) | 0.084 (6) | −0.003 (5) | 0.034 (5) | 0.008 (4) |
C52 | 0.078 (5) | 0.049 (4) | 0.076 (5) | 0.002 (4) | 0.024 (5) | 0.005 (4) |
C53 | 0.080 (6) | 0.050 (5) | 0.055 (4) | 0.009 (5) | −0.008 (4) | −0.006 (4) |
O1 | 0.074 (4) | 0.073 (4) | 0.079 (4) | −0.007 (3) | 0.027 (3) | −0.011 (3) |
O2 | 0.066 (3) | 0.091 (4) | 0.058 (3) | −0.013 (3) | 0.011 (3) | −0.011 (3) |
O3 | 0.112 (5) | 0.157 (7) | 0.067 (4) | 0.064 (5) | 0.007 (4) | 0.019 (4) |
O4 | 0.104 (5) | 0.155 (7) | 0.093 (5) | 0.046 (5) | 0.027 (4) | 0.050 (5) |
O6 | 0.072 (4) | 0.138 (6) | 0.123 (5) | −0.005 (4) | 0.038 (4) | 0.008 (5) |
O7 | 0.107 (5) | 0.130 (6) | 0.093 (4) | −0.040 (4) | 0.054 (4) | −0.021 (4) |
O9 | 0.084 (4) | 0.043 (3) | 0.074 (3) | −0.004 (3) | 0.033 (3) | −0.012 (2) |
O10 | 0.083 (4) | 0.093 (5) | 0.138 (5) | −0.019 (4) | 0.052 (4) | −0.039 (4) |
O11 | 0.110 (5) | 0.050 (4) | 0.104 (4) | 0.001 (3) | 0.013 (4) | −0.003 (3) |
O12 | 0.090 (4) | 0.054 (4) | 0.104 (4) | 0.018 (3) | 0.013 (3) | −0.008 (3) |
N1 | 0.050 (3) | 0.063 (4) | 0.051 (4) | 0.005 (3) | −0.002 (3) | −0.010 (3) |
N2 | 0.047 (3) | 0.047 (3) | 0.053 (3) | −0.001 (3) | 0.006 (3) | −0.004 (3) |
N3 | 0.049 (4) | 0.068 (4) | 0.050 (3) | 0.006 (3) | 0.010 (3) | 0.008 (3) |
N4 | 0.050 (3) | 0.057 (4) | 0.058 (4) | 0.006 (3) | −0.001 (3) | 0.000 (3) |
O5 | 0.130 (6) | 0.102 (5) | 0.116 (5) | −0.012 (5) | 0.075 (5) | −0.006 (4) |
O8 | 0.090 (4) | 0.077 (4) | 0.068 (3) | −0.022 (3) | 0.012 (3) | 0.003 (3) |
Cd1—N1 | 2.433 (6) | C26—O1 | 1.392 (8) |
Cd1—N2 | 2.321 (6) | C26—H26A | 0.9700 |
Cd1—N3 | 2.329 (6) | C26—H26B | 0.9700 |
Cd1—N4 | 2.374 (6) | C27—O1 | 1.370 (9) |
Cd1—O11 | 2.302 (6) | C27—C32 | 1.387 (10) |
Cd1—O12 | 2.462 (6) | C27—C28 | 1.401 (10) |
Cd1—C53 | 2.706 (8) | C28—C29 | 1.369 (11) |
C1—C6 | 1.344 (10) | C28—H28 | 0.9300 |
C1—C2 | 1.388 (11) | C29—C30 | 1.341 (12) |
C1—C36 | 1.526 (10) | C29—H29 | 0.9300 |
C2—C3 | 1.373 (13) | C30—C31 | 1.384 (12) |
C2—H2 | 0.9300 | C30—H30 | 0.9300 |
C3—C4 | 1.346 (16) | C31—C32 | 1.376 (10) |
C3—H3 | 0.9300 | C31—H31 | 0.9300 |
C4—C5 | 1.360 (15) | C32—C33 | 1.510 (9) |
C4—H4 | 0.9300 | C33—N1 | 1.487 (8) |
C5—C6 | 1.383 (13) | C33—H33A | 0.9700 |
C5—H5 | 0.9300 | C33—H33B | 0.9700 |
C6—O3 | 1.375 (10) | C34—N1 | 1.471 (9) |
C7—O3 | 1.357 (10) | C34—C35 | 1.509 (9) |
