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metal-organic compounds
The title compound, [Cu(C8H4O4)(C21H15N3)]·C8H6O4, consists of polymeric chains in which the terpyridine heterocycle chelates to the Cu atom in an N,N′,N′′-tridentate manner; the Cu atoms are also covalently bonded through the two singly-bonded carboxyl O atoms of the dicarboxylate dianions to give rise to a chain structure. An additional terephthalic acid molecule is hydrogen bonded to the chains. The asymmetric unit contains halves of two different half-molecule terephthalate ions; in each case, the complete ions are generated by inversion symmetry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031940/hb6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031940/hb6119Isup2.hkl |
CCDC reference: 262255
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O2
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.707 0.920 Tmin' and Tmax expected: 0.816 0.919 RR' = 0.866 Please check that your absorption correction is appropriate. REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.90 From the CIF: _diffrn_reflns_theta_full 27.90 From the CIF: _reflns_number_total 7024 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 7404 Completeness (_total/calc) 94.87% PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 N2 -CU1 -O1 -C1 11.20 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 O1 -CU1 -N2 -C18 -97.90 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21 O1 -CU1 -N2 -C14 86.90 0.60 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
catena-Poly[[[(4'-phenyl-2,2':6',2''-terpyridine-κ3N)copper(II)]- µ-terephthalato-κ2O:O'] terephthalic acid] top
Crystal data top
[Cu(C8H4O4)(C21H15N3)]·C8H6O4 | Z = 2 |
Mr = 703.14 | F(000) = 722 |
Triclinic, P1 | Dx = 1.510 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0952 (5) Å | Cell parameters from 4160 reflections |
b = 13.9570 (8) Å | θ = 2.2–26.0° |
c = 14.1416 (8) Å | µ = 0.77 mm−1 |
α = 93.925 (1)° | T = 295 K |
β = 91.488 (1)° | Prism, green |
γ = 103.777 (1)° | 0.26 × 0.18 × 0.11 mm |
V = 1546.70 (16) Å3 |
Data collection top
Bruker APEX area-dectector diffractometer | 7024 independent reflections |
Radiation source: fine-focus sealed tube | 5819 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.9°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.707, Tmax = 0.920 | k = −18→18 |
13572 measured reflections | l = −17→18 |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0744P)2 + 0.1147P] where P = (Fo2 + 2Fc2)/3 |
