In the title complex, [Cd(C
4H
4O
4S)(C
7H
6N
2)
3]·2H
2O, the Cd
II atom is surrounded by three benzimidazole ligands and one thiodiacetate dianion to complete a distorted octahedral CdN
3O
2S coordination geometry. The tridentate TDA chelates to the Cd
II atom in a facial mode. A C—H
π interaction and hydrogen bonding between neighboring complexes help to stabilize the crystal structure.
Supporting information
CCDC reference: 283963
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.011 Å
- R factor = 0.067
- wR factor = 0.167
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd - S .. 5.48 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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).
Tris(1
H-benzimidazole-
κN3)(thiodiacetato-
κ3O,
S,
O')cadmium(II) dihydrate
top
Crystal data top
[Cd(C4H4O4S)(C7H6N2)3]·2H2O | F(000) = 2640 |
Mr = 650.98 | Dx = 1.560 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 29359 reflections |
a = 10.6042 (3) Å | θ = 2.3–25.0° |
b = 20.1157 (8) Å | µ = 0.91 mm−1 |
c = 25.9795 (8) Å | T = 295 K |
V = 5541.7 (3) Å3 | Platelet, colorless |
Z = 8 | 0.26 × 0.22 × 0.07 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4866 independent reflections |
Radiation source: fine-focus sealed tube | 4125 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
Detector resolution: 10 pixels mm-1 | θmax = 25.2°, θmin = 1.6° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −24→24 |
Tmin = 0.782, Tmax = 0.929 | l = −31→31 |
36430 measured reflections | |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.33 | w = 1/[σ2(Fo2) + (0.0561P)2 + 17.5824P] where P = (Fo2 + 2Fc2)/3 |
4866 reflections | (Δ/σ)max = 0.001 |
352 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.97 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 | |
Cd | 0.25057 (5) | 0.22773 (2) | 0.123175 (17) | 0.03624 (18) | |
S | 0.17499 (19) | 0.23327 (9) | 0.22379 (7) | 0.0445 (4) | |
O1W | −0.2084 (6) | 0.4063 (3) | 0.2266 (2) | 0.0829 (19) | |
H1A | −0.2144 | 0.3711 | 0.2057 | 0.080* | |
H1B | −0.1193 | 0.4214 | 0.2271 | 0.080* | |
O2W | −0.0362 (7) | −0.0560 (4) | 0.2330 (4) | 0.138 (4) | |
H2A | −0.1280 | −0.0550 | 0.2297 | 0.080* | |
H2B | 0.0030 | −0.0271 | 0.2094 | 0.080* | |
