In the title compound, C
32H
26Cl
4N
4O
4S
2·2C
3H
7NO, the molecule of 3,3′-bis(2,4-dichlorophenoxyacetyl)-1,1′-(2,2′-dimethylbiphenyl-4,4′-diyl)dithiourea (BT) possesses a crystallographically imposed centre of symmetry at the mid-point of the central C—C bond. Intramolecular N—H
O and C—H
S hydrogen bonds contribute to the essential planarity of the BT skeleton, with a maximum deviation from the mean plane of 0.196 (2) Å for the S atoms.
Supporting information
CCDC reference: 620954
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.076
- wR factor = 0.161
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc.
PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.42
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C32 H26 Cl4 N4 O4 S2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C3 H7 N O
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
3,3'-Bis(2,4-dichlorophenoxyacetyl)-1,1'-(2,2'-dimethylbiphenyl-4,4'-
diyl)dithiourea
N,
N-dimethylformamide disolvate
top
Crystal data top
C32H26Cl4N4O4S2·2C3H7NO | Z = 1 |
Mr = 882.70 | F(000) = 458 |
Triclinic, P1 | Dx = 1.400 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.012 (2) Å | Cell parameters from 25 reflections |
b = 10.488 (2) Å | θ = 9–12° |
c = 11.124 (2) Å | µ = 0.44 mm−1 |
α = 67.78 (3)° | T = 293 K |
β = 77.92 (3)° | Prism, yellow |
γ = 78.07 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 1046.8 (4) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1798 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
ω/2θ scans | h = −11→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→12 |
Tmin = 0.881, Tmax = 0.958 | l = 0→13 |
4104 measured reflections | 3 standard reflections every 200 reflections |
4104 independent reflections | intensity decay: none |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.047P)2] where P = (Fo2 + 2Fc2)/3 |
4104 reflections | (Δ/σ)max = 0.001 |
300 parameters | Δρmax = 0.22 e Å−3 |
81 restraints | Δρmin = −0.24 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) |
Cl1 | 1.10379 (13) | 0.23531 (17) | 0.14612 (17) | 0.0898 (6) | |
Cl2 | 0.60665 (14) | 0.54598 (16) | 0.09552 (17) | 0.0982 (6) | |
S1 | 0.09276 (13) | 0.60688 (15) | 0.20113 (14) | 0.0694 (5) | |