C7—C8 | 1.507 (8) | C34—H34A | 0.9700 |
C7—H7A | 0.9700 | C34—H34B | 0.9700 |
C7—H7B | 0.9700 | C35—N2 | 1.475 (8) |
C8—O4 | 1.343 (11) | C35—H35A | 0.9700 |
C8—H8A | 0.9700 | C35—H35B | 0.9700 |
C8—H8B | 0.9700 | C36—N2 | 1.471 (8) |
C9—C14 | 1.385 (12) | C36—H36A | 0.9700 |
C9—O4 | 1.391 (11) | C36—H36B | 0.9700 |
C9—C10 | 1.392 (12) | C38—O7 | 1.197 (9) |
C10—C11 | 1.376 (15) | C38—O8 | 1.325 (9) |
C10—H10 | 0.9300 | C38—C39 | 1.478 (10) |
C11—C12 | 1.361 (16) | C39—C44 | 1.403 (10) |
C11—H11 | 0.9300 | C39—C40 | 1.404 (10) |
C12—C13 | 1.376 (13) | C40—C41 | 1.386 (10) |
C12—H12 | 0.9300 | C40—H40 | 0.9300 |
C13—C14 | 1.351 (11) | C41—C42 | 1.394 (11) |
C13—H13 | 0.9300 | C41—H41 | 0.9300 |
C14—C15 | 1.507 (10) | C42—C43 | 1.380 (10) |
C15—N4 | 1.475 (9) | C42—H42 | 0.9300 |
C15—H15A | 0.9700 | C43—C44 | 1.358 (10) |
C15—H15B | 0.9700 | C43—C45 | 1.492 (8) |
C16—N4 | 1.394 (10) | C44—H44 | 0.9300 |
C16—C17 | 1.506 (8) | C45—O6 | 1.214 (10) |
C16—H16A | 0.9700 | C45—O5 | 1.304 (11) |
C16—H16B | 0.9700 | C46—O9 | 1.246 (8) |
C17—N3 | 1.452 (10) | C46—O10 | 1.283 (9) |
C17—H17A | 0.9700 | C46—C47 | 1.490 (10) |
C17—H17B | 0.9700 | C47—C52 | 1.381 (9) |
C18—N3 | 1.461 (8) | C47—C48 | 1.382 (9) |
C18—C19 | 1.503 (10) | C48—C49 | 1.370 (10) |
C18—H18A | 0.9700 | C48—H48 | 0.9300 |
C18—H18B | 0.9700 | C49—C50 | 1.351 (10) |
C19—C20 | 1.376 (10) | C49—C53 | 1.518 (10) |
C19—C24 | 1.382 (10) | C50—C51 | 1.372 (10) |
C20—C21 | 1.379 (11) | C50—H50 | 0.9300 |
C20—H20 | 0.9300 | C51—C52 | 1.385 (10) |
C21—C22 | 1.372 (12) | C51—H51 | 0.9300 |
C21—H21 | 0.9300 | C52—H52 | 0.9300 |
C22—C23 | 1.402 (12) | C53—O12 | 1.239 (9) |
C22—H22 | 0.9300 | C53—O11 | 1.253 (10) |
C23—C24 | 1.371 (10) | N1—H1N | 0.85 (6) |
C23—H23 | 0.9300 | N2—H2N | 0.83 (2) |
C24—O2 | 1.380 (9) | N3—H3N | 0.82 (5) |
C25—O2 | 1.420 (8) | N4—H4N | 0.85 (6) |
C25—C26 | 1.489 (10) | O5—H5O | 0.85 (8) |
C25—H25A | 0.9700 | O8—H8O | 0.87 (2) |
C25—H25B | 0.9700 | ||
O11—Cd1—N2 | 93.5 (2) | C29—C28—H28 | 120.7 |
O11—Cd1—N3 | 127.9 (2) | C27—C28—H28 | 120.7 |
N2—Cd1—N3 | 135.4 (2) | C30—C29—C28 | 122.0 (9) |
O11—Cd1—N4 | 128.5 (2) | C30—C29—H29 | 119.0 |
N2—Cd1—N4 | 90.1 (2) | C28—C29—H29 | 119.0 |
N3—Cd1—N4 | 77.1 (2) | C29—C30—C31 | 119.4 (9) |
O11—Cd1—N1 | 88.9 (2) | C29—C30—H30 | 120.3 |
