In the crystal structure of the title two-dimensional complex, {[Cu(C
8H
4O
5)(C
5H
6N
2)
2]·H
2O}
n, the Cu atom has a distorted square-pyramidal coordination geometry. As well as O—H
O hydrogen bonds within a two-dimensional layer, there are N—H
O hydrogen bonds which connect layers into a three-dimensional network. In addition, there are significant π–π stacking interactions between layers.
Supporting information
CCDC reference: 283956
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.044
- wR factor = 0.128
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent N Ueq(max)/Ueq(min) ... 4.01 Ratio
PLAT420_ALERT_2_B D-H Without Acceptor >O1W - >H1B ... ?
| Author Response: The water molecule is disordered over two sites in a lattice
void. The location for H1B, that does not have an acceptor atom, was
refined isotropically. Alternate locations for H1B were investigated but
no other sensible positions for H1B could be found. It is possible that
the disorder of the water molecule may inhibit the determination of the
precise location of this H atom.
|
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.92 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 40.00 Perc.
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ?
| Author Response: The water molecule is disordered over two sites in a lattice
void. The location for H1B, that does not have an acceptor atom, was
refined isotropically. Alternate locations for H1B were investigated but
no other sensible positions for H1B could be found. It is possible that
the disorder of the water molecule may inhibit the determination of the
precise location of this H atom.
|
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3B ... ?
| Author Response: The water molecule is disordered over two sites in a lattice
void. The location for H1B, that does not have an acceptor atom, was
refined isotropically. Alternate locations for H1B were investigated but
no other sensible positions for H1B could be found. It is possible that
the disorder of the water molecule may inhibit the determination of the
precise location of this H atom.
|
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
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
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
2 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: SHELX97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Poly[[[
trans-bis(3-aminopyridine)copper(II)]-µ
3-5-hydroxy-1,3-
benzenedicarboxylato] monohydrate]
top
Crystal data top
[Cu(C8H4O5)(C5H6N2)2]·H2O | F(000) = 924 |
Mr = 449.90 | Dx = 1.588 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2213 reflections |
a = 10.3222 (9) Å | θ = 2.2–23.9° |
b = 11.5993 (10) Å | µ = 1.21 mm−1 |
c = 16.0222 (14) Å | T = 295 K |
β = 101.197 (2)° | Block, blue |
V = 1881.8 (3) Å3 | 0.25 × 0.25 × 0.19 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 3313 independent reflections |
Radiation source: fine-focus sealed tube | 2556 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→12 |
Tmin = 0.753, Tmax = 0.803 | k = −13→13 |
9360 measured reflections | l = −19→15 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0656P)25] where P = (Fo2 + 2Fc2)/3 |
3313 reflections | (Δ/σ)max = 0.002 |
284 parameters | Δρmax = 0.96 e Å−3 |
20 restraints | Δρmin = −0.54 e Å−3 |
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 | Occ. (<1) |
Cu1 | 0.90250 (4) | 0.88478 (4) | 0.08551 (3) | 0.02143 (18) | |
O1 | 0.7992 (2) | 0.9026 (2) | 0.17569 (16) | 0.0252 (6) | |
O2 | 0.7631 (3) | 0.7143 (2) | 0.18098 (18) | 0.0413 (8) | |
O3 | 0.6426 (3) | 1.0720 (2) | 0.42589 (17) | 0.0330 (7) | |
H3 | 0.6764 | 1.1186 | 0.3981 | 0.049* | |
O4 | 0.5331 (3) | 0.5673 (2) | 0.40923 (17) | 0.0322 (7) | |
O5 | 0.4911 (3) | 0.6934 (2) | 0.50539 (16) | 0.0306 (7) | |
N1 | 1.0558 (3) | 0.8425 (3) | 0.1798 (2) | 0.0257 (7) | |
N2 | 0.7363 (3) | 0.9075 (3) | −0.0030 (2) | 0.0336 (9) | |
N3 | 0.5948 (5) | 1.0976 (5) | −0.1753 (4) | 0.103 (2) | |
H3A | 0.5209 | 1.1098 | −0.2096 | 0.080* | |
H3B | 0.6614 | 1.1416 | −0.1767 | 0.080* | |
N4 | 1.2195 (5) | 0.9641 (4) | 0.3810 (3) | 0.0809 (16) | |
H4A | 1.2811 | 0.9475 | 0.4237 | 0.080* | |
H4B | 1.1814 | 1.0303 | 0.3783 | 0.080* | |
C1 | 0.7601 (4) | 0.8133 (3) | 0.2094 (2) | 0.0240 (9) | |
C2 | 0.7030 (4) | 0.8329 (3) | 0.2877 (2) | 0.0225 (8) | |
C3 | 0.6497 (3) | 0.7420 (3) | 0.3265 (2) | 0.0240 (9) | |
H3E | 0.6507 | 0.6676 | 0.3049 | 0.029* | |
C4 | 0.5946 (3) | 0.7631 (3) | 0.3981 (2) | 0.0211 (8) | |
C5 | 0.5929 (4) | 0.8734 (3) | 0.4300 (2) | 0.0235 (9) | |
H5 | 0.5556 | 0.8872 | 0.4775 | 0.028* | |
C6 | 0.6467 (4) | 0.9640 (3) | 0.3913 (2) | 0.0230 (9) | |
C7 | 0.7015 (4) | 0.9432 (3) | 0.3201 (2) | 0.0242 (9) | |
H7 | 0.7372 | 1.0039 | 0.2940 | 0.029* | |
C8 | 0.5354 (4) | 0.6649 (3) | 0.4397 (2) | 0.0215 (8) | |
C9 | 1.1141 (4) | 0.7392 (4) | 0.1826 (3) | 0.0392 (11) | |
H9 | 1.0912 | 0.6892 | 0.1367 | 0.047* | |
C10 | 1.2060 (5) | 0.7055 (5) | 0.2512 (3) | 0.0539 (14) | |
H10 | 1.2455 | 0.6334 | 0.2516 | 0.065* | |
C11 | 1.2408 (5) | 0.7788 (5) | 0.3203 (3) | 0.0528 (14) | |
H11 | 1.3029 | 0.7559 | 0.3675 | 0.063* | |
C12 | 1.1824 (5) | 0.8861 (4) | 0.3185 (3) | 0.0459 (13) | |
C13 | 1.0895 (4) | 0.9130 (4) | 0.2457 (3) | 0.0369 (11) | |
H13 | 1.0487 | 0.9847 | 0.2431 | 0.044* | |
C14 | 0.6302 (4) | 0.8386 (5) | −0.0024 (3) | 0.0481 (12) | |
H14 | 0.6381 | 0.7799 | 0.0378 | 0.058* | |
C15 | 0.5128 (5) | 0.8509 (5) | −0.0576 (3) | 0.0626 (15) | |
H15 | 0.4429 | 0.8011 | −0.0556 | 0.075* | |
C16 | 0.5000 (5) | 0.9380 (5) | −0.1158 (3) | 0.0580 (15) | |
H16 | 0.4202 | 0.9495 | −0.1533 | 0.070* | |
C17 | 0.6061 (5) | 1.0088 (5) | −0.1187 (3) | 0.0490 (13) | |
C18 | 0.7235 (4) | 0.9902 (4) | −0.0613 (3) | 0.0404 (11) | |
H18 | 0.7957 | 1.0372 | −0.0638 | 0.048* | |
O1W | 1.0218 (6) | 1.1469 (7) | 0.3830 (4) | 0.107 (3) | 0.791 (8) |
H1A | 0.943 (2) | 1.166 (6) | 0.3571 (18) | 0.080* | 0.791 (8) |
H1B | 1.023 (5) | 1.154 (5) | 0.4363 (8) | 0.080* | 0.791 (8) |
O1W' | 1.001 (3) | 1.054 (2) | 0.4668 (17) | 0.095 (9) | 0.209 (8) |
H1A' | 1.01 (3) | 0.981 (3) | 0.468 (13) | 0.080* | 0.209 (8) |
H1B' | 1.01 (3) | 1.079 (17) | 0.517 (6) | 0.080* | 0.209 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0289 (3) | 0.0206 (3) | 0.0176 (3) | 0.00384 (19) | 0.0114 (2) | 0.00045 (19) |
O1 | 0.0358 (15) | 0.0234 (15) | 0.0212 (14) | −0.0011 (12) | 0.0178 (12) | 0.0015 (11) |
O2 | 0.077 (2) | 0.0190 (17) | 0.0402 (18) | 0.0001 (15) | 0.0410 (17) | −0.0046 (13) |
O3 | 0.0631 (19) | 0.0139 (14) | 0.0295 (16) | −0.0057 (13) | 0.0277 (14) | −0.0035 (12) |
O4 | 0.0553 (18) | 0.0161 (15) | 0.0308 (16) | −0.0035 (13) | 0.0225 (14) | −0.0010 (12) |
O5 | 0.0495 (17) | 0.0230 (15) | 0.0266 (16) | −0.0074 (13) | 0.0257 (14) | −0.0017 (12) |
N1 | 0.0271 (17) | 0.0261 (18) | 0.0247 (18) | 0.0059 (15) | 0.0070 (14) | 0.0006 (15) |
N2 | 0.042 (2) | 0.039 (2) | 0.0207 (19) | 0.0084 (17) | 0.0091 (16) | −0.0007 (16) |
N3 | 0.078 (4) | 0.112 (5) | 0.113 (5) | −0.011 (3) | 0.005 (4) | 0.039 (4) |
N4 | 0.102 (4) | 0.073 (4) | 0.050 (3) | 0.011 (3) | −0.029 (3) | −0.008 (3) |
C1 | 0.032 (2) | 0.020 (2) | 0.023 (2) | 0.0021 (17) | 0.0122 (17) | 0.0002 (17) |
C2 | 0.033 (2) | 0.020 (2) | 0.018 (2) | 0.0001 (17) | 0.0131 (17) | −0.0009 (16) |
C3 | 0.035 (2) | 0.016 (2) | 0.025 (2) | 0.0003 (16) | 0.0148 (18) | −0.0020 (16) |
C4 | 0.029 (2) | 0.019 (2) | 0.018 (2) | 0.0002 (16) | 0.0090 (16) | 0.0006 (15) |
C5 | 0.033 (2) | 0.020 (2) | 0.021 (2) | 0.0019 (16) | 0.0159 (18) | 0.0005 (16) |
C6 | 0.033 (2) | 0.017 (2) | 0.022 (2) | 0.0005 (16) | 0.0105 (17) | −0.0016 (16) |
C7 | 0.034 (2) | 0.019 (2) | 0.023 (2) | −0.0022 (17) | 0.0146 (17) | 0.0057 (16) |
C8 | 0.026 (2) | 0.017 (2) | 0.022 (2) | −0.0022 (16) | 0.0068 (17) | 0.0017 (16) |
C9 | 0.045 (3) | 0.036 (3) | 0.038 (3) | 0.010 (2) | 0.010 (2) | 0.002 (2) |
C10 | 0.058 (3) | 0.043 (3) | 0.061 (4) | 0.019 (3) | 0.013 (3) | 0.014 (3) |
C11 | 0.045 (3) | 0.064 (4) | 0.046 (3) | 0.012 (3) | 0.001 (2) | 0.020 (3) |
C12 | 0.047 (3) | 0.053 (3) | 0.035 (3) | −0.001 (2) | 0.001 (2) | 0.004 (2) |
C13 | 0.039 (2) | 0.033 (3) | 0.039 (3) | 0.006 (2) | 0.007 (2) | 0.002 (2) |
C14 | 0.046 (3) | 0.058 (3) | 0.039 (3) | −0.009 (3) | 0.007 (2) | 0.012 (2) |
C15 | 0.055 (3) | 0.082 (4) | 0.049 (3) | −0.005 (3) | 0.006 (3) | 0.014 (3) |
C16 | 0.035 (3) | 0.083 (4) | 0.052 (3) | 0.000 (3) | 0.000 (2) | 0.006 (3) |
C17 | 0.061 (3) | 0.052 (3) | 0.031 (3) | 0.014 (3) | 0.004 (2) | 0.013 (2) |
C18 | 0.045 (3) | 0.043 (3) | 0.035 (3) | 0.003 (2) | 0.013 (2) | 0.004 (2) |
O1W | 0.081 (4) | 0.133 (6) | 0.103 (5) | 0.037 (4) | 0.007 (4) | −0.042 (4) |
O1W' | 0.083 (11) | 0.091 (12) | 0.110 (12) | 0.003 (9) | 0.020 (9) | −0.001 (8) |
Geometric parameters (Å, º) top
Cu1—O5i | 1.940 (2) | C4—C5 | 1.380 (5) |
Cu1—O1 | 1.966 (2) | C4—C8 | 1.508 (5) |
Cu1—N2 | 2.020 (3) | C5—C6 | 1.390 (5) |
Cu1—N1 | 2.025 (3) | C5—H5 | 0.9300 |
Cu1—O4ii | 2.216 (3) | C6—C7 | 1.389 (5) |
O1—C1 | 1.270 (4) | C7—H7 | 0.9300 |
O2—C1 | 1.238 (4) | C9—C10 | 1.362 (6) |
O3—C6 | 1.373 (4) | C9—H9 | 0.9300 |
O3—H3 | 0.8200 | C10—C11 | 1.388 (7) |
O4—C8 | 1.232 (4) | C10—H10 | 0.9300 |
O4—Cu1iii | 2.216 (3) | C11—C12 | 1.381 (7) |
O5—C8 | 1.269 (4) | C11—H11 | 0.9300 |
O5—Cu1iv | 1.940 (2) | C12—C13 | 1.394 (6) |
N1—C13 | 1.326 (5) | C13—H13 | 0.9300 |
N1—C9 | 1.338 (5) | C14—C15 | 1.362 (7) |
N2—C18 | 1.327 (5) | C14—H14 | 0.9300 |
N2—C14 | 1.358 (5) | C15—C16 | 1.364 (7) |
N3—C17 | 1.362 (7) | C15—H15 | 0.9300 |
N3—H3A | 0.8600 | C16—C17 | 1.376 (7) |
N3—H3B | 0.8600 | C16—H16 | 0.9300 |
N4—C12 | 1.349 (6) | C17—C18 | 1.389 (6) |
N4—H4A | 0.8600 | C18—H18 | 0.9300 |
N4—H4B | 0.8600 | O1W—H1A | 0.866 (8) |
C1—C2 | 1.504 (5) | O1W—H1B | 0.857 (10) |
C2—C7 | 1.382 (5) | O1W'—O1W'v | 1.64 (5) |
C2—C3 | 1.390 (5) | O1W'—H1B | 1.30 (6) |
C3—C4 | 1.397 (5) | O1W'—H1A' | 0.851 (11) |
C3—H3E | 0.9300 | O1W'—H1B' | 0.850 (11) |
| | | |
O5i—Cu1—O1 | 158.15 (11) | C7—C6—C5 | 119.8 (3) |
O5i—Cu1—N2 | 92.38 (12) | C2—C7—C6 | 120.3 (3) |
O1—Cu1—N2 | 89.71 (12) | C2—C7—H7 | 119.8 |
O5i—Cu1—N1 | 88.88 (12) | C6—C7—H7 | 119.8 |
O1—Cu1—N1 | 86.18 (11) | O4—C8—O5 | 125.8 (3) |
N2—Cu1—N1 | 171.87 (14) | O4—C8—C4 | 119.8 (3) |
O5i—Cu1—O4ii | 107.16 (11) | O5—C8—C4 | 114.4 (3) |
O1—Cu1—O4ii | 94.20 (10) | N1—C9—C10 | 121.5 (4) |
N2—Cu1—O4ii | 96.29 (13) | N1—C9—H9 | 119.3 |
N1—Cu1—O4ii | 91.01 (12) | C10—C9—H9 | 119.3 |
C1—O1—Cu1 | 119.3 (2) | C9—C10—C11 | 120.0 (5) |
C6—O3—H3 | 109.5 | C9—C10—H10 | 120.0 |
C8—O4—Cu1iii | 151.7 (3) | C11—C10—H10 | 120.0 |
C8—O5—Cu1iv | 136.0 (2) | C12—C11—C10 | 119.4 (4) |
C13—N1—C9 | 118.6 (4) | C12—C11—H11 | 120.3 |
C13—N1—Cu1 | 119.4 (3) | C10—C11—H11 | 120.3 |
C9—N1—Cu1 | 121.5 (3) | N4—C12—C11 | 121.9 (5) |
C18—N2—C14 | 117.4 (4) | N4—C12—C13 | 121.5 (5) |
C18—N2—Cu1 | 122.9 (3) | C11—C12—C13 | 116.5 (5) |
C14—N2—Cu1 | 119.6 (3) | N1—C13—C12 | 124.1 (4) |
C17—N3—H3A | 120.0 | N1—C13—H13 | 118.0 |
C17—N3—H3B | 120.0 | C12—C13—H13 | 118.0 |
H3A—N3—H3B | 120.0 | N2—C14—C15 | 123.5 (5) |
C12—N4—H4A | 120.0 | N2—C14—H14 | 118.3 |
C12—N4—H4B | 120.0 | C15—C14—H14 | 118.3 |
H4A—N4—H4B | 120.0 | C14—C15—C16 | 118.5 (5) |
O2—C1—O1 | 124.6 (3) | C14—C15—H15 | 120.8 |
O2—C1—C2 | 119.3 (3) | C16—C15—H15 | 120.8 |
O1—C1—C2 | 116.1 (3) | C15—C16—C17 | 119.5 (5) |
C7—C2—C3 | 120.0 (3) | C15—C16—H16 | 120.2 |
C7—C2—C1 | 119.2 (3) | C17—C16—H16 | 120.2 |
C3—C2—C1 | 120.8 (3) | N3—C17—C16 | 120.5 (5) |
C2—C3—C4 | 119.5 (3) | N3—C17—C18 | 120.6 (5) |
C2—C3—H3E | 120.2 | C16—C17—C18 | 118.9 (5) |
C4—C3—H3E | 120.2 | N2—C18—C17 | 122.2 (4) |
C5—C4—C3 | 120.3 (3) | N2—C18—H18 | 118.9 |
C5—C4—C8 | 120.0 (3) | C17—C18—H18 | 118.9 |
C3—C4—C8 | 119.7 (3) | H1A—O1W—H1B | 106.4 (14) |
C4—C5—C6 | 120.0 (3) | O1W'v—O1W'—H1B | 161 (3) |
C4—C5—H5 | 120.0 | H1B—O1W'—H1A' | 151 (10) |
C6—C5—H5 | 120.0 | O1W'v—O1W'—H1B' | 70 (10) |
O3—C6—C7 | 122.6 (3) | H1B—O1W'—H1B' | 93 (10) |
O3—C6—C5 | 117.6 (3) | H1A'—O1W'—H1B' | 109.6 (19) |
| | | |
O5i—Cu1—O1—C1 | 1.6 (5) | C1—C2—C7—C6 | 178.6 (3) |
N2—Cu1—O1—C1 | 97.3 (3) | O3—C6—C7—C2 | −180.0 (4) |
N1—Cu1—O1—C1 | −75.7 (3) | C5—C6—C7—C2 | −0.3 (6) |
O4ii—Cu1—O1—C1 | −166.4 (3) | Cu1iii—O4—C8—O5 | −67.8 (7) |
O5i—Cu1—N1—C13 | 148.1 (3) | Cu1iii—O4—C8—C4 | 112.3 (5) |
O1—Cu1—N1—C13 | −53.2 (3) | Cu1iv—O5—C8—O4 | −1.4 (6) |
O4ii—Cu1—N1—C13 | 40.9 (3) | Cu1iv—O5—C8—C4 | 178.5 (2) |
O5i—Cu1—N1—C9 | −40.0 (3) | C5—C4—C8—O4 | 177.5 (3) |
O1—Cu1—N1—C9 | 118.7 (3) | C3—C4—C8—O4 | −1.8 (5) |
O4ii—Cu1—N1—C9 | −147.1 (3) | C5—C4—C8—O5 | −2.4 (5) |
O5i—Cu1—N2—C18 | −79.3 (3) | C3—C4—C8—O5 | 178.4 (3) |
O1—Cu1—N2—C18 | 122.4 (3) | C13—N1—C9—C10 | 0.1 (6) |
O4ii—Cu1—N2—C18 | 28.2 (3) | Cu1—N1—C9—C10 | −171.9 (3) |
O5i—Cu1—N2—C14 | 102.9 (3) | N1—C9—C10—C11 | 0.3 (7) |
O1—Cu1—N2—C14 | −55.3 (3) | C9—C10—C11—C12 | −0.7 (7) |
O4ii—Cu1—N2—C14 | −149.5 (3) | C10—C11—C12—N4 | −175.0 (5) |
Cu1—O1—C1—O2 | −12.3 (5) | C10—C11—C12—C13 | 0.6 (7) |
Cu1—O1—C1—C2 | 169.6 (2) | C9—N1—C13—C12 | −0.2 (6) |
O2—C1—C2—C7 | 179.1 (4) | Cu1—N1—C13—C12 | 172.0 (4) |
O1—C1—C2—C7 | −2.6 (5) | N4—C12—C13—N1 | 175.4 (5) |
O2—C1—C2—C3 | −2.3 (6) | C11—C12—C13—N1 | −0.2 (7) |
O1—C1—C2—C3 | 175.9 (3) | C18—N2—C14—C15 | −0.6 (7) |
C7—C2—C3—C4 | 0.0 (6) | Cu1—N2—C14—C15 | 177.3 (4) |
C1—C2—C3—C4 | −178.5 (3) | N2—C14—C15—C16 | −1.0 (9) |
C2—C3—C4—C5 | 0.1 (6) | C14—C15—C16—C17 | 1.5 (9) |
C2—C3—C4—C8 | 179.4 (3) | C15—C16—C17—N3 | −178.8 (6) |
C3—C4—C5—C6 | −0.4 (6) | C15—C16—C17—C18 | −0.6 (8) |
C8—C4—C5—C6 | −179.6 (3) | C14—N2—C18—C17 | 1.6 (7) |
C4—C5—C6—O3 | −179.8 (3) | Cu1—N2—C18—C17 | −176.2 (3) |
C4—C5—C6—C7 | 0.4 (6) | N3—C17—C18—N2 | 177.2 (5) |
C3—C2—C7—C6 | 0.0 (6) | C16—C17—C18—N2 | −1.0 (7) |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x−1/2, −y+3/2, z+1/2; (v) −x+2, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2ii | 0.82 | 1.88 | 2.693 (4) | 171 |
N4—H4A···O3v | 0.86 | 2.40 | 3.172 (5) | 150 |
N4—H4B···O1W | 0.86 | 2.14 | 2.947 (8) | 155 |
N4—H4B···O1W′ | 0.86 | 2.57 | 3.05 (3) | 116 |
O1W—H1A···O2ii | 0.87 (1) | 2.17 (1) | 3.023 (6) | 168 (3) |
Symmetry codes: (ii) −x+3/2, y+1/2, −z+1/2; (v) −x+2, −y+2, −z+1. |