Download citation
Download citation
link to html
The prodrug cloxazolam [systematic name: 13-chloro-2-(2-chloro­phen­yl)-3-oxa-6,9-di­aza­tri­cyclo­[8.4.0.02,6]tetra­deca-1(10),11,13-trien-8-one], C17H14Cl2N2O2, crystallizes in the triclinic space group P\overline{1}, 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\overline{1} 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. C75, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619008404/sk3730sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008404/sk3730Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619008404/sk3730sup3.pdf
Halfsum and difference of coordinates (with mean values and s.u.'s) and Symmetry schemes for space groups #55 to #60

CCDC reference: 1922820

Computing details top

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[8.4.0.02,6]tetradeca-1(10),11,13-trien-8-one top
Crystal data top
C17H14Cl2N2O2Z = 16
Mr = 349.20F(000) = 2880
Triclinic, B1Dx = 1.521 Mg m3
a = 16.7989 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.0054 (7) ÅCell parameters from 2166 reflections
c = 22.1341 (7) Åθ = 3.1–25.4°
α = 78.897 (2)°µ = 0.44 mm1
β = 100.411 (4)°T = 150 K
γ = 90.042 (3)°Fragment, colourless
V = 6098.8 (4) Å30.22 × 0.16 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
7798 reflections with I > 2σ(I)
φ and ω scansRint = 0.114
Absorption correction: multi-scan
(SAINT; Bruker, 2012)
θmax = 26.5°, θmin = 2.1°
Tmin = 0.90, Tmax = 0.96h = 2121
83792 measured reflectionsk = 2121
12513 independent reflectionsl = 2727
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057H 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 reflectionsΔρmax = 0.82 e Å3
841 parametersΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
Cl1A0.44179 (5)0.10166 (5)0.59886 (4)0.0339 (2)
Cl2A0.13140 (5)0.19450 (5)0.55997 (4)0.0263 (2)
O1A0.26786 (12)0.31575 (13)0.71207 (10)0.0221 (5)
O2A0.22466 (14)0.52483 (14)0.59210 (12)0.0311 (6)
N1A0.16184 (15)0.33530 (15)0.62636 (12)0.0190 (6)
N2A0.31714 (16)0.42546 (16)0.60121 (13)0.0216 (6)
H2A0.3527 (15)0.4609 (15)0.6007 (16)0.026*
C1A0.23154 (18)0.28280 (19)0.65849 (14)0.0175 (7)
C2A0.19940 (18)0.20009 (18)0.68124 (14)0.0166 (7)
C3A0.21746 (19)0.16378 (19)0.74418 (15)0.0201 (7)
H3A0.2484070.1915830.7732110.024*
C4A0.1914 (2)0.0882 (2)0.76546 (16)0.0247 (8)
H4A0.2058760.0639680.8085230.030*
C5A0.1446 (2)0.0479 (2)0.72443 (16)0.0281 (8)
H5A0.1262050.0039480.7391050.034*
C6A0.1246 (2)0.0830 (2)0.66226 (16)0.0252 (8)
H6A0.0911400.0559870.6339270.030*
C7A0.15295 (18)0.15753 (19)0.64071 (14)0.0188 (7)
C8A0.20950 (19)0.3682 (2)0.72563 (16)0.0274 (8)
H8A0.2284500.4238230.7211070.033*
H8B0.1994040.3502270.7687720.033*
C9A0.1332 (2)0.3632 (2)0.67765 (15)0.0239 (8)
H9A0.0955570.3248340.6959600.029*
H9B0.1050940.4163760.6626300.029*
C10A0.17442 (19)0.39784 (19)0.57401 (15)0.0219 (8)
H10A0.1228440.4290540.5569640.026*
H10B0.1877350.3718110.5405630.026*
C11A0.2399 (2)0.4552 (2)0.58929 (15)0.0219 (8)
C12A0.34278 (19)0.34681 (19)0.60143 (14)0.0201 (7)
C13A0.30113 (18)0.27844 (19)0.62293 (14)0.0185 (7)
C14A0.33285 (19)0.2039 (2)0.62001 (15)0.0211 (7)
H14A0.3042900.1569440.6321110.025*
C15A0.40546 (19)0.1971 (2)0.59972 (15)0.0223 (8)
C16A0.44848 (19)0.2641 (2)0.58261 (15)0.0245 (8)
H16A0.4995850.2588630.5708530.029*
C17A0.41699 (19)0.3384 (2)0.58267 (15)0.0224 (8)
H17A0.4459160.3848210.5698170.027*
Cl1B0.05950 (5)0.52461 (5)0.41469 (5)0.0372 (2)
Cl2B0.36991 (5)0.59784 (5)0.44425 (4)0.0280 (2)
O1B0.22997 (13)0.79382 (13)0.28940 (10)0.0232 (5)
O2B0.26940 (13)0.94971 (14)0.40390 (11)0.0290 (6)
N1B0.33561 (15)0.77314 (15)0.37565 (12)0.0199 (6)
N2B0.17764 (16)0.85409 (16)0.39433 (13)0.0211 (6)
H2B0.1404 (15)0.8888 (15)0.3918 (15)0.025*
C1B0.26655 (19)0.73538 (19)0.34436 (14)0.0193 (7)
C2B0.29891 (18)0.66330 (19)0.32276 (14)0.0189 (7)