N2—Cd1—N1 | 77.4 (2) | C31—C30—H30 | 120.3 |
N3—Cd1—N1 | 86.6 (2) | C32—C31—C30 | 121.3 (8) |
N4—Cd1—N1 | 141.5 (2) | C32—C31—H31 | 119.3 |
O11—Cd1—O12 | 54.7 (2) | C30—C31—H31 | 119.3 |
N2—Cd1—O12 | 135.87 (19) | C31—C32—C27 | 118.2 (7) |
N3—Cd1—O12 | 87.1 (2) | C31—C32—C33 | 121.7 (7) |
N4—Cd1—O12 | 89.0 (2) | C27—C32—C33 | 120.0 (7) |
N1—Cd1—O12 | 125.1 (2) | N1—C33—C32 | 112.7 (6) |
C6—C1—C2 | 118.1 (9) | N1—C33—H33A | 109.0 |
C6—C1—C36 | 121.7 (8) | C32—C33—H33A | 109.0 |
C2—C1—C36 | 120.1 (7) | N1—C33—H33B | 109.0 |
C3—C2—C1 | 120.2 (10) | C32—C33—H33B | 109.0 |
C3—C2—H2 | 119.9 | H33A—C33—H33B | 107.8 |
C1—C2—H2 | 119.9 | N1—C34—C35 | 111.3 (6) |
C4—C3—C2 | 119.6 (12) | N1—C34—H34A | 109.4 |
C4—C3—H3 | 120.2 | C35—C34—H34A | 109.4 |
C2—C3—H3 | 120.2 | N1—C34—H34B | 109.4 |
C3—C4—C5 | 121.7 (12) | C35—C34—H34B | 109.4 |
C3—C4—H4 | 119.2 | H34A—C34—H34B | 108.0 |
C5—C4—H4 | 119.2 | N2—C35—C34 | 111.8 (6) |
C4—C5—C6 | 117.8 (11) | N2—C35—H35A | 109.3 |
C4—C5—H5 | 121.1 | C34—C35—H35A | 109.3 |
C6—C5—H5 | 121.1 | N2—C35—H35B | 109.3 |
C1—C6—O3 | 115.9 (8) | C34—C35—H35B | 109.3 |
C1—C6—C5 | 122.4 (10) | H35A—C35—H35B | 107.9 |
O3—C6—C5 | 121.7 (9) | N2—C36—C1 | 113.7 (6) |
O3—C7—C8 | 113.3 (8) | N2—C36—H36A | 108.8 |
O3—C7—H7A | 108.9 | C1—C36—H36A | 108.8 |
C8—C7—H7A | 108.9 | N2—C36—H36B | 108.8 |
O3—C7—H7B | 108.9 | C1—C36—H36B | 108.8 |
C8—C7—H7B | 108.9 | H36A—C36—H36B | 107.7 |
H7A—C7—H7B | 107.7 | O7—C38—O8 | 124.1 (8) |
O4—C8—C7 | 109.5 (8) | O7—C38—C39 | 123.4 (8) |
O4—C8—H8A | 109.8 | O8—C38—C39 | 112.6 (8) |
C7—C8—H8A | 109.8 | C44—C39—C40 | 119.0 (7) |
O4—C8—H8B | 109.8 | C44—C39—C38 | 122.2 (7) |
C7—C8—H8B | 109.8 | C40—C39—C38 | 118.8 (7) |
H8A—C8—H8B | 108.2 | C41—C40—C39 | 118.4 (8) |
C14—C9—O4 | 115.9 (8) | C41—C40—H40 | 120.8 |
C14—C9—C10 | 121.2 (11) | C39—C40—H40 | 120.8 |
O4—C9—C10 | 123.0 (10) | C40—C41—C42 | 121.3 (8) |
C11—C10—C9 | 118.7 (12) | C40—C41—H41 | 119.3 |
C11—C10—H10 | 120.7 | C42—C41—H41 | 119.3 |
C9—C10—H10 | 120.7 | C43—C42—C41 | 120.0 (8) |
C12—C11—C10 | 120.5 (11) | C43—C42—H42 | 120.0 |
C12—C11—H11 | 119.7 | C41—C42—H42 | 120.0 |
C10—C11—H11 | 119.7 | C44—C43—C42 | 119.4 (8) |
C11—C12—C13 | 119.4 (12) | C44—C43—C45 | 119.2 (8) |
C11—C12—H12 | 120.3 | C42—C43—C45 | 121.4 (8) |
C13—C12—H12 | 120.3 | C43—C44—C39 | 122.0 (7) |
