In the title compound, C
22H
14Cl
3N
3O
3, molecules are linked into two-dimensional layers in the
ab plane by C—H
N and C—H
Cl hydrogen bonds. The packing is further stabilized by π–π interactions. There are two molecules in the asymmetric unit.
Supporting information
CCDC reference: 613838
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.064
- wR factor = 0.150
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 5.62 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
2-(1
H-1,2,3-Benzotriazol-1-ylmethyl)-1-(4-chlorobenzoyl)ethyl
2,4-dichlorobenzoate
top
Crystal data top
C22H14Cl3N3O3 | F(000) = 1936 |
Mr = 474.71 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.941 (3) Å | Cell parameters from 2689 reflections |
b = 25.588 (6) Å | θ = 2.3–20.4° |
c = 13.780 (3) Å | µ = 0.47 mm−1 |
β = 100.508 (4)° | T = 293 K |
V = 4139.8 (15) Å3 | Column, colourless |
Z = 8 | 0.23 × 0.12 × 0.09 mm |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 8117 independent reflections |
Radiation source: fine-focus sealed tube | 4005 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 1.6° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −31→31 |
Tmin = 0.899, Tmax = 0.959 | l = −16→9 |
23763 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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3 |
8117 reflections | (Δ/σ)max = 0.001 |
559 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.22 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 | |
Cl1 | 0.18883 (14) | −0.09101 (5) | 0.10526 (13) | 0.1282 (6) | |
Cl2 | 0.34957 (8) | 0.32425 (4) | 0.10189 (9) | 0.0728 (3) | |
Cl3 | 0.03795 (10) | 0.46834 (4) | 0.13100 (9) | 0.0837 (4) | |
Cl4 | 0.30406 (13) | 0.79449 (4) | 0.31734 (10) | 0.1037 (5) | |
Cl5 | 0.15323 (8) | 0.37051 (4) | 0.42508 (8) | 0.0700 (3) | |
Cl6 | 0.47418 (10) | 0.23021 (4) | 0.39448 (9) | 0.0833 (4) | |
O1 | −0.0020 (2) | 0.15242 (10) | 0.1399 (2) | 0.0694 (8) | |
O2 | 0.14561 (19) | 0.21962 (9) | 0.24154 (18) | 0.0509 (6) | |
O3 | 0.2353 (2) | 0.22153 (10) | 0.1129 (2) | 0.0687 (8) | |
O4 | 0.4989 (3) | 0.54943 (12) | 0.3965 (2) | 0.0934 (10) | |
O5 | 0.3632 (2) | 0.47731 (10) | 0.2932 (2) | 0.0666 (8) | |
O6 | 0.2542 (3) | 0.47519 (11) | 0.4087 (2) | 0.0864 (10) | |
N1 | 0.0496 (2) | 0.14828 (11) | 0.3775 (2) | 0.0462 (7) | |
N2 | −0.0050 (3) | 0.10196 (11) | 0.3760 (2) | 0.0605 (9) | |
N3 | −0.1045 (3) | 0.10941 (13) | 0.3976 (2) | 0.0641 (9) | |
N4 | 0.4568 (2) | 0.54481 (11) | 0.1501 (2) | 0.0491 (8) | |
N5 | 0.5075 (3) | 0.59217 (11) | 0.1429 (2) | 0.0583 (9) | |
N6 | 0.6075 (3) | 0.58423 (13) | 0.1212 (2) | 0.0652 (9) | |
C1 | 0.2261 (3) | 0.06074 (14) | 0.1595 (3) | 0.0540 (10) | |