O1 | 0.5026 (3) | 0.3079 (3) | 0.2934 (3) | 0.0660 (11) | |
O2 | 0.2072 (3) | 0.1778 (3) | 0.4998 (4) | 0.0759 (12) | |
N1 | 0.2419 (3) | 0.3818 (4) | 0.3313 (4) | 0.0521 (11) | |
H1A | 0.3071 | 0.4244 | 0.2776 | 0.062* | |
N2 | 0.0101 (3) | 0.3886 (4) | 0.4105 (4) | 0.0531 (11) | |
H2A | 0.0417 | 0.3096 | 0.4641 | 0.064* | |
C1 | 0.9251 (5) | 0.2539 (6) | 0.1917 (6) | 0.0584 (15) | |
C2 | 0.8666 (5) | 0.1457 (6) | 0.2840 (5) | 0.0632 (16) | |
H2B | 0.9209 | 0.0617 | 0.3216 | 0.076* | |
C3 | 0.7241 (4) | 0.1609 (5) | 0.3224 (5) | 0.0631 (16) | |
H3A | 0.6833 | 0.0874 | 0.3870 | 0.076* | |
C4 | 0.6443 (4) | 0.2836 (5) | 0.2650 (5) | 0.0500 (13) | |
C5 | 0.7063 (5) | 0.3909 (5) | 0.1695 (5) | 0.0560 (14) | |
C6 | 0.8481 (5) | 0.3778 (6) | 0.1340 (5) | 0.0636 (15) | |
H6A | 0.8900 | 0.4519 | 0.0719 | 0.076* | |
C7 | 0.4364 (4) | 0.2019 (5) | 0.3981 (5) | 0.0621 (16) | |
H7A | 0.4727 | 0.1820 | 0.4786 | 0.075* | |
H7B | 0.4527 | 0.1172 | 0.3780 | 0.075* | |
C8 | 0.2826 (4) | 0.2543 (5) | 0.4144 (5) | 0.0565 (15) | |
C9 | 0.1066 (4) | 0.4568 (5) | 0.3191 (5) | 0.0465 (12) | |
C10 | −0.1358 (4) | 0.4248 (5) | 0.4338 (4) | 0.0430 (12) | |
C11 | −0.2087 (4) | 0.3241 (5) | 0.5275 (4) | 0.0454 (12) | |
C12 | −0.3521 (4) | 0.3575 (5) | 0.5509 (5) | 0.0522 (14) | |
H12A | −0.4023 | 0.2899 | 0.6132 | 0.063* | |
C13 | −0.4236 (4) | 0.4857 (5) | 0.4864 (5) | 0.0443 (12) | |
C14 | −0.3464 (4) | 0.5823 (5) | 0.3936 (5) | 0.0663 (17) | |
H14A | −0.3906 | 0.6689 | 0.3467 | 0.080* | |
C15 | −0.2028 (4) | 0.5528 (5) | 0.3682 (5) | 0.0649 (16) | |
H15A | −0.1524 | 0.6205 | 0.3064 | 0.078* | |
C16 | −0.1394 (4) | 0.1817 (5) | 0.6013 (5) | 0.0664 (16) | |
H16A | −0.0880 | 0.1387 | 0.5401 | 0.100* | |
H16B | −0.2080 | 0.1256 | 0.6581 | 0.100* | |
H16C | −0.0779 | 0.1900 | 0.6528 | 0.100* | |
O3 | 0.4798 (19) | 1.059 (3) | −0.2532 (19) | 0.112 (8) | 0.552 (10) |
N3 | 0.3106 (13) | 0.9633 (15) | −0.0826 (15) | 0.074 (4) | 0.552 (10) |
C17 | 0.1681 (13) | 0.9759 (15) | −0.0276 (13) | 0.128 (6) | 0.552 (10) |
H17A | 0.1201 | 1.0612 | −0.0807 | 0.191* | 0.552 (10) |
H17B | 0.1599 | 0.9761 | 0.0599 | 0.191* | 0.552 (10) |
H17C | 0.1286 | 0.8988 | −0.0252 | 0.191* | 0.552 (10) |
C18 | 0.4072 (17) | 0.8476 (16) | −0.0168 (17) | 0.135 (6) | 0.552 (10) |
H18A | 0.4992 | 0.8613 | −0.0608 | 0.203* | 0.552 (10) |
H18B | 0.3860 | 0.7630 | −0.0183 | 0.203* | 0.552 (10) |
H18C | 0.4005 | 0.8415 | 0.0725 | 0.203* | 0.552 (10) |
C19 | 0.3579 (15) | 1.0543 (12) | −0.2002 (13) | 0.091 (4) | 0.552 (10) |
H19A | 0.2918 | 1.1202 | −0.2465 | 0.109* | 0.552 (10) |
O3' | 0.501 (2) | 1.042 (5) | −0.276 (2) | 0.117 (9) | 0.448 (10) |
C17' | 0.2511 (19) | 1.0859 (19) | −0.1396 (19) | 0.133 (7) | 0.448 (10) |
H17D | 0.2877 | 1.1509 | −0.2215 | 0.199* | 0.448 (10) |
H17E | 0.2104 | 1.1338 | −0.0795 | 0.199* | 0.448 (10) |
H17F | 0.1822 | 1.0439 | −0.1541 | 0.199* | 0.448 (10) |
N3' | 0.3622 (17) | 0.978 (2) | −0.085 (2) | 0.078 (6) | 0.448 (10) |
C19' | 0.4837 (18) | 0.9633 (19) | −0.1593 (17) | 0.099 (6) | 0.448 (10) |
H19B | 0.5547 | 0.8950 | −0.1243 | 0.119* | 0.448 (10) |
C18' | 0.324 (2) | 0.873 (2) | 0.0403 (19) | 0.142 (8) | 0.448 (10) |
H18D | 0.4037 | 0.8069 | 0.0671 | 0.213* | 0.448 (10) |
H18E | 0.2555 | 0.8256 | 0.0318 | 0.213* | 0.448 (10) |
H18F | 0.2865 | 0.9157 | 0.1049 | 0.213* | 0.448 (10) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0357 (7) | 0.1138 (14) | 0.1264 (15) | −0.0080 (8) | 0.0093 (8) | −0.0618 (12) |
Cl2 | 0.0600 (9) | 0.0809 (12) | 0.1116 (14) | −0.0031 (8) | −0.0174 (9) | 0.0122 (10) |
S1 | 0.0463 (7) | 0.0692 (10) | 0.0670 (10) | −0.0047 (7) | −0.0022 (7) | −0.0003 (8) |
O1 | 0.0294 (16) | 0.067 (2) | 0.079 (3) | −0.0030 (16) | 0.0064 (17) | −0.011 (2) |
O2 | 0.0409 (19) | 0.057 (2) | 0.093 (3) | 0.0008 (17) | 0.0061 (19) | 0.001 (2) |
N1 | 0.032 (2) | 0.055 (3) | 0.057 (3) | −0.0072 (18) | 0.0042 (18) | −0.011 (2) |
N2 | 0.036 (2) | 0.045 (2) | 0.063 (3) | −0.0046 (18) | 0.0026 (19) | −0.007 (2) |
C1 | 0.036 (3) | 0.071 (4) | 0.076 (4) | −0.008 (3) | 0.006 (3) | −0.042 (3) |
C2 | 0.039 (3) | 0.064 (4) | 0.085 (4) | 0.010 (3) | −0.008 (3) | −0.033 (3) |
C3 | 0.039 (3) | 0.052 (3) | 0.080 (4) | 0.005 (2) | 0.000 (3) | −0.012 (3) |
C4 | 0.034 (2) | 0.053 (3) | 0.059 (3) | −0.001 (2) | −0.001 (2) | −0.020 (3) |
C5 | 0.046 (3) | 0.060 (3) | 0.055 (3) | −0.005 (3) | −0.006 (3) | −0.014 (3) |
C6 | 0.044 (3) | 0.071 (4) | 0.072 (4) | −0.022 (3) | 0.006 (3) | −0.020 (3) |