C14—C13—C12 | 122.4 (11) | C43—C44—H44 | 119.0 |
C14—C13—H13 | 118.8 | C39—C44—H44 | 119.0 |
C12—C13—H13 | 118.8 | O6—C45—O5 | 125.9 (8) |
C13—C14—C9 | 117.8 (8) | O6—C45—C43 | 121.5 (9) |
C13—C14—C15 | 123.1 (8) | O5—C45—C43 | 112.7 (9) |
C9—C14—C15 | 119.1 (8) | O9—C46—O10 | 124.3 (8) |
N4—C15—C14 | 113.5 (6) | O9—C46—C47 | 120.4 (7) |
N4—C15—H15A | 108.9 | O10—C46—C47 | 115.3 (7) |
C14—C15—H15A | 108.9 | C52—C47—C48 | 117.6 (7) |
N4—C15—H15B | 108.9 | C52—C47—C46 | 120.3 (7) |
C14—C15—H15B | 108.9 | C48—C47—C46 | 122.1 (7) |
H15A—C15—H15B | 107.7 | C49—C48—C47 | 121.5 (7) |
N4—C16—C17 | 117.0 (7) | C49—C48—H48 | 119.2 |
N4—C16—H16A | 108.1 | C47—C48—H48 | 119.2 |
C17—C16—H16A | 108.1 | C50—C49—C48 | 119.6 (7) |
N4—C16—H16B | 108.1 | C50—C49—C53 | 121.0 (8) |
C17—C16—H16B | 108.1 | C48—C49—C53 | 119.3 (8) |
H16A—C16—H16B | 107.3 | C49—C50—C51 | 121.2 (7) |
N3—C17—C16 | 112.8 (7) | C49—C50—H50 | 119.4 |
N3—C17—H17A | 109.0 | C51—C50—H50 | 119.4 |
C16—C17—H17A | 109.0 | C50—C51—C52 | 118.7 (8) |
N3—C17—H17B | 109.0 | C50—C51—H51 | 120.6 |
C16—C17—H17B | 109.0 | C52—C51—H51 | 120.6 |
H17A—C17—H17B | 107.8 | C47—C52—C51 | 121.3 (7) |
N3—C18—C19 | 113.5 (6) | C47—C52—H52 | 119.4 |
N3—C18—H18A | 108.9 | C51—C52—H52 | 119.4 |
C19—C18—H18A | 108.9 | O12—C53—O11 | 123.3 (8) |
N3—C18—H18B | 108.9 | O12—C53—C49 | 118.9 (9) |
C19—C18—H18B | 108.9 | O11—C53—C49 | 117.8 (8) |
H18A—C18—H18B | 107.7 | O12—C53—Cd1 | 65.3 (4) |
C20—C19—C24 | 116.8 (7) | O11—C53—Cd1 | 58.0 (4) |
C20—C19—C18 | 122.7 (7) | C49—C53—Cd1 | 174.5 (6) |
C24—C19—C18 | 120.5 (7) | C27—O1—C26 | 117.8 (6) |
C19—C20—C21 | 124.3 (8) | C24—O2—C25 | 118.1 (6) |
C19—C20—H20 | 117.8 | C7—O3—C6 | 118.3 (7) |
C21—C20—H20 | 117.8 | C8—O4—C9 | 120.1 (8) |
C22—C21—C20 | 117.1 (9) | C53—O11—Cd1 | 94.5 (5) |
C22—C21—H21 | 121.4 | C53—O12—Cd1 | 87.4 (5) |
C20—C21—H21 | 121.4 | C34—N1—C33 | 113.8 (6) |
C21—C22—C23 | 120.9 (8) | C34—N1—Cd1 | 104.0 (4) |
C21—C22—H22 | 119.6 | C33—N1—Cd1 | 117.3 (4) |
C23—C22—H22 | 119.6 | C34—N1—H1N | 105 (5) |
C24—C23—C22 | 119.3 (8) | C33—N1—H1N | 112 (5) |
C24—C23—H23 | 120.3 | Cd1—N1—H1N | 104 (5) |
C22—C23—H23 | 120.3 | C36—N2—C35 | 113.3 (6) |
C23—C24—O2 | 124.0 (7) | C36—N2—Cd1 | 118.0 (4) |
C23—C24—C19 | 121.6 (8) | C35—N2—Cd1 | 106.4 (4) |
O2—C24—C19 | 114.4 (7) | C36—N2—H2N | 110 (5) |