O1 | 0.0295 (5) | 0.2509 (3) | 0.12238 (17) | 0.0479 (12) | |
O2 | −0.1194 (5) | 0.3157 (3) | 0.1541 (2) | 0.0586 (14) | |
O3 | 0.1953 (5) | 0.1218 (2) | 0.14362 (18) | 0.0474 (12) | |
O4 | 0.0801 (7) | 0.0501 (3) | 0.1859 (3) | 0.083 (2) | |
N11 | 0.2987 (6) | 0.4478 (3) | 0.1346 (2) | 0.0503 (15) | |
H11 | 0.3221 | 0.4824 | 0.1515 | 0.060* | |
N13 | 0.2662 (6) | 0.3420 (3) | 0.1159 (2) | 0.0446 (14) | |
N21 | 0.3480 (6) | 0.1858 (3) | −0.0386 (2) | 0.0522 (16) | |
H21 | 0.4007 | 0.1891 | −0.0637 | 0.063* | |
N23 | 0.2642 (5) | 0.2013 (3) | 0.0385 (2) | 0.0398 (13) | |
N31 | 0.6681 (6) | 0.2399 (3) | 0.1349 (2) | 0.0544 (16) | |
H31 | 0.7347 | 0.2643 | 0.1332 | 0.065* | |
N33 | 0.4639 (5) | 0.2125 (3) | 0.1362 (2) | 0.0442 (14) | |
C1 | −0.0176 (6) | 0.2834 (3) | 0.1582 (3) | 0.0374 (15) | |
C2 | 0.0431 (7) | 0.2865 (3) | 0.2109 (3) | 0.0447 (17) | |
H2C | −0.0215 | 0.2768 | 0.2362 | 0.054* | |
H2D | 0.0702 | 0.3320 | 0.2166 | 0.054* | |
C3 | 0.1017 (9) | 0.1525 (3) | 0.2244 (3) | 0.056 (2) | |
H3A | 0.1257 | 0.1306 | 0.2562 | 0.067* | |
H3B | 0.0111 | 0.1590 | 0.2256 | 0.067* | |
C4 | 0.1298 (7) | 0.1053 (3) | 0.1807 (3) | 0.0421 (16) | |
C12 | 0.3109 (8) | 0.3843 (3) | 0.1495 (3) | 0.0482 (18) | |
H12 | 0.3474 | 0.3717 | 0.1806 | 0.058* | |
C14 | 0.1642 (7) | 0.3622 (4) | 0.0293 (3) | 0.0491 (18) | |
H14 | 0.1488 | 0.3179 | 0.0213 | 0.059* | |
C15 | 0.1326 (7) | 0.4127 (4) | −0.0039 (3) | 0.055 (2) | |
H15 | 0.0949 | 0.4023 | −0.0353 | 0.066* | |
C16 | 0.1556 (8) | 0.4792 (4) | 0.0081 (3) | 0.063 (2) | |
H16 | 0.1334 | 0.5118 | −0.0156 | 0.075* | |
C17 | 0.2099 (7) | 0.4982 (4) | 0.0537 (3) | 0.0498 (19) | |
H17 | 0.2243 | 0.5426 | 0.0618 | 0.060* | |
C18 | 0.2420 (7) | 0.4469 (3) | 0.0872 (3) | 0.0424 (16) | |
C19 | 0.2203 (6) | 0.3807 (3) | 0.0756 (3) | 0.0371 (15) | |
C22 | 0.3569 (6) | 0.2159 (4) | 0.0072 (3) | 0.0454 (17) | |
H22 | 0.4225 | 0.2443 | 0.0160 | 0.054* | |
C24 | 0.0713 (7) | 0.1289 (4) | 0.0232 (3) | 0.0488 (18) | |
H24 | 0.0337 | 0.1364 | 0.0550 | 0.059* | |
C25 | 0.0169 (8) | 0.0884 (4) | −0.0125 (3) | 0.060 (2) | |
H25 | −0.0601 | 0.0685 | −0.0051 | 0.072* | |
C26 | 0.0740 (9) | 0.0760 (4) | −0.0598 (3) | 0.064 (2) | |
H26 | 0.0356 | 0.0465 | −0.0825 | 0.077* | |