7024 reflections | (Δ/σ)max = 0.001 |
450 parameters | Δρmax = 0.61 e Å−3 |
2 restraints | Δρmin = −0.47 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.22179 (3) | 0.132123 (19) | 0.331863 (18) | 0.03213 (11) | |
O1 | 0.3647 (2) | 0.25793 (12) | 0.37261 (12) | 0.0433 (4) | |
O2 | 0.1476 (3) | 0.27967 (15) | 0.45626 (17) | 0.0707 (7) | |
O3 | 0.4304 (2) | 0.09956 (11) | 0.23849 (10) | 0.0341 (4) | |
O4 | 0.3489 (2) | −0.06372 (11) | 0.23495 (11) | 0.0368 (4) | |
O5 | 0.2041 (3) | −0.24825 (13) | 0.18840 (14) | 0.0517 (5) | |
H5o | 0.254 (5) | −0.1890 (12) | 0.206 (3) | 0.101 (14)* | |
O6 | 0.2555 (3) | −0.27656 (15) | 0.33843 (15) | 0.0636 (6) | |
O7 | −0.3031 (3) | −0.74479 (14) | 0.24618 (14) | 0.0525 (5) | |
H7o | −0.386 (3) | −0.7946 (18) | 0.242 (3) | 0.090 (13)* | |
O8 | −0.4262 (3) | −0.68005 (14) | 0.13282 (16) | 0.0647 (6) | |
N1 | 0.1101 (3) | 0.16966 (14) | 0.21283 (14) | 0.0354 (4) | |
N2 | 0.0531 (2) | 0.01088 (13) | 0.29813 (12) | 0.0286 (4) | |
N3 | 0.2513 (2) | 0.05599 (14) | 0.44482 (13) | 0.0333 (4) | |
C1 | 0.2936 (3) | 0.30856 (17) | 0.43008 (16) | 0.0384 (5) | |
C2 | 0.4012 (3) | 0.40809 (16) | 0.46680 (15) | 0.0339 (5) | |
C3 | 0.5752 (3) | 0.43206 (17) | 0.45393 (17) | 0.0401 (6) | |
H3 | 0.6259 | 0.3861 | 0.4232 | 0.048* | |
C4 | 0.3272 (3) | 0.47626 (17) | 0.51341 (18) | 0.0396 (5) | |
H4 | 0.2108 | 0.4602 | 0.5228 | 0.047* | |
C5 | 0.4080 (3) | 0.01388 (15) | 0.19648 (14) | 0.0273 (4) | |
C6 | 0.4550 (3) | 0.00686 (15) | 0.09451 (14) | 0.0260 (4) | |
C7 | 0.4823 (3) | 0.08976 (15) | 0.04183 (14) | 0.0290 (4) | |
H7 | 0.4701 | 0.1499 | 0.0697 | 0.035* | |
C8 | 0.4725 (3) | −0.08297 (15) | 0.05152 (14) | 0.0283 (4) | |
H8 | 0.4536 | −0.1387 | 0.0859 | 0.034* | |
C9 | 0.1513 (3) | 0.25602 (18) | 0.17377 (19) | 0.0433 (6) | |
H9 | 0.2306 | 0.3084 | 0.2056 | 0.052* | |
C10 | 0.0800 (4) | 0.2701 (2) | 0.0876 (2) | 0.0494 (7) | |
H10 | 0.1116 | 0.3310 | 0.0616 | 0.059* | |
C11 | −0.0380 (4) | 0.1934 (2) | 0.0406 (2) | 0.0489 (6) | |
H11 | −0.0880 | 0.2017 | −0.0172 | 0.059* | |
C12 | −0.0815 (3) | 0.10341 (19) | 0.08046 (18) | 0.0416 (6) | |
H12 | −0.1604 | 0.0503 | 0.0495 | 0.050* | |
C13 | −0.0065 (3) | 0.09362 (16) | 0.16653 (16) | 0.0328 (5) | |
C14 | −0.0410 (3) | 0.00151 (16) | 0.21704 (15) | 0.0301 (4) | |
C15 | −0.1538 (3) | −0.08669 (16) | 0.18814 (16) | 0.0342 (5) | |
H15 | −0.2183 | −0.0925 | 0.1317 | 0.041* | |
C16 | −0.1719 (3) | −0.16816 (16) | 0.24367 (15) | 0.0317 (5) | |
C17 | −0.0703 (3) | −0.15511 (16) | 0.32800 (15) | 0.0313 (5) | |
H17 | −0.0781 | −0.2071 | 0.3667 | 0.038* | |