C3B0.27977 (19)0.6571 (2)0.26003 (15)0.0219 (8)
H3B0.2468160.6979560.2309740.026*
C4B0.3078 (2)0.5926 (2)0.23923 (16)0.0255 (8)
H4B0.2931440.5890730.1963470.031*
C5B0.3567 (2)0.5335 (2)0.28007 (16)0.0268 (8)
H5B0.3763320.4895820.2655030.032*
C6B0.37733 (19)0.53847 (19)0.34271 (16)0.0227 (8)
H6B0.4120310.4984870.3712070.027*
C7B0.34721 (19)0.60164 (19)0.36335 (15)0.0208 (7)
C8B0.2893 (2)0.8515 (2)0.27406 (16)0.0290 (8)
H8C0.2706310.9060910.2757670.035*
H8D0.3002940.8514370.2316100.035*
C9B0.3646 (2)0.8246 (2)0.32358 (15)0.0253 (8)
H9C0.4032150.7944230.3069010.030*
H9D0.3919550.8714040.3373710.030*
C10B0.32046 (19)0.81352 (19)0.42507 (15)0.0222 (8)
H10C0.3713750.8376750.4417290.027*
H10D0.3067950.7725390.4595900.027*
C11B0.2542 (2)0.8781 (2)0.40683 (15)0.0230 (8)
C12B0.15265 (19)0.77494 (19)0.39666 (14)0.0195 (7)
C13B0.19657 (18)0.71490 (19)0.37979 (14)0.0177 (7)
C14B0.16651 (19)0.6380 (2)0.38664 (14)0.0217 (8)
H14B0.1963190.5958400.3773650.026*
C15B0.0936 (2)0.6223 (2)0.40684 (15)0.0238 (8)
C16B0.0477 (2)0.6828 (2)0.41827 (14)0.0225 (8)
H16B0.0040920.6723150.4290120.027*
C17B0.07729 (19)0.7582 (2)0.41402 (14)0.0200 (7)
H17B0.0463410.7998610.4229620.024*
Cl1C0.21788 (5)0.97584 (5)0.55699 (4)0.0303 (2)
Cl2C0.52394 (5)0.89904 (5)0.55007 (4)0.0317 (2)
O1C0.44587 (12)0.70457 (12)0.69951 (10)0.0210 (5)
O2C0.43689 (13)0.54536 (13)0.59902 (10)0.0249 (5)
N1C0.51236 (15)0.72824 (15)0.61500 (12)0.0189 (6)
N2C0.34539 (16)0.64188 (16)0.59928 (13)0.0215 (6)
H2C0.3110 (16)0.6051 (14)0.6030 (15)0.026*
C1C0.45569 (18)0.76476 (18)0.64492 (14)0.0174 (7)
C2C0.49747 (18)0.83628 (19)0.66819 (15)0.0198 (7)
C3C0.5028 (2)0.8431 (2)0.73045 (16)0.0261 (8)
H3C0.4761440.8055960.7570130.031*
C4C0.5458 (2)0.9031 (2)0.75479 (18)0.0310 (9)
H4C0.5470590.9076720.7970630.037*
C5C0.5865 (2)0.9559 (2)0.7171 (2)0.0348 (10)
H5C0.6186380.9952400.7339900.042*
C6C0.5810 (2)0.9520 (2)0.65483 (19)0.0324 (9)
H6C0.6086270.9890360.6287510.039*
C7C0.53524 (19)0.89418 (19)0.63055 (16)0.0238 (8)
C8C0.5184 (2)0.6549 (2)0.71875 (16)0.0284 (8)
H8E0.5056350.5976560.7211280.034*
H8F0.5473710.6621610.7602990.034*
C9C0.56966 (19)0.6825 (2)0.66833 (15)0.0230 (8)
H9E0.6136020.7167770.6833560.028*
H9F0.5938890.6359400.6565260.028*
C10C0.47522 (19)0.68132 (19)0.56904 (15)0.0210 (7)
H10E0.5191460.6557220.5544070.025*
H10F0.4444240.7188100.5324590.025*
C11C0.41896 (19)0.61660 (19)0.59092 (14)0.0184 (7)
C12C0.31884 (19)0.72264 (19)0.59138 (14)0.0182 (7)
C13C0.37007 (18)0.78333 (18)0.60755 (14)0.0168 (7)
C14C0.33746 (19)0.8615 (2)0.59500 (14)0.0205 (7)
H14C0.3713830.9042550.6036690.025*
C15C0.2565 (2)0.8773 (2)0.57016 (15)0.0233 (8)
C16C0.2052 (2)0.8168 (2)0.55805 (15)0.0236 (8)
H16C0.1489140.8282560.5431180.028*
C17C0.23628 (19)0.7394 (2)0.56785 (14)0.0205 (7)
H17C0.2016410.6974000.5586010.025*
Cl1D0.27872 (5)1.38511 (5)0.43509 (4)0.0273 (2)
Cl2D0.02595 (5)1.30909 (5)0.44167 (4)0.0268 (2)
O1D0.05252 (12)1.17806 (13)0.29885 (9)0.0208 (5)
O2D0.05983 (13)0.97141 (13)0.40548 (11)0.0279 (6)
N1D0.01540 (15)1.16405 (15)0.38226 (12)0.0193 (6)
N2D0.15034 (16)1.06948 (16)0.40216 (13)0.0216 (6)
H2D0.1847 (16)1.0350 (15)0.3989 (16)0.026*
C1D0.04150 (18)1.21429 (18)0.35117 (14)0.0171 (7)
C2D0.00026 (18)1.29714 (18)0.32485 (15)0.0175 (7)
C3D0.00403 (19)1.33234 (19)0.26206 (15)0.0216 (7)
H3D0.0217661.3057290.2364260.026*
C4D0.0448 (2)1.4049 (2)0.23603 (16)0.0270 (8)
H4D0.0450591.4284620.1934260.032*
C5D0.0849 (2)1.4431 (2)0.27159 (17)0.0284 (8)
H5D0.1151781.4916130.2530410.034*
C6D0.08124 (19)1.41100 (19)0.33437 (16)0.0228 (8)
H6D0.1087181.4372740.3592400.027*
C7D0.03684 (18)1.33973 (19)0.36075 (15)0.0204 (7)
C8D0.0184 (2)1.1356 (2)0.28092 (16)0.0289 (8)
H8G0.0043361.0787080.2819850.035*
H8H0.0465381.1600480.2381510.035*
C9D0.07166 (19)1.1424 (2)0.32936 (15)0.0244 (8)
H9G0.1149541.1843560.3120780.029*
