In the title compound, [CuCl(C
12H
8N
2)
2]
2(C
10H
4O
8)·2H
2O, the Cu
II cation has a five-coordinate environment made up of one chloride anion and four N atoms of two 1,10-phenanthroline ligands. Hydrogen bonds between the benzene-1,2,4,5-tetracarboxylate(2-) anion and water molecules produce a linear hydrogen-bonded chain. The anion lies on a special position of
site symmetry.
Supporting information
CCDC reference: 231823
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.091
- Data-to-parameter ratio = 11.7
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 ............ 2.00 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C25
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C29
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.37
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C28 - C29 = 1.53 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C3 = 2.95 Ang.
PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.855(10) ...... 4.00 su-Rat
O5 -H31 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.849(10) ...... 3.00 su-Rat
O5 -H30 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.855(10) ...... 4.00 su-Rat
O5 -H31 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.849(10) ...... 3.00 su-Rat
O5 -H30 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 2.02(4), Rep 2.025(14) ...... 2.86 su-Rat
H31 -O1 1.555 2.666
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis[bis(1,10-phenanthroline)chlorocopper(II)]
benzene-1,2,4,5-tetracarboxylate(2-) dihydrate
top
Crystal data top
[CuCl(C12H8N2)2]2(C10H4O8)·2H2O | Z = 1 |
Mr = 1206.96 | F(000) = 616 |
Triclinic, P1 | Dx = 1.607 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1324 (7) Å | Cell parameters from 426 reflections |
b = 11.3356 (8) Å | θ = 2.3–21.4° |
c = 12.2000 (9) Å | µ = 1.03 mm−1 |
α = 104.041 (1)° | T = 273 K |
β = 95.208 (1)° | Prism, blue |
γ = 110.685 (1)° | 0.34 × 0.28 × 0.13 mm |
V = 1247.48 (15) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4388 independent reflections |
Radiation source: fine-focus sealed tube | 3992 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→12 |
Tmin = 0.714, Tmax = 0.874 | k = −13→8 |
6633 measured reflections | l = −12→14 |
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)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.4259P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.005 |