C27 | 0.1842 (9) | 0.1057 (4) | −0.0739 (3) | 0.058 (2) | |
H27 | 0.2212 | 0.0978 | −0.1058 | 0.070* | |
C28 | 0.2380 (7) | 0.1482 (4) | −0.0383 (3) | 0.0444 (17) | |
C29 | 0.1854 (6) | 0.1587 (3) | 0.0101 (2) | 0.0371 (15) | |
C32 | 0.5476 (7) | 0.2609 (4) | 0.1342 (3) | 0.0512 (19) | |
H32 | 0.5254 | 0.3056 | 0.1325 | 0.061* | |
C34 | 0.5006 (7) | 0.0884 (3) | 0.1439 (3) | 0.0488 (18) | |
H34 | 0.4160 | 0.0762 | 0.1445 | 0.059* | |
C35 | 0.5947 (9) | 0.0417 (4) | 0.1476 (3) | 0.067 (2) | |
H35 | 0.5731 | −0.0029 | 0.1506 | 0.081* | |
C36 | 0.7220 (9) | 0.0594 (5) | 0.1468 (4) | 0.079 (3) | |
H36 | 0.7825 | 0.0261 | 0.1494 | 0.094* | |
C37 | 0.7607 (8) | 0.1242 (5) | 0.1424 (3) | 0.063 (2) | |
H37 | 0.8455 | 0.1359 | 0.1418 | 0.076* | |
C38 | 0.6638 (7) | 0.1719 (4) | 0.1389 (3) | 0.0434 (16) | |
C39 | 0.5371 (6) | 0.1552 (3) | 0.1394 (2) | 0.0375 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd | 0.0374 (3) | 0.0328 (3) | 0.0385 (3) | −0.0042 (2) | 0.0007 (2) | 0.00014 (19) |
S | 0.0577 (11) | 0.0388 (9) | 0.0371 (9) | 0.0010 (8) | −0.0089 (9) | −0.0030 (7) |
O1W | 0.081 (4) | 0.090 (5) | 0.077 (4) | 0.012 (4) | 0.004 (4) | −0.013 (4) |
O2W | 0.079 (5) | 0.100 (6) | 0.235 (10) | −0.002 (4) | 0.008 (6) | 0.104 (7) |
O1 | 0.045 (3) | 0.062 (3) | 0.037 (3) | 0.000 (2) | −0.007 (2) | −0.006 (2) |
O2 | 0.036 (3) | 0.069 (4) | 0.071 (4) | 0.008 (3) | −0.014 (3) | −0.017 (3) |
O3 | 0.062 (3) | 0.030 (2) | 0.050 (3) | −0.011 (2) | 0.020 (3) | −0.005 (2) |
O4 | 0.107 (5) | 0.035 (3) | 0.107 (5) | −0.023 (3) | 0.055 (4) | −0.014 (3) |
N11 | 0.064 (4) | 0.032 (3) | 0.055 (4) | 0.000 (3) | 0.004 (3) | −0.011 (3) |
N13 | 0.064 (4) | 0.021 (2) | 0.049 (3) | −0.006 (3) | −0.005 (3) | 0.006 (2) |
N21 | 0.051 (4) | 0.070 (4) | 0.036 (3) | 0.015 (3) | 0.008 (3) | 0.000 (3) |
N23 | 0.038 (3) | 0.038 (3) | 0.043 (3) | −0.005 (2) | 0.003 (3) | 0.001 (2) |
N31 | 0.039 (3) | 0.063 (4) | 0.060 (4) | −0.012 (3) | −0.005 (3) | 0.010 (3) |
N33 | 0.037 (3) | 0.038 (3) | 0.058 (4) | −0.001 (3) | −0.005 (3) | 0.006 (3) |
C1 | 0.038 (4) | 0.031 (3) | 0.042 (4) | −0.008 (3) | −0.004 (3) | 0.001 (3) |
C2 | 0.060 (5) | 0.038 (4) | 0.037 (3) | 0.004 (3) | −0.001 (3) | −0.006 (3) |
C3 | 0.088 (6) | 0.034 (4) | 0.047 (4) | −0.006 (4) | 0.014 (4) | 0.003 (3) |