H9H0.0968071.0907160.3425140.029*
C10D0.02069 (19)1.09544 (18)0.43008 (14)0.0200 (7)
H10G0.0238371.0634770.4447920.024*
H10H0.0506571.1161890.4662000.024*
C11D0.07751 (19)1.0396 (2)0.41118 (14)0.0204 (7)
C12D0.17715 (19)1.14651 (19)0.40877 (15)0.0204 (7)
C13D0.12618 (18)1.21568 (18)0.38960 (14)0.0163 (7)
C14D0.15921 (18)1.28817 (19)0.39954 (14)0.0179 (7)
H14D0.1257991.3356820.3883950.022*
C15D0.24007 (19)1.29189 (19)0.42545 (14)0.0200 (7)
C16D0.29060 (19)1.2249 (2)0.44117 (15)0.0231 (8)
H16D0.3465821.2288760.4570730.028*
C17D0.2592 (2)1.1516 (2)0.43361 (15)0.0248 (8)
H17D0.2933341.1045620.4453100.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0285 (5)0.0328 (5)0.0436 (6)0.0072 (4)0.0099 (4)0.0120 (4)
Cl2A0.0276 (5)0.0316 (5)0.0194 (4)0.0036 (4)0.0001 (4)0.0081 (4)
O1A0.0177 (12)0.0278 (13)0.0227 (12)0.0030 (10)0.0012 (10)0.0120 (10)
O2A0.0239 (13)0.0217 (14)0.0488 (16)0.0034 (11)0.0109 (12)0.0057 (12)
N1A0.0148 (14)0.0227 (15)0.0206 (15)0.0037 (11)0.0051 (12)0.0051 (12)
N2A0.0164 (15)0.0205 (16)0.0278 (16)0.0053 (12)0.0054 (13)0.0031 (13)
C1A0.0133 (16)0.0229 (18)0.0179 (17)0.0028 (13)0.0015 (13)0.0093 (14)
C2A0.0113 (16)0.0202 (17)0.0191 (18)0.0008 (13)0.0024 (13)0.0061 (14)
C3A0.0160 (17)0.0230 (19)0.0224 (19)0.0011 (14)0.0024 (14)0.0084 (15)
C4A0.0267 (19)0.0255 (19)0.0192 (18)0.0044 (16)0.0011 (15)0.0004 (15)
C5A0.031 (2)0.0204 (19)0.032 (2)0.0030 (16)0.0066 (17)0.0031 (16)
C6A0.0217 (18)0.0249 (19)0.030 (2)0.0042 (15)0.0017 (16)0.0111 (16)
C7A0.0135 (16)0.0236 (18)0.0195 (18)0.0019 (14)0.0013 (14)0.0064 (14)
C8A0.0224 (19)0.034 (2)0.030 (2)0.0010 (16)0.0073 (16)0.0150 (17)
C9A0.0229 (18)0.0238 (19)0.0271 (19)0.0009 (15)0.0102 (15)0.0052 (15)
C10A0.0157 (17)0.0262 (19)0.0225 (19)0.0002 (14)0.0036 (14)0.0017 (15)
C11A0.0222 (19)0.024 (2)0.0214 (18)0.0047 (15)0.0080 (15)0.0056 (15)
C12A0.0155 (17)0.0262 (19)0.0170 (17)0.0021 (14)0.0004 (14)0.0037 (15)
C13A0.0124 (16)0.0268 (19)0.0161 (17)0.0016 (14)0.0001 (13)0.0063 (14)
C14A0.0169 (17)0.0232 (19)0.0234 (19)0.0008 (14)0.0033 (15)0.0057 (15)
C15A0.0205 (18)0.030 (2)0.0178 (18)0.0033 (15)0.0032 (14)0.0081 (15)
C16A0.0118 (17)0.037 (2)0.0241 (19)0.0026 (16)0.0048 (14)0.0036 (16)
C17A0.0175 (18)0.032 (2)0.0173 (18)0.0002 (15)0.0050 (14)0.0011 (15)
Cl1B0.0294 (5)0.0280 (5)0.0536 (6)0.0114 (4)0.0088 (4)0.0055 (4)
Cl2B0.0318 (5)0.0287 (5)0.0199 (4)0.0010 (4)0.0012 (4)0.0015 (4)
O1B0.0177 (12)0.0244 (13)0.0233 (13)0.0025 (10)0.0012 (10)0.0030 (10)
O2B0.0231 (13)0.0231 (14)0.0438 (16)0.0026 (11)0.0109 (11)0.0098 (11)
N1B0.0179 (14)0.0200 (15)0.0226 (15)0.0014 (12)0.0062 (12)0.0043 (12)
N2B0.0138 (15)0.0259 (17)0.0244 (16)0.0025 (12)0.0042 (12)0.0059 (13)
C1B0.0168 (17)0.0214 (18)0.0188 (18)0.0001 (14)0.0040 (14)0.0011 (14)
C2B0.0136 (16)0.0228 (18)0.0202 (18)0.0020 (14)0.0045 (14)0.0025 (14)
C3B0.0204 (18)0.0236 (19)0.0203 (19)0.0032 (15)0.0033 (14)0.0017 (15)
C4B0.028 (2)0.0255 (19)0.0228 (19)0.0058 (16)0.0042 (16)0.0052 (16)
C5B0.028 (2)0.0209 (19)0.036 (2)0.0047 (16)0.0117 (17)0.0101 (16)
C6B0.0179 (17)0.0203 (18)0.030 (2)0.0015 (14)0.0034 (15)0.0055 (15)
C7B0.0180 (17)0.0230 (18)0.0205 (18)0.0045 (14)0.0034 (14)0.0020 (15)
C8B0.027 (2)0.028 (2)0.030 (2)0.0003 (16)0.0085 (16)0.0032 (16)
C9B0.0210 (18)0.0263 (19)0.031 (2)0.0036 (15)0.0102 (16)0.0056 (16)
C10B0.0178 (18)0.0254 (19)0.0223 (18)0.0001 (14)0.0033 (14)0.0027 (15)
C11B0.0235 (19)0.024 (2)0.0232 (19)0.0006 (15)0.0101 (15)0.0033 (15)
C12B0.0197 (18)0.0220 (18)0.0151 (17)0.0010 (14)0.0021 (14)0.0003 (14)
C13B0.0167 (17)0.0217 (18)0.0138 (17)0.0002 (14)0.0024 (13)0.0016 (14)
C14B0.0209 (18)0.0247 (19)0.0195 (18)0.0013 (15)0.0030 (15)0.0050 (15)
C15B0.0198 (18)0.0265 (19)0.0229 (19)0.0084 (15)0.0023 (15)0.0056 (15)
C16B0.0177 (17)0.036 (2)0.0165 (18)0.0045 (16)0.0040 (14)0.0105 (15)
C17B0.0156 (17)0.030 (2)0.0173 (17)0.0028 (15)0.0050 (14)0.0116 (15)