C18 | 0.0408 (3) | −0.06496 (16) | 0.35295 (15) | 0.0297 (4) | |
C19 | 0.1568 (3) | −0.03879 (17) | 0.43834 (15) | 0.0306 (5) | |
C21 | 0.1690 (3) | −0.1028 (2) | 0.50697 (17) | 0.0406 (5) | |
H21 | 0.1040 | −0.1677 | 0.5014 | 0.049* | |
C22 | 0.2815 (3) | −0.0673 (2) | 0.58490 (18) | 0.0471 (6) | |
H22 | 0.2920 | −0.1087 | 0.6323 | 0.057* | |
C23 | 0.3761 (3) | 0.0280 (2) | 0.59152 (17) | 0.0462 (6) | |
H23 | 0.4516 | 0.0521 | 0.6431 | 0.055* | |
C24 | 0.3580 (3) | 0.08801 (19) | 0.52058 (17) | 0.0397 (6) | |
H24 | 0.4221 | 0.1531 | 0.5254 | 0.048* | |
C25 | −0.2935 (3) | −0.26311 (16) | 0.21396 (16) | 0.0331 (5) | |
C26 | −0.3490 (3) | −0.28739 (18) | 0.11902 (18) | 0.0404 (5) | |
H26 | −0.3078 | −0.2435 | 0.0737 | 0.049* | |
C27 | −0.4636 (4) | −0.3752 (2) | 0.0917 (2) | 0.0491 (6) | |
H27 | −0.4987 | −0.3902 | 0.0282 | 0.059* | |
C28 | −0.5269 (4) | −0.4412 (2) | 0.1576 (2) | 0.0543 (7) | |
H28 | −0.6042 | −0.5006 | 0.1387 | 0.065* | |
C29 | −0.4747 (4) | −0.4185 (2) | 0.2517 (2) | 0.0564 (7) | |
H29 | −0.5173 | −0.4628 | 0.2965 | 0.068* | |
C30 | −0.3596 (3) | −0.33044 (19) | 0.27981 (19) | 0.0459 (6) | |
H30 | −0.3258 | −0.3158 | 0.3436 | 0.055* | |
C31 | 0.1891 (3) | −0.30418 (18) | 0.26161 (19) | 0.0426 (6) | |
C32 | 0.0712 (3) | −0.40404 (17) | 0.23867 (18) | 0.0391 (5) | |
C33 | −0.0239 (4) | −0.42740 (18) | 0.1541 (2) | 0.0471 (6) | |
H33 | −0.0066 | −0.3830 | 0.1072 | 0.056* | |
C34 | −0.1438 (4) | −0.51556 (19) | 0.1387 (2) | 0.0482 (6) | |
H34 | −0.2089 | −0.5296 | 0.0820 | 0.058* | |
C35 | −0.1685 (3) | −0.58383 (17) | 0.20703 (18) | 0.0392 (5) | |
C36 | −0.0665 (3) | −0.56292 (19) | 0.2900 (2) | 0.0464 (6) | |
H36 | −0.0770 | −0.6096 | 0.3348 | 0.056* | |
C37 | 0.0502 (4) | −0.47307 (19) | 0.3060 (2) | 0.0476 (6) | |
H37 | 0.1155 | −0.4587 | 0.3626 | 0.057* | |
C38 | −0.3120 (3) | −0.67397 (18) | 0.19068 (19) | 0.0423 (6) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03614 (17) | 0.02649 (16) | 0.02836 (16) | −0.00120 (11) | −0.00163 (11) | −0.00366 (10) |
O1 | 0.0492 (10) | 0.0315 (9) | 0.0403 (9) | −0.0045 (7) | 0.0035 (8) | −0.0101 (7) |
O2 | 0.0548 (12) | 0.0433 (11) | 0.0952 (17) | −0.0191 (9) | 0.0267 (12) | −0.0253 (11) |
O3 | 0.0417 (9) | 0.0259 (8) | 0.0282 (8) | −0.0032 (6) | 0.0061 (7) | −0.0043 (6) |
O4 | 0.0502 (10) | 0.0260 (8) | 0.0289 (8) | −0.0017 (7) | 0.0059 (7) | 0.0026 (6) |
O5 | 0.0642 (13) | 0.0306 (10) | 0.0501 (11) | −0.0086 (9) | 0.0047 (9) | 0.0028 (8) |
O6 | 0.0762 (15) | 0.0465 (11) | 0.0575 (13) | −0.0038 (10) | −0.0117 (11) | 0.0011 (10) |
