In the title cooordination polymer, {[Cu(C
6H
2O
4S)(C
10H
9N
3)(H
2O)]·C
3H
7NO·H
2O}
n, the Cu
II atom is in a square-pyramidal environment defined by an apically coordinated water molecule, carboxyl O atoms from two different thiophene-2,5-dicarboxylate dianions and the two N atoms of a chelating di-2-pyridylamine ligand. The thiophene-2,5-dicarboxylate dianion functions as a μ
2-bridging ligand to form a zigzag polymeric chain. In addition, N—H
O and O—H
O intermolecular hydrogen bonds link the chains into a three-dimensional network structure.
Supporting information
CCDC reference: 293992
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.031
- wR factor = 0.075
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13
O4 -CU1 -N3 -C12 -56.90 0.80 2.565 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17
O4 -CU1 -N3 -C16 120.10 0.70 2.565 1.555 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Rat
O5 -H5A 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.844(10) ...... 3.00 su-Rat
O5 -H5B 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.844(10) ...... 3.00 su-Rat
O5 -H5B 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Rat
O5 -H5A 1.555 1.555
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _reflns_number_total 4485
Count of symmetry unique reflns 2736
Completeness (_total/calc) 163.93%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1749
Fraction of Friedel pairs measured 0.639
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
catena-Poly[[[aqua(di-2-pyridylamine-
κ2N2,
N2')copper(II)]-µ- thiophene-2,5-dicarboxylato-
κ2O2:
O5]
N,
N-dimethylformamide monohydrate]
top
Crystal data top
[Cu(C6H2O4S)(C10H9N3)(H2O)]·C3H7NO·H2O | F(000) = 1060 |
Mr = 514.01 | Dx = 1.497 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 6159 reflections |
a = 7.067 (1) Å | θ = 2.9–25.7° |
b = 24.123 (2) Å | µ = 1.10 mm−1 |
c = 13.379 (1) Å | T = 298 K |
V = 2280.8 (4) Å3 | Block, blue |
Z = 4 | 0.46 × 0.41 × 0.17 mm |
Data collection top
Bruker APEX area-detector diffractometer | 4485 independent reflections |
Radiation source: fine-focus sealed tube | 4174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.633, Tmax = 0.836 | k = −30→28 |
13430 measured reflections | l = −17→12 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0436P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4485 reflections | Δρmax = 0.28 e Å−3 |