Cl1C0.0264 (5)0.0285 (5)0.0325 (5)0.0087 (4)0.0006 (4)0.0018 (4)
Cl2C0.0331 (5)0.0291 (5)0.0306 (5)0.0012 (4)0.0129 (4)0.0068 (4)
O1C0.0189 (12)0.0212 (12)0.0189 (12)0.0007 (10)0.0015 (10)0.0037 (10)
O2C0.0221 (13)0.0198 (13)0.0312 (14)0.0012 (10)0.0036 (11)0.0020 (10)
N1C0.0154 (14)0.0206 (15)0.0186 (15)0.0004 (11)0.0004 (12)0.0011 (12)
N2C0.0188 (16)0.0231 (16)0.0224 (15)0.0061 (12)0.0047 (12)0.0028 (13)
C1C0.0164 (16)0.0203 (17)0.0133 (16)0.0017 (14)0.0041 (13)0.0030 (13)
C2C0.0087 (16)0.0217 (18)0.0267 (19)0.0006 (13)0.0006 (14)0.0014 (15)
C3C0.0209 (18)0.029 (2)0.025 (2)0.0021 (15)0.0030 (15)0.0029 (16)
C4C0.031 (2)0.027 (2)0.032 (2)0.0056 (17)0.0060 (17)0.0093 (17)
C5C0.0192 (19)0.024 (2)0.058 (3)0.0007 (16)0.0056 (19)0.0106 (19)
C6C0.0206 (19)0.0181 (19)0.056 (3)0.0016 (15)0.0065 (18)0.0027 (18)
C7C0.0173 (17)0.0212 (18)0.031 (2)0.0026 (14)0.0041 (15)0.0001 (15)
C8C0.026 (2)0.030 (2)0.025 (2)0.0077 (16)0.0002 (16)0.0008 (16)
C9C0.0182 (17)0.0225 (18)0.0247 (19)0.0030 (14)0.0003 (15)0.0001 (15)
C10C0.0204 (18)0.0216 (18)0.0217 (18)0.0006 (14)0.0063 (15)0.0037 (15)
C11C0.0203 (18)0.0210 (19)0.0120 (17)0.0055 (15)0.0010 (14)0.0025 (14)
C12C0.0172 (17)0.0233 (18)0.0147 (17)0.0016 (14)0.0045 (14)0.0039 (14)
C13C0.0144 (16)0.0203 (18)0.0153 (17)0.0018 (14)0.0051 (13)0.0002 (14)
C14C0.0188 (18)0.0250 (19)0.0175 (17)0.0019 (15)0.0048 (14)0.0023 (14)
C15C0.0264 (19)0.0234 (19)0.0208 (19)0.0027 (15)0.0055 (15)0.0047 (15)
C16C0.0164 (17)0.033 (2)0.0210 (18)0.0035 (15)0.0026 (14)0.0057 (16)
C17C0.0166 (17)0.0263 (19)0.0196 (18)0.0016 (15)0.0035 (14)0.0070 (15)
Cl1D0.0259 (5)0.0281 (5)0.0273 (5)0.0101 (4)0.0017 (4)0.0071 (4)
Cl2D0.0301 (5)0.0315 (5)0.0215 (5)0.0034 (4)0.0079 (4)0.0089 (4)
O1D0.0200 (12)0.0259 (13)0.0172 (12)0.0002 (10)0.0008 (10)0.0079 (10)
O2D0.0236 (13)0.0206 (13)0.0405 (15)0.0007 (10)0.0041 (11)0.0101 (11)
N1D0.0151 (14)0.0193 (14)0.0228 (15)0.0028 (11)0.0023 (12)0.0037 (12)
N2D0.0183 (15)0.0203 (16)0.0265 (16)0.0022 (12)0.0040 (13)0.0059 (13)
C1D0.0171 (17)0.0226 (18)0.0130 (16)0.0018 (14)0.0035 (13)0.0058 (14)
C2D0.0112 (16)0.0200 (17)0.0207 (18)0.0035 (13)0.0007 (13)0.0046 (14)
C3D0.0167 (17)0.0237 (19)0.0227 (19)0.0018 (14)0.0001 (14)0.0033 (15)
C4D0.028 (2)0.026 (2)0.0225 (19)0.0031 (16)0.0011 (16)0.0019 (16)
C5D0.0204 (19)0.0212 (19)0.039 (2)0.0011 (15)0.0026 (17)0.0024 (17)
C6D0.0202 (18)0.0194 (18)0.032 (2)0.0036 (14)0.0073 (15)0.0095 (16)
C7D0.0146 (17)0.0229 (18)0.0245 (19)0.0038 (14)0.0027 (14)0.0073 (15)
C8D0.027 (2)0.036 (2)0.0226 (19)0.0081 (17)0.0025 (16)0.0115 (17)
C9D0.0176 (17)0.0248 (19)0.029 (2)0.0055 (14)0.0018 (15)0.0053 (16)
C10D0.0229 (18)0.0211 (18)0.0163 (17)0.0032 (14)0.0048 (14)0.0031 (14)
C11D0.0192 (18)0.0228 (19)0.0165 (17)0.0044 (15)0.0015 (14)0.0019 (15)
C12D0.0207 (18)0.0198 (18)0.0196 (18)0.0036 (14)0.0045 (14)0.0007 (14)
C13D0.0133 (16)0.0213 (18)0.0140 (17)0.0031 (14)0.0021 (13)0.0030 (14)
C14D0.0173 (17)0.0244 (18)0.0116 (16)0.0006 (14)0.0042 (14)0.0008 (14)
C15D0.0194 (18)0.0225 (18)0.0180 (18)0.0082 (15)0.0026 (14)0.0041 (14)
C16D0.0129 (17)0.030 (2)0.0235 (19)0.0052 (15)0.0001 (14)0.0006 (15)
C17D0.0210 (18)0.027 (2)0.0248 (19)0.0014 (15)0.0028 (15)0.0025 (16)
Geometric parameters (Å, º) top
Cl1A—C15A1.740 (3)Cl1C—C15C1.750 (3)
Cl2A—C7A1.747 (3)Cl2C—C7C1.743 (4)
O1A—C8A1.435 (4)O1C—C8C1.433 (4)
O1A—C1A1.445 (4)O1C—C1C1.459 (4)
O2A—C11A1.227 (4)O2C—C11C1.220 (4)
N1A—C1A1.459 (4)N1C—C1C1.455 (4)
N1A—C10A1.460 (4)N1C—C10C1.464 (4)
N1A—C9A1.466 (4)N1C—C9C1.470 (4)
N2A—C11A1.355 (4)N2C—C11C1.364 (4)
N2A—C12A1.404 (4)N2C—C12C1.413 (4)
N2A—H2A0.849 (10)N2C—H2C0.853 (10)
C1A—C13A1.532 (4)C1C—C13C1.524 (4)
C1A—C2A1.532 (4)C1C—C2C1.532 (4)
C2A—C3A1.389 (4)C2C—C3C1.392 (5)
C2A—C7A1.391 (4)C2C—C7C1.393 (4)
C3A—C4A1.380 (5)C3C—C4C1.387 (5)
C3A—H3A0.9500C3C—H3C0.9500
C4A—C5A1.377 (5)C4C—C5C1.374 (5)