C4 | 0.049 (4) | 0.026 (3) | 0.051 (4) | −0.001 (3) | 0.009 (4) | −0.002 (3) |
C12 | 0.066 (5) | 0.038 (4) | 0.041 (4) | −0.006 (4) | −0.003 (4) | −0.007 (3) |
C14 | 0.051 (4) | 0.041 (4) | 0.055 (4) | −0.006 (3) | −0.008 (4) | 0.008 (3) |
C15 | 0.053 (5) | 0.063 (5) | 0.049 (4) | 0.006 (4) | −0.004 (4) | 0.010 (4) |
C16 | 0.058 (5) | 0.063 (6) | 0.067 (5) | 0.015 (4) | 0.009 (5) | 0.026 (4) |
C17 | 0.047 (4) | 0.029 (4) | 0.073 (5) | 0.004 (3) | 0.014 (4) | 0.008 (3) |
C18 | 0.046 (4) | 0.028 (3) | 0.053 (4) | 0.002 (3) | 0.014 (4) | −0.004 (3) |
C19 | 0.033 (4) | 0.032 (3) | 0.047 (4) | −0.001 (3) | 0.004 (3) | 0.001 (3) |
C22 | 0.037 (4) | 0.050 (4) | 0.049 (4) | −0.009 (3) | 0.005 (3) | 0.000 (3) |
C24 | 0.042 (4) | 0.045 (4) | 0.059 (5) | 0.000 (3) | −0.006 (4) | 0.004 (3) |
C25 | 0.057 (5) | 0.043 (4) | 0.080 (6) | −0.003 (4) | −0.024 (5) | 0.005 (4) |
C26 | 0.083 (6) | 0.047 (5) | 0.064 (5) | 0.001 (4) | −0.035 (5) | −0.010 (4) |
C27 | 0.082 (6) | 0.054 (5) | 0.039 (4) | 0.016 (5) | −0.013 (4) | −0.010 (3) |
C28 | 0.042 (4) | 0.048 (4) | 0.043 (4) | 0.019 (3) | −0.004 (4) | 0.001 (3) |
C29 | 0.041 (4) | 0.030 (3) | 0.040 (4) | 0.005 (3) | −0.004 (3) | −0.003 (3) |
C32 | 0.035 (4) | 0.050 (4) | 0.068 (5) | −0.002 (3) | −0.003 (4) | 0.011 (4) |
C34 | 0.054 (5) | 0.042 (4) | 0.051 (4) | 0.003 (3) | −0.009 (4) | 0.004 (3) |
C35 | 0.079 (6) | 0.047 (5) | 0.076 (6) | 0.010 (4) | −0.010 (5) | −0.008 (4) |
C36 | 0.069 (6) | 0.080 (7) | 0.086 (7) | 0.030 (5) | −0.014 (5) | −0.015 (5) |
C37 | 0.046 (5) | 0.080 (6) | 0.064 (5) | 0.007 (4) | −0.008 (4) | −0.009 (4) |
C38 | 0.042 (4) | 0.052 (4) | 0.036 (3) | 0.001 (3) | −0.008 (3) | 0.000 (3) |
C39 | 0.038 (4) | 0.047 (4) | 0.028 (3) | −0.001 (3) | −0.002 (3) | 0.001 (3) |
Geometric parameters (Å, º) top
Cd—O1 | 2.390 (5) | C3—H3A | 0.9700 |
Cd—O3 | 2.272 (4) | C3—H3B | 0.9700 |
Cd—N13 | 2.313 (5) | C12—H12 | 0.9300 |
Cd—N23 | 2.268 (6) | C14—C15 | 1.375 (10) |
Cd—N33 | 2.308 (6) | C14—C19 | 1.391 (10) |
Cd—S | 2.7365 (18) | C14—H14 | 0.9300 |
S—C2 | 1.793 (7) | C15—C16 | 1.396 (12) |
S—C3 | 1.802 (7) | C15—H15 | 0.9300 |
O1W—H1A | 0.8953 | C16—C17 | 1.371 (12) |
O1W—H1B | 0.9919 | C16—H16 | 0.9300 |