C7 | 0.036 (3) | 0.055 (3) | 0.076 (4) | −0.003 (2) | 0.003 (3) | −0.009 (3) |
C8 | 0.034 (3) | 0.057 (4) | 0.065 (4) | −0.004 (2) | 0.003 (3) | −0.013 (3) |
C9 | 0.039 (2) | 0.045 (3) | 0.053 (3) | −0.007 (2) | 0.001 (2) | −0.018 (3) |
C10 | 0.029 (2) | 0.041 (3) | 0.055 (3) | 0.003 (2) | −0.001 (2) | −0.020 (3) |
C11 | 0.036 (2) | 0.040 (3) | 0.048 (3) | 0.001 (2) | −0.005 (2) | −0.008 (2) |
C12 | 0.032 (2) | 0.058 (3) | 0.059 (3) | −0.008 (2) | −0.001 (2) | −0.016 (3) |
C13 | 0.035 (2) | 0.043 (3) | 0.053 (3) | 0.001 (2) | −0.006 (2) | −0.018 (2) |
C14 | 0.038 (3) | 0.043 (3) | 0.088 (4) | 0.003 (2) | −0.002 (3) | 0.002 (3) |
C15 | 0.038 (3) | 0.042 (3) | 0.085 (4) | 0.000 (2) | 0.009 (3) | −0.002 (3) |
C16 | 0.042 (3) | 0.056 (3) | 0.077 (4) | 0.000 (2) | −0.008 (3) | −0.001 (3) |
O3 | 0.118 (9) | 0.084 (9) | 0.111 (12) | −0.015 (8) | 0.010 (8) | −0.022 (11) |
N3 | 0.106 (8) | 0.046 (6) | 0.072 (7) | −0.031 (7) | −0.021 (7) | −0.007 (5) |
C17 | 0.134 (9) | 0.119 (11) | 0.117 (11) | −0.019 (8) | 0.024 (8) | −0.050 (9) |
C18 | 0.170 (12) | 0.086 (10) | 0.121 (12) | −0.001 (9) | −0.051 (10) | 0.001 (8) |
C19 | 0.106 (8) | 0.057 (7) | 0.088 (9) | 0.002 (7) | −0.012 (7) | −0.010 (6) |
O3' | 0.140 (14) | 0.119 (16) | 0.092 (9) | −0.033 (11) | 0.027 (9) | −0.050 (9) |
C17' | 0.116 (11) | 0.114 (13) | 0.130 (13) | −0.005 (9) | 0.008 (10) | −0.019 (10) |
N3' | 0.078 (8) | 0.085 (11) | 0.077 (9) | −0.042 (7) | 0.000 (7) | −0.025 (7) |
C19' | 0.100 (9) | 0.099 (12) | 0.094 (10) | −0.019 (8) | 0.008 (8) | −0.039 (9) |
C18' | 0.147 (15) | 0.117 (13) | 0.112 (12) | −0.031 (11) | 0.017 (10) | 0.003 (9) |
Geometric parameters (Å, º) top
Cl1—C1 | 1.745 (5) | C13—C14 | 1.374 (6) |
Cl2—C5 | 1.726 (5) | C13—C13i | 1.486 (8) |
S1—C9 | 1.626 (5) | C14—C15 | 1.399 (6) |
O1—C4 | 1.380 (5) | C14—H14A | 0.9300 |
O1—C7 | 1.426 (5) | C15—H15A | 0.9300 |
O2—C8 | 1.220 (5) | C16—H16A | 0.9600 |
N1—C8 | 1.344 (6) | C16—H16B | 0.9600 |
N1—C9 | 1.424 (5) | C16—H16C | 0.9600 |
N1—H1A | 0.8600 | O3—C19 | 1.242 (10) |
N2—C9 | 1.342 (5) | N3—C19 | 1.352 (15) |
N2—C10 | 1.425 (5) | N3—C17 | 1.430 (13) |
N2—H2A | 0.8600 | N3—C18 | 1.443 (15) |
C1—C2 | 1.352 (7) | C17—H17A | 0.9600 |
C1—C6 | 1.363 (6) | C17—H17B | 0.9600 |
C2—C3 | 1.395 (6) | C17—H17C | 0.9600 |
C2—H2B | 0.9300 | C18—H18A | 0.9600 |
C3—C4 | 1.367 (6) | C18—H18B | 0.9600 |
C3—H3A | 0.9300 | C18—H18C | 0.9600 |
C4—C5 | 1.374 (6) | C19—H19A | 0.9300 |
C5—C6 | 1.385 (6) | O3'—C19' | 1.247 (10) |
C6—H6A | 0.9300 | C17'—N3' | 1.46 (2) |
C7—C8 | 1.521 (6) | C17'—H17D | 0.9600 |
C7—H7A | 0.9700 | C17'—H17E | 0.9600 |
C7—H7B | 0.9700 | C17'—H17F | 0.9600 |
C10—C15 | 1.369 (6) | N3'—C19' | 1.34 (2) |
C10—C11 | 1.380 (5) | N3'—C18' | 1.45 (3) |
C11—C12 | 1.399 (5) | C19'—H19B | 0.9300 |
C11—C16 | 1.506 (6) | C18'—H18D | 0.9600 |
C12—C13 | 1.387 (6) | C18'—H18E | 0.9600 |
C12—H12A | 0.9300 | C18'—H18F | 0.9600 |
| | | |
C4—O1—C7 | 117.4 (4) | C13—C14—C15 | 121.3 (4) |
C8—N1—C9 | 129.6 (4) | C13—C14—H14A | 119.4 |
C8—N1—H1A | 115.2 | C15—C14—H14A | 119.4 |
C9—N1—H1A | 115.2 | C10—C15—C14 | 120.4 (4) |
C9—N2—C10 | 131.0 (4) | C10—C15—H15A | 119.8 |
C9—N2—H2A | 114.5 | C14—C15—H15A | 119.8 |
C10—N2—H2A | 114.5 | C11—C16—H16A | 109.5 |
C2—C1—C6 | 121.6 (4) | C11—C16—H16B | 109.5 |
C2—C1—Cl1 | 119.4 (4) | H16A—C16—H16B | 109.5 |
C6—C1—Cl1 | 119.1 (4) | C11—C16—H16C | 109.5 |
C1—C2—C3 | 119.5 (5) | H16A—C16—H16C | 109.5 |
C1—C2—H2B | 120.2 | H16B—C16—H16C | 109.5 |
C3—C2—H2B | 120.2 | C19—N3—C17 | 121.5 (13) |
C4—C3—C2 | 120.0 (5) | C19—N3—C18 | 117.9 (14) |
C4—C3—H3A | 120.0 | C17—N3—C18 | 120.5 (13) |
C2—C3—H3A | 120.0 | N3—C17—H17A | 109.5 |
C3—C4—C5 | 119.2 (4) | N3—C17—H17B | 109.5 |
C3—C4—O1 | 124.5 (4) | H17A—C17—H17B | 109.5 |
C5—C4—O1 | 116.2 (4) | N3—C17—H17C | 109.5 |
C4—C5—C6 | 120.9 (5) | H17A—C17—H17C | 109.5 |
C4—C5—Cl2 | 119.7 (4) | H17B—C17—H17C | 109.5 |
C6—C5—Cl2 | 119.3 (4) | N3—C18—H18A | 109.5 |
C1—C6—C5 | 118.6 (5) | N3—C18—H18B | 109.5 |
C1—C6—H6A | 120.7 | H18A—C18—H18B | 109.5 |
C5—C6—H6A | 120.7 | N3—C18—H18C | 109.5 |
O1—C7—C8 | 107.8 (4) | H18A—C18—H18C | 109.5 |
O1—C7—H7A | 110.1 | H18B—C18—H18C | 109.5 |
C8—C7—H7A | 110.1 | O3—C19—N3 | 127.1 (14) |
O1—C7—H7B | 110.1 | O3—C19—H19A | 116.4 |
C8—C7—H7B | 110.1 | N3—C19—H19A | 116.4 |
H7A—C7—H7B | 108.5 | N3'—C17'—H17D | 109.5 |
O2—C8—N1 | 125.8 (4) | N3'—C17'—H17E | 109.5 |
O2—C8—C7 | 118.0 (4) | H17D—C17'—H17E | 109.5 |