O2—C25—C26 | 108.2 (6) | C35—N2—H2N | 105 (5) |
O2—C25—H25A | 110.1 | Cd1—N2—H2N | 103 (5) |
C26—C25—H25A | 110.1 | C17—N3—C18 | 108.4 (6) |
O2—C25—H25B | 110.1 | C17—N3—Cd1 | 107.8 (5) |
C26—C25—H25B | 110.1 | C18—N3—Cd1 | 112.8 (4) |
H25A—C25—H25B | 108.4 | C17—N3—H3N | 112 (5) |
O1—C26—C25 | 109.5 (7) | C18—N3—H3N | 110 (5) |
O1—C26—H26A | 109.8 | Cd1—N3—H3N | 106 (5) |
C25—C26—H26A | 109.8 | C16—N4—C15 | 116.7 (7) |
O1—C26—H26B | 109.8 | C16—N4—Cd1 | 106.7 (4) |
C25—C26—H26B | 109.8 | C15—N4—Cd1 | 114.6 (4) |
H26A—C26—H26B | 108.2 | C16—N4—H4N | 116 (5) |
O1—C27—C32 | 116.3 (7) | C15—N4—H4N | 99 (5) |
O1—C27—C28 | 123.2 (7) | Cd1—N4—H4N | 102 (5) |
C32—C27—C28 | 120.4 (8) | C45—O5—H5O | 105 (8) |
C29—C28—C27 | 118.5 (8) | C38—O8—H8O | 107 (7) |
C6—C1—C2—C3 | −0.4 (13) | N1—Cd1—C53—O12 | −134.0 (4) |
C36—C1—C2—C3 | 177.5 (8) | N2—Cd1—C53—O11 | −35.7 (5) |
C1—C2—C3—C4 | −1.8 (16) | N3—Cd1—C53—O11 | 140.9 (5) |
C2—C3—C4—C5 | 4.2 (18) | N4—Cd1—C53—O11 | −136.5 (5) |
C3—C4—C5—C6 | −4.2 (17) | N1—Cd1—C53—O11 | 48.8 (5) |
C2—C1—C6—O3 | 178.8 (7) | O12—Cd1—C53—O11 | −177.2 (8) |
C36—C1—C6—O3 | 0.9 (11) | C32—C27—O1—C26 | 140.3 (7) |
C2—C1—C6—C5 | 0.3 (12) | C28—C27—O1—C26 | −42.5 (10) |
C36—C1—C6—C5 | −177.6 (7) | C25—C26—O1—C27 | 175.0 (6) |
C4—C5—C6—C1 | 1.9 (14) | C23—C24—O2—C25 | −12.8 (11) |
C4—C5—C6—O3 | −176.5 (9) | C19—C24—O2—C25 | 168.9 (6) |
O3—C7—C8—O4 | 49.9 (13) | C26—C25—O2—C24 | −179.4 (6) |
C14—C9—C10—C11 | 1.2 (15) | C8—C7—O3—C6 | −175.5 (9) |
O4—C9—C10—C11 | −179.2 (9) | C1—C6—O3—C7 | 137.9 (9) |
C9—C10—C11—C12 | 0.4 (17) | C5—C6—O3—C7 | −43.6 (13) |
C10—C11—C12—C13 | −1.1 (18) | C7—C8—O4—C9 | 171.2 (8) |
C11—C12—C13—C14 | 0.1 (15) | C14—C9—O4—C8 | 163.9 (9) |
C12—C13—C14—C9 | 1.5 (13) | C10—C9—O4—C8 | −15.7 (14) |
C12—C13—C14—C15 | −176.5 (8) | O12—C53—O11—Cd1 | −3.1 (8) |
O4—C9—C14—C13 | 178.3 (7) | C49—C53—O11—Cd1 | 176.0 (5) |
C10—C9—C14—C13 | −2.2 (13) | N2—Cd1—O11—C53 | 148.4 (5) |
O4—C9—C14—C15 | −3.6 (11) | N3—Cd1—O11—C53 | −49.4 (6) |
C10—C9—C14—C15 | 175.9 (8) | N4—Cd1—O11—C53 | 55.5 (6) |
C13—C14—C15—N4 | 108.1 (9) | N1—Cd1—O11—C53 | −134.2 (5) |
C9—C14—C15—N4 | −69.9 (9) | O12—Cd1—O11—C53 | 1.6 (4) |
N4—C16—C17—N3 | −52.6 (13) | O11—C53—O12—Cd1 | 2.9 (8) |
N3—C18—C19—C20 | −101.1 (8) | C49—C53—O12—Cd1 | −176.2 (6) |