O7 | 0.0501 (11) | 0.0383 (10) | 0.0619 (12) | −0.0069 (9) | −0.0033 (9) | 0.0180 (9) |
O8 | 0.0682 (14) | 0.0402 (11) | 0.0742 (14) | −0.0092 (10) | −0.0246 (11) | 0.0121 (10) |
N1 | 0.0387 (10) | 0.0268 (9) | 0.0373 (10) | 0.0018 (8) | −0.0014 (8) | 0.0022 (8) |
N2 | 0.0296 (9) | 0.0268 (9) | 0.0265 (9) | 0.0016 (7) | −0.0016 (7) | 0.0018 (7) |
N3 | 0.0332 (10) | 0.0369 (10) | 0.0271 (9) | 0.0052 (8) | −0.0003 (8) | −0.0042 (8) |
C1 | 0.0457 (14) | 0.0277 (11) | 0.0344 (12) | −0.0044 (10) | −0.0004 (10) | −0.0024 (9) |
C2 | 0.0426 (13) | 0.0259 (11) | 0.0278 (11) | −0.0015 (9) | 0.0015 (9) | −0.0015 (8) |
C3 | 0.0446 (14) | 0.0307 (12) | 0.0413 (13) | 0.0045 (10) | 0.0048 (11) | −0.0079 (10) |
C4 | 0.0364 (12) | 0.0335 (12) | 0.0430 (13) | −0.0015 (10) | 0.0056 (10) | −0.0035 (10) |
C5 | 0.0256 (10) | 0.0271 (10) | 0.0265 (10) | 0.0016 (8) | −0.0013 (8) | 0.0000 (8) |
C6 | 0.0255 (10) | 0.0255 (10) | 0.0249 (10) | 0.0031 (8) | −0.0021 (8) | −0.0007 (8) |
C7 | 0.0345 (11) | 0.0238 (10) | 0.0276 (10) | 0.0063 (8) | 0.0004 (8) | −0.0023 (8) |
C8 | 0.0334 (11) | 0.0231 (10) | 0.0265 (10) | 0.0030 (8) | −0.0014 (8) | 0.0041 (8) |
C9 | 0.0473 (14) | 0.0309 (12) | 0.0480 (14) | 0.0022 (10) | −0.0019 (11) | 0.0045 (10) |
C10 | 0.0552 (16) | 0.0374 (14) | 0.0548 (16) | 0.0055 (12) | 0.0041 (13) | 0.0177 (12) |
C11 | 0.0504 (15) | 0.0491 (15) | 0.0452 (15) | 0.0045 (12) | −0.0048 (12) | 0.0179 (12) |
C12 | 0.0403 (13) | 0.0408 (14) | 0.0398 (13) | 0.0017 (10) | −0.0081 (10) | 0.0070 (10) |
C13 | 0.0316 (11) | 0.0311 (11) | 0.0344 (11) | 0.0048 (9) | −0.0018 (9) | 0.0037 (9) |
C14 | 0.0304 (11) | 0.0309 (11) | 0.0280 (10) | 0.0055 (9) | −0.0017 (8) | 0.0028 (8) |
C15 | 0.0343 (12) | 0.0328 (12) | 0.0321 (11) | 0.0024 (9) | −0.0078 (9) | 0.0027 (9) |
C16 | 0.0308 (11) | 0.0298 (11) | 0.0323 (11) | 0.0039 (9) | 0.0002 (9) | 0.0010 (9) |
C17 | 0.0313 (11) | 0.0294 (11) | 0.0320 (11) | 0.0035 (9) | 0.0024 (9) | 0.0058 (9) |
C18 | 0.0276 (10) | 0.0337 (11) | 0.0270 (10) | 0.0054 (9) | 0.0021 (8) | 0.0022 (8) |
C19 | 0.0268 (10) | 0.0378 (12) | 0.0257 (10) | 0.0054 (9) | 0.0015 (8) | 0.0005 (9) |
C21 | 0.0373 (13) | 0.0478 (14) | 0.0354 (12) | 0.0066 (11) | 0.0018 (10) | 0.0087 (11) |
C22 | 0.0441 (14) | 0.0680 (18) | 0.0321 (12) | 0.0171 (13) | −0.0003 (11) | 0.0115 (12) |
C23 | 0.0399 (14) | 0.0681 (18) | 0.0299 (12) | 0.0155 (13) | −0.0066 (10) | −0.0065 (12) |
C24 | 0.0346 (12) | 0.0469 (14) | 0.0334 (12) | 0.0060 (10) | −0.0022 (10) | −0.0112 (10) |