C4A—H4A0.9500C4C—H4C0.9500
C5A—C6A1.371 (5)C5C—C6C1.379 (5)
C5A—H5A0.9500C5C—H5C0.9500
C6A—C7A1.382 (4)C6C—C7C1.378 (5)
C6A—H6A0.9500C6C—H6C0.9500
C8A—C9A1.523 (5)C8C—C9C1.534 (5)
C8A—H8A0.9900C8C—H8E0.9900
C8A—H8B0.9900C8C—H8F0.9900
C9A—H9A0.9900C9C—H9E0.9900
C9A—H9B0.9900C9C—H9F0.9900
C10A—C11A1.505 (4)C10C—C11C1.516 (4)
C10A—H10A0.9900C10C—H10E0.9900
C10A—H10B0.9900C10C—H10F0.9900
C12A—C17A1.399 (4)C12C—C17C1.399 (4)
C12A—C13A1.405 (4)C12C—C13C1.401 (4)
C13A—C14A1.393 (4)C13C—C14C1.396 (4)
C14A—C15A1.386 (4)C14C—C15C1.377 (4)
C14A—H14A0.9500C14C—H14C0.9500
C15A—C16A1.376 (5)C15C—C16C1.376 (5)
C16A—C17A1.371 (5)C16C—C17C1.380 (4)
C16A—H16A0.9500C16C—H16C0.9500
C17A—H17A0.9500C17C—H17C0.9500
Cl1B—C15B1.743 (3)Cl1D—C15D1.749 (3)
Cl2B—C7B1.750 (3)Cl2D—C7D1.742 (3)
O1B—C8B1.436 (4)O1D—C8D1.427 (4)
O1B—C1B1.453 (4)O1D—C1D1.452 (4)
O2B—C11B1.235 (4)O2D—C11D1.222 (4)
N1B—C1B1.455 (4)N1D—C1D1.458 (4)
N1B—C10B1.457 (4)N1D—C10D1.464 (4)
N1B—C9B1.465 (4)N1D—C9D1.472 (4)
N2B—C11B1.347 (4)N2D—C11D1.357 (4)
N2B—C12B1.404 (4)N2D—C12D1.410 (4)
N2B—H2B0.847 (10)N2D—H2D0.845 (10)
C1B—C13B1.531 (4)C1D—C13D1.523 (4)
C1B—C2B1.532 (4)C1D—C2D1.531 (4)
C2B—C3B1.392 (4)C2D—C3D1.392 (4)
C2B—C7B1.393 (4)C2D—C7D1.395 (4)
C3B—C4B1.383 (5)C3D—C4D1.382 (5)
C3B—H3B0.9500C3D—H3D0.9500
C4B—C5B1.372 (5)C4D—C5D1.373 (5)
C4B—H4B0.9500C4D—H4D0.9500
C5B—C6B1.386 (5)C5D—C6D1.382 (5)
C5B—H5B0.9500C5D—H5D0.9500
C6B—C7B1.376 (4)C6D—C7D1.392 (4)
C6B—H6B0.9500C6D—H6D0.9500
C8B—C9B1.522 (5)C8D—C9D1.536 (5)
C8B—H8C0.9900C8D—H8G0.9900
C8B—H8D0.9900C8D—H8H0.9900
C9B—H9C0.9900C9D—H9G0.9900
C9B—H9D0.9900C9D—H9H0.9900
C10B—C11B1.509 (4)C10D—C11D1.512 (4)
C10B—H10C0.9900C10D—H10G0.9900
C10B—H10D0.9900C10D—H10H0.9900
C12B—C17B1.402 (4)C12D—C17D1.397 (4)
C12B—C13B1.405 (4)C12D—C13D1.405 (4)
C13B—C14B1.392 (4)C13D—C14D1.391 (4)
C14B—C15B1.386 (4)C14D—C15D1.382 (4)
C14B—H14B0.9500C14D—H14D0.9500
C15B—C16B1.375 (5)C15D—C16D1.372 (5)
C16B—C17B1.368 (5)C16D—C17D1.382 (5)
C16B—H16B0.9500C16D—H16D0.9500
C17B—H17B0.9500C17D—H17D0.9500
C8A—O1A—C1A108.9 (2)C8C—O1C—C1C108.0 (2)
C1A—N1A—C10A116.9 (2)C1C—N1C—C10C115.0 (2)
C1A—N1A—C9A103.2 (2)C1C—N1C—C9C103.2 (2)
C10A—N1A—C9A115.7 (3)C10C—N1C—C9C114.7 (2)
C11A—N2A—C12A127.1 (3)C11C—N2C—C12C125.6 (3)
C11A—N2A—H2A114 (2)C11C—N2C—H2C114 (2)
C12A—N2A—H2A117 (2)C12C—N2C—H2C119 (2)
O1A—C1A—N1A106.6 (2)N1C—C1C—O1C105.4 (2)
O1A—C1A—C13A103.8 (2)N1C—C1C—C13C116.5 (2)
N1A—C1A—C13A117.1 (3)O1C—C1C—C13C104.6 (2)
O1A—C1A—C2A109.2 (2)N1C—C1C—C2C107.0 (2)
N1A—C1A—C2A107.3 (2)O1C—C1C—C2C108.1 (2)
C13A—C1A—C2A112.5 (3)C13C—C1C—C2C114.6 (3)
C3A—C2A—C7A117.2 (3)C3C—C2C—C7C117.0 (3)
C3A—C2A—C1A120.4 (3)C3C—C2C—C1C119.9 (3)
C7A—C2A—C1A122.4 (3)C7C—C2C—C1C123.0 (3)
C4A—C3A—C2A121.4 (3)C4C—C3C—C2C121.9 (3)
C4A—C3A—H3A119.3C4C—C3C—H3C119.1
C2A—C3A—H3A119.3C2C—C3C—H3C119.1
C5A—C4A—C3A120.2 (3)C5C—C4C—C3C119.2 (4)
C5A—C4A—H4A119.9C5C—C4C—H4C120.4
C3A—C4A—H4A119.9C3C—C4C—H4C120.4
C6A—C5A—C4A119.6 (3)C4C—C5C—C6C120.3 (3)
C6A—C5A—H5A120.2C4C—C5C—H5C119.8
C4A—C5A—H5A120.2C6C—C5C—H5C119.8
C5A—C6A—C7A120.2 (3)C5C—C6C—C7C119.8 (3)
C5A—C6A—H6A119.9C5C—C6C—H6C120.1
C7A—C6A—H6A119.9C7C—C6C—H6C120.1
C6A—C7A—C2A121.5 (3)C6C—C7C—C2C121.6 (3)
C6A—C7A—Cl2A117.2 (2)C6C—C7C—Cl2C116.9 (3)
C2A—C7A—Cl2A121.2 (2)C2C—C7C—Cl2C121.5 (3)
O1A—C8A—C9A104.7 (3)O1C—C8C—C9C105.2 (2)
O1A—C8A—H8A110.8O1C—C8C—H8E110.7
C9A—C8A—H8A110.8C9C—C8C—H8E110.7
O1A—C8A—H8B110.8O1C—C8C—H8F110.7
C9A—C8A—H8B110.8C9C—C8C—H8F110.7
H8A—C8A—H8B108.9H8E—C8C—H8F108.8
N1A—C9A—C8A104.9 (3)N1C—C9C—C8C104.6 (2)
N1A—C9A—H9A110.8N1C—C9C—H9E110.8
C8A—C9A—H9A110.8C8C—C9C—H9E110.8
N1A—C9A—H9B110.8N1C—C9C—H9F110.8
C8A—C9A—H9B110.8C8C—C9C—H9F110.8
H9A—C9A—H9B108.8H9E—C9C—H9F108.9
N1A—C10A—C11A115.5 (3)N1C—C10C—C11C116.7 (3)
N1A—C10A—H10A108.4N1C—C10C—H10E108.1
C11A—C10A—H10A108.4C11C—C10C—H10E108.1
N1A—C10A—H10B108.4N1C—C10C—H10F108.1