4388 reflections | Δρmax = 0.46 e Å−3 |
374 parameters | Δρmin = −0.30 e Å−3 |
5 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0094 (12) |
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 | 0.24732 (2) | 0.91663 (2) | 0.20963 (2) | 0.03775 (12) | |
Cl1 | 0.34267 (6) | 0.82258 (6) | 0.06828 (5) | 0.04827 (16) | |
O1 | 0.88315 (19) | 0.6249 (2) | 0.50569 (19) | 0.0704 (6) | |
O2 | 0.7969 (2) | 0.6520 (3) | 0.3499 (2) | 0.1046 (10) | |
O3 | 0.5737 (2) | 0.5563 (3) | 0.21317 (18) | 0.0872 (8) | |
O4 | 0.3492 (2) | 0.4471 (2) | 0.20433 (16) | 0.0804 (7) | |
O5 | 0.0295 (3) | 0.4912 (3) | 0.3320 (2) | 0.0831 (7) | |
N1 | 0.05525 (19) | 0.76799 (18) | 0.15257 (15) | 0.0400 (4) | |
N2 | 0.11811 (18) | 1.02440 (18) | 0.17589 (14) | 0.0375 (4) | |
N3 | 0.23036 (18) | 0.94894 (17) | 0.38435 (15) | 0.0378 (4) | |
N4 | 0.43377 (19) | 1.07138 (18) | 0.28032 (15) | 0.0388 (4) | |
C1 | 0.0281 (3) | 0.6415 (2) | 0.1394 (2) | 0.0496 (6) | |
H1 | 0.1023 | 0.6176 | 0.1630 | 0.060* | |
C2 | −0.1086 (3) | 0.5432 (3) | 0.0912 (2) | 0.0571 (7) | |
H2 | −0.1243 | 0.4552 | 0.0825 | 0.068* | |
C3 | −0.2185 (3) | 0.5764 (3) | 0.0571 (2) | 0.0557 (7) | |
H3 | −0.3090 | 0.5110 | 0.0229 | 0.067* | |
C4 | −0.1952 (2) | 0.7099 (3) | 0.07352 (17) | 0.0471 (6) | |
C5 | −0.3044 (2) | 0.7565 (3) | 0.0456 (2) | 0.0571 (7) | |
H5 | −0.3984 | 0.6961 | 0.0153 | 0.068* | |
C6 | −0.2738 (3) | 0.8855 (3) | 0.0622 (2) | 0.0569 (7) | |
H6 | −0.3475 | 0.9126 | 0.0443 | 0.068* | |
C7 | −0.1307 (2) | 0.9824 (3) | 0.10656 (18) | 0.0453 (5) | |
C8 | −0.0908 (3) | 1.1183 (3) | 0.1232 (2) | 0.0534 (6) | |
H8 | −0.1598 | 1.1508 | 0.1052 | 0.064* | |
C9 | 0.0491 (3) | 1.2030 (3) | 0.1658 (2) | 0.0527 (6) | |
H9 | 0.0759 | 1.2932 | 0.1781 | 0.063* | |
C10 | 0.1514 (3) | 1.1520 (2) | 0.19067 (19) | 0.0437 (5) | |
H10 | 0.2468 | 1.2099 | 0.2187 | 0.052* | |
C11 | −0.0212 (2) | 0.9405 (2) | 0.13558 (16) | 0.0370 (5) | |
C12 | −0.0544 (2) | 0.8027 (2) | 0.12087 (16) | 0.0381 (5) | |
C13 | 0.1254 (2) | 0.8900 (2) | 0.4338 (2) | 0.0469 (5) | |
H13 | 0.0436 | 0.8204 | 0.3877 | 0.056* | |
C14 | 0.1332 (3) | 0.9284 (3) | 0.5524 (2) | 0.0550 (6) | |
H14 | 0.0563 | 0.8867 | 0.5842 | 0.066* | |
C15 | 0.2544 (3) | 1.0277 (3) | 0.6216 (2) | 0.0547 (6) | |
H15 | 0.2610 | 1.0529 | 0.7010 | 0.066* | |
C16 | 0.3686 (3) | 1.0915 (2) | 0.57306 (19) | 0.0417 (5) | |
C17 | 0.5020 (3) | 1.1935 (2) | 0.6385 (2) | 0.0484 (6) | |
H17 | 0.5166 | 1.2196 | 0.7185 | 0.058* | |
C18 | 0.6071 (3) | 1.2524 (2) | 0.5856 (2) | 0.0478 (6) | |
H18 | 0.6931 | 1.3179 | 0.6299 | 0.057* | |
C19 | 0.5883 (2) | 1.2159 (2) | 0.4626 (2) | 0.0411 (5) | |
C20 | 0.6901 (2) | 1.2768 (2) | 0.4022 (2) | 0.0499 (6) | |
H20 | 0.7772 | 1.3442 | 0.4421 | 0.060* | |
C21 | 0.6612 (3) | 1.2369 (2) | 0.2849 (2) | 0.0534 (6) | |
H21 | 0.7268 | 1.2791 | 0.2444 | 0.064* | |
C22 | 0.5324 (3) | 1.1324 (2) | 0.2260 (2) | 0.0484 (6) | |
H22 | 0.5150 | 1.1044 | 0.1459 | 0.058* | |
C23 | 0.4597 (2) | 1.1137 (2) | 0.39706 (18) | 0.0355 (4) | |
C24 | 0.3500 (2) | 1.0493 (2) | 0.45273 (17) | 0.0351 (4) | |
C25 | 0.4699 (3) | 0.4986 (2) | 0.2584 (2) | 0.0481 (6) | |
C26 | 0.3739 (2) | 0.4507 (2) | 0.42571 (18) | 0.0371 (5) | |
H26 | 0.2867 | 0.4166 | 0.3742 | 0.044* | |
C27 | 0.4987 (2) | 0.5034 (2) | 0.38457 (17) | 0.0361 (4) | |
C28 | 0.6304 (2) | 0.5549 (2) | 0.46221 (18) | 0.0363 (4) | |
C29 | 0.7826 (3) | 0.6148 (2) | 0.4387 (2) | 0.0482 (6) | |
H31 | 0.054 (4) | 0.446 (3) | 0.371 (3) | 0.113 (15)* | |
H30 | −0.016 (3) | 0.538 (3) | 0.361 (2) | 0.080 (11)* | |
H32 | 0.6417 (18) | 0.600 (4) | 0.2713 (15) | 0.139 (19)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.03054 (16) | 0.03856 (17) | 0.03669 (17) | 0.00831 (12) | 0.00643 (11) | 0.00573 (11) |
Cl1 | 0.0405 (3) | 0.0549 (3) | 0.0436 (3) | 0.0185 (3) | 0.0101 (2) | 0.0037 (3) |
O1 | 0.0376 (10) | 0.0858 (14) | 0.0859 (14) | 0.0096 (9) | 0.0137 (9) | 0.0430 (12) |
O2 | 0.0521 (12) | 0.173 (3) | 0.0727 (14) | 0.0040 (14) | 0.0254 (11) | 0.0625 (17) |
O3 | 0.0648 (13) | 0.148 (2) | 0.0498 (11) | 0.0264 (14) | 0.0246 (11) | 0.0472 (14) |
O4 | 0.0682 (13) | 0.1003 (17) | 0.0411 (10) | −0.0024 (12) | −0.0040 (9) | 0.0237 (10) |
O5 | 0.0890 (17) | 0.1016 (19) | 0.0873 (16) | 0.0590 (15) | 0.0328 (13) | 0.0392 (15) |
N1 | 0.0365 (10) | 0.0388 (10) | 0.0359 (9) | 0.0078 (8) | 0.0076 (7) | 0.0057 (8) |
N2 | 0.0348 (9) | 0.0411 (10) | 0.0326 (9) | 0.0124 (8) | 0.0078 (7) | 0.0071 (7) |
N3 | 0.0338 (9) | 0.0398 (10) | 0.0370 (9) | 0.0118 (8) | 0.0078 (7) | 0.0100 (8) |
N4 | 0.0340 (9) | 0.0398 (10) | 0.0385 (9) | 0.0104 (8) | 0.0093 (7) | 0.0090 (8) |
C1 | 0.0533 (14) | 0.0425 (13) | 0.0465 (13) | 0.0130 (11) | 0.0143 (11) | 0.0081 (10) |
C2 | 0.0639 (17) | 0.0403 (13) | 0.0476 (13) | 0.0014 (12) | 0.0189 (12) | 0.0043 (11) |
C3 | 0.0446 (14) | 0.0582 (16) | 0.0350 (11) | −0.0072 (12) | 0.0111 (10) | 0.0020 (11) |
C4 | 0.0362 (12) | 0.0610 (15) | 0.0265 (10) | 0.0018 (10) | 0.0092 (9) | 0.0068 (10) |
C5 | 0.0289 (11) | 0.089 (2) | 0.0360 (12) | 0.0066 (12) | 0.0051 (9) | 0.0139 (13) |
C6 | 0.0369 (13) | 0.099 (2) | 0.0378 (12) | 0.0285 (14) | 0.0098 (10) | 0.0221 (13) |
C7 | 0.0400 (12) | 0.0727 (17) | 0.0293 (10) | 0.0265 (11) | 0.0129 (9) | 0.0165 (10) |
C8 | 0.0615 (16) | 0.0778 (18) | 0.0401 (12) | 0.0451 (15) | 0.0177 (11) | 0.0212 (12) |
C9 | 0.0697 (17) | 0.0550 (15) | 0.0440 (13) | 0.0351 (13) | 0.0161 (12) | 0.0150 (11) |
C10 | 0.0482 (13) | 0.0426 (13) | 0.0374 (11) | 0.0168 (10) | 0.0096 (9) | 0.0074 (9) |
C11 | 0.0342 (11) | 0.0507 (13) | 0.0245 (9) | 0.0151 (9) | 0.0095 (8) | 0.0091 (9) |
C12 | 0.0311 (10) | 0.0485 (12) | 0.0266 (9) | 0.0081 (9) | 0.0079 (8) | 0.0072 (9) |
C13 | 0.0388 (12) | 0.0486 (13) | 0.0496 (13) | 0.0107 (10) | 0.0128 (10) | 0.0160 (11) |
C14 | 0.0563 (15) | 0.0610 (16) | 0.0518 (14) | 0.0199 (13) | 0.0256 (12) | 0.0228 (12) |
C15 | 0.0715 (17) | 0.0586 (15) | 0.0386 (12) | 0.0269 (14) | 0.0191 (12) | 0.0167 (11) |
C16 | 0.0528 (13) | 0.0386 (12) | 0.0377 (11) | 0.0225 (10) | 0.0080 (10) | 0.0112 (9) |
C17 | 0.0639 (15) | 0.0415 (12) | 0.0357 (11) | 0.0230 (12) | −0.0009 (10) | 0.0043 (10) |
C18 | 0.0495 (13) | 0.0351 (12) | 0.0483 (13) | 0.0157 (10) | −0.0078 (11) | 0.0015 (10) |
C19 | 0.0390 (12) | 0.0314 (11) | 0.0486 (12) | 0.0140 (9) | 0.0033 (9) | 0.0057 (9) |
C20 | 0.0364 (12) | 0.0337 (12) | 0.0677 (16) | 0.0064 (9) | 0.0066 (11) | 0.0063 (11) |
C21 | 0.0442 (13) | 0.0430 (13) | 0.0661 (16) | 0.0077 (11) | 0.0224 (12) | 0.0138 (12) |
C22 | 0.0451 (13) | 0.0486 (13) | 0.0482 (13) | 0.0126 (11) | 0.0175 (10) | 0.0137 (11) |
C23 | 0.0344 (10) | 0.0313 (10) | 0.0405 (11) | 0.0143 (9) | 0.0062 (8) | 0.0080 (9) |
C24 | 0.0384 (11) | 0.0336 (10) | 0.0359 (10) | 0.0176 (9) | 0.0073 (8) | 0.0095 (9) |
C25 | 0.0575 (15) | 0.0487 (13) | 0.0379 (12) | 0.0183 (12) | 0.0161 (11) | 0.0135 (10) |
C26 | 0.0378 (11) | 0.0330 (11) | 0.0366 (10) | 0.0116 (9) | 0.0069 (9) | 0.0070 (9) |
C27 | 0.0440 (12) | 0.0316 (10) | 0.0331 (10) | 0.0151 (9) | 0.0128 (9) | 0.0080 (8) |
C28 | 0.0374 (11) | 0.0311 (10) | 0.0403 (11) | 0.0117 (9) | 0.0152 (9) | 0.0100 (9) |
C29 | 0.0413 (13) | 0.0475 (13) | 0.0546 (14) | 0.0125 (10) | 0.0213 (11) | 0.0157 (11) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.9949 (18) | C8—C9 | 1.365 (4) |
Cu1—N2 | 2.1569 (18) | C8—H8 | 0.9300 |
Cu1—N3 | 2.1071 (17) | C9—C10 | 1.397 (3) |
Cu1—N4 | 2.0047 (18) | C9—H9 | 0.9300 |
Cu1—Cl1 | 2.2763 (6) | C10—H10 | 0.9300 |
O1—C29 | 1.200 (3) | C11—C12 | 1.438 (3) |
O2—C29 | 1.256 (3) | C13—C14 | 1.392 (3) |
O3—C25 | 1.278 (3) | C13—H13 | 0.9300 |
O3—H32 | 0.851 (10) | C14—C15 | 1.365 (4) |
O4—C25 | 1.197 (3) | C14—H14 | 0.9300 |
O5—H31 | 0.855 (10) | C15—C16 | 1.398 (3) |
O5—H30 | 0.849 (10) | C15—H15 | 0.9300 |
N1—C1 | 1.326 (3) | C16—C24 | 1.402 (3) |
N1—C12 | 1.358 (3) | C16—C17 | 1.433 (3) |
N2—C10 | 1.325 (3) | C17—C18 | 1.351 (4) |
N2—C11 | 1.355 (3) | C17—H17 | 0.9300 |
N3—C13 | 1.323 (3) | C18—C19 | 1.432 (3) |
N3—C24 | 1.357 (3) | C18—H18 | 0.9300 |
N4—C22 | 1.331 (3) | C19—C20 | 1.402 (3) |
N4—C23 | 1.356 (3) | C19—C23 | 1.405 (3) |
C1—C2 | 1.397 (4) | C20—C21 | 1.361 (4) |
C1—H1 | 0.9300 | C20—H20 | 0.9300 |
C2—C3 | 1.357 (4) | C21—C22 | 1.395 (3) |
C2—H2 | 0.9300 | C21—H21 | 0.9300 |
C3—C4 | 1.407 (4) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.426 (3) |
C4—C12 | 1.404 (3) | C25—C27 | 1.525 (3) |
C4—C5 | 1.431 (4) | C26—C28i | 1.388 (3) |
C5—C6 | 1.342 (4) | C26—C27 | 1.391 (3) |
C5—H5 | 0.9300 | C26—H26 | 0.9300 |
C6—C7 | 1.430 (4) | C27—C28 | 1.404 (3) |
C6—H6 | 0.9300 | C28—C26i | 1.388 (3) |
C7—C11 | 1.402 (3) | C28—C29 | 1.535 (3) |
C7—C8 | 1.405 (4) | | |
| | | |
N1—Cu1—N2 | 80.38 (7) | C7—C11—C12 | 119.8 (2) |
N1—Cu1—N3 | 94.34 (7) | N1—C12—C4 | 122.7 (2) |
N1—Cu1—N4 | 174.67 (7) | N1—C12—C11 | 117.33 (18) |
N1—Cu1—Cl1 | 92.15 (5) | C4—C12—C11 | 120.0 (2) |
N2—Cu1—N4 | 97.93 (7) | N3—C13—C14 | 122.4 (2) |
N2—Cu1—N3 | 93.90 (7) | N3—C13—H13 | 118.8 |
N2—Cu1—Cl1 | 121.04 (5) | C14—C13—H13 | 118.8 |
N3—Cu1—N4 | 80.70 (7) | C15—C14—C13 | 119.5 (2) |
N3—Cu1—Cl1 | 145.05 (5) | C15—C14—H14 | 120.2 |
N4—Cu1—Cl1 | 93.04 (5) | C13—C14—H14 | 120.2 |
C25—O3—H32 | 102.6 (11) | C14—C15—C16 | 119.9 (2) |
H31—O5—H30 | 118.9 (19) | C14—C15—H15 | 120.0 |
C1—N1—C12 | 118.74 (19) | C16—C15—H15 | 120.0 |
C1—N1—Cu1 | 126.14 (17) | C15—C16—C24 | 116.8 (2) |
C12—N1—Cu1 | 115.07 (14) | C15—C16—C17 | 124.2 (2) |
C10—N2—C11 | 118.37 (19) | C24—C16—C17 | 119.1 (2) |
C10—N2—Cu1 | 131.65 (15) | C18—C17—C16 | 121.0 (2) |
C11—N2—Cu1 | 109.95 (14) | C18—C17—H17 | 119.5 |
C13—N3—C24 | 118.23 (19) | C16—C17—H17 | 119.5 |
C13—N3—Cu1 | 130.97 (15) | C17—C18—C19 | 121.2 (2) |
C24—N3—Cu1 | 110.79 (13) | C17—C18—H18 | 119.4 |
C22—N4—C23 | 118.40 (19) | C19—C18—H18 | 119.4 |
C22—N4—Cu1 | 127.43 (16) | C20—C19—C23 | 117.2 (2) |
C23—N4—Cu1 | 114.15 (14) | C20—C19—C18 | 124.1 (2) |
N1—C1—C2 | 122.0 (2) | C23—C19—C18 | 118.7 (2) |
N1—C1—H1 | 119.0 | C21—C20—C19 | 119.8 (2) |
C2—C1—H1 | 119.0 | C21—C20—H20 | 120.1 |
C3—C2—C1 | 119.8 (3) | C19—C20—H20 | 120.1 |
C3—C2—H2 | 120.1 | C20—C21—C22 | 119.6 (2) |
C1—C2—H2 | 120.1 | C20—C21—H21 | 120.2 |
C2—C3—C4 | 119.9 (2) | C22—C21—H21 | 120.2 |
C2—C3—H3 | 120.1 | N4—C22—C21 | 122.3 (2) |
C4—C3—H3 | 120.1 | N4—C22—H22 | 118.9 |
C12—C4—C3 | 116.8 (2) | C21—C22—H22 | 118.9 |
C12—C4—C5 | 118.5 (2) | N4—C23—C19 | 122.64 (19) |
C3—C4—C5 | 124.6 (2) | N4—C23—C24 | 117.11 (18) |
C6—C5—C4 | 121.4 (2) | C19—C23—C24 | 120.25 (19) |
C6—C5—H5 | 119.3 | N3—C24—C16 | 123.1 (2) |
C4—C5—H5 | 119.3 | N3—C24—C23 | 117.13 (18) |
C5—C6—C7 | 121.6 (2) | C16—C24—C23 | 119.8 (2) |
C5—C6—H6 | 119.2 | O4—C25—O3 | 120.5 (2) |
C7—C6—H6 | 119.2 | O4—C25—C27 | 119.7 (2) |
C11—C7—C8 | 116.8 (2) | O3—C25—C27 | 119.6 (2) |
C11—C7—C6 | 118.6 (2) | C28i—C26—C27 | 124.9 (2) |
C8—C7—C6 | 124.6 (2) | C28i—C26—H26 | 117.5 |
C9—C8—C7 | 120.1 (2) | C27—C26—H26 | 117.5 |
C9—C8—H8 | 119.9 | C26—C27—C28 | 117.60 (19) |
C7—C8—H8 | 119.9 | C26—C27—C25 | 113.23 (19) |
C8—C9—C10 | 119.0 (2) | C28—C27—C25 | 129.2 (2) |
C8—C9—H9 | 120.5 | C26i—C28—C27 | 117.46 (19) |
C10—C9—H9 | 120.5 | C26i—C28—C29 | 114.4 (2) |
N2—C10—C9 | 122.7 (2) | C27—C28—C29 | 128.15 (19) |
N2—C10—H10 | 118.7 | O1—C29—O2 | 122.5 (2) |
C9—C10—H10 | 118.7 | O1—C29—C28 | 119.0 (2) |
N2—C11—C7 | 122.9 (2) | O2—C29—C28 | 118.5 (2) |
N2—C11—C12 | 117.23 (18) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H31···O1i | 0.86 (1) | 2.03 (1) | 2.864 (3) | 167 (3) |
O5—H30···O1ii | 0.85 (1) | 2.31 (2) | 3.096 (3) | 154 (3) |
O3—H32···O2 | 0.85 (1) | 1.59 (2) | 2.404 (3) | 158 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z. |