In the title compound, [Cu(C
8H
5O
5)Cl(C
12H
8N
2)(H
2O)]·2.5H
2O, the Cu
II atom is in a square-pyramidal geometry defined by one Cl
− anion, one aqua O atom, one carboxyl O atom belonging to one 5-hydroxyisophthalate anion, and two N atoms from a 1,10-phenanthroline molecule. O—H
O hydrogen bonds involving 5-hydroxyisophthalate anions, the aqua ligands and the uncoordinated water molecules, along with weak O—H
Cl hydrogen bonds, link the mononuclear units into a three-dimensional network structure.
Supporting information
CCDC reference: 272119
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- H-atom completeness 96%
- Disorder in solvent or counterion
- R factor = 0.050
- wR factor = 0.156
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.68
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O9 .. 3.14 Ang.
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C20 H20 Cl1 Cu1 N2 O8.5
Atom count from the _atom_site data: C20 H19 Cl1 Cu1 N2 O8.5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_sum C20 H20 Cl Cu N2 O8.5
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 40.00 40.00 0.00
H 40.00 38.00 2.00
Cl 2.00 2.00 0.00
Cu 2.00 2.00 0.00
N 4.00 4.00 0.00
O 17.00 17.00 0.00
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
1 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: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
Aquachloro[5-hydroxyisophthalato(1-)](1,10-phenanthroline)copper(II) 2.5-hydrate
top
Crystal data top
[Cu(C8H5O5)Cl(C12H8N2)(H2O)]·2.5H2O | Z = 2 |
Mr = 523.37 | F(000) = 536 |
Triclinic, P1 | Dx = 1.590 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8508 (10) Å | Cell parameters from 2931 reflections |
b = 10.7516 (12) Å | θ = 2.3–24.4° |
c = 12.7592 (15) Å | µ = 1.17 mm−1 |
α = 114.218 (2)° | T = 298 K |
β = 95.770 (2)° | Prism, blue |
γ = 94.022 (2)° | 0.33 × 0.15 × 0.13 mm |
V = 1093.4 (2) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3911 independent reflections |
Radiation source: fine-focus sealed tube | 3445 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 25.2°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.810, Tmax = 0.862 | k = −12→12 |
8038 measured reflections | l = −15→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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0785P)2 + 1.351P] where P = (Fo2 + 2Fc2)/3 |