C25 | 0.0315 (11) | 0.0301 (11) | 0.0352 (11) | 0.0038 (9) | −0.0030 (9) | −0.0001 (9) |
C26 | 0.0460 (14) | 0.0323 (12) | 0.0405 (13) | 0.0056 (10) | −0.0053 (11) | 0.0014 (10) |
C27 | 0.0538 (16) | 0.0404 (14) | 0.0478 (15) | 0.0058 (12) | −0.0156 (12) | −0.0068 (11) |
C28 | 0.0483 (16) | 0.0343 (14) | 0.071 (2) | −0.0061 (12) | −0.0094 (14) | −0.0016 (13) |
C29 | 0.0563 (17) | 0.0415 (15) | 0.0606 (18) | −0.0111 (13) | −0.0005 (14) | 0.0100 (13) |
C30 | 0.0475 (15) | 0.0398 (14) | 0.0427 (14) | −0.0049 (11) | −0.0033 (11) | 0.0067 (11) |
C31 | 0.0408 (14) | 0.0337 (13) | 0.0508 (15) | 0.0049 (10) | 0.0042 (12) | −0.0001 (11) |
C32 | 0.0360 (12) | 0.0310 (12) | 0.0490 (14) | 0.0054 (10) | 0.0034 (10) | 0.0033 (10) |
C33 | 0.0551 (16) | 0.0321 (13) | 0.0504 (15) | 0.0014 (11) | −0.0005 (12) | 0.0117 (11) |
C34 | 0.0536 (16) | 0.0363 (13) | 0.0487 (15) | −0.0004 (11) | −0.0085 (12) | 0.0047 (11) |
C35 | 0.0390 (13) | 0.0291 (12) | 0.0472 (14) | 0.0035 (10) | 0.0042 (11) | 0.0038 (10) |
C36 | 0.0480 (15) | 0.0377 (14) | 0.0512 (15) | 0.0026 (11) | 0.0026 (12) | 0.0151 (11) |
C37 | 0.0484 (15) | 0.0425 (14) | 0.0468 (15) | 0.0001 (12) | −0.0046 (12) | 0.0081 (11) |
C38 | 0.0470 (14) | 0.0308 (12) | 0.0462 (14) | 0.0036 (10) | 0.0028 (12) | 0.0026 (10) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.901 (2) | C12—H12 | 0.9300 |
Cu1—O3 | 2.280 (2) | C13—C14 | 1.485 (3) |
Cu1—N1 | 2.047 (2) | C14—C15 | 1.376 (3) |
Cu1—N2 | 1.927 (2) | C15—C16 | 1.407 (3) |
Cu1—N3 | 2.018 (2) | C15—H15 | 0.9300 |
O1—C1 | 1.277 (3) | C16—C17 | 1.407 (3) |
O2—C1 | 1.230 (3) | C16—C25 | 1.477 (3) |
O3—C5 | 1.269 (2) | C17—C18 | 1.378 (3) |
O4—C5 | 1.243 (2) | C17—H17 | 0.9300 |
O5—C31 | 1.330 (3) | C18—C19 | 1.480 (3) |
O5—H5o | 0.85 (1) | C19—C21 | 1.380 (3) |
O6—C31 | 1.197 (3) | C21—C22 | 1.396 (4) |
O7—C38 | 1.317 (3) | C21—H21 | 0.9300 |
O7—H7o | 0.84 (1) | C22—C23 | 1.363 (4) |
O8—C38 | 1.202 (3) | C22—H22 | 0.9300 |
N1—C9 | 1.334 (3) | C23—C24 | 1.376 (4) |
N1—C13 | 1.357 (3) | C23—H23 | 0.9300 |
N2—C18 | 1.341 (3) | C24—H24 | 0.9300 |
N2—C14 | 1.341 (3) | C25—C30 | 1.394 (3) |
N3—C24 | 1.340 (3) | C25—C26 | 1.398 (3) |
N3—C19 | 1.357 (3) | C26—C27 | 1.373 (3) |
C1—C2 | 1.503 (3) | C26—H26 | 0.9300 |
C2—C4 | 1.380 (3) | C27—C28 | 1.377 (4) |
C2—C3 | 1.388 (3) | C27—H27 | 0.9300 |
C3—C4i | 1.376 (3) | C28—C29 | 1.378 (4) |
C3—H3 | 0.9300 | C28—H28 | 0.9300 |
C4—C3i | 1.376 (3) | C29—C30 | 1.381 (3) |
C4—H4 | 0.9300 | C29—H29 | 0.9300 |
C5—C6 | 1.504 (3) | C30—H30 | 0.9300 |
C6—C8 | 1.395 (3) | C31—C32 | 1.499 (3) |
C6—C7 | 1.396 (3) | C32—C33 | 1.381 (4) |
C7—C8ii | 1.382 (3) | C32—C37 | 1.386 (4) |
C7—H7 | 0.9300 | C33—C34 | 1.374 (3) |
C8—C7ii | 1.382 (3) | C33—H33 | 0.9300 |
C8—H8 | 0.9300 | C34—C35 | 1.389 (4) |
C9—C10 | 1.382 (4) | C34—H34 | 0.9300 |
C9—H9 | 0.9300 | C35—C36 | 1.391 (4) |
C10—C11 | 1.372 (4) | C35—C38 | 1.495 (3) |
C10—H10 | 0.9300 | C36—C37 | 1.379 (3) |
C11—C12 | 1.383 (3) | C36—H36 | 0.9300 |
C11—H11 | 0.9300 | C37—H37 | 0.9300 |
C12—C13 | 1.376 (3) | ||
O1—Cu1—O3 | 89.94 (6) | C16—C15—H15 | 119.9 |
O1—Cu1—N1 | 99.11 (8) | C17—C16—C15 | 117.3 (2) |
O1—Cu1—N2 | 172.45 (7) | C17—C16—C25 | 121.8 (2) |
O1—Cu1—N3 | 100.18 (8) | C15—C16—C25 | 120.83 (19) |
O3—Cu1—N1 | 87.69 (7) | C18—C17—C16 | 119.7 (2) |
O3—Cu1—N2 | 97.43 (7) | C18—C17—H17 | 120.1 |
O3—Cu1—N3 | 101.00 (7) | C16—C17—H17 | 120.1 |
N1—Cu1—N2 | 79.65 (7) | N2—C18—C17 | 120.91 (19) |
N1—Cu1—N3 | 158.81 (8) | N2—C18—C19 | 112.32 (19) |
N2—Cu1—N3 | 80.07 (7) | C17—C18—C19 | 126.8 (2) |
C1—O1—Cu1 | 113.00 (15) | N3—C19—C21 | 121.8 (2) |
C5—O3—Cu1 | 118.42 (13) | N3—C19—C18 | 113.85 (19) |
C31—O5—H5o | 111 (3) | C21—C19—C18 | 124.3 (2) |
C38—O7—H7o | 116 (3) | C19—C21—C22 | 118.1 (2) |
C9—N1—C13 | 118.8 (2) | C19—C21—H21 | 120.9 |
C9—N1—Cu1 | 126.86 (17) | C22—C21—H21 | 120.9 |
C13—N1—Cu1 | 114.07 (15) | C23—C22—C21 | 120.1 (2) |
C18—N2—C14 | 121.29 (18) | C23—C22—H22 | 120.0 |
C18—N2—Cu1 | 119.05 (14) | C21—C22—H22 | 120.0 |
C14—N2—Cu1 | 119.48 (15) | C22—C23—C24 | 118.9 (2) |
C24—N3—C19 | 118.7 (2) | C22—C23—H23 | 120.5 |
C24—N3—Cu1 | 126.87 (17) | C24—C23—H23 | 120.5 |
C19—N3—Cu1 | 114.34 (14) | N3—C24—C23 | 122.4 (2) |
O2—C1—O1 | 123.8 (2) | N3—C24—H24 | 118.8 |
O2—C1—C2 | 120.4 (2) | C23—C24—H24 | 118.8 |
O1—C1—C2 | 115.8 (2) | C30—C25—C26 | 117.8 (2) |
C4—C2—C3 | 119.6 (2) | C30—C25—C16 | 121.2 (2) |
C4—C2—C1 | 120.1 (2) | C26—C25—C16 | 121.0 (2) |
C3—C2—C1 | 120.3 (2) | C27—C26—C25 | 120.9 (2) |
C4i—C3—C2 | 120.1 (2) | C27—C26—H26 | 119.5 |
C4i—C3—H3 | 120.0 | C25—C26—H26 | 119.5 |
C2—C3—H3 | 120.0 | C26—C27—C28 | 120.6 (2) |
C3i—C4—C2 | 120.3 (2) | C26—C27—H27 | 119.7 |
C3i—C4—H4 | 119.9 | C28—C27—H27 | 119.7 |
C2—C4—H4 | 119.9 | C27—C28—C29 | 119.5 (2) |
O4—C5—O3 | 123.53 (19) | C27—C28—H28 | 120.2 |
O4—C5—C6 | 118.78 (18) | C29—C28—H28 | 120.2 |
O3—C5—C6 | 117.69 (18) | C28—C29—C30 | 120.3 (3) |
C8—C6—C7 | 119.18 (19) | C28—C29—H29 | 119.8 |
C8—C6—C5 | 120.16 (19) | C30—C29—H29 | 119.8 |
C7—C6—C5 | 120.66 (18) | C29—C30—C25 | 120.9 (2) |
C8ii—C7—C6 | 120.31 (19) | C29—C30—H30 | 119.5 |
C8ii—C7—H7 | 119.8 | C25—C30—H30 | 119.5 |