C11A—C10A—H10B108.4C11C—C10C—H10F108.1
H10A—C10A—H10B107.5H10E—C10C—H10F107.3
O2A—C11A—N2A121.3 (3)O2C—C11C—N2C121.1 (3)
O2A—C11A—C10A122.3 (3)O2C—C11C—C10C122.3 (3)
N2A—C11A—C10A116.4 (3)N2C—C11C—C10C116.6 (3)
C17A—C12A—C13A120.0 (3)C17C—C12C—C13C120.6 (3)
C17A—C12A—N2A116.1 (3)C17C—C12C—N2C116.1 (3)
C13A—C12A—N2A123.7 (3)C13C—C12C—N2C123.3 (3)
C14A—C13A—C12A117.9 (3)C14C—C13C—C12C117.9 (3)
C14A—C13A—C1A119.5 (3)C14C—C13C—C1C119.8 (3)
C12A—C13A—C1A121.9 (3)C12C—C13C—C1C121.9 (3)
C15A—C14A—C13A121.0 (3)C15C—C14C—C13C120.5 (3)
C15A—C14A—H14A119.5C15C—C14C—H14C119.7
C13A—C14A—H14A119.5C13C—C14C—H14C119.7
C16A—C15A—C14A120.6 (3)C16C—C15C—C14C121.4 (3)
C16A—C15A—Cl1A121.2 (3)C16C—C15C—Cl1C119.6 (3)
C14A—C15A—Cl1A118.1 (3)C14C—C15C—Cl1C118.9 (3)
C17A—C16A—C15A119.5 (3)C15C—C16C—C17C119.3 (3)
C17A—C16A—H16A120.3C15C—C16C—H16C120.4
C15A—C16A—H16A120.3C17C—C16C—H16C120.4
C16A—C17A—C12A120.8 (3)C16C—C17C—C12C120.0 (3)
C16A—C17A—H17A119.6C16C—C17C—H17C120.0
C12A—C17A—H17A119.6C12C—C17C—H17C120.0
C8B—O1B—C1B108.5 (2)C8D—O1D—C1D108.5 (2)
C1B—N1B—C10B116.1 (2)C1D—N1D—C10D115.6 (2)
C1B—N1B—C9B103.1 (2)C1D—N1D—C9D102.7 (2)
C10B—N1B—C9B115.0 (3)C10D—N1D—C9D114.3 (2)
C11B—N2B—C12B126.8 (3)C11D—N2D—C12D126.3 (3)
C11B—N2B—H2B116 (2)C11D—N2D—H2D114 (2)
C12B—N2B—H2B116 (2)C12D—N2D—H2D118 (2)
O1B—C1B—N1B106.6 (2)O1D—C1D—N1D105.4 (2)
O1B—C1B—C13B103.4 (2)O1D—C1D—C13D105.0 (2)
N1B—C1B—C13B117.0 (3)N1D—C1D—C13D115.6 (2)
O1B—C1B—C2B108.6 (2)O1D—C1D—C2D108.2 (2)
N1B—C1B—C2B107.7 (2)N1D—C1D—C2D107.6 (2)
C13B—C1B—C2B113.1 (3)C13D—C1D—C2D114.4 (2)
C3B—C2B—C7B117.0 (3)C3D—C2D—C7D116.7 (3)
C3B—C2B—C1B119.9 (3)C3D—C2D—C1D120.4 (3)
C7B—C2B—C1B123.1 (3)C7D—C2D—C1D122.9 (3)
C4B—C3B—C2B121.2 (3)C4D—C3D—C2D121.8 (3)
C4B—C3B—H3B119.4C4D—C3D—H3D119.1
C2B—C3B—H3B119.4C2D—C3D—H3D119.1
C5B—C4B—C3B120.5 (3)C5D—C4D—C3D120.1 (3)
C5B—C4B—H4B119.7C5D—C4D—H4D119.9
C3B—C4B—H4B119.7C3D—C4D—H4D119.9
C4B—C5B—C6B119.5 (3)C4D—C5D—C6D120.0 (3)
C4B—C5B—H5B120.2C4D—C5D—H5D120.0
C6B—C5B—H5B120.2C6D—C5D—H5D120.0
C7B—C6B—C5B119.6 (3)C5D—C6D—C7D119.2 (3)
C7B—C6B—H6B120.2C5D—C6D—H6D120.4
C5B—C6B—H6B120.2C7D—C6D—H6D120.4
C6B—C7B—C2B122.1 (3)C6D—C7D—C2D121.9 (3)
C6B—C7B—Cl2B115.9 (2)C6D—C7D—Cl2D116.4 (2)
C2B—C7B—Cl2B121.9 (2)C2D—C7D—Cl2D121.7 (2)
O1B—C8B—C9B104.8 (3)O1D—C8D—C9D104.9 (3)
O1B—C8B—H8C110.8O1D—C8D—H8G110.8
C9B—C8B—H8C110.8C9D—C8D—H8G110.8
O1B—C8B—H8D110.8O1D—C8D—H8H110.8
C9B—C8B—H8D110.8C9D—C8D—H8H110.8
H8C—C8B—H8D108.9H8G—C8D—H8H108.8
N1B—C9B—C8B105.5 (3)N1D—C9D—C8D104.4 (3)
N1B—C9B—H9C110.6N1D—C9D—H9G110.9
C8B—C9B—H9C110.6C8D—C9D—H9G110.9
N1B—C9B—H9D110.6N1D—C9D—H9H110.9
C8B—C9B—H9D110.6C8D—C9D—H9H110.9
H9C—C9B—H9D108.8H9G—C9D—H9H108.9
N1B—C10B—C11B116.4 (3)N1D—C10D—C11D117.1 (3)
N1B—C10B—H10C108.2N1D—C10D—H10G108.0
C11B—C10B—H10C108.2C11D—C10D—H10G108.0
N1B—C10B—H10D108.2N1D—C10D—H10H108.0
C11B—C10B—H10D108.2C11D—C10D—H10H108.0
H10C—C10B—H10D107.3H10G—C10D—H10H107.3
O2B—C11B—N2B121.5 (3)O2D—C11D—N2D121.9 (3)
O2B—C11B—C10B121.7 (3)O2D—C11D—C10D122.3 (3)
N2B—C11B—C10B116.9 (3)N2D—C11D—C10D115.8 (3)
C17B—C12B—C13B119.8 (3)C17D—C12D—C13D120.8 (3)
C17B—C12B—N2B116.3 (3)C17D—C12D—N2D116.3 (3)
C13B—C12B—N2B123.8 (3)C13D—C12D—N2D122.9 (3)
C14B—C13B—C12B117.9 (3)C14D—C13D—C12D117.7 (3)
C14B—C13B—C1B119.9 (3)C14D—C13D—C1D120.2 (3)
C12B—C13B—C1B121.3 (3)C12D—C13D—C1D121.6 (3)
C15B—C14B—C13B120.9 (3)C15D—C14D—C13D120.8 (3)
C15B—C14B—H14B119.6C15D—C14D—H14D119.6
C13B—C14B—H14B119.6C13D—C14D—H14D119.6
C16B—C15B—C14B120.8 (3)C16D—C15D—C14D121.4 (3)
C16B—C15B—Cl1B120.6 (3)C16D—C15D—Cl1D119.9 (2)
C14B—C15B—Cl1B118.6 (3)C14D—C15D—Cl1D118.7 (2)
C17B—C16B—C15B119.3 (3)C15D—C16D—C17D119.3 (3)
C17B—C16B—H16B120.3C15D—C16D—H16D120.4
C15B—C16B—H16B120.3C17D—C16D—H16D120.4
C16B—C17B—C12B120.9 (3)C16D—C17D—C12D120.0 (3)
C16B—C17B—H17B119.5C16D—C17D—H17D120.0
C12B—C17B—H17B119.5C12D—C17D—H17D120.0
C8A—O1A—C1A—N1A19.2 (3)C10C—N1C—C1C—O1C88.5 (3)
C8A—O1A—C1A—C13A143.4 (3)C9C—N1C—C1C—O1C37.2 (3)
C8A—O1A—C1A—C2A96.4 (3)C10C—N1C—C1C—C13C26.9 (4)
C10A—N1A—C1A—O1A95.7 (3)C9C—N1C—C1C—C13C152.6 (3)
C9A—N1A—C1A—O1A32.6 (3)C10C—N1C—C1C—C2C156.7 (2)
C10A—N1A—C1A—C13A19.9 (4)C9C—N1C—C1C—C2C77.7 (3)
C9A—N1A—C1A—C13A148.2 (3)C8C—O1C—C1C—N1C27.1 (3)
C10A—N1A—C1A—C2A147.5 (3)C8C—O1C—C1C—C13C150.4 (3)
C9A—N1A—C1A—C2A84.2 (3)C8C—O1C—C1C—C2C87.0 (3)
O1A—C1A—C2A—C3A8.9 (4)N1C—C1C—C2C—C3C127.0 (3)
N1A—C1A—C2A—C3A124.0 (3)O1C—C1C—C2C—C3C14.0 (4)
C13A—C1A—C2A—C3A105.8 (3)C13C—C1C—C2C—C3C102.2 (3)
O1A—C1A—C2A—C7A172.4 (3)N1C—C1C—C2C—C7C49.4 (4)
N1A—C1A—C2A—C7A57.3 (4)O1C—C1C—C2C—C7C162.4 (3)
C13A—C1A—C2A—C7A73.0 (4)C13C—C1C—C2C—C7C81.4 (4)
C7A—C2A—C3A—C4A0.9 (5)C7C—C2C—C3C—C4C2.0 (5)
C1A—C2A—C3A—C4A177.8 (3)C1C—C2C—C3C—C4C174.6 (3)
C2A—C3A—C4A—C5A1.8 (5)C2C—C3C—C4C—C5C2.1 (5)
C3A—C4A—C5A—C6A0.6 (5)C3C—C4C—C5C—C6C3.6 (5)
C4A—C5A—C6A—C7A1.6 (5)C4C—C5C—C6C—C7C0.9 (5)
C5A—C6A—C7A—C2A2.5 (5)C5C—C6C—C7C—C2C3.5 (5)
C5A—C6A—C7A—Cl2A175.0 (3)C5C—C6C—C7C—Cl2C174.3 (3)
C3A—C2A—C7A—C6A1.3 (4)C3C—C2C—C7C—C6C4.8 (5)
C1A—C2A—C7A—C6A180.0 (3)C1C—C2C—C7C—C6C171.7 (3)
C3A—C2A—C7A—Cl2A176.2 (2)C3C—C2C—C7C—Cl2C172.9 (2)
C1A—C2A—C7A—Cl2A2.5 (4)C1C—C2C—C7C—Cl2C10.6 (4)
C1A—O1A—C8A—C9A1.8 (3)C1C—O1C—C8C—C9C6.0 (3)
C1A—N1A—C9A—C8A33.2 (3)C1C—N1C—C9C—C8C33.0 (3)
C10A—N1A—C9A—C8A95.8 (3)C10C—N1C—C9C—C8C92.9 (3)
O1A—C8A—C9A—N1A22.0 (3)O1C—C8C—C9C—N1C16.9 (3)
C1A—N1A—C10A—C11A57.6 (4)C1C—N1C—C10C—C11C53.3 (4)
C9A—N1A—C10A—C11A64.3 (4)C9C—N1C—C10C—C11C66.2 (4)
C12A—N2A—C11A—O2A178.0 (3)C12C—N2C—C11C—O2C179.8 (3)
C12A—N2A—C11A—C10A0.7 (5)C12C—N2C—C11C—C10C2.3 (4)
N1A—C10A—C11A—O2A107.6 (4)N1C—C10C—C11C—O2C109.6 (3)
N1A—C10A—C11A—N2A71.0 (4)N1C—C10C—C11C—N2C72.5 (4)
C11A—N2A—C12A—C17A147.8 (3)C11C—N2C—C12C—C17C145.5 (3)
C11A—N2A—C12A—C13A36.4 (5)C11C—N2C—C12C—C13C36.4 (5)
C17A—C12A—C13A—C14A5.0 (4)C17C—C12C—C13C—C14C4.8 (4)
N2A—C12A—C13A—C14A179.4 (3)N2C—C12C—C13C—C14C177.3 (3)
C17A—C12A—C13A—C1A164.9 (3)C17C—C12C—C13C—C1C167.7 (3)
N2A—C12A—C13A—C1A10.6 (5)N2C—C12C—C13C—C1C10.2 (5)
O1A—C1A—C13A—C14A111.7 (3)N1C—C1C—C13C—C14C123.4 (3)
N1A—C1A—C13A—C14A131.2 (3)O1C—C1C—C13C—C14C120.8 (3)
C2A—C1A—C13A—C14A6.2 (4)C2C—C1C—C13C—C14C2.6 (4)
O1A—C1A—C13A—C12A58.1 (4)N1C—C1C—C13C—C12C64.3 (4)
N1A—C1A—C13A—C12A59.0 (4)O1C—C1C—C13C—C12C51.6 (4)
C2A—C1A—C13A—C12A175.9 (3)C2C—C1C—C13C—C12C169.8 (3)
C12A—C13A—C14A—C15A3.4 (5)C12C—C13C—C14C—C15C2.9 (4)
C1A—C13A—C14A—C15A166.8 (3)C1C—C13C—C14C—C15C169.7 (3)
C13A—C14A—C15A—C16A0.8 (5)C13C—C14C—C15C—C16C1.2 (5)
C13A—C14A—C15A—Cl1A178.8 (2)C13C—C14C—C15C—Cl1C178.5 (2)
C14A—C15A—C16A—C17A3.3 (5)C14C—C15C—C16C—C17C3.5 (5)
Cl1A—C15A—C16A—C17A178.7 (3)Cl1C—C15C—C16C—C17C179.2 (2)
C15A—C16A—C17A—C12A1.7 (5)C15C—C16C—C17C—C12C1.7 (5)
C13A—C12A—C17A—C16A2.6 (5)C13C—C12C—C17C—C16C2.5 (5)
N2A—C12A—C17A—C16A178.5 (3)N2C—C12C—C17C—C16C179.4 (3)
C8B—O1B—C1B—N1B20.9 (3)C8D—O1D—C1D—N1D26.3 (3)
C8B—O1B—C1B—C13B144.8 (3)C8D—O1D—C1D—C13D148.9 (2)
C8B—O1B—C1B—C2B94.8 (3)C8D—O1D—C1D—C2D88.5 (3)
C10B—N1B—C1B—O1B93.5 (3)C10D—N1D—C1D—O1D87.6 (3)
C9B—N1B—C1B—O1B33.1 (3)C9D—N1D—C1D—O1D37.5 (3)
C10B—N1B—C1B—C13B21.5 (4)C10D—N1D—C1D—C13D27.8 (4)
C9B—N1B—C1B—C13B148.2 (3)C9D—N1D—C1D—C13D153.0 (3)
C10B—N1B—C1B—C2B150.1 (3)C10D—N1D—C1D—C2D157.1 (2)
C9B—N1B—C1B—C2B83.3 (3)C9D—N1D—C1D—C2D77.7 (3)
O1B—C1B—C2B—C3B9.5 (4)O1D—C1D—C2D—C3D13.9 (4)
N1B—C1B—C2B—C3B124.6 (3)N1D—C1D—C2D—C3D127.3 (3)
C13B—C1B—C2B—C3B104.6 (3)C13D—C1D—C2D—C3D102.7 (3)
O1B—C1B—C2B—C7B170.9 (3)O1D—C1D—C2D—C7D163.9 (3)
N1B—C1B—C2B—C7B55.9 (4)N1D—C1D—C2D—C7D50.5 (4)
C13B—C1B—C2B—C7B74.9 (4)C13D—C1D—C2D—C7D79.5 (4)
C7B—C2B—C3B—C4B0.2 (5)C7D—C2D—C3D—C4D1.6 (5)
C1B—C2B—C3B—C4B179.7 (3)C1D—C2D—C3D—C4D176.3 (3)
C2B—C3B—C4B—C5B1.2 (5)C2D—C3D—C4D—C5D2.3 (5)
C3B—C4B—C5B—C6B0.6 (5)C3D—C4D—C5D—C6D3.2 (5)