306 parameters | Δρmin = −0.35 e Å−3 |
6 restraints | Absolute structure: Flack (1983), 5538 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.012 (11) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.37248 (4) | 0.361767 (10) | 0.31324 (3) | 0.02829 (8) | |
S1 | 0.18998 (10) | 0.52931 (3) | 0.03113 (6) | 0.04299 (17) | |
O1 | 0.2441 (3) | 0.39926 (7) | 0.20203 (15) | 0.0373 (4) | |
O2 | 0.4530 (3) | 0.46381 (11) | 0.1561 (2) | 0.0749 (9) | |
O3 | 0.0218 (3) | 0.61444 (7) | −0.10425 (15) | 0.0439 (5) | |
O4 | −0.2718 (3) | 0.58068 (8) | −0.09834 (16) | 0.0428 (5) | |
O5 | 0.6477 (3) | 0.40404 (10) | 0.2890 (2) | 0.0593 (7) | |
H5A | 0.745 (4) | 0.4076 (18) | 0.325 (3) | 0.089* | |
O6 | 0.1613 (4) | 0.31322 (14) | 0.8349 (3) | 0.0946 (11) | |
O7 | 0.7557 (4) | 0.30210 (16) | 0.8343 (2) | 0.0857 (9) | |
N1 | 0.4492 (3) | 0.31666 (8) | 0.43208 (16) | 0.0320 (4) | |
N2 | 0.4104 (3) | 0.23093 (9) | 0.35201 (17) | 0.0341 (5) | |
H2 | 0.3609 | 0.1988 | 0.3618 | 0.041* | |
N3 | 0.4437 (3) | 0.29830 (8) | 0.22521 (15) | 0.0298 (4) | |
N4 | 0.2849 (6) | 0.39889 (15) | 0.8154 (3) | 0.0881 (10) | |
C1 | 0.2936 (4) | 0.44285 (11) | 0.1568 (2) | 0.0397 (6) | |
C2 | 0.1414 (4) | 0.47032 (11) | 0.0978 (2) | 0.0382 (6) | |
C3 | −0.0432 (4) | 0.45562 (12) | 0.0887 (3) | 0.0467 (7) | |
H3 | −0.0954 | 0.4246 | 0.1195 | 0.056* | |
C4 | −0.1477 (4) | 0.49215 (13) | 0.0277 (3) | 0.0472 (7) | |
H4 | −0.2762 | 0.4881 | 0.0145 | 0.057* | |
C5 | −0.0395 (4) | 0.53408 (10) | −0.0098 (2) | 0.0361 (6) | |
C6 | −0.0991 (4) | 0.58013 (10) | −0.0762 (2) | 0.0344 (5) | |
C7 | 0.4980 (4) | 0.34447 (13) | 0.5167 (2) | 0.0449 (6) | |
H7 | 0.5027 | 0.3830 | 0.5143 | 0.054* | |
C8 | 0.5404 (5) | 0.31912 (15) | 0.6050 (2) | 0.0541 (8) | |
H8 | 0.5750 | 0.3397 | 0.6608 | 0.065* | |
C9 | 0.5304 (5) | 0.26160 (15) | 0.6090 (2) | 0.0525 (8) | |
H9 | 0.5535 | 0.2431 | 0.6688 | 0.063* | |
C10 | 0.4867 (4) | 0.23256 (12) | 0.5249 (2) | 0.0432 (7) | |
H10 | 0.4818 | 0.1940 | 0.5263 | 0.052* | |
C11 | 0.4492 (4) | 0.26128 (10) | 0.43643 (18) | 0.0314 (5) | |
C12 | 0.4409 (4) | 0.24547 (10) | 0.25298 (17) | 0.0287 (5) | |
C13 | 0.4699 (4) | 0.20183 (11) | 0.1853 (2) | 0.0386 (6) | |
H13 | 0.4600 | 0.1651 | 0.2059 | 0.046* | |
C14 | 0.5127 (4) | 0.21450 (13) | 0.0890 (2) | 0.0464 (7) | |
H14 | 0.5327 | 0.1863 | 0.0427 | 0.056* | |