H1A | 0.2859 | 0.0845 | 0.1720 | 0.065* | |
C2 | 0.2485 (3) | 0.00954 (15) | 0.1407 (3) | 0.0630 (11) | |
H2A | 0.3224 | −0.0010 | 0.1382 | 0.076* | |
C3 | 0.1612 (4) | −0.02578 (15) | 0.1257 (3) | 0.0674 (12) | |
C4 | 0.0506 (4) | −0.01005 (18) | 0.1252 (3) | 0.0849 (15) | |
H4A | −0.0087 | −0.0341 | 0.1136 | 0.102* | |
C5 | 0.0296 (3) | 0.04127 (17) | 0.1418 (3) | 0.0715 (13) | |
H5A | −0.0451 | 0.0520 | 0.1407 | 0.086* | |
C6 | 0.1162 (3) | 0.07786 (14) | 0.1604 (3) | 0.0474 (9) | |
C7 | 0.0878 (3) | 0.13301 (13) | 0.1781 (3) | 0.0475 (9) | |
C8 | 0.1714 (3) | 0.16467 (12) | 0.2522 (3) | 0.0479 (10) | |
H8A | 0.2491 | 0.1585 | 0.2410 | 0.057* | |
C9 | 0.1640 (3) | 0.14984 (13) | 0.3572 (3) | 0.0505 (10) | |
H9A | 0.1986 | 0.1157 | 0.3713 | 0.061* | |
H9B | 0.2081 | 0.1747 | 0.4017 | 0.061* | |
C10 | −0.0177 (3) | 0.18717 (14) | 0.4019 (2) | 0.0443 (9) | |
C11 | −0.1170 (3) | 0.16142 (16) | 0.4145 (3) | 0.0513 (10) | |
C12 | −0.2075 (4) | 0.18997 (19) | 0.4392 (3) | 0.0734 (13) | |
H12A | −0.2751 | 0.1737 | 0.4463 | 0.088* | |
C13 | −0.1936 (4) | 0.2417 (2) | 0.4524 (3) | 0.0748 (13) | |
H13A | −0.2530 | 0.2613 | 0.4690 | 0.090* | |
C14 | −0.0913 (4) | 0.26768 (16) | 0.4418 (3) | 0.0702 (12) | |
H14A | −0.0849 | 0.3035 | 0.4524 | 0.084* | |
C15 | −0.0018 (3) | 0.24083 (14) | 0.4162 (3) | 0.0550 (10) | |
H15A | 0.0655 | 0.2574 | 0.4088 | 0.066* | |
C16 | 0.1829 (3) | 0.24369 (14) | 0.1659 (3) | 0.0480 (9) | |
C17 | 0.1478 (3) | 0.29951 (13) | 0.1587 (2) | 0.0443 (9) | |
C18 | 0.2157 (3) | 0.33770 (14) | 0.1281 (2) | 0.0460 (9) | |
C19 | 0.1817 (3) | 0.38916 (14) | 0.1194 (3) | 0.0555 (10) | |
H19A | 0.2285 | 0.4143 | 0.0990 | 0.067* | |
C20 | 0.0777 (3) | 0.40298 (14) | 0.1412 (3) | 0.0546 (10) | |
C21 | 0.0072 (3) | 0.36609 (15) | 0.1714 (3) | 0.0618 (11) | |
H21A | −0.0633 | 0.3755 | 0.1855 | 0.074* | |
C22 | 0.0435 (3) | 0.31490 (14) | 0.1799 (3) | 0.0550 (10) | |
H22A | −0.0034 | 0.2899 | 0.2007 | 0.066* | |
C23 | 0.4700 (3) | 0.65960 (18) | 0.3577 (3) | 0.0700 (13) | |
H23A | 0.5453 | 0.6483 | 0.3708 | 0.084* | |
C24 | 0.4469 (4) | 0.71155 (19) | 0.3493 (3) | 0.0778 (14) | |
H24A | 0.5061 | 0.7356 | 0.3553 | 0.093* | |
C25 | 0.3352 (4) | 0.72842 (14) | 0.3318 (3) | 0.0622 (11) | |
C26 | 0.2473 (3) | 0.69359 (15) | 0.3251 (3) | 0.0635 (11) | |
H26A | 0.1724 | 0.7053 | 0.3159 | 0.076* | |
C27 | 0.2714 (3) | 0.64102 (15) | 0.3319 (3) | 0.0615 (11) | |
H27A | 0.2120 | 0.6171 | 0.3264 | 0.074* | |
C28 | 0.3827 (3) | 0.62320 (15) | 0.3469 (3) | 0.0519 (10) | |
C29 | 0.4116 (3) | 0.56666 (16) | 0.3480 (3) | 0.0602 (11) | |
C30 | 0.3334 (3) | 0.53129 (14) | 0.2762 (3) | 0.0567 (10) | |
H30A | 0.2545 | 0.5365 | 0.2851 | 0.068* | |
C31 | 0.3419 (3) | 0.54325 (14) | 0.1696 (3) | 0.0561 (11) | |
H31A | 0.2993 | 0.5169 | 0.1275 | 0.067* | |
H31B | 0.3059 | 0.5767 | 0.1517 | 0.067* | |
C32 | 0.5269 (3) | 0.50557 (14) | 0.1315 (2) | 0.0453 (9) | |
C33 | 0.6229 (3) | 0.53121 (16) | 0.1136 (3) | 0.0539 (10) | |
C34 | 0.7153 (3) | 0.50336 (19) | 0.0908 (3) | 0.0680 (12) | |
H34A | 0.7805 | 0.5204 | 0.0795 | 0.082* | |
C35 | 0.7062 (4) | 0.45066 (19) | 0.0859 (3) | 0.0745 (13) | |
H35A | 0.7664 | 0.4311 | 0.0709 | 0.089* | |
C36 | 0.6073 (4) | 0.42477 (16) | 0.1030 (3) | 0.0725 (13) | |
H36A | 0.6035 | 0.3885 | 0.0983 | 0.087* | |
C37 | 0.5167 (3) | 0.45166 (15) | 0.1265 (3) | 0.0627 (11) | |
H37A | 0.4517 | 0.4346 | 0.1385 | 0.075* | |
C38 | 0.3182 (3) | 0.45311 (15) | 0.3655 (3) | 0.0565 (10) | |
C39 | 0.3575 (3) | 0.39840 (14) | 0.3768 (3) | 0.0497 (9) | |
C40 | 0.2895 (3) | 0.35862 (14) | 0.4027 (3) | 0.0478 (9) | |
C41 | 0.3262 (3) | 0.30722 (14) | 0.4100 (3) | 0.0522 (10) | |
H41A | 0.2800 | 0.2812 | 0.4284 | 0.063* | |
C42 | 0.4318 (3) | 0.29507 (15) | 0.3898 (3) | 0.0566 (10) | |
C43 | 0.5033 (3) | 0.33369 (16) | 0.3666 (3) | 0.0665 (12) | |
H43A | 0.5760 | 0.3256 | 0.3559 | 0.080* | |
C44 | 0.4645 (3) | 0.38449 (16) | 0.3597 (3) | 0.0651 (12) | |
H44A | 0.5120 | 0.4105 | 0.3430 | 0.078* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1429 (13) | 0.0509 (8) | 0.1896 (16) | 0.0010 (8) | 0.0269 (11) | −0.0382 (9) |
Cl2 | 0.0584 (6) | 0.0550 (7) | 0.1106 (10) | 0.0032 (5) | 0.0301 (6) | 0.0125 (6) |
Cl3 | 0.0913 (8) | 0.0437 (6) | 0.1139 (10) | 0.0169 (6) | 0.0129 (7) | 0.0040 (6) |
Cl4 | 0.1603 (13) | 0.0464 (7) | 0.1180 (12) | −0.0195 (7) | 0.0612 (9) | −0.0129 (6) |
Cl5 | 0.0590 (6) | 0.0637 (7) | 0.0923 (9) | 0.0005 (5) | 0.0272 (6) | 0.0036 (6) |
Cl6 | 0.0940 (9) | 0.0562 (7) | 0.1076 (10) | 0.0183 (6) | 0.0390 (7) | 0.0087 (6) |
O1 | 0.0497 (16) | 0.0625 (18) | 0.091 (2) | 0.0138 (14) | 0.0004 (15) | 0.0056 (15) |
O2 | 0.0566 (15) | 0.0340 (14) | 0.0667 (19) | 0.0031 (11) | 0.0238 (13) | 0.0063 (12) |
O3 | 0.092 (2) | 0.0484 (17) | 0.077 (2) | 0.0024 (15) | 0.0455 (17) | −0.0039 (14) |
O4 | 0.071 (2) | 0.105 (3) | 0.097 (3) | 0.0188 (18) | −0.0042 (18) | 0.0031 (19) |
O5 | 0.0702 (17) | 0.0469 (17) | 0.092 (2) | 0.0053 (13) | 0.0390 (15) | 0.0128 (15) |
O6 | 0.115 (3) | 0.066 (2) | 0.094 (3) | 0.0184 (18) | 0.061 (2) | 0.0090 (17) |
N1 | 0.0492 (19) | 0.0365 (18) | 0.054 (2) | −0.0014 (15) | 0.0122 (15) | 0.0031 (14) |
N2 | 0.069 (2) | 0.0386 (19) | 0.078 (3) | −0.0141 (17) | 0.0236 (19) | 0.0010 (16) |
N3 | 0.065 (2) | 0.052 (2) | 0.080 (3) | −0.0179 (17) | 0.0246 (19) | −0.0044 (18) |
N4 | 0.0463 (18) | 0.0381 (18) | 0.063 (2) | −0.0033 (15) | 0.0116 (15) | 0.0019 (15) |