N3—C18—C19—C24 | 81.9 (9) | O11—Cd1—O12—C53 | −1.6 (4) |
C24—C19—C20—C21 | 0.5 (12) | N2—Cd1—O12—C53 | −53.2 (5) |
C18—C19—C20—C21 | −176.6 (8) | N3—Cd1—O12—C53 | 140.5 (5) |
C19—C20—C21—C22 | 0.9 (13) | N4—Cd1—O12—C53 | −142.4 (5) |
C20—C21—C22—C23 | −0.9 (14) | N1—Cd1—O12—C53 | 56.7 (5) |
C21—C22—C23—C24 | −0.5 (13) | C35—C34—N1—C33 | −85.7 (7) |
C22—C23—C24—O2 | −176.2 (7) | C35—C34—N1—Cd1 | 43.0 (6) |
C22—C23—C24—C19 | 2.1 (12) | C32—C33—N1—C34 | −53.0 (8) |
C20—C19—C24—C23 | −2.0 (11) | C32—C33—N1—Cd1 | −174.6 (5) |
C18—C19—C24—C23 | 175.1 (7) | O11—Cd1—N1—C34 | −108.0 (5) |
C20—C19—C24—O2 | 176.4 (6) | N2—Cd1—N1—C34 | −14.1 (4) |
C18—C19—C24—O2 | −6.5 (10) | N3—Cd1—N1—C34 | 124.0 (4) |
O2—C25—C26—O1 | 56.7 (8) | N4—Cd1—N1—C34 | 59.7 (6) |
O1—C27—C28—C29 | −176.8 (7) | O12—Cd1—N1—C34 | −152.0 (4) |
C32—C27—C28—C29 | 0.3 (11) | C53—Cd1—N1—C34 | −128.3 (5) |
C27—C28—C29—C30 | 2.4 (13) | O11—Cd1—N1—C33 | 18.6 (5) |
C28—C29—C30—C31 | −2.4 (15) | N2—Cd1—N1—C33 | 112.5 (5) |
C29—C30—C31—C32 | −0.3 (14) | N3—Cd1—N1—C33 | −109.4 (5) |
C30—C31—C32—C27 | 2.9 (12) | N4—Cd1—N1—C33 | −173.7 (4) |
C30—C31—C32—C33 | −172.6 (8) | O12—Cd1—N1—C33 | −25.4 (6) |
O1—C27—C32—C31 | 174.4 (7) | C53—Cd1—N1—C33 | −1.7 (6) |
C28—C27—C32—C31 | −2.9 (11) | C1—C36—N2—C35 | 67.6 (8) |
O1—C27—C32—C33 | −10.0 (10) | C1—C36—N2—Cd1 | −167.2 (5) |
C28—C27—C32—C33 | 172.7 (6) | C34—C35—N2—C36 | 177.0 (6) |
C31—C32—C33—N1 | 108.6 (8) | C34—C35—N2—Cd1 | 45.8 (6) |
C27—C32—C33—N1 | −66.9 (9) | O11—Cd1—N2—C36 | −56.5 (5) |
N1—C34—C35—N2 | −64.3 (8) | N3—Cd1—N2—C36 | 143.7 (4) |
C6—C1—C36—N2 | 83.3 (8) | N4—Cd1—N2—C36 | 72.0 (5) |
C2—C1—C36—N2 | −94.5 (8) | N1—Cd1—N2—C36 | −144.6 (5) |
O7—C38—C39—C44 | −164.4 (8) | O12—Cd1—N2—C36 | −16.7 (6) |
O8—C38—C39—C44 | 15.6 (11) | C53—Cd1—N2—C36 | −40.9 (5) |
O7—C38—C39—C40 | 16.9 (13) | O11—Cd1—N2—C35 | 72.1 (4) |
O8—C38—C39—C40 | −163.2 (7) | N3—Cd1—N2—C35 | −87.7 (5) |
C44—C39—C40—C41 | 0.2 (11) | N4—Cd1—N2—C35 | −159.4 (4) |
C38—C39—C40—C41 | 179.1 (8) | N1—Cd1—N2—C35 | −16.0 (4) |
C39—C40—C41—C42 | −0.9 (13) | O12—Cd1—N2—C35 | 111.9 (4) |
C40—C41—C42—C43 | 1.0 (13) | C53—Cd1—N2—C35 | 87.7 (4) |
C41—C42—C43—C44 | −0.4 (12) | C16—C17—N3—C18 | 159.4 (8) |
C41—C42—C43—C45 | 179.3 (8) | C16—C17—N3—Cd1 | 37.0 (10) |
C42—C43—C44—C39 | −0.4 (12) | C19—C18—N3—C17 | 70.6 (8) |
C45—C43—C44—C39 | 180.0 (7) | C19—C18—N3—Cd1 | −170.1 (5) |
C40—C39—C44—C43 | 0.4 (11) | O11—Cd1—N3—C17 | 114.7 (6) |
C38—C39—C44—C43 | −178.4 (7) | N2—Cd1—N3—C17 | −91.1 (6) |
C44—C43—C45—O6 | 5.1 (13) | N4—Cd1—N3—C17 | −14.4 (6) |
C42—C43—C45—O6 | −174.6 (9) | N1—Cd1—N3—C17 | −159.3 (6) |
C44—C43—C45—O5 | −174.3 (8) | O12—Cd1—N3—C17 | 75.3 (6) |
C42—C43—C45—O5 | 6.0 (11) | C53—Cd1—N3—C17 | 93.1 (6) |
O9—C46—C47—C52 | −33.8 (10) | O11—Cd1—N3—C18 | −4.9 (6) |
O10—C46—C47—C52 | 145.5 (7) | N2—Cd1—N3—C18 | 149.3 (4) |
O9—C46—C47—C48 | 147.6 (7) | N4—Cd1—N3—C18 | −134.0 (5) |
O10—C46—C47—C48 | −33.0 (10) | N1—Cd1—N3—C18 | 81.1 (5) |
C52—C47—C48—C49 | 1.0 (10) | O12—Cd1—N3—C18 | −44.3 (4) |
C46—C47—C48—C49 | 179.6 (6) | C53—Cd1—N3—C18 | −26.5 (5) |
C47—C48—C49—C50 | −1.1 (10) | C17—C16—N4—C15 | −94.1 (9) |
C47—C48—C49—C53 | 178.7 (6) | C17—C16—N4—Cd1 | 35.4 (10) |
C48—C49—C50—C51 | 0.1 (11) | C14—C15—N4—C16 | −51.4 (9) |
C53—C49—C50—C51 | −179.7 (7) | C14—C15—N4—Cd1 | −177.1 (5) |
C49—C50—C51—C52 | 0.9 (11) | O11—Cd1—N4—C16 | −139.1 (6) |
C48—C47—C52—C51 | 0.0 (10) | N2—Cd1—N4—C16 | 126.3 (6) |
C46—C47—C52—C51 | −178.6 (7) | N3—Cd1—N4—C16 | −10.5 (6) |
C50—C51—C52—C47 | −1.0 (11) | N1—Cd1—N4—C16 | 56.7 (7) |
C50—C49—C53—O12 | −1.0 (10) | O12—Cd1—N4—C16 | −97.8 (6) |
C48—C49—C53—O12 | 179.2 (6) | C53—Cd1—N4—C16 | −115.1 (6) |
C50—C49—C53—O11 | 179.9 (7) | O11—Cd1—N4—C15 | −8.3 (6) |
C48—C49—C53—O11 | 0.1 (10) | N2—Cd1—N4—C15 | −102.9 (5) |
O11—Cd1—C53—O12 | 177.2 (8) | N3—Cd1—N4—C15 | 120.2 (5) |
N2—Cd1—C53—O12 | 141.4 (4) | N1—Cd1—N4—C15 | −172.5 (4) |
N3—Cd1—C53—O12 | −41.9 (5) | O12—Cd1—N4—C15 | 33.0 (5) |
N4—Cd1—C53—O12 | 40.6 (5) | C53—Cd1—N4—C15 | 15.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O8 | 0.82 (5) | 2.42 (4) | 3.148 (8) | 147 (6) |
N4—H4N···O4 | 0.85 (6) | 2.46 (6) | 3.043 (8) | 127 (6) |
N2—H2N···O9i | 0.83 (2) | 2.10 (3) | 2.901 (7) | 163 (6) |
O8—H8O···O9i | 0.87 (2) | 1.76 (3) | 2.605 (7) | 166 (9) |
O5—H5O···O10ii | 0.85 (8) | 1.71 (8) | 2.548 (9) | 170 (12) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C8H4O4)(C36H44N4O4)]·C8H6O4 |
Mr | 1039.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 12.912 (3), 23.330 (5), 16.086 (3) |
β (°) | 103.37 (3) |
V (Å3) | 4714.4 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.53 |
Crystal size (mm) | 0.34 × 0.29 × 0.21 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.842, 0.913 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43452, 10582, 4951 |
Rint | 0.158 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.085, 0.185, 1.02 |
No. of reflections | 10582 |
No. of parameters | 640 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.68, −0.71 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).
Cd1—N1 | 2.433 (6) | Cd1—N4 | 2.374 (6) |
Cd1—N2 | 2.321 (6) | Cd1—O11 | 2.302 (6) |
Cd1—N3 | 2.329 (6) | Cd1—O12 | 2.462 (6) |
O11—Cd1—N2 | 93.5 (2) | N3—Cd1—N1 | 86.6 (2) |
O11—Cd1—N3 | 127.9 (2) | N4—Cd1—N1 | 141.5 (2) |
N2—Cd1—N3 | 135.4 (2) | O11—Cd1—O12 | 54.7 (2) |
O11—Cd1—N4 | 128.5 (2) | N2—Cd1—O12 | 135.87 (19) |
N2—Cd1—N4 | 90.1 (2) | N3—Cd1—O12 | 87.1 (2) |
N3—Cd1—N4 | 77.1 (2) | N4—Cd1—O12 | 89.0 (2) |
O11—Cd1—N1 | 88.9 (2) | N1—Cd1—O12 | 125.1 (2) |
N2—Cd1—N1 | 77.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O8 | 0.82 (5) | 2.42 (4) | 3.148 (8) | 147 (6) |
N4—H4N···O4 | 0.85 (6) | 2.46 (6) | 3.043 (8) | 127 (6) |
N2—H2N···O9i | 0.83 (2) | 2.10 (3) | 2.901 (7) | 163 (6) |
O8—H8O···O9i | 0.87 (2) | 1.76 (3) | 2.605 (7) | 166 (9) |
O5—H5O···O10ii | 0.85 (8) | 1.71 (8) | 2.548 (9) | 170 (12) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, z−1/2. |
As part of an investigation of the supramolecular chemistry of crown ether systems, we present here the crystal structure of the title compound.
In the title compound, the CdII atom displays a psudo-square-pyramidal coordination geometry, defined by four N atoms from the macrocyclic ligand in the basal plane and two O atoms of the carboxylate group of a benzene-1,3-dicarboxylate ligand (Fig. 1). The bond distances (Cd—N, Cd—O) and angles (N—Cd—N, N—Cd—O) are normal (Table 1) (Banerjee et al., 2005; Liu et al., 2005). The complex molecules are linked by N—H···O hydrogen bonds, forming a one-dimensional chain structure along the b-axis (Table 2). The uncoordinated benzene-1,3-dicarboxylic acid molecules are located on both sides of the chain. The adjacent chains are further connected through N—H···O and O—H···O hydrogen bonds between the complex molecule and the benzene-1,3-dicarboxylic acid, resulting in a two-dimensional supramolecular network (Fig. 2) (Sarkar et al., 2008).