3911 reflections | (Δ/σ)max < 0.001 |
313 parameters | Δρmax = 1.28 e Å−3 |
8 restraints | Δρmin = −0.48 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | 0.94701 (6) | 0.88662 (5) | 0.27984 (4) | 0.0333 (2) | |
Cl1 | 0.71061 (13) | 0.81084 (12) | 0.12694 (9) | 0.0453 (3) | |
O1 | 0.8466 (3) | 1.0061 (3) | 0.4076 (2) | 0.0381 (9) | |
O2 | 0.8222 (4) | 1.1817 (3) | 0.3593 (3) | 0.0441 (11) | |
O3 | 0.5900 (4) | 1.5828 (3) | 0.6309 (3) | 0.0504 (11) | |
O4 | 0.4699 (4) | 1.5535 (3) | 0.7659 (3) | 0.0513 (11) | |
O5 | 0.5235 (4) | 1.0742 (3) | 0.7163 (3) | 0.0433 (11) | |
O6 | 1.0255 (4) | 1.0405 (3) | 0.2450 (3) | 0.0465 (11) | |
N1 | 1.0769 (4) | 0.7580 (3) | 0.1751 (3) | 0.0343 (10) | |
N2 | 0.9214 (4) | 0.7356 (3) | 0.3333 (3) | 0.0316 (10) | |
C1 | 1.1576 (5) | 0.7746 (5) | 0.0982 (4) | 0.0438 (16) | |
C2 | 1.2382 (6) | 0.6717 (5) | 0.0289 (4) | 0.0483 (16) | |
C3 | 1.2338 (5) | 0.5497 (5) | 0.0374 (4) | 0.0449 (16) | |
C4 | 1.1475 (5) | 0.5275 (4) | 0.1163 (4) | 0.0362 (12) | |
C5 | 1.1344 (5) | 0.4027 (4) | 0.1335 (4) | 0.0431 (14) | |
C6 | 1.0536 (5) | 0.3911 (4) | 0.2119 (4) | 0.0437 (16) | |
C7 | 0.9789 (5) | 0.5027 (4) | 0.2857 (4) | 0.0357 (12) | |
C8 | 0.8968 (5) | 0.4998 (4) | 0.3735 (4) | 0.0400 (14) | |
C9 | 0.8330 (5) | 0.6126 (5) | 0.4384 (4) | 0.0426 (14) | |
C10 | 0.8470 (5) | 0.7303 (4) | 0.4165 (4) | 0.0361 (12) | |
C11 | 0.9878 (4) | 0.6238 (4) | 0.2693 (3) | 0.0304 (11) | |
C12 | 1.0726 (4) | 0.6367 (4) | 0.1839 (3) | 0.0306 (12) | |
C13 | 0.7970 (5) | 1.1183 (4) | 0.4205 (3) | 0.0321 (11) | |
C14 | 0.7030 (4) | 1.1791 (4) | 0.5174 (3) | 0.0306 (11) | |
C15 | 0.6647 (4) | 1.3110 (4) | 0.5493 (3) | 0.0320 (12) | |
C16 | 0.5796 (4) | 1.3663 (4) | 0.6400 (4) | 0.0322 (11) | |
C17 | 0.5296 (4) | 1.2880 (4) | 0.6971 (4) | 0.0338 (12) | |
C18 | 0.5679 (4) | 1.1562 (4) | 0.6636 (3) | 0.0322 (12) | |
C19 | 0.6560 (5) | 1.1026 (4) | 0.5756 (3) | 0.0330 (12) | |
C20 | 0.5481 (5) | 1.5121 (4) | 0.6773 (4) | 0.0365 (12) | |
O7 | 0.6859 (4) | 0.8519 (4) | 0.6776 (5) | 0.0858 (19) | |
O8 | 0.3877 (6) | 0.7989 (4) | 0.8158 (4) | 0.0815 (19) | |
O9 | 0.3090 (15) | 0.0112 (8) | 0.0159 (7) | 0.097 (4) | 0.500 |
H1 | 1.16040 | 0.85700 | 0.09050 | 0.0520* | |
H2 | 1.29500 | 0.68680 | −0.02320 | 0.0580* | |
H3 | 1.28760 | 0.48120 | −0.00860 | 0.0540* | |
H4 | 0.45840 | 1.63460 | 0.78510 | 0.0770* | |