C15 | 0.5265 (4) | 0.26952 (14) | 0.0597 (2) | 0.0456 (7) | |
H15 | 0.5595 | 0.2788 | −0.0054 | 0.055* | |
C16 | 0.4900 (4) | 0.30991 (12) | 0.1296 (2) | 0.0398 (6) | |
H16 | 0.4976 | 0.3469 | 0.1101 | 0.048* | |
C17 | 0.1109 (12) | 0.4222 (3) | 0.7847 (8) | 0.179 (4) | |
H17A | 0.0286 | 0.3933 | 0.7614 | 0.269* | |
H17B | 0.1330 | 0.4482 | 0.7317 | 0.269* | |
H17C | 0.0530 | 0.4409 | 0.8402 | 0.269* | |
C18 | 0.4481 (11) | 0.4341 (2) | 0.8216 (8) | 0.165 (4) | |
H18A | 0.4186 | 0.4661 | 0.8615 | 0.248* | |
H18B | 0.4842 | 0.4457 | 0.7557 | 0.248* | |
H18C | 0.5506 | 0.4141 | 0.8519 | 0.248* | |
C19 | 0.2885 (7) | 0.3470 (2) | 0.8387 (3) | 0.0781 (12) | |
H19 | 0.4041 | 0.3336 | 0.8616 | 0.094* | |
H7A | 0.739 (5) | 0.2673 (6) | 0.830 (4) | 0.11 (2)* | |
H7B | 0.873 (2) | 0.3091 (14) | 0.841 (4) | 0.083 (15)* | |
H5B | 0.645 (7) | 0.4238 (18) | 0.237 (2) | 0.108 (19)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02809 (14) | 0.02259 (13) | 0.03420 (14) | 0.00414 (10) | 0.00069 (13) | −0.00008 (13) |
S1 | 0.0334 (3) | 0.0348 (3) | 0.0607 (4) | −0.0029 (3) | −0.0029 (3) | 0.0216 (3) |
O1 | 0.0366 (10) | 0.0260 (9) | 0.0492 (11) | 0.0012 (7) | −0.0078 (8) | 0.0125 (8) |
O2 | 0.0384 (13) | 0.0715 (17) | 0.115 (2) | −0.0144 (11) | −0.0176 (13) | 0.0545 (16) |
O3 | 0.0457 (11) | 0.0307 (10) | 0.0553 (12) | 0.0002 (8) | 0.0046 (9) | 0.0149 (9) |
O4 | 0.0349 (11) | 0.0353 (10) | 0.0583 (13) | 0.0092 (8) | 0.0048 (9) | 0.0186 (9) |
O5 | 0.0380 (11) | 0.0594 (14) | 0.081 (2) | −0.0112 (10) | −0.0150 (11) | 0.0262 (13) |
O6 | 0.0739 (19) | 0.098 (2) | 0.112 (3) | −0.0003 (17) | 0.0048 (18) | 0.021 (2) |
O7 | 0.072 (2) | 0.109 (3) | 0.076 (2) | 0.0086 (17) | 0.0026 (16) | 0.0011 (17) |
N1 | 0.0312 (11) | 0.0338 (11) | 0.0310 (11) | 0.0031 (9) | 0.0000 (9) | 0.0009 (9) |
N2 | 0.0425 (12) | 0.0233 (10) | 0.0366 (11) | −0.0027 (9) | 0.0000 (9) | 0.0022 (9) |
N3 | 0.0290 (10) | 0.0284 (11) | 0.0319 (11) | 0.0053 (8) | 0.0016 (9) | 0.0014 (8) |
N4 | 0.115 (3) | 0.066 (2) | 0.083 (2) | 0.017 (2) | 0.014 (3) | −0.001 (2) |
C1 | 0.0356 (14) | 0.0334 (13) | 0.0501 (16) | 0.0052 (11) | −0.0028 (12) | 0.0094 (12) |
C2 | 0.0361 (14) | 0.0284 (13) | 0.0501 (16) | 0.0017 (10) | 0.0001 (12) | 0.0167 (12) |
C3 | 0.0378 (16) | 0.0353 (14) | 0.067 (2) | −0.0035 (12) | −0.0004 (14) | 0.0258 (14) |
C4 | 0.0295 (13) | 0.0436 (17) | 0.069 (2) | −0.0022 (11) | −0.0042 (13) | 0.0242 (15) |