O2W—H2A | 0.9772 | C17—C18 | 1.392 (10) |
O2W—H2B | 0.9422 | C17—H17 | 0.9300 |
O1—C1 | 1.242 (8) | C18—C19 | 1.386 (9) |
O2—C1 | 1.264 (8) | C22—H22 | 0.9300 |
O3—C4 | 1.233 (8) | C24—C25 | 1.363 (10) |
O4—C4 | 1.237 (8) | C24—C29 | 1.393 (10) |
N11—C12 | 1.340 (9) | C24—H24 | 0.9300 |
N11—C18 | 1.369 (9) | C25—C26 | 1.392 (12) |
N11—H11 | 0.8600 | C25—H25 | 0.9300 |
N13—C12 | 1.309 (8) | C26—C27 | 1.363 (12) |
N13—C19 | 1.391 (8) | C26—H26 | 0.9300 |
N21—C22 | 1.339 (9) | C27—C28 | 1.382 (10) |
N21—C28 | 1.390 (10) | C27—H27 | 0.9300 |
N21—H21 | 0.8600 | C28—C29 | 1.393 (9) |
N23—C22 | 1.309 (8) | C32—H32 | 0.9300 |
N23—C29 | 1.405 (8) | C34—C35 | 1.373 (11) |
N31—C32 | 1.346 (10) | C34—C39 | 1.404 (9) |
N31—C38 | 1.373 (9) | C34—H34 | 0.9300 |
N31—H31 | 0.8600 | C35—C36 | 1.396 (13) |
N33—C32 | 1.319 (9) | C35—H35 | 0.9300 |
N33—C39 | 1.392 (8) | C36—C37 | 1.371 (14) |
C1—C2 | 1.513 (9) | C36—H36 | 0.9300 |
C2—H2C | 0.9700 | C37—C38 | 1.409 (11) |
C2—H2D | 0.9700 | C37—H37 | 0.9300 |
C3—C4 | 1.510 (9) | C38—C39 | 1.384 (10) |
| | | |
O1—Cd—O3 | 86.10 (19) | C15—C14—C19 | 116.8 (7) |
O1—Cd—N13 | 82.8 (2) | C15—C14—H14 | 121.6 |
O1—Cd—N23 | 95.72 (17) | C19—C14—H14 | 121.6 |
O1—Cd—N33 | 171.32 (19) | C14—C15—C16 | 121.6 (8) |
O1—Cd—S | 73.33 (11) | C14—C15—H15 | 119.2 |
O3—Cd—N13 | 165.82 (19) | C16—C15—H15 | 119.2 |
O3—Cd—N23 | 91.32 (18) | C17—C16—C15 | 122.3 (7) |
O3—Cd—N33 | 95.39 (19) | C17—C16—H16 | 118.9 |
O3—Cd—S | 74.89 (12) | C15—C16—H16 | 118.9 |
N13—Cd—N23 | 98.6 (2) | C16—C17—C18 | 115.9 (7) |
N13—Cd—N33 | 94.2 (2) | C16—C17—H17 | 122.0 |
N23—Cd—N33 | 92.8 (2) | C18—C17—H17 | 122.0 |
N13—Cd—S | 93.37 (15) | N11—C18—C19 | 106.3 (6) |
N23—Cd—S | 162.70 (14) | N11—C18—C17 | 131.3 (7) |
N33—Cd—S | 98.77 (16) | C19—C18—C17 | 122.3 (7) |
C2—S—C3 | 101.8 (4) | C18—C19—C14 | 121.1 (6) |
C2—S—Cd | 94.2 (2) | C18—C19—N13 | 108.3 (6) |
C3—S—Cd | 95.7 (2) | C14—C19—N13 | 130.6 (6) |
H1A—O1W—H1B | 108.5 | N23—C22—N21 | 113.5 (6) |
H2A—O2W—H2B | 111.7 | N23—C22—H22 | 123.3 |
C1—O1—Cd | 119.4 (4) | N21—C22—H22 | 123.3 |
C4—O3—Cd | 125.5 (4) | C25—C24—C29 | 117.3 (8) |
C12—N11—C18 | 106.9 (6) | C25—C24—H24 | 121.3 |
C12—N11—H11 | 126.6 | C29—C24—H24 | 121.3 |
C18—N11—H11 | 126.6 | C24—C25—C26 | 121.6 (8) |
C12—N13—C19 | 105.4 (6) | C24—C25—H25 | 119.2 |
C12—N13—Cd | 128.1 (5) | C26—C25—H25 | 119.2 |
C19—N13—Cd | 126.3 (4) | C27—C26—C25 | 122.2 (7) |
C22—N21—C28 | 107.4 (6) | C27—C26—H26 | 118.9 |
C22—N21—H21 | 126.3 | C25—C26—H26 | 118.9 |
C28—N21—H21 | 126.3 | C26—C27—C28 | 116.4 (7) |
C22—N23—C29 | 104.9 (6) | C26—C27—H27 | 121.8 |
C22—N23—Cd | 126.7 (5) | C28—C27—H27 | 121.8 |
C29—N23—Cd | 127.9 (4) | C27—C28—N21 | 132.8 (7) |
C32—N31—C38 | 106.3 (6) | C27—C28—C29 | 122.2 (7) |
C32—N31—H31 | 126.8 | N21—C28—C29 | 105.0 (6) |
C38—N31—H31 | 126.8 | C24—C29—C28 | 120.2 (7) |
C32—N33—C39 | 103.8 (6) | C24—C29—N23 | 130.6 (6) |
C32—N33—Cd | 123.8 (5) | C28—C29—N23 | 109.2 (6) |
C39—N33—Cd | 131.7 (4) | N33—C32—N31 | 114.0 (7) |
O1—C1—O2 | 123.4 (6) | N33—C32—H32 | 123.0 |
O1—C1—C2 | 121.9 (6) | N31—C32—H32 | 123.0 |
O2—C1—C2 | 114.8 (6) | C35—C34—C39 | 117.4 (7) |
C1—C2—S | 118.5 (5) | C35—C34—H34 | 121.3 |
C1—C2—H2C | 107.7 | C39—C34—H34 | 121.3 |
S—C2—H2C | 107.7 | C34—C35—C36 | 121.8 (8) |
C1—C2—H2D | 107.7 | C34—C35—H35 | 119.1 |
S—C2—H2D | 107.7 | C36—C35—H35 | 119.1 |
H2C—C2—H2D | 107.1 | C37—C36—C35 | 122.2 (8) |
C4—C3—S | 118.3 (5) | C37—C36—H36 | 118.9 |
C4—C3—H3A | 107.7 | C35—C36—H36 | 118.9 |
S—C3—H3A | 107.7 | C36—C37—C38 | 115.7 (8) |
C4—C3—H3B | 107.7 | C36—C37—H37 | 122.1 |
S—C3—H3B | 107.7 | C38—C37—H37 | 122.1 |
H3A—C3—H3B | 107.1 | N31—C38—C39 | 106.0 (6) |
O3—C4—O4 | 124.6 (7) | N31—C38—C37 | 131.2 (7) |
O3—C4—C3 | 122.0 (6) | C39—C38—C37 | 122.8 (7) |
O4—C4—C3 | 113.4 (6) | C38—C39—N33 | 109.8 (6) |
N13—C12—N11 | 113.0 (6) | C38—C39—C34 | 120.0 (7) |
N13—C12—H12 | 123.5 | N33—C39—C34 | 130.1 (6) |
N11—C12—H12 | 123.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2 | 0.89 | 2.01 | 2.786 (8) | 144 |
O1W—H1B···O2Wi | 0.99 | 2.00 | 2.899 (10) | 149 |
O2W—H2A···O1Wii | 0.98 | 1.90 | 2.817 (10) | 155 |
O2W—H2B···O4 | 0.94 | 1.86 | 2.752 (11) | 158 |
N11—H11···O4iii | 0.86 | 1.93 | 2.768 (9) | 164 |
N21—H21···O1iv | 0.86 | 2.38 | 3.172 (8) | 154 |
N21—H21···O2iv | 0.86 | 2.36 | 3.021 (7) | 134 |
N31—H31···O2v | 0.86 | 1.94 | 2.766 (8) | 161 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x−1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) x+1/2, −y+1/2, −z; (v) x+1, y, z. |