N1—C8—C7 | 116.3 (4) | N3'—C17'—H17F | 109.5 |
N2—C9—N1 | 112.4 (4) | H17D—C17'—H17F | 109.5 |
N2—C9—S1 | 130.7 (4) | H17E—C17'—H17F | 109.5 |
N1—C9—S1 | 116.8 (3) | C19'—N3'—C18' | 122 (2) |
C15—C10—C11 | 120.5 (4) | C19'—N3'—C17' | 120.2 (18) |
C15—C10—N2 | 122.8 (4) | C18'—N3'—C17' | 116.2 (18) |
C11—C10—N2 | 116.7 (4) | O3'—C19'—N3' | 119 (2) |
C10—C11—C12 | 117.5 (4) | O3'—C19'—H19B | 120.3 |
C10—C11—C16 | 122.3 (4) | N3'—C19'—H19B | 120.3 |
C12—C11—C16 | 120.2 (4) | N3'—C18'—H18D | 109.5 |
C13—C12—C11 | 123.7 (4) | N3'—C18'—H18E | 109.5 |
C13—C12—H12A | 118.2 | H18D—C18'—H18E | 109.5 |
C11—C12—H12A | 118.2 | N3'—C18'—H18F | 109.5 |
C14—C13—C12 | 116.6 (4) | H18D—C18'—H18F | 109.5 |
C14—C13—C13i | 122.1 (5) | H18E—C18'—H18F | 109.5 |
C12—C13—C13i | 121.2 (5) | | |
| | | |
C6—C1—C2—C3 | −0.6 (9) | C8—N1—C9—N2 | 3.7 (7) |
Cl1—C1—C2—C3 | 178.9 (4) | C8—N1—C9—S1 | −176.4 (4) |
C1—C2—C3—C4 | 1.2 (8) | C9—N2—C10—C15 | −7.5 (8) |
C2—C3—C4—C5 | 0.1 (8) | C9—N2—C10—C11 | 172.8 (5) |
C2—C3—C4—O1 | 178.2 (5) | C15—C10—C11—C12 | 0.8 (7) |
C7—O1—C4—C3 | 6.0 (7) | N2—C10—C11—C12 | −179.5 (4) |
C7—O1—C4—C5 | −175.9 (5) | C15—C10—C11—C16 | 179.6 (5) |
C3—C4—C5—C6 | −2.1 (8) | N2—C10—C11—C16 | −0.7 (7) |
O1—C4—C5—C6 | 179.7 (5) | C10—C11—C12—C13 | −0.7 (7) |
C3—C4—C5—Cl2 | 179.5 (4) | C16—C11—C12—C13 | −179.5 (5) |
O1—C4—C5—Cl2 | 1.3 (7) | C11—C12—C13—C14 | 1.0 (8) |
C2—C1—C6—C5 | −1.3 (8) | C11—C12—C13—C13i | 178.8 (6) |
Cl1—C1—C6—C5 | 179.2 (4) | C12—C13—C14—C15 | −1.4 (8) |
C4—C5—C6—C1 | 2.7 (8) | C13i—C13—C14—C15 | −179.2 (6) |
Cl2—C5—C6—C1 | −178.9 (4) | C11—C10—C15—C14 | −1.2 (8) |
C4—O1—C7—C8 | 177.7 (4) | N2—C10—C15—C14 | 179.1 (5) |
C9—N1—C8—O2 | −1.5 (9) | C13—C14—C15—C10 | 1.6 (9) |
C9—N1—C8—C7 | 177.8 (5) | C17—N3—C19—O3 | 175 (3) |
O1—C7—C8—O2 | 179.8 (5) | C18—N3—C19—O3 | −9 (3) |
O1—C7—C8—N1 | 0.5 (7) | C18'—N3'—C19'—O3' | 165 (3) |
C10—N2—C9—N1 | −179.8 (4) | C17'—N3'—C19'—O3' | 0 (4) |
C10—N2—C9—S1 | 0.3 (8) | | |
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 |
N1—H1A···O1 | 0.86 | 2.09 | 2.558 (5) | 114 |
N2—H2A···O2 | 0.86 | 1.93 | 2.669 (5) | 143 |
C15—H15A···S1 | 0.93 | 2.49 | 3.182 (5) | 131 |
C18—H18A···O3 | 0.96 | 2.36 | 2.80 (3) | 107 |