C6—C7—H7 | 119.8 | O6—C31—O5 | 124.0 (2) |
C7ii—C8—C6 | 120.51 (19) | O6—C31—C32 | 123.6 (2) |
C7ii—C8—H8 | 119.7 | O5—C31—C32 | 112.3 (2) |
C6—C8—H8 | 119.7 | C33—C32—C37 | 119.0 (2) |
N1—C9—C10 | 122.1 (2) | C33—C32—C31 | 121.8 (2) |
N1—C9—H9 | 119.0 | C37—C32—C31 | 119.2 (2) |
C10—C9—H9 | 119.0 | C34—C33—C32 | 120.7 (2) |
C11—C10—C9 | 119.3 (2) | C34—C33—H33 | 119.6 |
C11—C10—H10 | 120.4 | C32—C33—H33 | 119.6 |
C9—C10—H10 | 120.4 | C33—C34—C35 | 120.4 (2) |
C10—C11—C12 | 119.1 (2) | C33—C34—H34 | 119.8 |
C10—C11—H11 | 120.4 | C35—C34—H34 | 119.8 |
C12—C11—H11 | 120.4 | C34—C35—C36 | 119.0 (2) |
C13—C12—C11 | 119.1 (2) | C34—C35—C38 | 118.2 (2) |
C13—C12—H12 | 120.5 | C36—C35—C38 | 122.7 (2) |
C11—C12—H12 | 120.5 | C37—C36—C35 | 120.1 (2) |
N1—C13—C12 | 121.7 (2) | C37—C36—H36 | 120.0 |
N1—C13—C14 | 113.62 (19) | C35—C36—H36 | 120.0 |
C12—C13—C14 | 124.7 (2) | C36—C37—C32 | 120.7 (2) |
N2—C14—C15 | 120.5 (2) | C36—C37—H37 | 119.7 |
N2—C14—C13 | 112.71 (18) | C32—C37—H37 | 119.7 |
C15—C14—C13 | 126.74 (19) | O8—C38—O7 | 123.4 (2) |
C14—C15—C16 | 120.2 (2) | O8—C38—C35 | 122.6 (2) |
C14—C15—H15 | 119.9 | O7—C38—C35 | 114.0 (2) |
N2—Cu1—O1—C1 | 11.2 (6) | Cu1—N2—C14—C15 | 175.44 (17) |
N3—Cu1—O1—C1 | −80.07 (18) | C18—N2—C14—C13 | −179.25 (19) |
N1—Cu1—O1—C1 | 91.12 (18) | Cu1—N2—C14—C13 | −4.1 (2) |
O3—Cu1—O1—C1 | 178.77 (17) | N1—C13—C14—N2 | −1.3 (3) |
O1—Cu1—O3—C5 | 173.75 (16) | C12—C13—C14—N2 | 178.0 (2) |
N2—Cu1—O3—C5 | −7.88 (16) | N1—C13—C14—C15 | 179.1 (2) |
N3—Cu1—O3—C5 | 73.39 (16) | C12—C13—C14—C15 | −1.6 (4) |
N1—Cu1—O3—C5 | −87.13 (16) | N2—C14—C15—C16 | 0.1 (3) |
O1—Cu1—N1—C9 | 7.8 (2) | C13—C14—C15—C16 | 179.6 (2) |
N2—Cu1—N1—C9 | −179.7 (2) | C14—C15—C16—C17 | −0.3 (3) |
N3—Cu1—N1—C9 | 163.2 (2) | C14—C15—C16—C25 | 179.5 (2) |
O3—Cu1—N1—C9 | −81.7 (2) | C15—C16—C17—C18 | 0.1 (3) |
O1—Cu1—N1—C13 | −178.54 (16) | C25—C16—C17—C18 | −179.7 (2) |
N2—Cu1—N1—C13 | −6.10 (16) | C14—N2—C18—C17 | −0.5 (3) |
N3—Cu1—N1—C13 | −23.2 (3) | Cu1—N2—C18—C17 | −175.66 (16) |
O3—Cu1—N1—C13 | 91.89 (16) | C14—N2—C18—C19 | 179.44 (19) |
O1—Cu1—N2—C18 | −97.9 (6) | Cu1—N2—C18—C19 | 4.3 (2) |
N3—Cu1—N2—C18 | −5.33 (16) | C16—C17—C18—N2 | 0.3 (3) |
N1—Cu1—N2—C18 | −179.14 (17) | C16—C17—C18—C19 | −179.7 (2) |
O3—Cu1—N2—C18 | 94.60 (16) | C24—N3—C19—C21 | −0.6 (3) |
O1—Cu1—N2—C14 | 86.9 (6) | Cu1—N3—C19—C21 | 176.33 (17) |
N3—Cu1—N2—C14 | 179.45 (17) | C24—N3—C19—C18 | 178.56 (19) |
N1—Cu1—N2—C14 | 5.65 (16) | Cu1—N3—C19—C18 | −4.5 (2) |
O3—Cu1—N2—C14 | −80.62 (17) | N2—C18—C19—N3 | 0.4 (3) |
O1—Cu1—N3—C24 | −5.8 (2) | C17—C18—C19—N3 | −179.7 (2) |
N2—Cu1—N3—C24 | −178.1 (2) | N2—C18—C19—C21 | 179.5 (2) |
N1—Cu1—N3—C24 | −161.0 (2) | C17—C18—C19—C21 | −0.5 (4) |
O3—Cu1—N3—C24 | 86.18 (19) | N3—C19—C21—C22 | 0.4 (4) |
O1—Cu1—N3—C19 | 177.61 (15) | C18—C19—C21—C22 | −178.6 (2) |
N2—Cu1—N3—C19 | 5.28 (15) | C19—C21—C22—C23 | −0.2 (4) |
N1—Cu1—N3—C19 | 22.4 (3) | C21—C22—C23—C24 | 0.2 (4) |
O3—Cu1—N3—C19 | −90.45 (15) | C19—N3—C24—C23 | 0.6 (3) |
Cu1—O1—C1—O2 | −0.4 (3) | Cu1—N3—C24—C23 | −175.95 (18) |
Cu1—O1—C1—C2 | 178.71 (15) | C22—C23—C24—N3 | −0.4 (4) |
O2—C1—C2—C4 | −13.9 (4) | C17—C16—C25—C30 | 23.7 (3) |
O1—C1—C2—C4 | 166.9 (2) | C15—C16—C25—C30 | −156.1 (2) |
O2—C1—C2—C3 | 166.2 (3) | C17—C16—C25—C26 | −157.8 (2) |
O1—C1—C2—C3 | −12.9 (3) | C15—C16—C25—C26 | 22.4 (3) |
C4—C2—C3—C4i | −0.7 (4) | C30—C25—C26—C27 | −0.7 (4) |
C1—C2—C3—C4i | 179.2 (2) | C16—C25—C26—C27 | −179.2 (2) |
C3—C2—C4—C3i | 0.7 (4) | C25—C26—C27—C28 | 0.3 (4) |
C1—C2—C4—C3i | −179.2 (2) | C26—C27—C28—C29 | 0.2 (5) |
Cu1—O3—C5—O4 | −43.1 (3) | C27—C28—C29—C30 | −0.1 (5) |
Cu1—O3—C5—C6 | 136.49 (15) | C28—C29—C30—C25 | −0.3 (5) |
O4—C5—C6—C8 | −15.7 (3) | C26—C25—C30—C29 | 0.7 (4) |
O3—C5—C6—C8 | 164.61 (19) | C16—C25—C30—C29 | 179.2 (2) |
O4—C5—C6—C7 | 164.5 (2) | O6—C31—C32—C33 | 169.4 (3) |
O3—C5—C6—C7 | −15.2 (3) | O5—C31—C32—C33 | −7.3 (4) |
C8—C6—C7—C8ii | −0.5 (3) | O6—C31—C32—C37 | −7.1 (4) |
C5—C6—C7—C8ii | 179.23 (19) | O5—C31—C32—C37 | 176.2 (2) |
C7—C6—C8—C7ii | 0.5 (3) | C37—C32—C33—C34 | 3.3 (4) |
C5—C6—C8—C7ii | −179.23 (19) | C31—C32—C33—C34 | −173.3 (2) |
C13—N1—C9—C10 | −0.5 (4) | C32—C33—C34—C35 | −1.5 (4) |
Cu1—N1—C9—C10 | 172.9 (2) | C33—C34—C35—C36 | −2.0 (4) |
N1—C9—C10—C11 | 0.5 (4) | C33—C34—C35—C38 | 174.1 (2) |
C9—C10—C11—C12 | −0.5 (4) | C34—C35—C36—C37 | 3.8 (4) |
C10—C11—C12—C13 | 0.6 (4) | C38—C35—C36—C37 | −172.1 (2) |
C9—N1—C13—C12 | 0.5 (4) | C35—C36—C37—C32 | −2.1 (4) |
Cu1—N1—C13—C12 | −173.64 (19) | C33—C32—C37—C36 | −1.5 (4) |
C9—N1—C13—C14 | 179.8 (2) | C31—C32—C37—C36 | 175.2 (2) |
Cu1—N1—C13—C14 | 5.7 (2) | C34—C35—C38—O8 | −16.0 (4) |
C11—C12—C13—N1 | −0.6 (4) | C36—C35—C38—O8 | 159.9 (3) |
C11—C12—C13—C14 | −179.8 (2) | C34—C35—C38—O7 | 165.0 (2) |
C18—N2—C14—C15 | 0.3 (3) | C36—C35—C38—O7 | −19.1 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5o···O4 | 0.85 (1) | 1.75 (1) | 2.594 (2) | 176 (4) |
O7—H7o···O3iii | 0.84 (1) | 1.82 (1) | 2.666 (2) | 177 (4) |
Symmetry code: (iii) x−1, y−1, z. |
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