C4B—C5B—C6B—C7B1.3 (5)C4D—C5D—C6D—C7D0.2 (5)
C5B—C6B—C7B—C2B2.7 (5)C5D—C6D—C7D—C2D3.8 (5)
C5B—C6B—C7B—Cl2B174.8 (2)C5D—C6D—C7D—Cl2D173.1 (2)
C3B—C2B—C7B—C6B2.1 (5)C3D—C2D—C7D—C6D4.7 (5)
C1B—C2B—C7B—C6B178.3 (3)C1D—C2D—C7D—C6D173.2 (3)
C3B—C2B—C7B—Cl2B175.3 (2)C3D—C2D—C7D—Cl2D172.1 (2)
C1B—C2B—C7B—Cl2B4.3 (4)C1D—C2D—C7D—Cl2D10.0 (4)
C1B—O1B—C8B—C9B0.3 (3)C1D—O1D—C8D—C9D4.4 (3)
C1B—N1B—C9B—C8B32.5 (3)C1D—N1D—C9D—C8D34.2 (3)
C10B—N1B—C9B—C8B94.8 (3)C10D—N1D—C9D—C8D91.8 (3)
O1B—C8B—C9B—N1B20.3 (3)O1D—C8D—C9D—N1D18.8 (3)
C1B—N1B—C10B—C11B56.6 (4)C1D—N1D—C10D—C11D52.7 (4)
C9B—N1B—C10B—C11B63.8 (4)C9D—N1D—C10D—C11D66.2 (4)
C12B—N2B—C11B—O2B179.3 (3)C12D—N2D—C11D—O2D178.7 (3)
C12B—N2B—C11B—C10B0.2 (5)C12D—N2D—C11D—C10D0.0 (5)
N1B—C10B—C11B—O2B110.2 (4)N1D—C10D—C11D—O2D110.3 (3)
N1B—C10B—C11B—N2B70.2 (4)N1D—C10D—C11D—N2D71.0 (4)
C11B—N2B—C12B—C17B148.0 (3)C11D—N2D—C12D—C17D143.4 (3)
C11B—N2B—C12B—C13B35.3 (5)C11D—N2D—C12D—C13D39.0 (5)
C17B—C12B—C13B—C14B5.9 (4)C17D—C12D—C13D—C14D3.6 (5)
N2B—C12B—C13B—C14B177.5 (3)N2D—C12D—C13D—C14D178.9 (3)
C17B—C12B—C13B—C1B163.5 (3)C17D—C12D—C13D—C1D168.0 (3)
N2B—C12B—C13B—C1B13.1 (5)N2D—C12D—C13D—C1D9.5 (5)
O1B—C1B—C13B—C14B114.2 (3)O1D—C1D—C13D—C14D119.9 (3)
N1B—C1B—C13B—C14B129.0 (3)N1D—C1D—C13D—C14D124.4 (3)
C2B—C1B—C13B—C14B3.1 (4)C2D—C1D—C13D—C14D1.5 (4)
O1B—C1B—C13B—C12B55.0 (4)O1D—C1D—C13D—C12D51.4 (4)
N1B—C1B—C13B—C12B61.8 (4)N1D—C1D—C13D—C12D64.2 (4)
C2B—C1B—C13B—C12B172.3 (3)C2D—C1D—C13D—C12D169.9 (3)
C12B—C13B—C14B—C15B2.8 (5)C12D—C13D—C14D—C15D2.1 (4)
C1B—C13B—C14B—C15B166.7 (3)C1D—C13D—C14D—C15D169.5 (3)
C13B—C14B—C15B—C16B2.5 (5)C13D—C14D—C15D—C16D1.1 (5)
C13B—C14B—C15B—Cl1B179.8 (2)C13D—C14D—C15D—Cl1D178.5 (2)
C14B—C15B—C16B—C17B4.8 (5)C14D—C15D—C16D—C17D3.0 (5)
Cl1B—C15B—C16B—C17B177.6 (2)Cl1D—C15D—C16D—C17D179.7 (3)
C15B—C16B—C17B—C12B1.6 (5)C15D—C16D—C17D—C12D1.5 (5)
C13B—C12B—C17B—C16B3.8 (5)C13D—C12D—C17D—C16D1.8 (5)
N2B—C12B—C17B—C16B179.4 (3)N2D—C12D—C17D—C16D179.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O2C0.85 (1)2.01 (1)2.863 (3)180 (4)
C6A—H6A···O2Di0.952.603.399 (4)142
C10A—H10B···Cl1Dii0.992.993.844 (3)146
N2B—H2B···O2D0.85 (1)2.05 (1)2.886 (3)168 (3)
C6B—H6B···O2Ciii0.952.583.359 (4)140
C9B—H9D···Cl1Aiii0.992.973.729 (3)134
N2C—H2C···O2A0.85 (1)2.01 (1)2.846 (3)168 (3)
C6C—H6C···O2Biv0.952.463.338 (4)154
C17C—H17C···Cl2Dv0.952.953.606 (3)127
N2D—H2D···O2B0.85 (1)2.01 (1)2.846 (3)172 (3)
C6D—H6D···O2Av0.952.533.428 (4)158
C10D—H10H···Cl2Avi0.992.823.807 (3)173
Symmetry codes: (i) x, y+1, z+1; (ii) x, y1, 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) top
Group No.D—H···AD—HH···AD···AD—H···A
#1C3A—H3A···O1A0.952.342.722 (4)104
#1C3B—H3B···O1B0.952.312.703 (4)104
#1C3C—H3C···O1C0.952.332.703 (4)103
#1C3D—H3D···O1D0.952.342.711 (4)103
#2N2A—H2A···O2C0.85 (1)2.01 (1)2.863 (3)180 (4)
#2N2B—H2B···O2D0.85 (1)2.05 (1)2.886 (3)168 (3)
#2N2C—H2C···O2A0.85 (1)2.01 (1)2.846 (3)168 (3)
#2N2D—H2D···O2B0.85 (1)2.01 (1)2.846 (3)172 (3)
#3C6A—H6A···O2Di0.952.603.399 (4)142
#3C6B—H6B···O2Ciii0.952.583.359 (3)140
#3C6C—H6C···O2Biv0.952.463.338 (4)154
#3C6D—H6D···O2Av0.952.533.428 (4)158
#4C10A—H10B···Cl1Dii0.992.993.844 (3)146
#4C9B—H9C···O1Dvii0.992.543.270 (4)130
#4C9B—H9D···Cl1Aiii0.992.973.729 (3)134
#4C4B—H4B···Cl1Dvii0.952.893.815 (3)165
#4C4D—H4D···O2Cviii0.952.573.446 (4)154
#4C9A—H9A···O1Cix0.992.503.254 (4)133
#5C10D—H10H···Cl2Avi0.992.823.807 (3)173
#5C17C—H17C···Cl2Div0.952.953.606 (3)127
#5Cl1A···Cl2Ciiin.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. top
2.0 (3)90.5 (7)90.6 (5)c90.090.00
90.6 (7)1.2 (2)88.9 (1)b90.004 (3)090.0
91.8 (1)89.5 (1)1.5 (3)a090.004 (3)90.0
ACBDAB–CDADBCabc
91.2 (7)91.1 (5)0ADBC1.5 (3)88.9 (1)90.6 (5)
90.7 (6)091.1 (5)ABCD89.5 (1)1.2 (2)90.5 (7)
090.7 (6)91.2 (7)ACBD91.8 (1)90.6 (7)2.0 (3)
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds