The prodrug cloxazolam [systematic name: 13-chloro-2-(2-chlorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0
2,6]tetradeca-1(10),11,13-trien-8-one], C
17H
14Cl
2N
2O
2, crystallizes in the triclinic space group
P, with four chemically identical independent molecules in the asymmetric unit. However, in order to facilitate the analysis of the striking pseudosymmetry relating the four independent molecules, the structure has been analysed and reported in the nonconventional centred
B space-group setting. Pseudosymmetry is an eminently local property, valid only in the realm of the unit-cell boundary and not propagating to the whole crystal structure. It has been analyzed using the
MP procedure described in the preceding article [Baggio (2019).
Acta Cryst. C
75, 837–850]. The molecules consist of a rigid core made up of three rings (five-, six- and seven-membered) and an extra six-membered ring joined to the latter group by a single C—C bond, together with a clamping intramolecular C—H
O interaction preventing free rotation and providing additional rigidity. The four molecules in the asymmetric unit pair into dimers with almost exact twofold pseudosymmetry, further linked into (001) slabs as the building bricks of the structure. Interpenetration of slabs finally leads to a three-dimensional structure of unusual compactness for an organic structure, with a Kitaigorodskii packing index of
ca 0.71.
Supporting information
CCDC reference: 1922820
Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
13-Chloro-2-(2-chlorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0
2,6]tetradeca-1(10),11,13-trien-8-one
top
Crystal data top
C17H14Cl2N2O2 | Z = 16 |
Mr = 349.20 | F(000) = 2880 |
Triclinic, B1 | Dx = 1.521 Mg m−3 |
a = 16.7989 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.0054 (7) Å | Cell parameters from 2166 reflections |
c = 22.1341 (7) Å | θ = 3.1–25.4° |
α = 78.897 (2)° | µ = 0.44 mm−1 |
β = 100.411 (4)° | T = 150 K |
γ = 90.042 (3)° | Fragment, colourless |
V = 6098.8 (4) Å3 | 0.22 × 0.16 × 0.12 mm |
Data collection top
Bruker APEXII CCD diffractometer | 7798 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.114 |
Absorption correction: multi-scan (SAINT; Bruker, 2012) | θmax = 26.5°, θmin = 2.1° |
Tmin = 0.90, Tmax = 0.96 | h = −21→21 |
83792 measured reflections | k = −21→21 |
12513 independent reflections | l = −27→27 |
Refinement top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0509P)2 + 3.6398P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
12513 reflections | Δρmax = 0.82 e Å−3 |
841 parameters | Δρmin = −0.30 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1A | 0.44179 (5) | 0.10166 (5) | 0.59886 (4) | 0.0339 (2) | |
Cl2A | 0.13140 (5) | 0.19450 (5) | 0.55997 (4) | 0.0263 (2) | |
O1A | 0.26786 (12) | 0.31575 (13) | 0.71207 (10) | 0.0221 (5) | |
O2A | 0.22466 (14) | 0.52483 (14) | 0.59210 (12) | 0.0311 (6) | |
N1A | 0.16184 (15) | 0.33530 (15) | 0.62636 (12) | 0.0190 (6) | |
N2A | 0.31714 (16) | 0.42546 (16) | 0.60121 (13) | 0.0216 (6) | |
H2A | 0.3527 (15) | 0.4609 (15) | 0.6007 (16) | 0.026* | |
C1A | 0.23154 (18) | 0.28280 (19) | 0.65849 (14) | 0.0175 (7) | |
C2A | 0.19940 (18) | 0.20009 (18) | 0.68124 (14) | 0.0166 (7) | |
C3A | 0.21746 (19) | 0.16378 (19) | 0.74418 (15) | 0.0201 (7) | |
H3A | 0.248407 | 0.191583 | 0.773211 | 0.024* | |
C4A | 0.1914 (2) | 0.0882 (2) | 0.76546 (16) | 0.0247 (8) | |
H4A | 0.205876 | 0.063968 | 0.808523 | 0.030* | |
C5A | 0.1446 (2) | 0.0479 (2) | 0.72443 (16) | 0.0281 (8) | |
H5A | 0.126205 | −0.003948 | 0.739105 | 0.034* | |
C6A | 0.1246 (2) | 0.0830 (2) | 0.66226 (16) | 0.0252 (8) | |
H6A | 0.091140 | 0.055987 | 0.633927 | 0.030* | |
C7A | 0.15295 (18) | 0.15753 (19) | 0.64071 (14) | 0.0188 (7) | |
C8A | 0.20950 (19) | 0.3682 (2) | 0.72563 (16) | 0.0274 (8) | |
H8A | 0.228450 | 0.423823 | 0.721107 | 0.033* | |
H8B | 0.199404 | 0.350227 | 0.768772 | 0.033* | |
C9A | 0.1332 (2) | 0.3632 (2) | 0.67765 (15) | 0.0239 (8) | |
H9A | 0.095557 | 0.324834 | 0.695960 | 0.029* | |
H9B | 0.105094 | 0.416376 | 0.662630 | 0.029* | |
C10A | 0.17442 (19) | 0.39784 (19) | 0.57401 (15) | 0.0219 (8) | |
H10A | 0.122844 | 0.429054 | 0.556964 | 0.026* | |
H10B | 0.187735 | 0.371811 | 0.540563 | 0.026* | |
C11A | 0.2399 (2) | 0.4552 (2) | 0.58929 (15) | 0.0219 (8) | |
C12A | 0.34278 (19) | 0.34681 (19) | 0.60143 (14) | 0.0201 (7) | |
C13A | 0.30113 (18) | 0.27844 (19) | 0.62293 (14) | 0.0185 (7) | |
C14A | 0.33285 (19) | 0.2039 (2) | 0.62001 (15) | 0.0211 (7) | |
H14A | 0.304290 | 0.156944 | 0.632111 | 0.025* | |
C15A | 0.40546 (19) | 0.1971 (2) | 0.59972 (15) | 0.0223 (8) | |
C16A | 0.44848 (19) | 0.2641 (2) | 0.58261 (15) | 0.0245 (8) | |
H16A | 0.499585 | 0.258863 | 0.570853 | 0.029* | |
C17A | 0.41699 (19) | 0.3384 (2) | 0.58267 (15) | 0.0224 (8) | |
H17A | 0.445916 | 0.384821 | 0.569817 | 0.027* | |
Cl1B | 0.05950 (5) | 0.52461 (5) | 0.41469 (5) | 0.0372 (2) | |
Cl2B | 0.36991 (5) | 0.59784 (5) | 0.44425 (4) | 0.0280 (2) | |
O1B | 0.22997 (13) | 0.79382 (13) | 0.28940 (10) | 0.0232 (5) | |
O2B | 0.26940 (13) | 0.94971 (14) | 0.40390 (11) | 0.0290 (6) | |
N1B | 0.33561 (15) | 0.77314 (15) | 0.37565 (12) | 0.0199 (6) | |
N2B | 0.17764 (16) | 0.85409 (16) | 0.39433 (13) | 0.0211 (6) | |
H2B | 0.1404 (15) | 0.8888 (15) | 0.3918 (15) | 0.025* | |
C1B | 0.26655 (19) | 0.73538 (19) | 0.34436 (14) | 0.0193 (7) | |
C2B | 0.29891 (18) | 0.66330 (19) | 0.32276 (14) | 0.0189 (7) | |
C3B | 0.27977 (19) | 0.6571 (2) | 0.26003 (15) | 0.0219 (8) | |
H3B | 0.246816 | 0.697956 | 0.230974 | 0.026* | |
C4B | 0.3078 (2) | 0.5926 (2) | 0.23923 (16) | 0.0255 (8) | |
H4B | 0.293144 | 0.589073 | 0.196347 | 0.031* | |
C5B | 0.3567 (2) | 0.5335 (2) | 0.28007 (16) | 0.0268 (8) | |
H5B | 0.376332 | 0.489582 | 0.265503 | 0.032* | |
C6B | 0.37733 (19) | 0.53847 (19) | 0.34271 (16) | 0.0227 (8) | |
H6B | 0.412031 | 0.498487 | 0.371207 | 0.027* | |
C7B | 0.34721 (19) | 0.60164 (19) | 0.36335 (15) | 0.0208 (7) | |
C8B | 0.2893 (2) | 0.8515 (2) | 0.27406 (16) | 0.0290 (8) | |
H8C | 0.270631 | 0.906091 | 0.275767 | 0.035* | |
H8D | 0.300294 | 0.851437 | 0.231610 | 0.035* | |
C9B | 0.3646 (2) | 0.8246 (2) | 0.32358 (15) | 0.0253 (8) | |
H9C | 0.403215 | 0.794423 | 0.306901 | 0.030* | |
H9D | 0.391955 | 0.871404 | 0.337371 | 0.030* | |
C10B | 0.32046 (19) | 0.81352 (19) | 0.42507 (15) | 0.0222 (8) | |
H10C | 0.371375 | 0.837675 | 0.441729 | 0.027* | |
H10D | 0.306795 | 0.772539 | 0.459590 | 0.027* | |
C11B | 0.2542 (2) | 0.8781 (2) | 0.40683 (15) | 0.0230 (8) | |
C12B | 0.15265 (19) | 0.77494 (19) | 0.39666 (14) | 0.0195 (7) | |
C13B | 0.19657 (18) | 0.71490 (19) | 0.37979 (14) | 0.0177 (7) | |
C14B | 0.16651 (19) | 0.6380 (2) | 0.38664 (14) | 0.0217 (8) | |
H14B | 0.196319 | 0.595840 | 0.377365 | 0.026* | |
C15B | 0.0936 (2) | 0.6223 (2) | 0.40684 (15) | 0.0238 (8) | |
C16B | 0.0477 (2) | 0.6828 (2) | 0.41827 (14) | 0.0225 (8) | |
H16B | −0.004092 | 0.672315 | 0.429012 | 0.027* | |
C17B | 0.07729 (19) | 0.7582 (2) | 0.41402 (14) | 0.0200 (7) | |
H17B | 0.046341 | 0.799861 | 0.422962 | 0.024* | |
Cl1C | 0.21788 (5) | 0.97584 (5) | 0.55699 (4) | 0.0303 (2) | |
Cl2C | 0.52394 (5) | 0.89904 (5) | 0.55007 (4) | 0.0317 (2) | |
O1C | 0.44587 (12) | 0.70457 (12) | 0.69951 (10) | 0.0210 (5) | |
O2C | 0.43689 (13) | 0.54536 (13) | 0.59902 (10) | 0.0249 (5) | |
N1C | 0.51236 (15) | 0.72824 (15) | 0.61500 (12) | 0.0189 (6) | |
N2C | 0.34539 (16) | 0.64188 (16) | 0.59928 (13) | 0.0215 (6) | |
H2C | 0.3110 (16) | 0.6051 (14) | 0.6030 (15) | 0.026* | |
C1C | 0.45569 (18) | 0.76476 (18) | 0.64492 (14) | 0.0174 (7) | |
C2C | 0.49747 (18) | 0.83628 (19) | 0.66819 (15) | 0.0198 (7) | |
C3C | 0.5028 (2) | 0.8431 (2) | 0.73045 (16) | 0.0261 (8) | |
H3C | 0.476144 | 0.805596 | 0.757013 | 0.031* | |
C4C | 0.5458 (2) | 0.9031 (2) | 0.75479 (18) | 0.0310 (9) | |
H4C | 0.547059 | 0.907672 | 0.797063 | 0.037* | |
C5C | 0.5865 (2) | 0.9559 (2) | 0.7171 (2) | 0.0348 (10) | |
H5C | 0.618638 | 0.995240 | 0.733990 | 0.042* | |
C6C | 0.5810 (2) | 0.9520 (2) | 0.65483 (19) | 0.0324 (9) | |
H6C | 0.608627 | 0.989036 | 0.628751 | 0.039* | |
C7C | 0.53524 (19) | 0.89418 (19) | 0.63055 (16) | 0.0238 (8) | |
C8C | 0.5184 (2) | 0.6549 (2) | 0.71875 (16) | 0.0284 (8) | |
H8E | 0.505635 | 0.597656 | 0.721128 | 0.034* | |
H8F | 0.547371 | 0.662161 | 0.760299 | 0.034* | |
C9C | 0.56966 (19) | 0.6825 (2) | 0.66833 (15) | 0.0230 (8) | |
H9E | 0.613602 | 0.716777 | 0.683356 | 0.028* | |
H9F | 0.593889 | 0.635940 | 0.656526 | 0.028* | |
C10C | 0.47522 (19) | 0.68132 (19) | 0.56904 (15) | 0.0210 (7) | |
H10E | 0.519146 | 0.655722 | 0.554407 | 0.025* | |
H10F | 0.444424 | 0.718810 | 0.532459 | 0.025* | |
C11C | 0.41896 (19) | 0.61660 (19) | 0.59092 (14) | 0.0184 (7) | |
C12C | 0.31884 (19) | 0.72264 (19) | 0.59138 (14) | 0.0182 (7) | |
C13C | 0.37007 (18) | 0.78333 (18) | 0.60755 (14) | 0.0168 (7) | |
C14C | 0.33746 (19) | 0.8615 (2) | 0.59500 (14) | 0.0205 (7) | |
H14C | 0.371383 | 0.904255 | 0.603669 | 0.025* | |
C15C | 0.2565 (2) | 0.8773 (2) | 0.57016 (15) | 0.0233 (8) | |
C16C | 0.2052 (2) | 0.8168 (2) | 0.55805 (15) | 0.0236 (8) | |
H16C | 0.148914 | 0.828256 | 0.543118 | 0.028* | |
C17C | 0.23628 (19) | 0.7394 (2) | 0.56785 (14) | 0.0205 (7) | |
H17C | 0.201641 | 0.697400 | 0.558601 | 0.025* | |
Cl1D | 0.27872 (5) | 1.38511 (5) | 0.43509 (4) | 0.0273 (2) | |
Cl2D | −0.02595 (5) | 1.30909 (5) | 0.44167 (4) | 0.0268 (2) | |
O1D | 0.05252 (12) | 1.17806 (13) | 0.29885 (9) | 0.0208 (5) | |
O2D | 0.05983 (13) | 0.97141 (13) | 0.40548 (11) | 0.0279 (6) | |
N1D | −0.01540 (15) | 1.16405 (15) | 0.38226 (12) | 0.0193 (6) | |
N2D | 0.15034 (16) | 1.06948 (16) | 0.40216 (13) | 0.0216 (6) | |
H2D | 0.1847 (16) | 1.0350 (15) | 0.3989 (16) | 0.026* | |
C1D | 0.04150 (18) | 1.21429 (18) | 0.35117 (14) | 0.0171 (7) | |
C2D | 0.00026 (18) | 1.29714 (18) | 0.32485 (15) | 0.0175 (7) | |
C3D | −0.00403 (19) | 1.33234 (19) | 0.26206 (15) | 0.0216 (7) | |
H3D | 0.021766 | 1.305729 | 0.236426 | 0.026* | |
C4D | −0.0448 (2) | 1.4049 (2) | 0.23603 (16) | 0.0270 (8) | |
H4D | −0.045059 | 1.428462 | 0.193426 | 0.032* | |
C5D | −0.0849 (2) | 1.4431 (2) | 0.27159 (17) | 0.0284 (8) | |
H5D | −0.115178 | 1.491613 | 0.253041 | 0.034* | |
C6D | −0.08124 (19) | 1.41100 (19) | 0.33437 (16) | 0.0228 (8) | |
H6D | −0.108718 | 1.437274 | 0.359240 | 0.027* | |
C7D | −0.03684 (18) | 1.33973 (19) | 0.36075 (15) | 0.0204 (7) | |
C8D | −0.0184 (2) | 1.1356 (2) | 0.28092 (16) | 0.0289 (8) | |
H8G | −0.004336 | 1.078708 | 0.281985 | 0.035* | |
H8H | −0.046538 | 1.160048 | 0.238151 | 0.035* | |
C9D | −0.07166 (19) | 1.1424 (2) | 0.32936 (15) | 0.0244 (8) | |
H9G | −0.114954 | 1.184356 | 0.312078 | 0.029* | |
H9H | −0.096807 | 1.090716 | 0.342514 | 0.029* | |
C10D | 0.02069 (19) | 1.09544 (18) | 0.43008 (14) | 0.0200 (7) | |
H10G | −0.023837 | 1.063477 | 0.444792 | 0.024* | |
H10H | 0.050657 | 1.116189 | 0.466200 | 0.024* | |
C11D | 0.07751 (19) | 1.0396 (2) | 0.41118 (14) | 0.0204 (7) | |
C12D | 0.17715 (19) | 1.14651 (19) | 0.40877 (15) | 0.0204 (7) | |
C13D | 0.12618 (18) | 1.21568 (18) | 0.38960 (14) | 0.0163 (7) | |
C14D | 0.15921 (18) | 1.28817 (19) | 0.39954 (14) | 0.0179 (7) | |
H14D | 0.125799 | 1.335682 | 0.388395 | 0.022* | |
C15D | 0.24007 (19) | 1.29189 (19) | 0.42545 (14) | 0.0200 (7) | |
C16D | 0.29060 (19) | 1.2249 (2) | 0.44117 (15) | 0.0231 (8) | |
H16D | 0.346582 | 1.228876 | 0.457073 | 0.028* | |
C17D | 0.2592 (2) | 1.1516 (2) | 0.43361 (15) | 0.0248 (8) | |
H17D | 0.293334 | 1.104562 | 0.445310 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1A | 0.0285 (5) | 0.0328 (5) | 0.0436 (6) | 0.0072 (4) | 0.0099 (4) | −0.0120 (4) |
Cl2A | 0.0276 (5) | 0.0316 (5) | 0.0194 (4) | −0.0036 (4) | −0.0001 (4) | −0.0081 (4) |
O1A | 0.0177 (12) | 0.0278 (13) | 0.0227 (12) | −0.0030 (10) | 0.0012 (10) | −0.0120 (10) |
O2A | 0.0239 (13) | 0.0217 (14) | 0.0488 (16) | −0.0034 (11) | 0.0109 (12) | −0.0057 (12) |
N1A | 0.0148 (14) | 0.0227 (15) | 0.0206 (15) | −0.0037 (11) | 0.0051 (12) | −0.0051 (12) |
N2A | 0.0164 (15) | 0.0205 (16) | 0.0278 (16) | −0.0053 (12) | 0.0054 (13) | −0.0031 (13) |
C1A | 0.0133 (16) | 0.0229 (18) | 0.0179 (17) | −0.0028 (13) | 0.0015 (13) | −0.0093 (14) |
C2A | 0.0113 (16) | 0.0202 (17) | 0.0191 (18) | −0.0008 (13) | 0.0024 (13) | −0.0061 (14) |
C3A | 0.0160 (17) | 0.0230 (19) | 0.0224 (19) | −0.0011 (14) | 0.0024 (14) | −0.0084 (15) |
C4A | 0.0267 (19) | 0.0255 (19) | 0.0192 (18) | 0.0044 (16) | 0.0011 (15) | −0.0004 (15) |
C5A | 0.031 (2) | 0.0204 (19) | 0.032 (2) | −0.0030 (16) | 0.0066 (17) | −0.0031 (16) |
C6A | 0.0217 (18) | 0.0249 (19) | 0.030 (2) | −0.0042 (15) | 0.0017 (16) | −0.0111 (16) |
C7A | 0.0135 (16) | 0.0236 (18) | 0.0195 (18) | 0.0019 (14) | 0.0013 (14) | −0.0064 (14) |
C8A | 0.0224 (19) | 0.034 (2) | 0.030 (2) | −0.0010 (16) | 0.0073 (16) | −0.0150 (17) |
C9A | 0.0229 (18) | 0.0238 (19) | 0.0271 (19) | −0.0009 (15) | 0.0102 (15) | −0.0052 (15) |
C10A | 0.0157 (17) | 0.0262 (19) | 0.0225 (19) | 0.0002 (14) | 0.0036 (14) | −0.0017 (15) |
C11A | 0.0222 (19) | 0.024 (2) | 0.0214 (18) | −0.0047 (15) | 0.0080 (15) | −0.0056 (15) |
C12A | 0.0155 (17) | 0.0262 (19) | 0.0170 (17) | −0.0021 (14) | −0.0004 (14) | −0.0037 (15) |
C13A | 0.0124 (16) | 0.0268 (19) | 0.0161 (17) | −0.0016 (14) | −0.0001 (13) | −0.0063 (14) |
C14A | 0.0169 (17) | 0.0232 (19) | 0.0234 (19) | −0.0008 (14) | 0.0033 (15) | −0.0057 (15) |
C15A | 0.0205 (18) | 0.030 (2) | 0.0178 (18) | 0.0033 (15) | 0.0032 (14) | −0.0081 (15) |
C16A | 0.0118 (17) | 0.037 (2) | 0.0241 (19) | 0.0026 (16) | 0.0048 (14) | −0.0036 (16) |
C17A | 0.0175 (18) | 0.032 (2) | 0.0173 (18) | −0.0002 (15) | 0.0050 (14) | −0.0011 (15) |
Cl1B | 0.0294 (5) | 0.0280 (5) | 0.0536 (6) | −0.0114 (4) | 0.0088 (4) | −0.0055 (4) |
Cl2B | 0.0318 (5) | 0.0287 (5) | 0.0199 (4) | 0.0010 (4) | −0.0012 (4) | −0.0015 (4) |
O1B | 0.0177 (12) | 0.0244 (13) | 0.0233 (13) | 0.0025 (10) | 0.0012 (10) | 0.0030 (10) |
O2B | 0.0231 (13) | 0.0231 (14) | 0.0438 (16) | −0.0026 (11) | 0.0109 (11) | −0.0098 (11) |
N1B | 0.0179 (14) | 0.0200 (15) | 0.0226 (15) | −0.0014 (12) | 0.0062 (12) | −0.0043 (12) |
N2B | 0.0138 (15) | 0.0259 (17) | 0.0244 (16) | 0.0025 (12) | 0.0042 (12) | −0.0059 (13) |
C1B | 0.0168 (17) | 0.0214 (18) | 0.0188 (18) | 0.0001 (14) | 0.0040 (14) | −0.0011 (14) |
C2B | 0.0136 (16) | 0.0228 (18) | 0.0202 (18) | −0.0020 (14) | 0.0045 (14) | −0.0025 (14) |
C3B | 0.0204 (18) | 0.0236 (19) | 0.0203 (19) | −0.0032 (15) | 0.0033 (14) | −0.0017 (15) |
C4B | 0.028 (2) | 0.0255 (19) | 0.0228 (19) | −0.0058 (16) | 0.0042 (16) | −0.0052 (16) |
C5B | 0.028 (2) | 0.0209 (19) | 0.036 (2) | −0.0047 (16) | 0.0117 (17) | −0.0101 (16) |
C6B | 0.0179 (17) | 0.0203 (18) | 0.030 (2) | −0.0015 (14) | 0.0034 (15) | −0.0055 (15) |
C7B | 0.0180 (17) | 0.0230 (18) | 0.0205 (18) | −0.0045 (14) | 0.0034 (14) | −0.0020 (15) |
C8B | 0.027 (2) | 0.028 (2) | 0.030 (2) | −0.0003 (16) | 0.0085 (16) | 0.0032 (16) |
C9B | 0.0210 (18) | 0.0263 (19) | 0.031 (2) | −0.0036 (15) | 0.0102 (16) | −0.0056 (16) |
C10B | 0.0178 (18) | 0.0254 (19) | 0.0223 (18) | 0.0001 (14) | 0.0033 (14) | −0.0027 (15) |
C11B | 0.0235 (19) | 0.024 (2) | 0.0232 (19) | 0.0006 (15) | 0.0101 (15) | −0.0033 (15) |
C12B | 0.0197 (18) | 0.0220 (18) | 0.0151 (17) | −0.0010 (14) | 0.0021 (14) | −0.0003 (14) |
C13B | 0.0167 (17) | 0.0217 (18) | 0.0138 (17) | −0.0002 (14) | 0.0024 (13) | −0.0016 (14) |
C14B | 0.0209 (18) | 0.0247 (19) | 0.0195 (18) | −0.0013 (15) | 0.0030 (15) | −0.0050 (15) |
C15B | 0.0198 (18) | 0.0265 (19) | 0.0229 (19) | −0.0084 (15) | −0.0023 (15) | −0.0056 (15) |
C16B | 0.0177 (17) | 0.036 (2) | 0.0165 (18) | −0.0045 (16) | 0.0040 (14) | −0.0105 (15) |
C17B | 0.0156 (17) | 0.030 (2) | 0.0173 (17) | −0.0028 (15) | 0.0050 (14) | −0.0116 (15) |
Cl1C | 0.0264 (5) | 0.0285 (5) | 0.0325 (5) | 0.0087 (4) | 0.0006 (4) | −0.0018 (4) |
Cl2C | 0.0331 (5) | 0.0291 (5) | 0.0306 (5) | 0.0012 (4) | 0.0129 (4) | 0.0068 (4) |
O1C | 0.0189 (12) | 0.0212 (12) | 0.0189 (12) | −0.0007 (10) | 0.0015 (10) | 0.0037 (10) |
O2C | 0.0221 (13) | 0.0198 (13) | 0.0312 (14) | −0.0012 (10) | 0.0036 (11) | −0.0020 (10) |
N1C | 0.0154 (14) | 0.0206 (15) | 0.0186 (15) | −0.0004 (11) | 0.0004 (12) | −0.0011 (12) |
N2C | 0.0188 (16) | 0.0231 (16) | 0.0224 (15) | −0.0061 (12) | 0.0047 (12) | −0.0028 (13) |
C1C | 0.0164 (16) | 0.0203 (17) | 0.0133 (16) | −0.0017 (14) | 0.0041 (13) | 0.0030 (13) |
C2C | 0.0087 (16) | 0.0217 (18) | 0.0267 (19) | −0.0006 (13) | 0.0006 (14) | −0.0014 (15) |
C3C | 0.0209 (18) | 0.029 (2) | 0.025 (2) | 0.0021 (15) | −0.0030 (15) | −0.0029 (16) |
C4C | 0.031 (2) | 0.027 (2) | 0.032 (2) | 0.0056 (17) | −0.0060 (17) | −0.0093 (17) |
C5C | 0.0192 (19) | 0.024 (2) | 0.058 (3) | −0.0007 (16) | −0.0056 (19) | −0.0106 (19) |
C6C | 0.0206 (19) | 0.0181 (19) | 0.056 (3) | −0.0016 (15) | 0.0065 (18) | −0.0027 (18) |
C7C | 0.0173 (17) | 0.0212 (18) | 0.031 (2) | 0.0026 (14) | 0.0041 (15) | 0.0001 (15) |
C8C | 0.026 (2) | 0.030 (2) | 0.025 (2) | 0.0077 (16) | −0.0002 (16) | 0.0008 (16) |
C9C | 0.0182 (17) | 0.0225 (18) | 0.0247 (19) | 0.0030 (14) | −0.0003 (15) | 0.0001 (15) |
C10C | 0.0204 (18) | 0.0216 (18) | 0.0217 (18) | −0.0006 (14) | 0.0063 (15) | −0.0037 (15) |
C11C | 0.0203 (18) | 0.0210 (19) | 0.0120 (17) | −0.0055 (15) | −0.0010 (14) | −0.0025 (14) |
C12C | 0.0172 (17) | 0.0233 (18) | 0.0147 (17) | −0.0016 (14) | 0.0045 (14) | −0.0039 (14) |
C13C | 0.0144 (16) | 0.0203 (18) | 0.0153 (17) | 0.0018 (14) | 0.0051 (13) | −0.0002 (14) |
C14C | 0.0188 (18) | 0.0250 (19) | 0.0175 (17) | −0.0019 (15) | 0.0048 (14) | −0.0023 (14) |
C15C | 0.0264 (19) | 0.0234 (19) | 0.0208 (19) | 0.0027 (15) | 0.0055 (15) | −0.0047 (15) |
C16C | 0.0164 (17) | 0.033 (2) | 0.0210 (18) | 0.0035 (15) | 0.0026 (14) | −0.0057 (16) |
C17C | 0.0166 (17) | 0.0263 (19) | 0.0196 (18) | −0.0016 (15) | 0.0035 (14) | −0.0070 (15) |
Cl1D | 0.0259 (5) | 0.0281 (5) | 0.0273 (5) | −0.0101 (4) | 0.0017 (4) | −0.0071 (4) |
Cl2D | 0.0301 (5) | 0.0315 (5) | 0.0215 (5) | −0.0034 (4) | 0.0079 (4) | −0.0089 (4) |
O1D | 0.0200 (12) | 0.0259 (13) | 0.0172 (12) | −0.0002 (10) | 0.0008 (10) | −0.0079 (10) |
O2D | 0.0236 (13) | 0.0206 (13) | 0.0405 (15) | −0.0007 (10) | 0.0041 (11) | −0.0101 (11) |
N1D | 0.0151 (14) | 0.0193 (14) | 0.0228 (15) | −0.0028 (11) | 0.0023 (12) | −0.0037 (12) |
N2D | 0.0183 (15) | 0.0203 (16) | 0.0265 (16) | 0.0022 (12) | 0.0040 (13) | −0.0059 (13) |
C1D | 0.0171 (17) | 0.0226 (18) | 0.0130 (16) | −0.0018 (14) | 0.0035 (13) | −0.0058 (14) |
C2D | 0.0112 (16) | 0.0200 (17) | 0.0207 (18) | −0.0035 (13) | 0.0007 (13) | −0.0046 (14) |
C3D | 0.0167 (17) | 0.0237 (19) | 0.0227 (19) | −0.0018 (14) | 0.0001 (14) | −0.0033 (15) |
C4D | 0.028 (2) | 0.026 (2) | 0.0225 (19) | −0.0031 (16) | −0.0011 (16) | 0.0019 (16) |
C5D | 0.0204 (19) | 0.0212 (19) | 0.039 (2) | −0.0011 (15) | −0.0026 (17) | −0.0024 (17) |
C6D | 0.0202 (18) | 0.0194 (18) | 0.032 (2) | −0.0036 (14) | 0.0073 (15) | −0.0095 (16) |
C7D | 0.0146 (17) | 0.0229 (18) | 0.0245 (19) | −0.0038 (14) | 0.0027 (14) | −0.0073 (15) |
C8D | 0.027 (2) | 0.036 (2) | 0.0226 (19) | −0.0081 (17) | −0.0025 (16) | −0.0115 (17) |
C9D | 0.0176 (17) | 0.0248 (19) | 0.029 (2) | −0.0055 (14) | −0.0018 (15) | −0.0053 (16) |
C10D | 0.0229 (18) | 0.0211 (18) | 0.0163 (17) | −0.0032 (14) | 0.0048 (14) | −0.0031 (14) |
C11D | 0.0192 (18) | 0.0228 (19) | 0.0165 (17) | 0.0044 (15) | −0.0015 (14) | −0.0019 (15) |
C12D | 0.0207 (18) | 0.0198 (18) | 0.0196 (18) | −0.0036 (14) | 0.0045 (14) | −0.0007 (14) |
C13D | 0.0133 (16) | 0.0213 (18) | 0.0140 (17) | −0.0031 (14) | 0.0021 (13) | −0.0030 (14) |
C14D | 0.0173 (17) | 0.0244 (18) | 0.0116 (16) | 0.0006 (14) | 0.0042 (14) | −0.0008 (14) |
C15D | 0.0194 (18) | 0.0225 (18) | 0.0180 (18) | −0.0082 (15) | 0.0026 (14) | −0.0041 (14) |
C16D | 0.0129 (17) | 0.030 (2) | 0.0235 (19) | −0.0052 (15) | 0.0001 (14) | −0.0006 (15) |
C17D | 0.0210 (18) | 0.027 (2) | 0.0248 (19) | −0.0014 (15) | 0.0028 (15) | −0.0025 (16) |
Geometric parameters (Å, º) top
Cl1A—C15A | 1.740 (3) | Cl1C—C15C | 1.750 (3) |
Cl2A—C7A | 1.747 (3) | Cl2C—C7C | 1.743 (4) |
O1A—C8A | 1.435 (4) | O1C—C8C | 1.433 (4) |
O1A—C1A | 1.445 (4) | O1C—C1C | 1.459 (4) |
O2A—C11A | 1.227 (4) | O2C—C11C | 1.220 (4) |
N1A—C1A | 1.459 (4) | N1C—C1C | 1.455 (4) |
N1A—C10A | 1.460 (4) | N1C—C10C | 1.464 (4) |
N1A—C9A | 1.466 (4) | N1C—C9C | 1.470 (4) |
N2A—C11A | 1.355 (4) | N2C—C11C | 1.364 (4) |
N2A—C12A | 1.404 (4) | N2C—C12C | 1.413 (4) |
N2A—H2A | 0.849 (10) | N2C—H2C | 0.853 (10) |
C1A—C13A | 1.532 (4) | C1C—C13C | 1.524 (4) |
C1A—C2A | 1.532 (4) | C1C—C2C | 1.532 (4) |
C2A—C3A | 1.389 (4) | C2C—C3C | 1.392 (5) |
C2A—C7A | 1.391 (4) | C2C—C7C | 1.393 (4) |
C3A—C4A | 1.380 (5) | C3C—C4C | 1.387 (5) |
C3A—H3A | 0.9500 | C3C—H3C | 0.9500 |
C4A—C5A | 1.377 (5) | C4C—C5C | 1.374 (5) |
C4A—H4A | 0.9500 | C4C—H4C | 0.9500 |
C5A—C6A | 1.371 (5) | C5C—C6C | 1.379 (5) |
C5A—H5A | 0.9500 | C5C—H5C | 0.9500 |
C6A—C7A | 1.382 (4) | C6C—C7C | 1.378 (5) |
C6A—H6A | 0.9500 | C6C—H6C | 0.9500 |
C8A—C9A | 1.523 (5) | C8C—C9C | 1.534 (5) |
C8A—H8A | 0.9900 | C8C—H8E | 0.9900 |
C8A—H8B | 0.9900 | C8C—H8F | 0.9900 |
C9A—H9A | 0.9900 | C9C—H9E | 0.9900 |
C9A—H9B | 0.9900 | C9C—H9F | 0.9900 |
C10A—C11A | 1.505 (4) | C10C—C11C | 1.516 (4) |
C10A—H10A | 0.9900 | C10C—H10E | 0.9900 |
C10A—H10B | 0.9900 | C10C—H10F | 0.9900 |
C12A—C17A | 1.399 (4) | C12C—C17C | 1.399 (4) |
C12A—C13A | 1.405 (4) | C12C—C13C | 1.401 (4) |
C13A—C14A | 1.393 (4) | C13C—C14C | 1.396 (4) |
C14A—C15A | 1.386 (4) | C14C—C15C | 1.377 (4) |
C14A—H14A | 0.9500 | C14C—H14C | 0.9500 |
C15A—C16A | 1.376 (5) | C15C—C16C | 1.376 (5) |
C16A—C17A | 1.371 (5) | C16C—C17C | 1.380 (4) |
C16A—H16A | 0.9500 | C16C—H16C | 0.9500 |
C17A—H17A | 0.9500 | C17C—H17C | 0.9500 |
Cl1B—C15B | 1.743 (3) | Cl1D—C15D | 1.749 (3) |
Cl2B—C7B | 1.750 (3) | Cl2D—C7D | 1.742 (3) |
O1B—C8B | 1.436 (4) | O1D—C8D | 1.427 (4) |
O1B—C1B | 1.453 (4) | O1D—C1D | 1.452 (4) |
O2B—C11B | 1.235 (4) | O2D—C11D | 1.222 (4) |
N1B—C1B | 1.455 (4) | N1D—C1D | 1.458 (4) |
N1B—C10B | 1.457 (4) | N1D—C10D | 1.464 (4) |
N1B—C9B | 1.465 (4) | N1D—C9D | 1.472 (4) |
N2B—C11B | 1.347 (4) | N2D—C11D | 1.357 (4) |
N2B—C12B | 1.404 (4) | N2D—C12D | 1.410 (4) |
N2B—H2B | 0.847 (10) | N2D—H2D | 0.845 (10) |
C1B—C13B | 1.531 (4) | C1D—C13D | 1.523 (4) |
C1B—C2B | 1.532 (4) | C1D—C2D | 1.531 (4) |
C2B—C3B | 1.392 (4) | C2D—C3D | 1.392 (4) |
C2B—C7B | 1.393 (4) | C2D—C7D | 1.395 (4) |
C3B—C4B | 1.383 (5) | C3D—C4D | 1.382 (5) |
C3B—H3B | 0.9500 | C3D—H3D | 0.9500 |
C4B—C5B | 1.372 (5) | C4D—C5D | 1.373 (5) |
C4B—H4B | 0.9500 | C4D—H4D | 0.9500 |
C5B—C6B | 1.386 (5) | C5D—C6D | 1.382 (5) |
C5B—H5B | 0.9500 | C5D—H5D | 0.9500 |
C6B—C7B | 1.376 (4) | C6D—C7D | 1.392 (4) |
C6B—H6B | 0.9500 | C6D—H6D | 0.9500 |
C8B—C9B | 1.522 (5) | C8D—C9D | 1.536 (5) |
C8B—H8C | 0.9900 | C8D—H8G | 0.9900 |
C8B—H8D | 0.9900 | C8D—H8H | 0.9900 |
C9B—H9C | 0.9900 | C9D—H9G | 0.9900 |
C9B—H9D | 0.9900 | C9D—H9H | 0.9900 |
C10B—C11B | 1.509 (4) | C10D—C11D | 1.512 (4) |
C10B—H10C | 0.9900 | C10D—H10G | 0.9900 |
C10B—H10D | 0.9900 | C10D—H10H | 0.9900 |
C12B—C17B | 1.402 (4) | C12D—C17D | 1.397 (4) |
C12B—C13B | 1.405 (4) | C12D—C13D | 1.405 (4) |
C13B—C14B | 1.392 (4) | C13D—C14D | 1.391 (4) |
C14B—C15B | 1.386 (4) | C14D—C15D | 1.382 (4) |
C14B—H14B | 0.9500 | C14D—H14D | 0.9500 |
C15B—C16B | 1.375 (5) | C15D—C16D | 1.372 (5) |
C16B—C17B | 1.368 (5) | C16D—C17D | 1.382 (5) |
C16B—H16B | 0.9500 | C16D—H16D | 0.9500 |
C17B—H17B | 0.9500 | C17D—H17D | 0.9500 |
| | | |
C8A—O1A—C1A | 108.9 (2) | C8C—O1C—C1C | 108.0 (2) |
C1A—N1A—C10A | 116.9 (2) | C1C—N1C—C10C | 115.0 (2) |
C1A—N1A—C9A | 103.2 (2) | C1C—N1C—C9C | 103.2 (2) |
C10A—N1A—C9A | 115.7 (3) | C10C—N1C—C9C | 114.7 (2) |
C11A—N2A—C12A | 127.1 (3) | C11C—N2C—C12C | 125.6 (3) |
C11A—N2A—H2A | 114 (2) | C11C—N2C—H2C | 114 (2) |
C12A—N2A—H2A | 117 (2) | C12C—N2C—H2C | 119 (2) |
O1A—C1A—N1A | 106.6 (2) | N1C—C1C—O1C | 105.4 (2) |
O1A—C1A—C13A | 103.8 (2) | N1C—C1C—C13C | 116.5 (2) |
N1A—C1A—C13A | 117.1 (3) | O1C—C1C—C13C | 104.6 (2) |
O1A—C1A—C2A | 109.2 (2) | N1C—C1C—C2C | 107.0 (2) |
N1A—C1A—C2A | 107.3 (2) | O1C—C1C—C2C | 108.1 (2) |
C13A—C1A—C2A | 112.5 (3) | C13C—C1C—C2C | 114.6 (3) |
C3A—C2A—C7A | 117.2 (3) | C3C—C2C—C7C | 117.0 (3) |
C3A—C2A—C1A | 120.4 (3) | C3C—C2C—C1C | 119.9 (3) |
C7A—C2A—C1A | 122.4 (3) | C7C—C2C—C1C | 123.0 (3) |
C4A—C3A—C2A | 121.4 (3) | C4C—C3C—C2C | 121.9 (3) |
C4A—C3A—H3A | 119.3 | C4C—C3C—H3C | 119.1 |
C2A—C3A—H3A | 119.3 | C2C—C3C—H3C | 119.1 |
C5A—C4A—C3A | 120.2 (3) | C5C—C4C—C3C | 119.2 (4) |
C5A—C4A—H4A | 119.9 | C5C—C4C—H4C | 120.4 |
C3A—C4A—H4A | 119.9 | C3C—C4C—H4C | 120.4 |
C6A—C5A—C4A | 119.6 (3) | C4C—C5C—C6C | 120.3 (3) |
C6A—C5A—H5A | 120.2 | C4C—C5C—H5C | 119.8 |
C4A—C5A—H5A | 120.2 | C6C—C5C—H5C | 119.8 |
C5A—C6A—C7A | 120.2 (3) | C5C—C6C—C7C | 119.8 (3) |
C5A—C6A—H6A | 119.9 | C5C—C6C—H6C | 120.1 |
C7A—C6A—H6A | 119.9 | C7C—C6C—H6C | 120.1 |
C6A—C7A—C2A | 121.5 (3) | C6C—C7C—C2C | 121.6 (3) |
C6A—C7A—Cl2A | 117.2 (2) | C6C—C7C—Cl2C | 116.9 (3) |
C2A—C7A—Cl2A | 121.2 (2) | C2C—C7C—Cl2C | 121.5 (3) |
O1A—C8A—C9A | 104.7 (3) | O1C—C8C—C9C | 105.2 (2) |
O1A—C8A—H8A | 110.8 | O1C—C8C—H8E | 110.7 |
C9A—C8A—H8A | 110.8 | C9C—C8C—H8E | 110.7 |
O1A—C8A—H8B | 110.8 | O1C—C8C—H8F | 110.7 |
C9A—C8A—H8B | 110.8 | C9C—C8C—H8F | 110.7 |
H8A—C8A—H8B | 108.9 | H8E—C8C—H8F | 108.8 |
N1A—C9A—C8A | 104.9 (3) | N1C—C9C—C8C | 104.6 (2) |
N1A—C9A—H9A | 110.8 | N1C—C9C—H9E | 110.8 |
C8A—C9A—H9A | 110.8 | C8C—C9C—H9E | 110.8 |
N1A—C9A—H9B | 110.8 | N1C—C9C—H9F | 110.8 |
C8A—C9A—H9B | 110.8 | C8C—C9C—H9F | 110.8 |
H9A—C9A—H9B | 108.8 | H9E—C9C—H9F | 108.9 |
N1A—C10A—C11A | 115.5 (3) | N1C—C10C—C11C | 116.7 (3) |
N1A—C10A—H10A | 108.4 | N1C—C10C—H10E | 108.1 |
C11A—C10A—H10A | 108.4 | C11C—C10C—H10E | 108.1 |
N1A—C10A—H10B | 108.4 | N1C—C10C—H10F | 108.1 |
C11A—C10A—H10B | 108.4 | C11C—C10C—H10F | 108.1 |
H10A—C10A—H10B | 107.5 | H10E—C10C—H10F | 107.3 |
O2A—C11A—N2A | 121.3 (3) | O2C—C11C—N2C | 121.1 (3) |
O2A—C11A—C10A | 122.3 (3) | O2C—C11C—C10C | 122.3 (3) |
N2A—C11A—C10A | 116.4 (3) | N2C—C11C—C10C | 116.6 (3) |
C17A—C12A—C13A | 120.0 (3) | C17C—C12C—C13C | 120.6 (3) |
C17A—C12A—N2A | 116.1 (3) | C17C—C12C—N2C | 116.1 (3) |
C13A—C12A—N2A | 123.7 (3) | C13C—C12C—N2C | 123.3 (3) |
C14A—C13A—C12A | 117.9 (3) | C14C—C13C—C12C | 117.9 (3) |
C14A—C13A—C1A | 119.5 (3) | C14C—C13C—C1C | 119.8 (3) |
C12A—C13A—C1A | 121.9 (3) | C12C—C13C—C1C | 121.9 (3) |
C15A—C14A—C13A | 121.0 (3) | C15C—C14C—C13C | 120.5 (3) |
C15A—C14A—H14A | 119.5 | C15C—C14C—H14C | 119.7 |
C13A—C14A—H14A | 119.5 | C13C—C14C—H14C | 119.7 |
C16A—C15A—C14A | 120.6 (3) | C16C—C15C—C14C | 121.4 (3) |
C16A—C15A—Cl1A | 121.2 (3) | C16C—C15C—Cl1C | 119.6 (3) |
C14A—C15A—Cl1A | 118.1 (3) | C14C—C15C—Cl1C | 118.9 (3) |
C17A—C16A—C15A | 119.5 (3) | C15C—C16C—C17C | 119.3 (3) |
C17A—C16A—H16A | 120.3 | C15C—C16C—H16C | 120.4 |
C15A—C16A—H16A | 120.3 | C17C—C16C—H16C | 120.4 |
C16A—C17A—C12A | 120.8 (3) | C16C—C17C—C12C | 120.0 (3) |
C16A—C17A—H17A | 119.6 | C16C—C17C—H17C | 120.0 |
C12A—C17A—H17A | 119.6 | C12C—C17C—H17C | 120.0 |
C8B—O1B—C1B | 108.5 (2) | C8D—O1D—C1D | 108.5 (2) |
C1B—N1B—C10B | 116.1 (2) | C1D—N1D—C10D | 115.6 (2) |
C1B—N1B—C9B | 103.1 (2) | C1D—N1D—C9D | 102.7 (2) |
C10B—N1B—C9B | 115.0 (3) | C10D—N1D—C9D | 114.3 (2) |
C11B—N2B—C12B | 126.8 (3) | C11D—N2D—C12D | 126.3 (3) |
C11B—N2B—H2B | 116 (2) | C11D—N2D—H2D | 114 (2) |
C12B—N2B—H2B | 116 (2) | C12D—N2D—H2D | 118 (2) |
O1B—C1B—N1B | 106.6 (2) | O1D—C1D—N1D | 105.4 (2) |
O1B—C1B—C13B | 103.4 (2) | O1D—C1D—C13D | 105.0 (2) |
N1B—C1B—C13B | 117.0 (3) | N1D—C1D—C13D | 115.6 (2) |
O1B—C1B—C2B | 108.6 (2) | O1D—C1D—C2D | 108.2 (2) |
N1B—C1B—C2B | 107.7 (2) | N1D—C1D—C2D | 107.6 (2) |
C13B—C1B—C2B | 113.1 (3) | C13D—C1D—C2D | 114.4 (2) |
C3B—C2B—C7B | 117.0 (3) | C3D—C2D—C7D | 116.7 (3) |
C3B—C2B—C1B | 119.9 (3) | C3D—C2D—C1D | 120.4 (3) |
C7B—C2B—C1B | 123.1 (3) | C7D—C2D—C1D | 122.9 (3) |
C4B—C3B—C2B | 121.2 (3) | C4D—C3D—C2D | 121.8 (3) |
C4B—C3B—H3B | 119.4 | C4D—C3D—H3D | 119.1 |
C2B—C3B—H3B | 119.4 | C2D—C3D—H3D | 119.1 |
C5B—C4B—C3B | 120.5 (3) | C5D—C4D—C3D | 120.1 (3) |
C5B—C4B—H4B | 119.7 | C5D—C4D—H4D | 119.9 |
C3B—C4B—H4B | 119.7 | C3D—C4D—H4D | 119.9 |
C4B—C5B—C6B | 119.5 (3) | C4D—C5D—C6D | 120.0 (3) |
C4B—C5B—H5B | 120.2 | C4D—C5D—H5D | 120.0 |
C6B—C5B—H5B | 120.2 | C6D—C5D—H5D | 120.0 |
C7B—C6B—C5B | 119.6 (3) | C5D—C6D—C7D | 119.2 (3) |
C7B—C6B—H6B | 120.2 | C5D—C6D—H6D | 120.4 |
C5B—C6B—H6B | 120.2 | C7D—C6D—H6D | 120.4 |
C6B—C7B—C2B | 122.1 (3) | C6D—C7D—C2D | 121.9 (3) |
C6B—C7B—Cl2B | 115.9 (2) | C6D—C7D—Cl2D | 116.4 (2) |
C2B—C7B—Cl2B | 121.9 (2) | C2D—C7D—Cl2D | 121.7 (2) |
O1B—C8B—C9B | 104.8 (3) | O1D—C8D—C9D | 104.9 (3) |
O1B—C8B—H8C | 110.8 | O1D—C8D—H8G | 110.8 |
C9B—C8B—H8C | 110.8 | C9D—C8D—H8G | 110.8 |
O1B—C8B—H8D | 110.8 | O1D—C8D—H8H | 110.8 |
C9B—C8B—H8D | 110.8 | C9D—C8D—H8H | 110.8 |
H8C—C8B—H8D | 108.9 | H8G—C8D—H8H | 108.8 |
N1B—C9B—C8B | 105.5 (3) | N1D—C9D—C8D | 104.4 (3) |
N1B—C9B—H9C | 110.6 | N1D—C9D—H9G | 110.9 |
C8B—C9B—H9C | 110.6 | C8D—C9D—H9G | 110.9 |
N1B—C9B—H9D | 110.6 | N1D—C9D—H9H | 110.9 |
C8B—C9B—H9D | 110.6 | C8D—C9D—H9H | 110.9 |
H9C—C9B—H9D | 108.8 | H9G—C9D—H9H | 108.9 |
N1B—C10B—C11B | 116.4 (3) | N1D—C10D—C11D | 117.1 (3) |
N1B—C10B—H10C | 108.2 | N1D—C10D—H10G | 108.0 |
C11B—C10B—H10C | 108.2 | C11D—C10D—H10G | 108.0 |
N1B—C10B—H10D | 108.2 | N1D—C10D—H10H | 108.0 |
C11B—C10B—H10D | 108.2 | C11D—C10D—H10H | 108.0 |
H10C—C10B—H10D | 107.3 | H10G—C10D—H10H | 107.3 |
O2B—C11B—N2B | 121.5 (3) | O2D—C11D—N2D | 121.9 (3) |
O2B—C11B—C10B | 121.7 (3) | O2D—C11D—C10D | 122.3 (3) |
N2B—C11B—C10B | 116.9 (3) | N2D—C11D—C10D | 115.8 (3) |
C17B—C12B—C13B | 119.8 (3) | C17D—C12D—C13D | 120.8 (3) |
C17B—C12B—N2B | 116.3 (3) | C17D—C12D—N2D | 116.3 (3) |
C13B—C12B—N2B | 123.8 (3) | C13D—C12D—N2D | 122.9 (3) |
C14B—C13B—C12B | 117.9 (3) | C14D—C13D—C12D | 117.7 (3) |
C14B—C13B—C1B | 119.9 (3) | C14D—C13D—C1D | 120.2 (3) |
C12B—C13B—C1B | 121.3 (3) | C12D—C13D—C1D | 121.6 (3) |
C15B—C14B—C13B | 120.9 (3) | C15D—C14D—C13D | 120.8 (3) |
C15B—C14B—H14B | 119.6 | C15D—C14D—H14D | 119.6 |
C13B—C14B—H14B | 119.6 | C13D—C14D—H14D | 119.6 |
C16B—C15B—C14B | 120.8 (3) | C16D—C15D—C14D | 121.4 (3) |
C16B—C15B—Cl1B | 120.6 (3) | C16D—C15D—Cl1D | 119.9 (2) |
C14B—C15B—Cl1B | 118.6 (3) | C14D—C15D—Cl1D | 118.7 (2) |
C17B—C16B—C15B | 119.3 (3) | C15D—C16D—C17D | 119.3 (3) |
C17B—C16B—H16B | 120.3 | C15D—C16D—H16D | 120.4 |
C15B—C16B—H16B | 120.3 | C17D—C16D—H16D | 120.4 |
C16B—C17B—C12B | 120.9 (3) | C16D—C17D—C12D | 120.0 (3) |
C16B—C17B—H17B | 119.5 | C16D—C17D—H17D | 120.0 |
C12B—C17B—H17B | 119.5 | C12D—C17D—H17D | 120.0 |
| | | |
C8A—O1A—C1A—N1A | 19.2 (3) | C10C—N1C—C1C—O1C | 88.5 (3) |
C8A—O1A—C1A—C13A | 143.4 (3) | C9C—N1C—C1C—O1C | −37.2 (3) |
C8A—O1A—C1A—C2A | −96.4 (3) | C10C—N1C—C1C—C13C | −26.9 (4) |
C10A—N1A—C1A—O1A | 95.7 (3) | C9C—N1C—C1C—C13C | −152.6 (3) |
C9A—N1A—C1A—O1A | −32.6 (3) | C10C—N1C—C1C—C2C | −156.7 (2) |
C10A—N1A—C1A—C13A | −19.9 (4) | C9C—N1C—C1C—C2C | 77.7 (3) |
C9A—N1A—C1A—C13A | −148.2 (3) | C8C—O1C—C1C—N1C | 27.1 (3) |
C10A—N1A—C1A—C2A | −147.5 (3) | C8C—O1C—C1C—C13C | 150.4 (3) |
C9A—N1A—C1A—C2A | 84.2 (3) | C8C—O1C—C1C—C2C | −87.0 (3) |
O1A—C1A—C2A—C3A | −8.9 (4) | N1C—C1C—C2C—C3C | −127.0 (3) |
N1A—C1A—C2A—C3A | −124.0 (3) | O1C—C1C—C2C—C3C | −14.0 (4) |
C13A—C1A—C2A—C3A | 105.8 (3) | C13C—C1C—C2C—C3C | 102.2 (3) |
O1A—C1A—C2A—C7A | 172.4 (3) | N1C—C1C—C2C—C7C | 49.4 (4) |
N1A—C1A—C2A—C7A | 57.3 (4) | O1C—C1C—C2C—C7C | 162.4 (3) |
C13A—C1A—C2A—C7A | −73.0 (4) | C13C—C1C—C2C—C7C | −81.4 (4) |
C7A—C2A—C3A—C4A | 0.9 (5) | C7C—C2C—C3C—C4C | −2.0 (5) |
C1A—C2A—C3A—C4A | −177.8 (3) | C1C—C2C—C3C—C4C | 174.6 (3) |
C2A—C3A—C4A—C5A | −1.8 (5) | C2C—C3C—C4C—C5C | −2.1 (5) |
C3A—C4A—C5A—C6A | 0.6 (5) | C3C—C4C—C5C—C6C | 3.6 (5) |
C4A—C5A—C6A—C7A | 1.6 (5) | C4C—C5C—C6C—C7C | −0.9 (5) |
C5A—C6A—C7A—C2A | −2.5 (5) | C5C—C6C—C7C—C2C | −3.5 (5) |
C5A—C6A—C7A—Cl2A | 175.0 (3) | C5C—C6C—C7C—Cl2C | 174.3 (3) |
C3A—C2A—C7A—C6A | 1.3 (4) | C3C—C2C—C7C—C6C | 4.8 (5) |
C1A—C2A—C7A—C6A | 180.0 (3) | C1C—C2C—C7C—C6C | −171.7 (3) |
C3A—C2A—C7A—Cl2A | −176.2 (2) | C3C—C2C—C7C—Cl2C | −172.9 (2) |
C1A—C2A—C7A—Cl2A | 2.5 (4) | C1C—C2C—C7C—Cl2C | 10.6 (4) |
C1A—O1A—C8A—C9A | 1.8 (3) | C1C—O1C—C8C—C9C | −6.0 (3) |
C1A—N1A—C9A—C8A | 33.2 (3) | C1C—N1C—C9C—C8C | 33.0 (3) |
C10A—N1A—C9A—C8A | −95.8 (3) | C10C—N1C—C9C—C8C | −92.9 (3) |
O1A—C8A—C9A—N1A | −22.0 (3) | O1C—C8C—C9C—N1C | −16.9 (3) |
C1A—N1A—C10A—C11A | −57.6 (4) | C1C—N1C—C10C—C11C | −53.3 (4) |
C9A—N1A—C10A—C11A | 64.3 (4) | C9C—N1C—C10C—C11C | 66.2 (4) |
C12A—N2A—C11A—O2A | 178.0 (3) | C12C—N2C—C11C—O2C | 179.8 (3) |
C12A—N2A—C11A—C10A | −0.7 (5) | C12C—N2C—C11C—C10C | −2.3 (4) |
N1A—C10A—C11A—O2A | −107.6 (4) | N1C—C10C—C11C—O2C | −109.6 (3) |
N1A—C10A—C11A—N2A | 71.0 (4) | N1C—C10C—C11C—N2C | 72.5 (4) |
C11A—N2A—C12A—C17A | 147.8 (3) | C11C—N2C—C12C—C17C | 145.5 (3) |
C11A—N2A—C12A—C13A | −36.4 (5) | C11C—N2C—C12C—C13C | −36.4 (5) |
C17A—C12A—C13A—C14A | −5.0 (4) | C17C—C12C—C13C—C14C | −4.8 (4) |
N2A—C12A—C13A—C14A | 179.4 (3) | N2C—C12C—C13C—C14C | 177.3 (3) |
C17A—C12A—C13A—C1A | 164.9 (3) | C17C—C12C—C13C—C1C | 167.7 (3) |
N2A—C12A—C13A—C1A | −10.6 (5) | N2C—C12C—C13C—C1C | −10.2 (5) |
O1A—C1A—C13A—C14A | 111.7 (3) | N1C—C1C—C13C—C14C | −123.4 (3) |
N1A—C1A—C13A—C14A | −131.2 (3) | O1C—C1C—C13C—C14C | 120.8 (3) |
C2A—C1A—C13A—C14A | −6.2 (4) | C2C—C1C—C13C—C14C | 2.6 (4) |
O1A—C1A—C13A—C12A | −58.1 (4) | N1C—C1C—C13C—C12C | 64.3 (4) |
N1A—C1A—C13A—C12A | 59.0 (4) | O1C—C1C—C13C—C12C | −51.6 (4) |
C2A—C1A—C13A—C12A | −175.9 (3) | C2C—C1C—C13C—C12C | −169.8 (3) |
C12A—C13A—C14A—C15A | 3.4 (5) | C12C—C13C—C14C—C15C | 2.9 (4) |
C1A—C13A—C14A—C15A | −166.8 (3) | C1C—C13C—C14C—C15C | −169.7 (3) |
C13A—C14A—C15A—C16A | 0.8 (5) | C13C—C14C—C15C—C16C | 1.2 (5) |
C13A—C14A—C15A—Cl1A | 178.8 (2) | C13C—C14C—C15C—Cl1C | 178.5 (2) |
C14A—C15A—C16A—C17A | −3.3 (5) | C14C—C15C—C16C—C17C | −3.5 (5) |
Cl1A—C15A—C16A—C17A | 178.7 (3) | Cl1C—C15C—C16C—C17C | 179.2 (2) |
C15A—C16A—C17A—C12A | 1.7 (5) | C15C—C16C—C17C—C12C | 1.7 (5) |
C13A—C12A—C17A—C16A | 2.6 (5) | C13C—C12C—C17C—C16C | 2.5 (5) |
N2A—C12A—C17A—C16A | 178.5 (3) | N2C—C12C—C17C—C16C | −179.4 (3) |
C8B—O1B—C1B—N1B | 20.9 (3) | C8D—O1D—C1D—N1D | 26.3 (3) |
C8B—O1B—C1B—C13B | 144.8 (3) | C8D—O1D—C1D—C13D | 148.9 (2) |
C8B—O1B—C1B—C2B | −94.8 (3) | C8D—O1D—C1D—C2D | −88.5 (3) |
C10B—N1B—C1B—O1B | 93.5 (3) | C10D—N1D—C1D—O1D | 87.6 (3) |
C9B—N1B—C1B—O1B | −33.1 (3) | C9D—N1D—C1D—O1D | −37.5 (3) |
C10B—N1B—C1B—C13B | −21.5 (4) | C10D—N1D—C1D—C13D | −27.8 (4) |
C9B—N1B—C1B—C13B | −148.2 (3) | C9D—N1D—C1D—C13D | −153.0 (3) |
C10B—N1B—C1B—C2B | −150.1 (3) | C10D—N1D—C1D—C2D | −157.1 (2) |
C9B—N1B—C1B—C2B | 83.3 (3) | C9D—N1D—C1D—C2D | 77.7 (3) |
O1B—C1B—C2B—C3B | −9.5 (4) | O1D—C1D—C2D—C3D | −13.9 (4) |
N1B—C1B—C2B—C3B | −124.6 (3) | N1D—C1D—C2D—C3D | −127.3 (3) |
C13B—C1B—C2B—C3B | 104.6 (3) | C13D—C1D—C2D—C3D | 102.7 (3) |
O1B—C1B—C2B—C7B | 170.9 (3) | O1D—C1D—C2D—C7D | 163.9 (3) |
N1B—C1B—C2B—C7B | 55.9 (4) | N1D—C1D—C2D—C7D | 50.5 (4) |
C13B—C1B—C2B—C7B | −74.9 (4) | C13D—C1D—C2D—C7D | −79.5 (4) |
C7B—C2B—C3B—C4B | −0.2 (5) | C7D—C2D—C3D—C4D | −1.6 (5) |
C1B—C2B—C3B—C4B | −179.7 (3) | C1D—C2D—C3D—C4D | 176.3 (3) |
C2B—C3B—C4B—C5B | −1.2 (5) | C2D—C3D—C4D—C5D | −2.3 (5) |
C3B—C4B—C5B—C6B | 0.6 (5) | C3D—C4D—C5D—C6D | 3.2 (5) |
C4B—C5B—C6B—C7B | 1.3 (5) | C4D—C5D—C6D—C7D | −0.2 (5) |
C5B—C6B—C7B—C2B | −2.7 (5) | C5D—C6D—C7D—C2D | −3.8 (5) |
C5B—C6B—C7B—Cl2B | 174.8 (2) | C5D—C6D—C7D—Cl2D | 173.1 (2) |
C3B—C2B—C7B—C6B | 2.1 (5) | C3D—C2D—C7D—C6D | 4.7 (5) |
C1B—C2B—C7B—C6B | −178.3 (3) | C1D—C2D—C7D—C6D | −173.2 (3) |
C3B—C2B—C7B—Cl2B | −175.3 (2) | C3D—C2D—C7D—Cl2D | −172.1 (2) |
C1B—C2B—C7B—Cl2B | 4.3 (4) | C1D—C2D—C7D—Cl2D | 10.0 (4) |
C1B—O1B—C8B—C9B | −0.3 (3) | C1D—O1D—C8D—C9D | −4.4 (3) |
C1B—N1B—C9B—C8B | 32.5 (3) | C1D—N1D—C9D—C8D | 34.2 (3) |
C10B—N1B—C9B—C8B | −94.8 (3) | C10D—N1D—C9D—C8D | −91.8 (3) |
O1B—C8B—C9B—N1B | −20.3 (3) | O1D—C8D—C9D—N1D | −18.8 (3) |
C1B—N1B—C10B—C11B | −56.6 (4) | C1D—N1D—C10D—C11D | −52.7 (4) |
C9B—N1B—C10B—C11B | 63.8 (4) | C9D—N1D—C10D—C11D | 66.2 (4) |
C12B—N2B—C11B—O2B | −179.3 (3) | C12D—N2D—C11D—O2D | −178.7 (3) |
C12B—N2B—C11B—C10B | 0.2 (5) | C12D—N2D—C11D—C10D | 0.0 (5) |
N1B—C10B—C11B—O2B | −110.2 (4) | N1D—C10D—C11D—O2D | −110.3 (3) |
N1B—C10B—C11B—N2B | 70.2 (4) | N1D—C10D—C11D—N2D | 71.0 (4) |
C11B—N2B—C12B—C17B | 148.0 (3) | C11D—N2D—C12D—C17D | 143.4 (3) |
C11B—N2B—C12B—C13B | −35.3 (5) | C11D—N2D—C12D—C13D | −39.0 (5) |
C17B—C12B—C13B—C14B | −5.9 (4) | C17D—C12D—C13D—C14D | −3.6 (5) |
N2B—C12B—C13B—C14B | 177.5 (3) | N2D—C12D—C13D—C14D | 178.9 (3) |
C17B—C12B—C13B—C1B | 163.5 (3) | C17D—C12D—C13D—C1D | 168.0 (3) |
N2B—C12B—C13B—C1B | −13.1 (5) | N2D—C12D—C13D—C1D | −9.5 (5) |
O1B—C1B—C13B—C14B | 114.2 (3) | O1D—C1D—C13D—C14D | 119.9 (3) |
N1B—C1B—C13B—C14B | −129.0 (3) | N1D—C1D—C13D—C14D | −124.4 (3) |
C2B—C1B—C13B—C14B | −3.1 (4) | C2D—C1D—C13D—C14D | 1.5 (4) |
O1B—C1B—C13B—C12B | −55.0 (4) | O1D—C1D—C13D—C12D | −51.4 (4) |
N1B—C1B—C13B—C12B | 61.8 (4) | N1D—C1D—C13D—C12D | 64.2 (4) |
C2B—C1B—C13B—C12B | −172.3 (3) | C2D—C1D—C13D—C12D | −169.9 (3) |
C12B—C13B—C14B—C15B | 2.8 (5) | C12D—C13D—C14D—C15D | 2.1 (4) |
C1B—C13B—C14B—C15B | −166.7 (3) | C1D—C13D—C14D—C15D | −169.5 (3) |
C13B—C14B—C15B—C16B | 2.5 (5) | C13D—C14D—C15D—C16D | 1.1 (5) |
C13B—C14B—C15B—Cl1B | −179.8 (2) | C13D—C14D—C15D—Cl1D | 178.5 (2) |
C14B—C15B—C16B—C17B | −4.8 (5) | C14D—C15D—C16D—C17D | −3.0 (5) |
Cl1B—C15B—C16B—C17B | 177.6 (2) | Cl1D—C15D—C16D—C17D | 179.7 (3) |
C15B—C16B—C17B—C12B | 1.6 (5) | C15D—C16D—C17D—C12D | 1.5 (5) |
C13B—C12B—C17B—C16B | 3.8 (5) | C13D—C12D—C17D—C16D | 1.8 (5) |
N2B—C12B—C17B—C16B | −179.4 (3) | N2D—C12D—C17D—C16D | 179.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O2C | 0.85 (1) | 2.01 (1) | 2.863 (3) | 180 (4) |
C6A—H6A···O2Di | 0.95 | 2.60 | 3.399 (4) | 142 |
C10A—H10B···Cl1Dii | 0.99 | 2.99 | 3.844 (3) | 146 |
N2B—H2B···O2D | 0.85 (1) | 2.05 (1) | 2.886 (3) | 168 (3) |
C6B—H6B···O2Ciii | 0.95 | 2.58 | 3.359 (4) | 140 |
C9B—H9D···Cl1Aiii | 0.99 | 2.97 | 3.729 (3) | 134 |
N2C—H2C···O2A | 0.85 (1) | 2.01 (1) | 2.846 (3) | 168 (3) |
C6C—H6C···O2Biv | 0.95 | 2.46 | 3.338 (4) | 154 |
C17C—H17C···Cl2Dv | 0.95 | 2.95 | 3.606 (3) | 127 |
N2D—H2D···O2B | 0.85 (1) | 2.01 (1) | 2.846 (3) | 172 (3) |
C6D—H6D···O2Av | 0.95 | 2.53 | 3.428 (4) | 158 |
C10D—H10H···Cl2Avi | 0.99 | 2.82 | 3.807 (3) | 173 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) −x, −y+2, −z+1; (vi) x, y+1, z. |
Hydrogen-bond geometry (Å, °) for (I) topGroup No. | D—H···A | D—H | H···A | D···A | D—H···A |
#1 | C3A—H3A···O1A | 0.95 | 2.34 | 2.722 (4) | 104 |
#1 | C3B—H3B···O1B | 0.95 | 2.31 | 2.703 (4) | 104 |
#1 | C3C—H3C···O1C | 0.95 | 2.33 | 2.703 (4) | 103 |
#1 | C3D—H3D···O1D | 0.95 | 2.34 | 2.711 (4) | 103 |
| | | | | |
#2 | N2A—H2A···O2C | 0.85 (1) | 2.01 (1) | 2.863 (3) | 180 (4) |
#2 | N2B—H2B···O2D | 0.85 (1) | 2.05 (1) | 2.886 (3) | 168 (3) |
#2 | N2C—H2C···O2A | 0.85 (1) | 2.01 (1) | 2.846 (3) | 168 (3) |
#2 | N2D—H2D···O2B | 0.85 (1) | 2.01 (1) | 2.846 (3) | 172 (3) |
| | | | | |
#3 | C6A—H6A···O2Di | 0.95 | 2.60 | 3.399 (4) | 142 |
#3 | C6B—H6B···O2Ciii | 0.95 | 2.58 | 3.359 (3) | 140 |
#3 | C6C—H6C···O2Biv | 0.95 | 2.46 | 3.338 (4) | 154 |
#3 | C6D—H6D···O2Av | 0.95 | 2.53 | 3.428 (4) | 158 |
| | | | | |
#4 | C10A—H10B···Cl1Dii | 0.99 | 2.99 | 3.844 (3) | 146 |
#4 | C9B—H9C···O1Dvii | 0.99 | 2.54 | 3.270 (4) | 130 |
#4 | C9B—H9D···Cl1Aiii | 0.99 | 2.97 | 3.729 (3) | 134 |
#4 | C4B—H4B···Cl1Dvii | 0.95 | 2.89 | 3.815 (3) | 165 |
#4 | C4D—H4D···O2Cviii | 0.95 | 2.57 | 3.446 (4) | 154 |
#4 | C9A—H9A···O1Cix | 0.99 | 2.50 | 3.254 (4) | 133 |
| | | | | |
#5 | C10D—H10H···Cl2Avi | 0.99 | 2.82 | 3.807 (3) | 173 |
#5 | C17C—H17C···Cl2Div | 0.95 | 2.95 | 3.606 (3) | 127 |
#5 | Cl1A···Cl2Ciii | n.a. | n.a. | 3.449 (2) | n.a. |
Symmetry codes:
(i) -x, -y+1, -z+1;
(ii) x, y-1, z;
(iii) -x+1, -y+1, -z+1;
(iv) -x+1, -y+2, -z+1;
(v) -x, -y+2, -z+1;
(vi) x, y+1, z.;
(vii) -x+1/2, -y+2, -z+1/2;
(viii) x-1/2, y+1, z-1/2;
(ix) -x+1/2, -y+1, -z+3/2. |
Internal angles (°) between the reference frame axis, as well as those
between the 2 and 21 loci. top2.0 (3) | 90.5 (7) | 90.6 (5) | c† | 90.0 | 90.0 | 0 |
90.6 (7) | 1.2 (2) | 88.9 (1) | b† | 90.004 (3) | 0 | 90.0 |
91.8 (1) | 89.5 (1) | 1.5 (3) | a† | 0 | 90.004 (3) | 90.0 |
| | | | | | |
AC–BD | AB–CD | AD–BC | | a† | b† | c† |
| | | | | | |
91.2 (7) | 91.1 (5) | 0 | AD–BC | 1.5 (3) | 88.9 (1) | 90.6 (5) |
90.7 (6) | 0 | 91.1 (5) | AB–CD | 89.5 (1) | 1.2 (2) | 90.5 (7) |
0 | 90.7 (6) | 91.2 (7) | AC–BD | 91.8 (1) | 90.6 (7) | 2.0 (3) |