H5 | 0.46590 | 1.11260 | 0.76280 | 0.0650* | |
H5A | 1.18340 | 0.32930 | 0.08880 | 0.0510* | |
H6 | 1.04510 | 0.30850 | 0.21940 | 0.0530* | |
H6A | 0.98170 | 1.10770 | 0.27840 | 0.0700* | |
H6B | 1.11680 | 1.08780 | 0.27830 | 0.0700* | |
H8 | 0.88620 | 0.42120 | 0.38710 | 0.0480* | |
H9 | 0.78000 | 0.61200 | 0.49750 | 0.0510* | |
H10 | 0.80260 | 0.80670 | 0.46170 | 0.0430* | |
H15 | 0.69580 | 1.36260 | 0.51020 | 0.0390* | |
H17 | 0.47120 | 1.32420 | 0.75690 | 0.0410* | |
H19 | 0.68390 | 1.01480 | 0.55540 | 0.0390* | |
H7A | 0.656 (5) | 0.775 (3) | 0.675 (5) | 0.0540* | |
H7B | 0.621 (4) | 0.905 (4) | 0.682 (5) | 0.0540* | |
H8A | 0.339 (5) | 0.794 (5) | 0.756 (2) | 0.0540* | |
H8B | 0.372 (6) | 0.849 (5) | 0.8802 (19) | 0.0540* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0409 (3) | 0.0250 (3) | 0.0390 (3) | 0.0099 (2) | 0.0165 (2) | 0.0151 (2) |
Cl1 | 0.0472 (6) | 0.0468 (6) | 0.0403 (6) | 0.0129 (5) | 0.0144 (5) | 0.0138 (5) |
O1 | 0.0536 (18) | 0.0276 (15) | 0.0397 (16) | 0.0145 (13) | 0.0190 (14) | 0.0166 (13) |
O2 | 0.059 (2) | 0.0340 (16) | 0.0525 (19) | 0.0175 (14) | 0.0257 (16) | 0.0255 (15) |
O3 | 0.075 (2) | 0.0291 (16) | 0.054 (2) | 0.0148 (15) | 0.0217 (17) | 0.0203 (15) |
O4 | 0.069 (2) | 0.0313 (17) | 0.059 (2) | 0.0224 (16) | 0.0286 (17) | 0.0174 (16) |
O5 | 0.0533 (19) | 0.0332 (16) | 0.055 (2) | 0.0164 (14) | 0.0281 (15) | 0.0238 (15) |
O6 | 0.0532 (19) | 0.0305 (16) | 0.065 (2) | 0.0114 (14) | 0.0282 (16) | 0.0239 (15) |
N1 | 0.0366 (18) | 0.0308 (18) | 0.0358 (18) | 0.0076 (14) | 0.0096 (15) | 0.0128 (15) |
N2 | 0.0358 (18) | 0.0268 (17) | 0.0347 (18) | 0.0076 (14) | 0.0096 (15) | 0.0137 (14) |
C1 | 0.053 (3) | 0.040 (2) | 0.044 (3) | 0.007 (2) | 0.016 (2) | 0.021 (2) |
C2 | 0.053 (3) | 0.053 (3) | 0.040 (2) | 0.011 (2) | 0.020 (2) | 0.017 (2) |
C3 | 0.047 (3) | 0.043 (3) | 0.040 (2) | 0.016 (2) | 0.016 (2) | 0.009 (2) |
C4 | 0.035 (2) | 0.034 (2) | 0.033 (2) | 0.0075 (17) | 0.0054 (17) | 0.0070 (18) |
C5 | 0.048 (3) | 0.031 (2) | 0.044 (2) | 0.0157 (19) | 0.010 (2) | 0.0070 (19) |
C6 | 0.055 (3) | 0.026 (2) | 0.049 (3) | 0.0108 (19) | 0.006 (2) | 0.014 (2) |
C7 | 0.037 (2) | 0.026 (2) | 0.040 (2) | 0.0049 (17) | 0.0016 (18) | 0.0106 (17) |
C8 | 0.051 (3) | 0.030 (2) | 0.044 (2) | 0.0029 (19) | 0.006 (2) | 0.021 (2) |
C9 | 0.050 (3) | 0.040 (2) | 0.044 (2) | 0.006 (2) | 0.015 (2) | 0.022 (2) |
C10 | 0.042 (2) | 0.032 (2) | 0.037 (2) | 0.0102 (18) | 0.0128 (18) | 0.0146 (18) |
C11 | 0.032 (2) | 0.0250 (19) | 0.031 (2) | 0.0048 (16) | 0.0020 (16) | 0.0090 (16) |
C12 | 0.032 (2) | 0.028 (2) | 0.031 (2) | 0.0035 (16) | 0.0031 (16) | 0.0120 (17) |
C13 | 0.037 (2) | 0.0226 (19) | 0.035 (2) | 0.0061 (16) | 0.0084 (17) | 0.0092 (17) |
C14 | 0.033 (2) | 0.0233 (19) | 0.033 (2) | 0.0043 (16) | 0.0039 (16) | 0.0095 (16) |
C15 | 0.037 (2) | 0.026 (2) | 0.034 (2) | 0.0038 (16) | 0.0059 (17) | 0.0133 (17) |
C16 | 0.034 (2) | 0.0229 (19) | 0.038 (2) | 0.0052 (16) | 0.0050 (17) | 0.0108 (17) |
C17 | 0.033 (2) | 0.029 (2) | 0.037 (2) | 0.0070 (17) | 0.0109 (17) | 0.0098 (18) |
C18 | 0.034 (2) | 0.028 (2) | 0.037 (2) | 0.0045 (16) | 0.0088 (17) | 0.0150 (18) |
C19 | 0.036 (2) | 0.025 (2) | 0.038 (2) | 0.0067 (16) | 0.0078 (17) | 0.0123 (17) |
C20 | 0.040 (2) | 0.027 (2) | 0.038 (2) | 0.0083 (17) | 0.0063 (18) | 0.0083 (18) |
O7 | 0.055 (2) | 0.038 (2) | 0.171 (5) | 0.0106 (18) | 0.024 (3) | 0.048 (3) |
O8 | 0.122 (4) | 0.058 (3) | 0.061 (3) | 0.045 (3) | 0.009 (3) | 0.017 (2) |
O9 | 0.214 (11) | 0.044 (4) | 0.049 (5) | 0.031 (6) | 0.044 (6) | 0.027 (4) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.5463 (12) | C5—C6 | 1.327 (6) |
Cu1—O1 | 1.957 (3) | C6—C7 | 1.440 (7) |
Cu1—O6 | 1.980 (4) | C7—C8 | 1.405 (6) |
Cu1—N1 | 2.009 (4) | C7—C11 | 1.399 (7) |
Cu1—N2 | 2.010 (4) | C8—C9 | 1.357 (7) |
O1—C13 | 1.265 (6) | C9—C10 | 1.404 (7) |
O2—C13 | 1.255 (6) | C11—C12 | 1.430 (5) |
O3—C20 | 1.200 (6) | C13—C14 | 1.506 (5) |
O4—C20 | 1.320 (6) | C14—C19 | 1.384 (6) |
O5—C18 | 1.369 (6) | C14—C15 | 1.383 (6) |
O4—H4 | 0.8200 | C15—C16 | 1.391 (5) |
O5—H5 | 0.8200 | C16—C20 | 1.496 (7) |
O6—H6A | 0.8200 | C16—C17 | 1.397 (7) |
O6—H6B | 0.8900 | C17—C18 | 1.380 (6) |
O7—H7A | 0.84 (4) | C18—C19 | 1.382 (5) |
O7—H7B | 0.83 (4) | C1—H1 | 0.9300 |
O8—H8B | 0.81 (3) | C2—H2 | 0.9300 |
O8—H8A | 0.82 (3) | C3—H3 | 0.9300 |
N1—C1 | 1.331 (6) | C5—H5A | 0.9300 |
N1—C12 | 1.352 (6) | C6—H6 | 0.9300 |
N2—C10 | 1.322 (6) | C8—H8 | 0.9300 |
N2—C11 | 1.359 (5) | C9—H9 | 0.9300 |
C1—C2 | 1.396 (7) | C10—H10 | 0.9300 |
C2—C3 | 1.358 (8) | C15—H15 | 0.9300 |
C3—C4 | 1.407 (7) | C17—H17 | 0.9300 |
C4—C5 | 1.445 (7) | C19—H19 | 0.9300 |
C4—C12 | 1.398 (6) | | |
| | | |
Cl1—Cu1—O1 | 95.62 (8) | N1—C12—C4 | 123.7 (4) |
Cl1—Cu1—O6 | 94.93 (11) | C4—C12—C11 | 119.8 (4) |
Cl1—Cu1—N1 | 94.68 (10) | O1—C13—C14 | 116.8 (4) |
Cl1—Cu1—N2 | 98.51 (11) | O2—C13—C14 | 118.6 (4) |
O1—Cu1—O6 | 92.98 (14) | O1—C13—O2 | 124.5 (4) |
O1—Cu1—N1 | 167.95 (13) | C13—C14—C19 | 119.6 (4) |
O1—Cu1—N2 | 90.42 (14) | C15—C14—C19 | 119.9 (3) |
O6—Cu1—N1 | 92.33 (15) | C13—C14—C15 | 120.5 (4) |
O6—Cu1—N2 | 165.74 (15) | C14—C15—C16 | 119.8 (4) |
N1—Cu1—N2 | 81.89 (14) | C15—C16—C17 | 120.3 (4) |
Cu1—O1—C13 | 127.8 (3) | C17—C16—C20 | 121.1 (4) |
C20—O4—H4 | 109.00 | C15—C16—C20 | 118.6 (4) |
C18—O5—H5 | 109.00 | C16—C17—C18 | 119.2 (4) |
Cu1—O6—H6B | 121.00 | C17—C18—C19 | 120.6 (4) |
H6A—O6—H6B | 92.00 | O5—C18—C19 | 117.2 (4) |
Cu1—O6—H6A | 109.00 | O5—C18—C17 | 122.2 (3) |
H7A—O7—H7B | 117 (4) | C14—C19—C18 | 120.3 (4) |
H8A—O8—H8B | 124 (5) | O4—C20—C16 | 112.8 (4) |
Cu1—N1—C12 | 112.6 (3) | O3—C20—C16 | 123.0 (4) |
C1—N1—C12 | 118.2 (4) | O3—C20—O4 | 124.2 (4) |
Cu1—N1—C1 | 129.2 (3) | C2—C1—H1 | 119.00 |
C10—N2—C11 | 118.3 (4) | N1—C1—H1 | 119.00 |
Cu1—N2—C11 | 112.4 (3) | C3—C2—H2 | 120.00 |
Cu1—N2—C10 | 129.3 (3) | C1—C2—H2 | 120.00 |
N1—C1—C2 | 121.8 (5) | C2—C3—H3 | 120.00 |
C1—C2—C3 | 120.2 (5) | C4—C3—H3 | 120.00 |
C2—C3—C4 | 119.7 (5) | C4—C5—H5A | 119.00 |
C3—C4—C5 | 124.8 (4) | C6—C5—H5A | 120.00 |
C5—C4—C12 | 118.6 (4) | C5—C6—H6 | 119.00 |
C3—C4—C12 | 116.5 (4) | C7—C6—H6 | 119.00 |
C4—C5—C6 | 121.1 (4) | C9—C8—H8 | 120.00 |
C5—C6—C7 | 121.9 (4) | C7—C8—H8 | 120.00 |
C6—C7—C8 | 125.1 (4) | C8—C9—H9 | 120.00 |
C6—C7—C11 | 118.0 (4) | C10—C9—H9 | 120.00 |
C8—C7—C11 | 117.0 (4) | N2—C10—H10 | 119.00 |
C7—C8—C9 | 119.5 (5) | C9—C10—H10 | 119.00 |
C8—C9—C10 | 120.1 (4) | C16—C15—H15 | 120.00 |
N2—C10—C9 | 121.9 (4) | C14—C15—H15 | 120.00 |
N2—C11—C12 | 116.2 (4) | C16—C17—H17 | 120.00 |
N2—C11—C7 | 123.3 (4) | C18—C17—H17 | 120.00 |
C7—C11—C12 | 120.6 (4) | C18—C19—H19 | 120.00 |
N1—C12—C11 | 116.6 (4) | C14—C19—H19 | 120.00 |
| | | |
Cl1—Cu1—O1—C13 | −68.5 (3) | C3—C4—C12—C11 | −177.5 (4) |
O6—Cu1—O1—C13 | 26.8 (3) | C5—C4—C12—C11 | 1.2 (6) |
N2—Cu1—O1—C13 | −167.1 (3) | C4—C5—C6—C7 | −1.8 (7) |
Cl1—Cu1—N1—C1 | 84.2 (4) | C5—C6—C7—C11 | 2.8 (7) |
Cl1—Cu1—N1—C12 | −92.8 (3) | C5—C6—C7—C8 | −177.3 (5) |
O6—Cu1—N1—C1 | −11.0 (4) | C6—C7—C8—C9 | 179.2 (4) |
O6—Cu1—N1—C12 | 172.1 (3) | C6—C7—C11—N2 | 179.7 (4) |
N2—Cu1—N1—C1 | −177.9 (4) | C6—C7—C11—C12 | −1.8 (6) |
N2—Cu1—N1—C12 | 5.2 (3) | C11—C7—C8—C9 | −1.0 (6) |
Cl1—Cu1—N2—C10 | −89.4 (4) | C8—C7—C11—C12 | 178.3 (4) |
Cl1—Cu1—N2—C11 | 88.1 (3) | C8—C7—C11—N2 | −0.2 (6) |
O1—Cu1—N2—C10 | 6.3 (4) | C7—C8—C9—C10 | 1.0 (7) |
O1—Cu1—N2—C11 | −176.1 (3) | C8—C9—C10—N2 | 0.1 (7) |
N1—Cu1—N2—C10 | 177.0 (4) | N2—C11—C12—C4 | 178.5 (4) |
N1—Cu1—N2—C11 | −5.4 (3) | C7—C11—C12—N1 | −179.1 (4) |
Cu1—O1—C13—O2 | −9.8 (6) | N2—C11—C12—N1 | −0.5 (5) |
Cu1—O1—C13—C14 | 171.0 (2) | C7—C11—C12—C4 | −0.1 (6) |
Cu1—N1—C1—C2 | −177.7 (3) | O2—C13—C14—C19 | 171.2 (4) |
C1—N1—C12—C4 | −0.4 (6) | O2—C13—C14—C15 | −9.5 (6) |
C1—N1—C12—C11 | 178.6 (4) | O1—C13—C14—C15 | 169.8 (3) |
Cu1—N1—C12—C11 | −4.1 (4) | O1—C13—C14—C19 | −9.6 (5) |
C12—N1—C1—C2 | −0.9 (6) | C13—C14—C15—C16 | −179.1 (3) |
Cu1—N1—C12—C4 | 177.0 (3) | C15—C14—C19—C18 | 1.5 (6) |
C11—N2—C10—C9 | −1.2 (6) | C19—C14—C15—C16 | 0.2 (5) |
C10—N2—C11—C7 | 1.2 (6) | C13—C14—C19—C18 | −179.1 (3) |
Cu1—N2—C11—C7 | −176.6 (3) | C14—C15—C16—C17 | −1.5 (6) |
Cu1—N2—C11—C12 | 4.8 (4) | C14—C15—C16—C20 | 176.3 (4) |
Cu1—N2—C10—C9 | 176.3 (3) | C20—C16—C17—C18 | −176.7 (4) |
C10—N2—C11—C12 | −177.3 (4) | C15—C16—C17—C18 | 1.1 (6) |
N1—C1—C2—C3 | 1.1 (7) | C17—C16—C20—O3 | 179.5 (4) |
C1—C2—C3—C4 | 0.1 (7) | C15—C16—C20—O3 | 1.7 (7) |
C2—C3—C4—C5 | −179.8 (5) | C15—C16—C20—O4 | −178.3 (4) |
C2—C3—C4—C12 | −1.2 (7) | C17—C16—C20—O4 | −0.5 (6) |
C12—C4—C5—C6 | −0.2 (7) | C16—C17—C18—C19 | 0.7 (6) |
C3—C4—C5—C6 | 178.3 (5) | C16—C17—C18—O5 | 179.6 (4) |
C5—C4—C12—N1 | −179.9 (4) | C17—C18—C19—C14 | −2.0 (6) |
C3—C4—C12—N1 | 1.4 (6) | O5—C18—C19—C14 | 179.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O8i | 0.82 | 1.82 | 2.623 (6) | 167 |
O5—H5···Cl1ii | 0.82 | 2.18 | 2.998 (4) | 172 |
O6—H6A···O2 | 0.82 | 1.86 | 2.601 (5) | 149 |
O6—H6B···O7iii | 0.89 | 1.77 | 2.642 (5) | 167 |
O7—H7A···O3iv | 0.84 (4) | 1.93 (4) | 2.754 (6) | 167 (6) |
O7—H7B···O5 | 0.83 (4) | 1.97 (5) | 2.771 (6) | 162 (4) |
O8—H8A···O2ii | 0.82 (3) | 2.05 (4) | 2.844 (6) | 163 (4) |
O8—H8B···O9v | 0.81 (3) | 2.05 (4) | 2.831 (10) | 162 (5) |
C1—H1···O9vi | 0.93 | 2.57 | 3.371 (11) | 144 |
C8—H8···O2iv | 0.93 | 2.47 | 3.364 (6) | 162 |
C10—H10···O1 | 0.93 | 2.52 | 3.014 (6) | 113 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+2, −y+2, −z+1; (iv) x, y−1, z; (v) x, y+1, z+1; (vi) x+1, y+1, z. |