N5 | 0.062 (2) | 0.041 (2) | 0.074 (3) | −0.0107 (16) | 0.0174 (18) | −0.0034 (16) |
N6 | 0.057 (2) | 0.058 (2) | 0.084 (3) | −0.0144 (17) | 0.0220 (19) | −0.0084 (18) |
C1 | 0.046 (2) | 0.052 (3) | 0.061 (3) | −0.0015 (18) | 0.0017 (19) | −0.0048 (19) |
C2 | 0.058 (3) | 0.049 (3) | 0.080 (3) | 0.004 (2) | 0.007 (2) | −0.009 (2) |
C3 | 0.086 (3) | 0.039 (2) | 0.076 (3) | 0.000 (2) | 0.012 (2) | −0.013 (2) |
C4 | 0.082 (3) | 0.063 (3) | 0.114 (4) | −0.025 (3) | 0.029 (3) | −0.019 (3) |
C5 | 0.058 (3) | 0.064 (3) | 0.096 (4) | −0.007 (2) | 0.025 (2) | −0.015 (2) |
C6 | 0.050 (2) | 0.044 (2) | 0.047 (2) | −0.0018 (18) | 0.0073 (18) | 0.0045 (17) |
C7 | 0.047 (2) | 0.041 (2) | 0.058 (3) | 0.0034 (18) | 0.0170 (19) | 0.0090 (18) |
C8 | 0.045 (2) | 0.034 (2) | 0.067 (3) | 0.0037 (16) | 0.0175 (19) | 0.0059 (18) |
C9 | 0.043 (2) | 0.042 (2) | 0.067 (3) | 0.0045 (16) | 0.0090 (19) | 0.0053 (19) |
C10 | 0.044 (2) | 0.045 (2) | 0.043 (2) | 0.0016 (18) | 0.0050 (17) | 0.0004 (17) |
C11 | 0.050 (2) | 0.062 (3) | 0.044 (3) | −0.005 (2) | 0.0160 (18) | −0.0004 (19) |
C12 | 0.062 (3) | 0.090 (4) | 0.075 (3) | −0.007 (3) | 0.029 (2) | −0.006 (3) |
C13 | 0.069 (3) | 0.086 (4) | 0.075 (3) | 0.021 (3) | 0.029 (2) | −0.006 (3) |
C14 | 0.093 (3) | 0.051 (3) | 0.067 (3) | 0.009 (3) | 0.016 (3) | −0.001 (2) |
C15 | 0.056 (2) | 0.047 (3) | 0.063 (3) | 0.003 (2) | 0.014 (2) | −0.0036 (19) |
C16 | 0.050 (2) | 0.043 (2) | 0.053 (3) | −0.0064 (18) | 0.014 (2) | −0.0048 (19) |
C17 | 0.055 (2) | 0.038 (2) | 0.039 (2) | −0.0018 (18) | 0.0047 (18) | −0.0010 (16) |
C18 | 0.050 (2) | 0.043 (2) | 0.044 (2) | −0.0028 (18) | 0.0073 (18) | −0.0002 (17) |
C19 | 0.059 (3) | 0.043 (2) | 0.062 (3) | −0.0015 (19) | 0.006 (2) | 0.0104 (19) |
C20 | 0.065 (3) | 0.040 (2) | 0.054 (3) | 0.009 (2) | −0.002 (2) | 0.0006 (18) |
C21 | 0.058 (3) | 0.056 (3) | 0.073 (3) | 0.011 (2) | 0.015 (2) | 0.006 (2) |
C22 | 0.059 (3) | 0.045 (2) | 0.064 (3) | −0.0024 (19) | 0.017 (2) | 0.0046 (19) |
C23 | 0.058 (3) | 0.072 (3) | 0.080 (3) | −0.022 (2) | 0.012 (2) | −0.019 (2) |
C24 | 0.075 (3) | 0.075 (3) | 0.091 (4) | −0.039 (3) | 0.035 (3) | −0.025 (3) |
C25 | 0.090 (3) | 0.041 (2) | 0.060 (3) | −0.015 (2) | 0.027 (2) | −0.0097 (19) |
C26 | 0.063 (3) | 0.050 (3) | 0.079 (3) | −0.005 (2) | 0.018 (2) | −0.012 (2) |
C27 | 0.058 (3) | 0.044 (2) | 0.083 (3) | −0.014 (2) | 0.014 (2) | −0.004 (2) |
C28 | 0.049 (2) | 0.057 (3) | 0.051 (3) | −0.008 (2) | 0.0139 (18) | −0.0045 (19) |
C29 | 0.055 (3) | 0.063 (3) | 0.065 (3) | 0.001 (2) | 0.017 (2) | 0.004 (2) |
C30 | 0.051 (2) | 0.042 (2) | 0.081 (3) | 0.0018 (18) | 0.023 (2) | 0.007 (2) |
C31 | 0.049 (2) | 0.045 (2) | 0.074 (3) | 0.0017 (18) | 0.013 (2) | 0.001 (2) |
C32 | 0.039 (2) | 0.046 (2) | 0.049 (3) | −0.0022 (18) | 0.0038 (17) | 0.0010 (18) |
C33 | 0.051 (2) | 0.056 (3) | 0.054 (3) | −0.001 (2) | 0.0060 (19) | −0.0037 (19) |
C34 | 0.051 (3) | 0.083 (4) | 0.071 (3) | −0.001 (2) | 0.014 (2) | −0.010 (2) |
C35 | 0.060 (3) | 0.085 (4) | 0.079 (3) | 0.023 (3) | 0.013 (2) | −0.004 (3) |
C36 | 0.083 (3) | 0.049 (3) | 0.084 (4) | 0.019 (2) | 0.012 (3) | 0.004 (2) |
C37 | 0.062 (3) | 0.045 (3) | 0.079 (3) | −0.001 (2) | 0.008 (2) | 0.005 (2) |
C38 | 0.065 (3) | 0.049 (3) | 0.061 (3) | −0.003 (2) | 0.027 (2) | −0.001 (2) |
C39 | 0.052 (2) | 0.050 (3) | 0.050 (3) | −0.0001 (19) | 0.0161 (19) | −0.0012 (18) |
C40 | 0.051 (2) | 0.050 (2) | 0.044 (2) | −0.0022 (19) | 0.0121 (17) | −0.0022 (18) |
C41 | 0.057 (2) | 0.048 (3) | 0.053 (3) | −0.0071 (19) | 0.0153 (19) | 0.0030 (19) |
C42 | 0.069 (3) | 0.052 (3) | 0.053 (3) | 0.005 (2) | 0.020 (2) | 0.0054 (19) |
C43 | 0.062 (3) | 0.063 (3) | 0.083 (3) | 0.012 (2) | 0.034 (2) | 0.017 (2) |
C44 | 0.062 (3) | 0.061 (3) | 0.079 (3) | −0.005 (2) | 0.030 (2) | 0.013 (2) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.734 (4) | C14—H14A | 0.9300 |
Cl2—C18 | 1.736 (4) | C15—H15A | 0.9300 |
Cl3—C20 | 1.737 (4) | C16—C17 | 1.487 (5) |
Cl4—C25 | 1.735 (4) | C17—C18 | 1.384 (4) |
Cl5—C40 | 1.737 (4) | C17—C22 | 1.387 (5) |
Cl6—C42 | 1.733 (4) | C18—C19 | 1.377 (5) |
O1—C7 | 1.211 (4) | C19—C20 | 1.375 (5) |
O2—C16 | 1.354 (4) | C19—H19A | 0.9300 |
O2—C8 | 1.441 (4) | C20—C21 | 1.379 (5) |
O3—C16 | 1.189 (4) | C21—C22 | 1.378 (5) |
O4—C29 | 1.214 (4) | C21—H21A | 0.9300 |
O5—C38 | 1.364 (4) | C22—H22A | 0.9300 |
O5—C30 | 1.435 (4) | C23—C24 | 1.358 (6) |
O6—C38 | 1.194 (4) | C23—C28 | 1.386 (5) |
N1—N2 | 1.351 (4) | C23—H23A | 0.9300 |
N1—C10 | 1.359 (4) | C24—C25 | 1.381 (5) |
N1—C9 | 1.444 (4) | C24—H24A | 0.9300 |
N2—N3 | 1.290 (4) | C25—C26 | 1.367 (5) |
N3—C11 | 1.364 (4) | C26—C27 | 1.375 (5) |
N4—C32 | 1.362 (4) | C26—H26A | 0.9300 |
N4—N5 | 1.367 (4) | C27—C28 | 1.384 (5) |
N4—C31 | 1.446 (4) | C27—H27A | 0.9300 |
N5—N6 | 1.299 (4) | C28—C29 | 1.487 (5) |
N6—C33 | 1.376 (5) | C29—C30 | 1.527 (5) |
C1—C2 | 1.371 (5) | C30—C31 | 1.522 (5) |
C1—C6 | 1.385 (5) | C30—H30A | 0.9800 |
C1—H1A | 0.9300 | C31—H31A | 0.9700 |
C2—C3 | 1.367 (5) | C31—H31B | 0.9700 |
C2—H2A | 0.9300 | C32—C33 | 1.381 (5) |
C3—C4 | 1.379 (5) | C32—C37 | 1.386 (5) |
C4—C5 | 1.364 (5) | C33—C34 | 1.396 (5) |
C4—H4A | 0.9300 | C34—C35 | 1.354 (5) |
C5—C6 | 1.384 (5) | C34—H34A | 0.9300 |
C5—H5A | 0.9300 | C35—C36 | 1.411 (6) |
C6—C7 | 1.482 (5) | C35—H35A | 0.9300 |
C7—C8 | 1.525 (5) | C36—C37 | 1.370 (5) |
C8—C9 | 1.514 (5) | C36—H36A | 0.9300 |
C8—H8A | 0.9800 | C37—H37A | 0.9300 |
C9—H9A | 0.9700 | C38—C39 | 1.476 (5) |
C9—H9B | 0.9700 | C39—C44 | 1.388 (5) |
C10—C15 | 1.395 (5) | C39—C40 | 1.389 (5) |
C10—C11 | 1.396 (5) | C40—C41 | 1.384 (5) |
C11—C12 | 1.396 (5) | C41—C42 | 1.375 (5) |
C12—C13 | 1.343 (5) | C41—H41A | 0.9300 |
C12—H12A | 0.9300 | C42—C43 | 1.381 (5) |
C13—C14 | 1.421 (6) | C43—C44 | 1.378 (5) |
C13—H13A | 0.9300 | C43—H43A | 0.9300 |
C14—C15 | 1.369 (5) | C44—H44A | 0.9300 |
| | | |
C16—O2—C8 | 115.3 (3) | C22—C21—C20 | 118.5 (4) |
C38—O5—C30 | 115.9 (3) | C22—C21—H21A | 120.8 |
N2—N1—C10 | 109.9 (3) | C20—C21—H21A | 120.8 |
N2—N1—C9 | 119.5 (3) | C21—C22—C17 | 122.2 (4) |
C10—N1—C9 | 130.6 (3) | C21—C22—H22A | 118.9 |
N3—N2—N1 | 109.2 (3) | C17—C22—H22A | 118.9 |
N2—N3—C11 | 108.5 (3) | C24—C23—C28 | 120.8 (4) |
C32—N4—N5 | 110.1 (3) | C24—C23—H23A | 119.6 |
C32—N4—C31 | 130.7 (3) | C28—C23—H23A | 119.6 |
N5—N4—C31 | 119.1 (3) | C23—C24—C25 | 119.7 (4) |
N6—N5—N4 | 108.5 (3) | C23—C24—H24A | 120.2 |
N5—N6—C33 | 108.2 (3) | C25—C24—H24A | 120.2 |
C2—C1—C6 | 121.5 (4) | C26—C25—C24 | 120.9 (4) |
C2—C1—H1A | 119.3 | C26—C25—Cl4 | 118.8 (4) |
C6—C1—H1A | 119.3 | C24—C25—Cl4 | 120.3 (3) |
C3—C2—C1 | 119.4 (4) | C25—C26—C27 | 119.0 (4) |
C3—C2—H2A | 120.3 | C25—C26—H26A | 120.5 |
C1—C2—H2A | 120.3 | C27—C26—H26A | 120.5 |
C2—C3—C4 | 120.7 (4) | C26—C27—C28 | 121.0 (4) |
C2—C3—Cl1 | 119.9 (3) | C26—C27—H27A | 119.5 |
C4—C3—Cl1 | 119.3 (3) | C28—C27—H27A | 119.5 |
C5—C4—C3 | 119.1 (4) | C27—C28—C23 | 118.5 (4) |
C5—C4—H4A | 120.5 | C27—C28—C29 | 122.5 (3) |
C3—C4—H4A | 120.5 | C23—C28—C29 | 118.9 (4) |
C4—C5—C6 | 121.8 (4) | O4—C29—C28 | 122.2 (4) |
C4—C5—H5A | 119.1 | O4—C29—C30 | 120.3 (4) |
C6—C5—H5A | 119.1 | C28—C29—C30 | 117.2 (3) |
C5—C6—C1 | 117.5 (4) | O5—C30—C31 | 107.0 (3) |
C5—C6—C7 | 119.2 (3) | O5—C30—C29 | 111.1 (3) |
C1—C6—C7 | 123.3 (3) | C31—C30—C29 | 111.4 (3) |
O1—C7—C6 | 122.0 (3) | O5—C30—H30A | 109.1 |
O1—C7—C8 | 119.5 (3) | C31—C30—H30A | 109.1 |
C6—C7—C8 | 118.3 (3) | C29—C30—H30A | 109.1 |
O2—C8—C9 | 107.0 (3) | N4—C31—C30 | 114.7 (3) |
O2—C8—C7 | 110.4 (3) | N4—C31—H31A | 108.6 |
C9—C8—C7 | 111.2 (3) | C30—C31—H31A | 108.6 |
O2—C8—H8A | 109.4 | N4—C31—H31B | 108.6 |
C9—C8—H8A | 109.4 | C30—C31—H31B | 108.6 |
C7—C8—H8A | 109.4 | H31A—C31—H31B | 107.6 |
N1—C9—C8 | 114.5 (3) | N4—C32—C33 | 104.0 (3) |
N1—C9—H9A | 108.6 | N4—C32—C37 | 133.7 (3) |
C8—C9—H9A | 108.6 | C33—C32—C37 | 122.2 (4) |
N1—C9—H9B | 108.6 | N6—C33—C32 | 109.2 (3) |
C8—C9—H9B | 108.6 | N6—C33—C34 | 130.0 (4) |
H9A—C9—H9B | 107.6 | C32—C33—C34 | 120.9 (4) |
N1—C10—C15 | 133.2 (3) | C35—C34—C33 | 117.4 (4) |
N1—C10—C11 | 103.9 (3) | C35—C34—H34A | 121.3 |
C15—C10—C11 | 122.9 (3) | C33—C34—H34A | 121.3 |
N3—C11—C10 | 108.5 (3) | C34—C35—C36 | 121.4 (4) |
N3—C11—C12 | 131.8 (4) | C34—C35—H35A | 119.3 |
C10—C11—C12 | 119.8 (4) | C36—C35—H35A | 119.3 |
C13—C12—C11 | 117.8 (4) | C37—C36—C35 | 121.7 (4) |
C13—C12—H12A | 121.1 | C37—C36—H36A | 119.2 |
C11—C12—H12A | 121.1 | C35—C36—H36A | 119.2 |
C12—C13—C14 | 122.3 (4) | C36—C37—C32 | 116.4 (4) |
C12—C13—H13A | 118.9 | C36—C37—H37A | 121.8 |
C14—C13—H13A | 118.9 | C32—C37—H37A | 121.8 |
C15—C14—C13 | 121.2 (4) | O6—C38—O5 | 121.5 (4) |
C15—C14—H14A | 119.4 | O6—C38—C39 | 128.0 (4) |
C13—C14—H14A | 119.4 | O5—C38—C39 | 110.4 (3) |
C14—C15—C10 | 116.0 (4) | C44—C39—C40 | 117.1 (3) |
C14—C15—H15A | 122.0 | C44—C39—C38 | 120.7 (3) |
C10—C15—H15A | 122.0 | C40—C39—C38 | 122.2 (3) |
O3—C16—O2 | 122.7 (4) | C41—C40—C39 | 121.5 (3) |
O3—C16—C17 | 126.2 (4) | C41—C40—Cl5 | 116.6 (3) |
O2—C16—C17 | 111.1 (3) | C39—C40—Cl5 | 121.9 (3) |
C18—C17—C22 | 117.5 (3) | C42—C41—C40 | 119.4 (3) |
C18—C17—C16 | 121.7 (3) | C42—C41—H41A | 120.3 |
C22—C17—C16 | 120.8 (3) | C40—C41—H41A | 120.3 |
C19—C18—C17 | 121.4 (3) | C41—C42—C43 | 120.9 (4) |
C19—C18—Cl2 | 116.1 (3) | C41—C42—Cl6 | 118.8 (3) |
C17—C18—Cl2 | 122.4 (3) | C43—C42—Cl6 | 120.3 (3) |
C20—C19—C18 | 119.4 (4) | C44—C43—C42 | 118.5 (4) |
C20—C19—H19A | 120.3 | C44—C43—H43A | 120.8 |
C18—C19—H19A | 120.3 | C42—C43—H43A | 120.8 |
C19—C20—C21 | 121.0 (3) | C43—C44—C39 | 122.6 (4) |
C19—C20—Cl3 | 118.3 (3) | C43—C44—H44A | 118.7 |
C21—C20—Cl3 | 120.7 (3) | C39—C44—H44A | 118.7 |
| | | |
C10—N1—N2—N3 | 0.5 (4) | C20—C21—C22—C17 | −0.4 (6) |
C9—N1—N2—N3 | 179.0 (3) | C18—C17—C22—C21 | 0.1 (5) |
N1—N2—N3—C11 | −0.4 (4) | C16—C17—C22—C21 | −178.2 (3) |
C32—N4—N5—N6 | −0.6 (4) | C28—C23—C24—C25 | 1.3 (6) |
C31—N4—N5—N6 | −177.3 (3) | C23—C24—C25—C26 | 1.5 (6) |
N4—N5—N6—C33 | 0.3 (4) | C23—C24—C25—Cl4 | −178.1 (3) |
C6—C1—C2—C3 | −2.2 (6) | C24—C25—C26—C27 | −2.6 (6) |
C1—C2—C3—C4 | 2.8 (7) | Cl4—C25—C26—C27 | 177.0 (3) |
C1—C2—C3—Cl1 | −178.2 (3) | C25—C26—C27—C28 | 0.9 (6) |
C2—C3—C4—C5 | −1.3 (7) | C26—C27—C28—C23 | 1.8 (6) |
Cl1—C3—C4—C5 | 179.6 (3) | C26—C27—C28—C29 | −175.8 (4) |
C3—C4—C5—C6 | −0.8 (7) | C24—C23—C28—C27 | −3.0 (6) |
C4—C5—C6—C1 | 1.3 (6) | C24—C23—C28—C29 | 174.7 (4) |
C4—C5—C6—C7 | −179.9 (4) | C27—C28—C29—O4 | −150.3 (4) |
C2—C1—C6—C5 | 0.2 (6) | C23—C28—C29—O4 | 32.1 (6) |
C2—C1—C6—C7 | −178.5 (3) | C27—C28—C29—C30 | 36.4 (5) |
C5—C6—C7—O1 | −31.0 (5) | C23—C28—C29—C30 | −141.2 (4) |
C1—C6—C7—O1 | 147.7 (4) | C38—O5—C30—C31 | −154.0 (3) |
C5—C6—C7—C8 | 144.8 (4) | C38—O5—C30—C29 | 84.2 (4) |
C1—C6—C7—C8 | −36.5 (5) | O4—C29—C30—O5 | 13.4 (5) |