C5 | 0.0328 (14) | 0.0286 (13) | 0.0468 (15) | 0.0061 (11) | 0.0012 (11) | 0.0086 (11) |
C6 | 0.0372 (14) | 0.0283 (12) | 0.0379 (13) | 0.0094 (10) | 0.0065 (11) | 0.0050 (10) |
C7 | 0.0473 (16) | 0.0499 (16) | 0.0376 (15) | −0.0004 (13) | −0.0031 (12) | −0.0079 (13) |
C8 | 0.0560 (19) | 0.072 (2) | 0.0340 (15) | 0.0020 (16) | −0.0043 (14) | −0.0112 (14) |
C9 | 0.0526 (19) | 0.076 (2) | 0.0285 (15) | 0.0057 (16) | 0.0004 (13) | 0.0127 (14) |
C10 | 0.0433 (16) | 0.0447 (16) | 0.0416 (15) | 0.0054 (12) | 0.0048 (12) | 0.0142 (13) |
C11 | 0.0276 (12) | 0.0352 (13) | 0.0315 (12) | 0.0026 (10) | 0.0033 (10) | 0.0032 (10) |
C12 | 0.0236 (11) | 0.0287 (12) | 0.0338 (13) | 0.0014 (9) | −0.0017 (10) | 0.0015 (10) |
C13 | 0.0420 (16) | 0.0300 (13) | 0.0438 (15) | 0.0072 (11) | −0.0065 (12) | −0.0079 (11) |
C14 | 0.0486 (18) | 0.0502 (17) | 0.0404 (15) | 0.0098 (13) | −0.0032 (12) | −0.0165 (14) |
C15 | 0.0411 (16) | 0.068 (2) | 0.0274 (13) | 0.0093 (14) | 0.0037 (11) | −0.0028 (13) |
C16 | 0.0398 (15) | 0.0423 (15) | 0.0373 (15) | 0.0053 (12) | 0.0028 (11) | 0.0084 (11) |
C17 | 0.217 (9) | 0.108 (5) | 0.211 (13) | 0.064 (6) | −0.050 (8) | 0.006 (6) |
C18 | 0.183 (7) | 0.083 (4) | 0.229 (9) | −0.022 (4) | 0.088 (7) | −0.032 (6) |
C19 | 0.070 (3) | 0.092 (3) | 0.072 (3) | 0.011 (2) | 0.006 (2) | 0.015 (2) |
Geometric parameters (Å, º) top
Cu1—O4i | 1.958 (2) | C3—C4 | 1.410 (4) |
Cu1—O1 | 1.963 (2) | C3—H3 | 0.9300 |
Cu1—N3 | 1.996 (2) | C4—C5 | 1.363 (4) |
Cu1—N1 | 2.002 (2) | C4—H4 | 0.9300 |
Cu1—O5 | 2.220 (2) | C5—C6 | 1.484 (4) |
S1—C2 | 1.714 (3) | C7—C8 | 1.363 (5) |
S1—C5 | 1.715 (3) | C7—H7 | 0.9300 |
O1—C1 | 1.262 (3) | C8—C9 | 1.390 (5) |
O2—C1 | 1.235 (4) | C8—H8 | 0.9300 |
O3—C6 | 1.248 (3) | C9—C10 | 1.361 (5) |
O4—C6 | 1.255 (3) | C9—H9 | 0.9300 |
O4—Cu1ii | 1.958 (2) | C10—C11 | 1.397 (4) |
O5—H5A | 0.842 (10) | C10—H10 | 0.9300 |
O5—H5B | 0.844 (10) | C12—C13 | 1.404 (3) |
O6—C19 | 1.213 (6) | C13—C14 | 1.358 (4) |
O7—H7A | 0.849 (10) | C13—H13 | 0.9300 |
O7—H7B | 0.849 (10) | C14—C15 | 1.387 (4) |
N1—C11 | 1.337 (3) | C14—H14 | 0.9300 |
N1—C7 | 1.361 (4) | C15—C16 | 1.375 (4) |
N2—C11 | 1.374 (3) | C15—H15 | 0.9300 |
N2—C12 | 1.388 (3) | C16—H16 | 0.9300 |
N2—H2 | 0.8600 | C17—H17A | 0.9600 |
N3—C12 | 1.328 (3) | C17—H17B | 0.9600 |
N3—C16 | 1.350 (3) | C17—H17C | 0.9600 |
N4—C19 | 1.292 (6) | C18—H18A | 0.9600 |
N4—C17 | 1.412 (8) | C18—H18B | 0.9600 |
N4—C18 | 1.435 (7) | C18—H18C | 0.9600 |
C1—C2 | 1.490 (4) | C19—H19 | 0.9300 |
C2—C3 | 1.358 (4) | | |
| | | |
O4i—Cu1—O1 | 87.90 (8) | O4—C6—C5 | 115.2 (2) |
O4i—Cu1—N3 | 172.76 (8) | N1—C7—C8 | 123.8 (3) |
O1—Cu1—N3 | 91.30 (8) | N1—C7—H7 | 118.1 |
O4i—Cu1—N1 | 90.23 (9) | C8—C7—H7 | 118.1 |
O1—Cu1—N1 | 167.87 (8) | C7—C8—C9 | 118.1 (3) |
N3—Cu1—N1 | 89.05 (9) | C7—C8—H8 | 121.0 |
O4i—Cu1—O5 | 94.65 (10) | C9—C8—H8 | 121.0 |
O1—Cu1—O5 | 94.73 (8) | C10—C9—C8 | 119.5 (3) |
N3—Cu1—O5 | 92.59 (10) | C10—C9—H9 | 120.2 |
N1—Cu1—O5 | 97.37 (9) | C8—C9—H9 | 120.2 |
C2—S1—C5 | 91.85 (13) | C9—C10—C11 | 119.2 (3) |
C1—O1—Cu1 | 128.24 (18) | C9—C10—H10 | 120.4 |
C6—O4—Cu1ii | 120.20 (17) | C11—C10—H10 | 120.4 |
Cu1—O5—H5A | 133 (3) | N1—C11—N2 | 119.8 (2) |
Cu1—O5—H5B | 111 (3) | N1—C11—C10 | 122.2 (2) |
H5A—O5—H5B | 116 (4) | N2—C11—C10 | 118.1 (2) |
H7A—O7—H7B | 109.7 (17) | N3—C12—N2 | 120.8 (2) |
C11—N1—C7 | 117.1 (2) | N3—C12—C13 | 122.5 (2) |
C11—N1—Cu1 | 125.28 (17) | N2—C12—C13 | 116.7 (2) |
C7—N1—Cu1 | 117.52 (19) | C14—C13—C12 | 118.4 (3) |
C11—N2—C12 | 128.3 (2) | C14—C13—H13 | 120.8 |
C11—N2—H2 | 115.9 | C12—C13—H13 | 120.8 |
C12—N2—H2 | 115.9 | C13—C14—C15 | 119.9 (3) |
C12—N3—C16 | 117.9 (2) | C13—C14—H14 | 120.0 |
C12—N3—Cu1 | 124.56 (17) | C15—C14—H14 | 120.0 |
C16—N3—Cu1 | 117.47 (18) | C16—C15—C14 | 118.2 (3) |
C19—N4—C17 | 118.2 (5) | C16—C15—H15 | 120.9 |
C19—N4—C18 | 123.0 (5) | C14—C15—H15 | 120.9 |
C17—N4—C18 | 118.8 (6) | N3—C16—C15 | 122.9 (3) |
O2—C1—O1 | 126.7 (3) | N3—C16—H16 | 118.6 |
O2—C1—C2 | 118.2 (2) | C15—C16—H16 | 118.6 |
O1—C1—C2 | 115.1 (2) | N4—C17—H17A | 109.5 |
C3—C2—C1 | 128.7 (2) | N4—C17—H17B | 109.5 |
C3—C2—S1 | 111.3 (2) | H17A—C17—H17B | 109.5 |
C1—C2—S1 | 120.0 (2) | N4—C17—H17C | 109.5 |
C2—C3—C4 | 113.1 (2) | H17A—C17—H17C | 109.5 |
C2—C3—H3 | 123.5 | H17B—C17—H17C | 109.5 |
C4—C3—H3 | 123.5 | N4—C18—H18A | 109.5 |
C5—C4—C3 | 112.5 (2) | N4—C18—H18B | 109.5 |
C5—C4—H4 | 123.8 | H18A—C18—H18B | 109.5 |
C3—C4—H4 | 123.8 | N4—C18—H18C | 109.5 |
C4—C5—C6 | 128.0 (3) | H18A—C18—H18C | 109.5 |
C4—C5—S1 | 111.3 (2) | H18B—C18—H18C | 109.5 |
C6—C5—S1 | 120.7 (2) | O6—C19—N4 | 128.7 (5) |
O3—C6—O4 | 126.0 (2) | O6—C19—H19 | 115.6 |
O3—C6—C5 | 118.8 (2) | N4—C19—H19 | 115.6 |
| | | |
O4i—Cu1—O1—C1 | 76.9 (2) | Cu1ii—O4—C6—O3 | 1.4 (4) |
N3—Cu1—O1—C1 | −110.3 (2) | Cu1ii—O4—C6—C5 | −179.24 (18) |
N1—Cu1—O1—C1 | 158.2 (4) | C4—C5—C6—O3 | −178.9 (3) |
O5—Cu1—O1—C1 | −17.6 (3) | S1—C5—C6—O3 | 2.1 (4) |
O4i—Cu1—N1—C11 | 146.4 (2) | C4—C5—C6—O4 | 1.7 (5) |
O1—Cu1—N1—C11 | 65.3 (5) | S1—C5—C6—O4 | −177.4 (2) |
N3—Cu1—N1—C11 | −26.4 (2) | C11—N1—C7—C8 | −2.1 (4) |
O5—Cu1—N1—C11 | −118.9 (2) | Cu1—N1—C7—C8 | 175.3 (2) |
O4i—Cu1—N1—C7 | −30.7 (2) | N1—C7—C8—C9 | −1.0 (5) |
O1—Cu1—N1—C7 | −111.8 (4) | C7—C8—C9—C10 | 2.6 (5) |
N3—Cu1—N1—C7 | 156.5 (2) | C8—C9—C10—C11 | −1.2 (4) |
O5—Cu1—N1—C7 | 64.0 (2) | C7—N1—C11—N2 | −176.8 (2) |
O4i—Cu1—N3—C12 | −56.9 (8) | Cu1—N1—C11—N2 | 6.1 (3) |
O1—Cu1—N3—C12 | −140.4 (2) | C7—N1—C11—C10 | 3.6 (4) |
N1—Cu1—N3—C12 | 27.5 (2) | Cu1—N1—C11—C10 | −173.55 (19) |
O5—Cu1—N3—C12 | 124.8 (2) | C12—N2—C11—N1 | 27.9 (4) |
O4i—Cu1—N3—C16 | 120.1 (7) | C12—N2—C11—C10 | −152.4 (3) |
O1—Cu1—N3—C16 | 36.6 (2) | C9—C10—C11—N1 | −2.0 (4) |
N1—Cu1—N3—C16 | −155.6 (2) | C9—C10—C11—N2 | 178.3 (3) |
O5—Cu1—N3—C16 | −58.2 (2) | C16—N3—C12—N2 | 174.5 (3) |
Cu1—O1—C1—O2 | 18.7 (5) | Cu1—N3—C12—N2 | −8.6 (3) |
Cu1—O1—C1—C2 | −162.29 (19) | C16—N3—C12—C13 | −4.9 (4) |
O2—C1—C2—C3 | −178.8 (4) | Cu1—N3—C12—C13 | 172.06 (19) |
O1—C1—C2—C3 | 2.1 (5) | C11—N2—C12—N3 | −26.8 (4) |
O2—C1—C2—S1 | 0.1 (4) | C11—N2—C12—C13 | 152.6 (2) |
O1—C1—C2—S1 | −179.0 (2) | N3—C12—C13—C14 | 3.7 (4) |
C5—S1—C2—C3 | −0.3 (3) | N2—C12—C13—C14 | −175.7 (3) |
C5—S1—C2—C1 | −179.3 (3) | C12—C13—C14—C15 | −0.1 (4) |
C1—C2—C3—C4 | 178.8 (3) | C13—C14—C15—C16 | −2.0 (4) |
S1—C2—C3—C4 | −0.1 (4) | C12—N3—C16—C15 | 2.7 (4) |
C2—C3—C4—C5 | 0.6 (5) | Cu1—N3—C16—C15 | −174.5 (2) |
C3—C4—C5—C6 | −179.9 (3) | C14—C15—C16—N3 | 0.8 (4) |
C3—C4—C5—S1 | −0.8 (4) | C17—N4—C19—O6 | 2.9 (9) |
C2—S1—C5—C4 | 0.6 (3) | C18—N4—C19—O6 | −178.7 (6) |
C2—S1—C5—C6 | 179.8 (2) | | |
Symmetry codes: (i) −x, −y+1, z+1/2; (ii) −x, −y+1, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5B···O2 | 0.84 (1) | 1.99 (3) | 2.671 (3) | 138 (4) |
O7—H7B···O6iii | 0.85 (1) | 2.05 (2) | 2.879 (5) | 168 (4) |
O7—H7A···O6iv | 0.85 (1) | 2.02 (1) | 2.861 (5) | 170 (5) |
N2—H2···O3v | 0.86 | 2.24 | 2.910 (3) | 134 |
O5—H5A···O3vi | 0.84 (1) | 1.98 (2) | 2.773 (3) | 158 (4) |
Symmetry codes: (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z; (v) −x+1/2, y−1/2, z+1/2; (vi) −x+1, −y+1, z+1/2. |