C16—O2—C8—C9 | 159.5 (3) | C28—C29—C30—O5 | −173.2 (3) |
C16—O2—C8—C7 | −79.4 (3) | O4—C29—C30—C31 | −105.8 (4) |
O1—C7—C8—O2 | −18.8 (5) | C28—C29—C30—C31 | 67.6 (4) |
C6—C7—C8—O2 | 165.3 (3) | C32—N4—C31—C30 | 82.8 (4) |
O1—C7—C8—C9 | 99.9 (4) | N5—N4—C31—C30 | −101.2 (4) |
C6—C7—C8—C9 | −76.1 (4) | O5—C30—C31—N4 | −71.1 (4) |
N2—N1—C9—C8 | 98.2 (4) | C29—C30—C31—N4 | 50.5 (4) |
C10—N1—C9—C8 | −83.6 (4) | N5—N4—C32—C33 | 0.6 (4) |
O2—C8—C9—N1 | 72.1 (3) | C31—N4—C32—C33 | 176.9 (3) |
C7—C8—C9—N1 | −48.5 (4) | N5—N4—C32—C37 | −178.0 (4) |
N2—N1—C10—C15 | 178.0 (4) | C31—N4—C32—C37 | −1.7 (7) |
C9—N1—C10—C15 | −0.4 (6) | N5—N6—C33—C32 | 0.1 (4) |
N2—N1—C10—C11 | −0.3 (4) | N5—N6—C33—C34 | 179.3 (4) |
C9—N1—C10—C11 | −178.6 (3) | N4—C32—C33—N6 | −0.4 (4) |
N2—N3—C11—C10 | 0.2 (4) | C37—C32—C33—N6 | 178.4 (3) |
N2—N3—C11—C12 | 179.3 (4) | N4—C32—C33—C34 | −179.7 (3) |
N1—C10—C11—N3 | 0.1 (4) | C37—C32—C33—C34 | −0.9 (6) |
C15—C10—C11—N3 | −178.4 (3) | N6—C33—C34—C35 | −178.3 (4) |
N1—C10—C11—C12 | −179.2 (3) | C32—C33—C34—C35 | 0.8 (6) |
C15—C10—C11—C12 | 2.3 (6) | C33—C34—C35—C36 | 0.1 (6) |
N3—C11—C12—C13 | 179.3 (4) | C34—C35—C36—C37 | −0.8 (7) |
C10—C11—C12—C13 | −1.6 (6) | C35—C36—C37—C32 | 0.7 (6) |
C11—C12—C13—C14 | 0.1 (6) | N4—C32—C37—C36 | 178.5 (4) |
C12—C13—C14—C15 | 0.8 (7) | C33—C32—C37—C36 | 0.1 (5) |
C13—C14—C15—C10 | −0.3 (6) | C30—O5—C38—O6 | 3.0 (6) |
N1—C10—C15—C14 | −179.3 (4) | C30—O5—C38—C39 | −178.7 (3) |
C11—C10—C15—C14 | −1.3 (5) | O6—C38—C39—C44 | −149.7 (4) |
C8—O2—C16—O3 | −1.5 (5) | O5—C38—C39—C44 | 32.1 (5) |
C8—O2—C16—C17 | 177.6 (3) | O6—C38—C39—C40 | 31.6 (6) |
O3—C16—C17—C18 | −34.8 (5) | O5—C38—C39—C40 | −146.5 (3) |
O2—C16—C17—C18 | 146.2 (3) | C44—C39—C40—C41 | −0.7 (5) |
O3—C16—C17—C22 | 143.4 (4) | C38—C39—C40—C41 | 177.9 (3) |
O2—C16—C17—C22 | −35.7 (4) | C44—C39—C40—Cl5 | −179.4 (3) |
C22—C17—C18—C19 | 0.3 (5) | C38—C39—C40—Cl5 | −0.8 (5) |
C16—C17—C18—C19 | 178.5 (3) | C39—C40—C41—C42 | −1.0 (5) |
C22—C17—C18—Cl2 | 178.5 (3) | Cl5—C40—C41—C42 | 177.8 (3) |
C16—C17—C18—Cl2 | −3.3 (5) | C40—C41—C42—C43 | 2.9 (6) |
C17—C18—C19—C20 | −0.2 (5) | C40—C41—C42—Cl6 | −177.4 (3) |
Cl2—C18—C19—C20 | −178.5 (3) | C41—C42—C43—C44 | −2.9 (6) |
C18—C19—C20—C21 | −0.2 (6) | Cl6—C42—C43—C44 | 177.4 (3) |
C18—C19—C20—Cl3 | 179.2 (3) | C42—C43—C44—C39 | 1.1 (6) |
C19—C20—C21—C22 | 0.5 (6) | C40—C39—C44—C43 | 0.7 (6) |
Cl3—C20—C21—C22 | −178.9 (3) | C38—C39—C44—C43 | −178.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N6i | 0.97 | 2.43 | 3.171 (5) | 132 |
C31—H31B···N3ii | 0.97 | 2.52 | 3.287 (5) | 136 |
C36—H36A···Cl4i | 0.93 | 2.81 | 3.608 (4) | 144 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |