organic compounds
8-{1-[(4′-Fluoro-[1,1′-biphenyl]-4-yl)methyl]piperidin-4-yl}-3,4-dihydroquinolin-2(1H)-one chloroform 0.25-solvate
aDepartment of Chemistry, King Fahad University of Petroleum & Minerals, 31261 Dahran, Saudi Arabia, and bInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland
*Correspondence e-mail: nullah@kfupm.edu.sa
In the 27H27FN2O·0.25CHCl3, there are two independent molecules (A and B) together with a partially disordered chloroform molecule situated about an inversion center. The conformation of the two molecules is very similar. The bridging piperidine rings each have a chair conformation while the piperidin-2-one rings of the quinoline moiety have screw-boat conformations. The benzene rings of the biphenyl moiety are inclined to one another by 26.37 (4) and 23.75 (15)° in molecules A and B, respectively. The mean plane of the central piperidine ring [r.m.s. deviation = 0.241 (2) Å in both molecules A and B] is inclined to the benzene ring of the quinoline moiety by 80.06 (4) in A and 83.75 (15)° in B, while it is inclined to the adjacent benzene ring of the biphenyl group by 73.623 (15) in A and 75.65 (14)° in B. In the crystal, individual molecules are linked by pairs of N—H⋯O hydrogen bonds, forming A–A and B–B inversion dimers with R22(8) ring motifs. The dimers are stabilized by C—H⋯O hydrogen bonds and linked via C—H⋯F and C—H⋯N hydrogen bonds into a three-dimensional network. Several C—H⋯π interactions are also present.
of the title compound, CCCDC reference: 978441
Related literature
For the synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones, see: Ullah (2013). For the synthesis of new 4-aryl-1-(biarylmethylene)piperidines, structural analogs of Adoprazine (SLV313), see: Ullah & Al-Shaheri (2012). For the synthesis of the title compound, see: Ullah (2012) and Eastwood (2000). For standard bond-length data, see: Allen et al. (1987). For a description of hydrogen-bond motifs, see: Bernstein et al. (1995)
Experimental
Crystal data
|
Data collection: X-AREA (Stoe & Cie, 2009); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 978441
10.1107/S160053681303448X/lr2120sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681303448X/lr2120Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681303448X/lr2120Isup3.cml
The synthesis of the title compound has been previously described (Ullah, 2012; Eastwood, 2000). Rod-like colourless crystals of the title compound were obtained by slow evaporation of a solution in chloroform.
Crystal data, data collection and structure
details are summarized in Table 1. The NH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95, 1.00 and 0.99 Å for CH(aromatic), methine, and methylene H atoms, respectives, with Uiso(H) = 1.2Ueq(C).In ongoing efforts to develop new antipsychotics, we have synthesized a series of compounds which are structural analogs of adoprazine and bifeprunox and have disclosed their dual D2 and 5-HT1A receptor binding affinities and structure-activity relationship (Ullah, 2013; Ullah & Al-Shaheri, 2012). Herein, we describe the
of one such molecule, a piperidine quinoline derivative.The molecular structure of the two independent moleules (A and B) of the title compound are illustrated in Fig. 1. The compound crystallizes with a partially disordered chloroform molecule situated about an inversion center. The bond lengths (Allen et al., 1987) and bond angles are within normal values.
The conformation of the two molecules is very similar. The piperidine rings, N1/C13—C15/C25/C26 and N3/C40—C42/C52/C53, in molecules A and B, respectively, each have a chair conformation and their mean planes are inclined to the benzene ring to which they are attached by 80.06 (14) ° in molecule A and 83.75 (15)° in molecule B. The piperidin-2-one rings of the quinoline moiety, N2/C17—C21 in A and N4/C44—C48 in B, have screw boat conformations. The two benzene rings of the biphenyl moiety are inclined to one another by 26.37 (14) and 23.75 (15) ° in molecules A and B, respectively.
In the crystal, individual molecules are linked by pairs of N—H···O hydrogen bonds forming A—A and B—B inversion dimers (Table 1 and Fig. 2), with R22(8) ring motifs (Bernstein et al., 1995). The dimers, are stabilized by C—H···O hydrogen bonds, and linked via C—H···F and C—H···N hydrogen bonds forming a three-dimensional network (Fig. 2). The network is further stabilized by a number of C—H···π interactions (Table 1).
In ongoing efforts to develop new antipsychotics, we have synthesized a series of compounds which are structural analogs of adoprazine and bifeprunox and have disclosed their dual D2 and 5-HT1A receptor binding affinities and structure-activity relationship (Ullah, 2013; Ullah & Al-Shaheri, 2012). Herein, we describe the
of one such molecule, a piperidine quinoline derivative.The molecular structure of the two independent moleules (A and B) of the title compound are illustrated in Fig. 1. The compound crystallizes with a partially disordered chloroform molecule situated about an inversion center. The bond lengths (Allen et al., 1987) and bond angles are within normal values.
The conformation of the two molecules is very similar. The piperidine rings, N1/C13—C15/C25/C26 and N3/C40—C42/C52/C53, in molecules A and B, respectively, each have a chair conformation and their mean planes are inclined to the benzene ring to which they are attached by 80.06 (14) ° in molecule A and 83.75 (15)° in molecule B. The piperidin-2-one rings of the quinoline moiety, N2/C17—C21 in A and N4/C44—C48 in B, have screw boat conformations. The two benzene rings of the biphenyl moiety are inclined to one another by 26.37 (14) and 23.75 (15) ° in molecules A and B, respectively.
In the crystal, individual molecules are linked by pairs of N—H···O hydrogen bonds forming A—A and B—B inversion dimers (Table 1 and Fig. 2), with R22(8) ring motifs (Bernstein et al., 1995). The dimers, are stabilized by C—H···O hydrogen bonds, and linked via C—H···F and C—H···N hydrogen bonds forming a three-dimensional network (Fig. 2). The network is further stabilized by a number of C—H···π interactions (Table 1).
For the synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones, see: Ullah (2013). For the synthesis of new 4-aryl-1-(biarylmethylene)piperidines, structural analogs of Adoprazine (SLV313), see: Ullah & Al-Shaheri (2012). For the synthesis of the title compound, see: Ullah (2012) and Eastwood (2000). For standard bond-length data, see: Allen et al. (1987). For a description of hydrogen-bond motifs,see: Bernstein et al. (1995)
The synthesis of the title compound has been previously described (Ullah, 2012; Eastwood, 2000). Rod-like colourless crystals of the title compound were obtained by slow evaporation of a solution in chloroform.
detailsCrystal data, data collection and structure
details are summarized in Table 1. The NH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95, 1.00 and 0.99 Å for CH(aromatic), methine, and methylene H atoms, respectives, with Uiso(H) = 1.2Ueq(C).Data collection: X-AREA (Stoe & Cie, 2009); cell
X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. A view of the two independent molecules (A and B) of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The C-bound H atoms and the disordered chloroform molecule of solvent has been omitted for clarity. | |
Fig. 2. A partial view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity). |
C27H27FN2O·0.25CHCl3 | Z = 4 |
Mr = 444.35 | F(000) = 938 |
Triclinic, P1 | Dx = 1.297 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6955 (8) Å | Cell parameters from 8114 reflections |
b = 16.618 (2) Å | θ = 1.5–26.0° |
c = 18.224 (2) Å | µ = 0.17 mm−1 |
α = 79.206 (9)° | T = 173 K |
β = 87.563 (9)° | Rod, colourless |
γ = 83.976 (9)° | 0.45 × 0.30 × 0.15 mm |
V = 2276.1 (4) Å3 |
Stoe IPDS 2 diffractometer | 8614 independent reflections |
Radiation source: fine-focus sealed tube | 3481 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.093 |
φ + ω scans | θmax = 25.7°, θmin = 1.5° |
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009) | h = −9→9 |
Tmin = 0.764, Tmax = 1.000 | k = −20→20 |
27043 measured reflections | l = −22→22 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.115 | (Δ/σ)max < 0.001 |
S = 0.69 | Δρmax = 0.63 e Å−3 |
8614 reflections | Δρmin = −0.60 e Å−3 |
595 parameters | Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0034 (5) |
C27H27FN2O·0.25CHCl3 | γ = 83.976 (9)° |
Mr = 444.35 | V = 2276.1 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.6955 (8) Å | Mo Kα radiation |
b = 16.618 (2) Å | µ = 0.17 mm−1 |
c = 18.224 (2) Å | T = 173 K |
α = 79.206 (9)° | 0.45 × 0.30 × 0.15 mm |
β = 87.563 (9)° |
Stoe IPDS 2 diffractometer | 8614 independent reflections |
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009) | 3481 reflections with I > 2σ(I) |
Tmin = 0.764, Tmax = 1.000 | Rint = 0.093 |
27043 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.69 | Δρmax = 0.63 e Å−3 |
8614 reflections | Δρmin = −0.60 e Å−3 |
595 parameters |
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. The crystal diffracted weakly beyond 19° in θ despite is size. This we believe is due to the presence of disordered solvent of crystallization. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 0.7833 (3) | 0.46774 (11) | 0.43761 (10) | 0.0520 (6) | |
O1 | −0.2054 (3) | 0.00085 (13) | 0.53754 (12) | 0.0385 (6) | |
N1 | 0.4532 (3) | −0.07591 (14) | 0.25646 (12) | 0.0246 (6) | |
N2 | −0.0871 (3) | −0.09665 (15) | 0.47441 (13) | 0.0232 (6) | |
H2N | 0.009 (4) | −0.0712 (18) | 0.4712 (16) | 0.034 (9)* | |
C2 | 0.7566 (4) | 0.39930 (19) | 0.40904 (18) | 0.0326 (8) | |
C3 | 0.8092 (4) | 0.32282 (19) | 0.44942 (17) | 0.0346 (8) | |
H3 | 0.8624 | 0.3169 | 0.4965 | 0.042* | |
C4 | 0.7826 (4) | 0.25500 (19) | 0.41952 (16) | 0.0292 (8) | |
H4 | 0.8186 | 0.2017 | 0.4468 | 0.035* | |
C5 | 0.7046 (4) | 0.26184 (17) | 0.35058 (16) | 0.0239 (7) | |
C6 | 0.6540 (4) | 0.34185 (18) | 0.31198 (16) | 0.0282 (7) | |
H6 | 0.6013 | 0.3490 | 0.2647 | 0.034* | |
C7 | 0.6794 (4) | 0.41019 (19) | 0.34164 (17) | 0.0321 (8) | |
H7 | 0.6436 | 0.4640 | 0.3154 | 0.039* | |
C8 | 0.6745 (4) | 0.18862 (17) | 0.31910 (15) | 0.0246 (7) | |
C9 | 0.7798 (4) | 0.11402 (18) | 0.33780 (16) | 0.0301 (8) | |
H9 | 0.8726 | 0.1101 | 0.3715 | 0.036* | |
C10 | 0.7510 (4) | 0.04604 (18) | 0.30805 (16) | 0.0284 (7) | |
H10 | 0.8233 | −0.0039 | 0.3227 | 0.034* | |
C11 | 0.6193 (4) | 0.04847 (18) | 0.25737 (16) | 0.0256 (7) | |
C12 | 0.5943 (4) | −0.02544 (18) | 0.22348 (16) | 0.0295 (8) | |
H12A | 0.5712 | −0.0061 | 0.1697 | 0.035* | |
H12B | 0.7057 | −0.0615 | 0.2271 | 0.035* | |
C13 | 0.2788 (4) | −0.03846 (18) | 0.23558 (16) | 0.0286 (7) | |
H13A | 0.2746 | −0.0207 | 0.1807 | 0.034* | |
H13B | 0.2503 | 0.0108 | 0.2588 | 0.034* | |
C14 | 0.1447 (4) | −0.09995 (18) | 0.26140 (15) | 0.0284 (7) | |
H14A | 0.1728 | −0.1493 | 0.2383 | 0.034* | |
H14B | 0.0266 | −0.0748 | 0.2458 | 0.034* | |
C15 | 0.1482 (4) | −0.12460 (17) | 0.34640 (15) | 0.0234 (7) | |
H15 | 0.1244 | −0.0730 | 0.3674 | 0.028* | |
C16 | 0.0118 (4) | −0.18178 (17) | 0.38047 (15) | 0.0219 (7) | |
C17 | −0.0964 (4) | −0.16765 (17) | 0.44165 (15) | 0.0227 (7) | |
C18 | −0.2169 (4) | −0.06471 (19) | 0.51550 (16) | 0.0268 (7) | |
C19 | −0.3732 (4) | −0.11199 (18) | 0.53351 (17) | 0.0303 (8) | |
H19A | −0.4592 | −0.0943 | 0.4933 | 0.036* | |
H19B | −0.4293 | −0.1003 | 0.5808 | 0.036* | |
C20 | −0.3202 (4) | −0.20388 (18) | 0.54119 (17) | 0.0335 (8) | |
H20A | −0.2500 | −0.2233 | 0.5865 | 0.040* | |
H20B | −0.4263 | −0.2336 | 0.5470 | 0.040* | |
C21 | −0.2159 (4) | −0.22272 (18) | 0.47433 (15) | 0.0250 (7) | |
C22 | −0.2296 (4) | −0.29239 (19) | 0.44420 (17) | 0.0319 (8) | |
H22 | −0.3118 | −0.3297 | 0.4651 | 0.038* | |
C23 | −0.1250 (4) | −0.30808 (19) | 0.38413 (17) | 0.0358 (8) | |
H23 | −0.1343 | −0.3562 | 0.3640 | 0.043* | |
C24 | −0.0059 (4) | −0.25301 (18) | 0.35321 (17) | 0.0318 (8) | |
H24 | 0.0658 | −0.2645 | 0.3120 | 0.038* | |
C25 | 0.3338 (4) | −0.16133 (18) | 0.36797 (16) | 0.0299 (8) | |
H25A | 0.3407 | −0.1750 | 0.4231 | 0.036* | |
H25B | 0.3613 | −0.2130 | 0.3483 | 0.036* | |
C26 | 0.4679 (4) | −0.10162 (18) | 0.33715 (15) | 0.0280 (7) | |
H26A | 0.4492 | −0.0527 | 0.3613 | 0.034* | |
H26B | 0.5870 | −0.1285 | 0.3489 | 0.034* | |
C27 | 0.5138 (4) | 0.12268 (18) | 0.23943 (16) | 0.0293 (8) | |
H27 | 0.4217 | 0.1265 | 0.2055 | 0.035* | |
C28 | 0.5396 (4) | 0.19087 (18) | 0.26978 (15) | 0.0264 (7) | |
H28 | 0.4639 | 0.2401 | 0.2567 | 0.032* | |
F2 | 1.3617 (3) | 0.62544 (12) | 0.38567 (11) | 0.0588 (6) | |
O2 | 0.2877 (3) | 0.54027 (12) | −0.01363 (13) | 0.0377 (6) | |
N3 | 0.9771 (3) | 0.20169 (14) | 0.05422 (13) | 0.0270 (6) | |
N4 | 0.4096 (3) | 0.42911 (14) | −0.05795 (14) | 0.0229 (6) | |
H4N | 0.502 (4) | 0.4311 (17) | −0.0344 (15) | 0.022 (8)* | |
C29 | 1.3188 (5) | 0.5689 (2) | 0.3462 (2) | 0.0410 (9) | |
C30 | 1.3440 (4) | 0.5841 (2) | 0.27003 (19) | 0.0393 (9) | |
H30 | 1.3864 | 0.6341 | 0.2452 | 0.047* | |
C31 | 1.3064 (4) | 0.52515 (18) | 0.23002 (17) | 0.0319 (8) | |
H31 | 1.3235 | 0.5351 | 0.1773 | 0.038* | |
C32 | 1.2437 (4) | 0.45105 (18) | 0.26552 (16) | 0.0283 (7) | |
C33 | 1.2175 (4) | 0.44066 (19) | 0.34284 (18) | 0.0362 (8) | |
H33 | 1.1721 | 0.3918 | 0.3684 | 0.043* | |
C34 | 1.2546 (5) | 0.4982 (2) | 0.38355 (19) | 0.0421 (9) | |
H34 | 1.2362 | 0.4893 | 0.4362 | 0.051* | |
C35 | 1.2088 (4) | 0.38639 (18) | 0.22319 (16) | 0.0273 (7) | |
C36 | 1.2923 (4) | 0.37995 (18) | 0.15466 (16) | 0.0297 (8) | |
H36 | 1.3708 | 0.4190 | 0.1337 | 0.036* | |
C37 | 1.2634 (4) | 0.31827 (18) | 0.11671 (16) | 0.0299 (8) | |
H37 | 1.3212 | 0.3163 | 0.0699 | 0.036* | |
C38 | 1.1510 (4) | 0.25863 (18) | 0.14560 (16) | 0.0277 (7) | |
C39 | 1.1252 (4) | 0.18953 (18) | 0.10479 (16) | 0.0300 (8) | |
H39A | 1.2334 | 0.1787 | 0.0754 | 0.036* | |
H39B | 1.1117 | 0.1393 | 0.1427 | 0.036* | |
C40 | 0.8066 (4) | 0.20082 (18) | 0.09254 (16) | 0.0281 (7) | |
H40A | 0.7850 | 0.2494 | 0.1171 | 0.034* | |
H40B | 0.8058 | 0.1508 | 0.1317 | 0.034* | |
C41 | 0.6633 (4) | 0.20212 (18) | 0.03805 (16) | 0.0298 (7) | |
H41A | 0.5490 | 0.2004 | 0.0650 | 0.036* | |
H41B | 0.6834 | 0.1530 | 0.0141 | 0.036* | |
C42 | 0.6609 (4) | 0.28031 (17) | −0.02180 (16) | 0.0256 (7) | |
H42 | 0.6425 | 0.3284 | 0.0045 | 0.031* | |
C43 | 0.5169 (4) | 0.29027 (17) | −0.07819 (16) | 0.0253 (7) | |
C44 | 0.4001 (4) | 0.36189 (17) | −0.09489 (15) | 0.0221 (7) | |
C45 | 0.2736 (4) | 0.48745 (18) | −0.05182 (16) | 0.0268 (7) | |
C46 | 0.1135 (4) | 0.48381 (18) | −0.09304 (16) | 0.0298 (8) | |
H46A | 0.0512 | 0.5397 | −0.1055 | 0.036* | |
H46B | 0.0348 | 0.4480 | −0.0608 | 0.036* | |
C47 | 0.1570 (4) | 0.45047 (18) | −0.16440 (16) | 0.0331 (8) | |
H47A | 0.0477 | 0.4413 | −0.1870 | 0.040* | |
H47B | 0.2170 | 0.4913 | −0.2006 | 0.040* | |
C48 | 0.2733 (4) | 0.37045 (18) | −0.14847 (15) | 0.0244 (7) | |
C49 | 0.2579 (4) | 0.3066 (2) | −0.18601 (17) | 0.0357 (8) | |
H49 | 0.1688 | 0.3113 | −0.2215 | 0.043* | |
C50 | 0.3729 (5) | 0.2356 (2) | −0.17158 (18) | 0.0406 (9) | |
H50 | 0.3650 | 0.1922 | −0.1982 | 0.049* | |
C51 | 0.4987 (4) | 0.22842 (19) | −0.11845 (18) | 0.0365 (8) | |
H51 | 0.5758 | 0.1793 | −0.1090 | 0.044* | |
C52 | 0.8422 (4) | 0.28231 (19) | −0.06015 (17) | 0.0343 (8) | |
H52A | 0.8639 | 0.2359 | −0.0874 | 0.041* | |
H52B | 0.8460 | 0.3342 | −0.0969 | 0.041* | |
C53 | 0.9835 (4) | 0.27626 (19) | −0.00341 (16) | 0.0323 (8) | |
H53A | 1.0994 | 0.2752 | −0.0291 | 0.039* | |
H53B | 0.9680 | 0.3254 | 0.0205 | 0.039* | |
C54 | 1.0668 (4) | 0.26511 (19) | 0.21371 (16) | 0.0310 (8) | |
H54 | 0.9889 | 0.2258 | 0.2348 | 0.037* | |
C55 | 1.0941 (4) | 0.32725 (19) | 0.25114 (17) | 0.0321 (8) | |
H55 | 1.0333 | 0.3301 | 0.2972 | 0.039* | |
Cl1 | −0.0132 (2) | −0.03511 (9) | 0.07915 (8) | 0.1134 (6) | |
Cl2 | 0.3096 (5) | 0.02001 (16) | 0.00809 (15) | 0.1066 (10) | 0.5 |
C61 | 0.0799 (10) | 0.0456 (5) | −0.0014 (4) | 0.065 (3) | 0.5 |
H61 | 0.0458 | 0.1028 | 0.0074 | 0.078* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0699 (16) | 0.0417 (12) | 0.0472 (12) | −0.0041 (11) | −0.0038 (11) | −0.0153 (9) |
O1 | 0.0344 (15) | 0.0437 (14) | 0.0431 (13) | −0.0094 (11) | 0.0146 (11) | −0.0231 (11) |
N1 | 0.0206 (15) | 0.0286 (14) | 0.0239 (13) | −0.0027 (11) | 0.0034 (11) | −0.0039 (11) |
N2 | 0.0214 (16) | 0.0278 (14) | 0.0214 (13) | −0.0080 (12) | 0.0059 (12) | −0.0053 (11) |
C2 | 0.034 (2) | 0.0292 (18) | 0.0378 (19) | −0.0041 (15) | 0.0051 (16) | −0.0143 (15) |
C3 | 0.036 (2) | 0.042 (2) | 0.0248 (17) | −0.0015 (17) | −0.0018 (15) | −0.0050 (15) |
C4 | 0.028 (2) | 0.0304 (18) | 0.0256 (17) | 0.0000 (15) | 0.0004 (15) | 0.0024 (14) |
C5 | 0.0143 (17) | 0.0274 (17) | 0.0272 (16) | −0.0016 (13) | 0.0046 (13) | 0.0008 (13) |
C6 | 0.0225 (19) | 0.0342 (18) | 0.0252 (16) | 0.0005 (14) | −0.0013 (14) | −0.0007 (14) |
C7 | 0.031 (2) | 0.0285 (18) | 0.0326 (18) | 0.0009 (15) | 0.0026 (16) | 0.0016 (14) |
C8 | 0.0224 (18) | 0.0273 (17) | 0.0208 (16) | −0.0038 (14) | 0.0057 (14) | 0.0037 (13) |
C9 | 0.0227 (19) | 0.0321 (18) | 0.0326 (18) | −0.0013 (15) | −0.0010 (15) | 0.0007 (14) |
C10 | 0.0239 (19) | 0.0255 (17) | 0.0325 (18) | 0.0013 (14) | 0.0040 (15) | 0.0004 (14) |
C11 | 0.0199 (18) | 0.0294 (17) | 0.0252 (16) | −0.0046 (14) | 0.0067 (14) | 0.0008 (13) |
C12 | 0.0224 (19) | 0.0355 (18) | 0.0288 (17) | 0.0000 (15) | 0.0056 (14) | −0.0047 (14) |
C13 | 0.0276 (19) | 0.0342 (18) | 0.0224 (16) | −0.0037 (15) | 0.0004 (14) | −0.0008 (13) |
C14 | 0.0255 (19) | 0.0346 (18) | 0.0241 (16) | −0.0009 (15) | −0.0008 (14) | −0.0038 (13) |
C15 | 0.0262 (19) | 0.0217 (16) | 0.0221 (15) | −0.0038 (14) | 0.0021 (14) | −0.0036 (12) |
C16 | 0.0207 (18) | 0.0253 (16) | 0.0191 (15) | −0.0026 (13) | −0.0024 (13) | −0.0022 (13) |
C17 | 0.0220 (18) | 0.0223 (16) | 0.0234 (16) | −0.0012 (13) | −0.0049 (14) | −0.0028 (13) |
C18 | 0.0237 (19) | 0.0329 (18) | 0.0237 (16) | −0.0031 (15) | 0.0029 (14) | −0.0051 (14) |
C19 | 0.0236 (19) | 0.0388 (19) | 0.0290 (17) | −0.0057 (15) | 0.0076 (14) | −0.0076 (14) |
C20 | 0.031 (2) | 0.0373 (19) | 0.0302 (18) | −0.0106 (16) | 0.0086 (15) | −0.0002 (14) |
C21 | 0.0227 (19) | 0.0294 (17) | 0.0213 (16) | −0.0057 (14) | −0.0007 (14) | 0.0011 (13) |
C22 | 0.030 (2) | 0.0321 (19) | 0.0339 (18) | −0.0129 (15) | −0.0029 (16) | −0.0012 (15) |
C23 | 0.043 (2) | 0.0285 (18) | 0.039 (2) | −0.0099 (16) | −0.0018 (17) | −0.0094 (15) |
C24 | 0.034 (2) | 0.0345 (19) | 0.0287 (17) | −0.0047 (16) | −0.0002 (15) | −0.0088 (15) |
C25 | 0.030 (2) | 0.0294 (17) | 0.0280 (17) | −0.0042 (15) | −0.0040 (15) | 0.0027 (13) |
C26 | 0.0262 (19) | 0.0284 (17) | 0.0261 (16) | −0.0036 (14) | −0.0007 (14) | 0.0041 (13) |
C27 | 0.025 (2) | 0.0354 (19) | 0.0243 (16) | −0.0023 (15) | −0.0008 (14) | 0.0028 (14) |
C28 | 0.0244 (19) | 0.0280 (17) | 0.0234 (16) | 0.0000 (14) | 0.0005 (14) | 0.0023 (13) |
F2 | 0.0776 (17) | 0.0417 (12) | 0.0624 (14) | −0.0126 (11) | 0.0063 (12) | −0.0215 (11) |
O2 | 0.0299 (14) | 0.0277 (12) | 0.0601 (15) | 0.0020 (10) | −0.0085 (12) | −0.0207 (12) |
N3 | 0.0241 (15) | 0.0250 (14) | 0.0285 (14) | 0.0009 (12) | 0.0010 (12) | 0.0011 (11) |
N4 | 0.0198 (16) | 0.0209 (14) | 0.0279 (14) | −0.0004 (12) | −0.0049 (12) | −0.0042 (11) |
C29 | 0.043 (2) | 0.033 (2) | 0.050 (2) | −0.0023 (17) | 0.0032 (18) | −0.0158 (17) |
C30 | 0.034 (2) | 0.0284 (18) | 0.052 (2) | 0.0012 (16) | 0.0015 (18) | −0.0027 (17) |
C31 | 0.028 (2) | 0.0289 (18) | 0.0334 (18) | 0.0002 (15) | 0.0020 (15) | 0.0059 (15) |
C32 | 0.0228 (19) | 0.0303 (17) | 0.0277 (17) | 0.0029 (14) | 0.0024 (14) | 0.0009 (14) |
C33 | 0.038 (2) | 0.0308 (18) | 0.0366 (19) | −0.0049 (16) | 0.0088 (16) | 0.0011 (15) |
C34 | 0.053 (3) | 0.037 (2) | 0.037 (2) | −0.0014 (18) | 0.0091 (18) | −0.0112 (17) |
C35 | 0.0188 (18) | 0.0306 (18) | 0.0267 (17) | 0.0031 (14) | 0.0007 (14) | 0.0062 (14) |
C36 | 0.026 (2) | 0.0289 (17) | 0.0308 (18) | −0.0031 (15) | 0.0048 (15) | 0.0016 (14) |
C37 | 0.0256 (19) | 0.0353 (19) | 0.0242 (16) | 0.0025 (15) | 0.0035 (14) | 0.0024 (14) |
C38 | 0.0176 (18) | 0.0297 (18) | 0.0310 (18) | 0.0027 (14) | −0.0036 (14) | 0.0048 (14) |
C39 | 0.0243 (19) | 0.0326 (18) | 0.0297 (17) | 0.0035 (15) | −0.0003 (15) | −0.0005 (14) |
C40 | 0.0236 (19) | 0.0277 (17) | 0.0290 (17) | −0.0023 (14) | 0.0038 (14) | 0.0038 (13) |
C41 | 0.0272 (19) | 0.0262 (17) | 0.0335 (17) | −0.0010 (14) | 0.0046 (15) | −0.0007 (13) |
C42 | 0.0259 (19) | 0.0174 (15) | 0.0327 (17) | 0.0014 (14) | −0.0017 (15) | −0.0045 (13) |
C43 | 0.0255 (19) | 0.0211 (16) | 0.0300 (17) | −0.0033 (14) | 0.0008 (14) | −0.0061 (13) |
C44 | 0.0225 (18) | 0.0248 (16) | 0.0197 (15) | −0.0058 (14) | 0.0053 (13) | −0.0050 (12) |
C45 | 0.027 (2) | 0.0199 (16) | 0.0312 (17) | −0.0012 (14) | 0.0022 (15) | −0.0016 (14) |
C46 | 0.0243 (19) | 0.0268 (17) | 0.0376 (18) | 0.0020 (14) | −0.0048 (15) | −0.0064 (14) |
C47 | 0.031 (2) | 0.0364 (19) | 0.0283 (17) | −0.0003 (15) | −0.0059 (15) | 0.0025 (14) |
C48 | 0.0232 (19) | 0.0299 (17) | 0.0195 (15) | −0.0026 (14) | 0.0025 (14) | −0.0038 (13) |
C49 | 0.034 (2) | 0.045 (2) | 0.0306 (18) | −0.0065 (17) | −0.0046 (16) | −0.0130 (16) |
C50 | 0.045 (2) | 0.038 (2) | 0.045 (2) | −0.0045 (18) | −0.0018 (18) | −0.0236 (17) |
C51 | 0.036 (2) | 0.0311 (19) | 0.045 (2) | 0.0018 (16) | −0.0028 (17) | −0.0153 (16) |
C52 | 0.029 (2) | 0.0350 (19) | 0.0353 (19) | −0.0037 (15) | −0.0014 (16) | 0.0027 (14) |
C53 | 0.0258 (19) | 0.0354 (18) | 0.0305 (18) | −0.0044 (15) | −0.0002 (15) | 0.0080 (14) |
C54 | 0.025 (2) | 0.0368 (19) | 0.0284 (17) | −0.0086 (15) | 0.0061 (15) | 0.0021 (15) |
C55 | 0.026 (2) | 0.040 (2) | 0.0279 (17) | −0.0042 (16) | 0.0051 (15) | −0.0010 (15) |
Cl1 | 0.1568 (15) | 0.1040 (11) | 0.0755 (9) | −0.0122 (10) | −0.0064 (9) | −0.0063 (8) |
Cl2 | 0.157 (3) | 0.0827 (18) | 0.0861 (18) | 0.0011 (19) | 0.0029 (19) | −0.0392 (14) |
C61 | 0.055 (6) | 0.074 (6) | 0.065 (5) | 0.038 (5) | −0.047 (5) | −0.027 (4) |
F1—C2 | 1.374 (3) | N3—C39 | 1.470 (4) |
O1—C18 | 1.242 (3) | N3—C53 | 1.470 (3) |
N1—C13 | 1.454 (4) | N4—C45 | 1.366 (4) |
N1—C26 | 1.458 (3) | N4—C44 | 1.417 (4) |
N1—C12 | 1.480 (4) | N4—H4N | 0.86 (3) |
N2—C18 | 1.347 (4) | C29—C30 | 1.372 (5) |
N2—C17 | 1.428 (4) | C29—C34 | 1.372 (4) |
N2—H2N | 0.88 (3) | C30—C31 | 1.386 (4) |
C2—C7 | 1.360 (4) | C30—H30 | 0.9500 |
C2—C3 | 1.374 (4) | C31—C32 | 1.403 (4) |
C3—C4 | 1.377 (4) | C31—H31 | 0.9500 |
C3—H3 | 0.9500 | C32—C33 | 1.396 (4) |
C4—C5 | 1.396 (4) | C32—C35 | 1.487 (4) |
C4—H4 | 0.9500 | C33—C34 | 1.374 (4) |
C5—C6 | 1.407 (4) | C33—H33 | 0.9500 |
C5—C8 | 1.482 (4) | C34—H34 | 0.9500 |
C6—C7 | 1.381 (4) | C35—C36 | 1.397 (4) |
C6—H6 | 0.9500 | C35—C55 | 1.401 (4) |
C7—H7 | 0.9500 | C36—C37 | 1.380 (4) |
C8—C28 | 1.395 (4) | C36—H36 | 0.9500 |
C8—C9 | 1.402 (4) | C37—C38 | 1.398 (4) |
C9—C10 | 1.383 (4) | C37—H37 | 0.9500 |
C9—H9 | 0.9500 | C38—C54 | 1.392 (4) |
C10—C11 | 1.392 (4) | C38—C39 | 1.514 (4) |
C10—H10 | 0.9500 | C39—H39A | 0.9900 |
C11—C27 | 1.396 (4) | C39—H39B | 0.9900 |
C11—C12 | 1.507 (4) | C40—C41 | 1.511 (4) |
C12—H12A | 0.9900 | C40—H40A | 0.9900 |
C12—H12B | 0.9900 | C40—H40B | 0.9900 |
C13—C14 | 1.526 (4) | C41—C42 | 1.531 (4) |
C13—H13A | 0.9900 | C41—H41A | 0.9900 |
C13—H13B | 0.9900 | C41—H41B | 0.9900 |
C14—C15 | 1.527 (4) | C42—C43 | 1.519 (4) |
C14—H14A | 0.9900 | C42—C52 | 1.534 (4) |
C14—H14B | 0.9900 | C42—H42 | 1.0000 |
C15—C16 | 1.524 (4) | C43—C51 | 1.391 (4) |
C15—C25 | 1.531 (4) | C43—C44 | 1.407 (4) |
C15—H15 | 1.0000 | C44—C48 | 1.388 (4) |
C16—C24 | 1.388 (4) | C45—C46 | 1.482 (4) |
C16—C17 | 1.403 (4) | C46—C47 | 1.518 (4) |
C17—C21 | 1.401 (4) | C46—H46A | 0.9900 |
C18—C19 | 1.497 (4) | C46—H46B | 0.9900 |
C19—C20 | 1.520 (4) | C47—C48 | 1.510 (4) |
C19—H19A | 0.9900 | C47—H47A | 0.9900 |
C19—H19B | 0.9900 | C47—H47B | 0.9900 |
C20—C21 | 1.495 (4) | C48—C49 | 1.383 (4) |
C20—H20A | 0.9900 | C49—C50 | 1.389 (4) |
C20—H20B | 0.9900 | C49—H49 | 0.9500 |
C21—C22 | 1.386 (4) | C50—C51 | 1.378 (4) |
C22—C23 | 1.379 (4) | C50—H50 | 0.9500 |
C22—H22 | 0.9500 | C51—H51 | 0.9500 |
C23—C24 | 1.391 (4) | C52—C53 | 1.515 (4) |
C23—H23 | 0.9500 | C52—H52A | 0.9900 |
C24—H24 | 0.9500 | C52—H52B | 0.9900 |
C25—C26 | 1.524 (4) | C53—H53A | 0.9900 |
C25—H25A | 0.9900 | C53—H53B | 0.9900 |
C25—H25B | 0.9900 | C54—C55 | 1.377 (4) |
C26—H26A | 0.9900 | C54—H54 | 0.9500 |
C26—H26B | 0.9900 | C55—H55 | 0.9500 |
C27—C28 | 1.386 (4) | Cl1—C61i | 1.573 (7) |
C27—H27 | 0.9500 | Cl1—C61 | 1.960 (9) |
C28—H28 | 0.9500 | Cl2—C61 | 1.782 (8) |
F2—C29 | 1.359 (4) | C61—Cl1i | 1.573 (7) |
O2—C45 | 1.234 (3) | C61—H61 | 1.0000 |
N3—C40 | 1.460 (4) | ||
C13—N1—C26 | 112.0 (2) | C45—N4—H4N | 117.3 (19) |
C13—N1—C12 | 113.8 (2) | C44—N4—H4N | 118.5 (19) |
C26—N1—C12 | 112.2 (2) | F2—C29—C30 | 118.6 (3) |
C18—N2—C17 | 124.3 (3) | F2—C29—C34 | 119.2 (3) |
C18—N2—H2N | 114 (2) | C30—C29—C34 | 122.2 (3) |
C17—N2—H2N | 122 (2) | C29—C30—C31 | 118.7 (3) |
C7—C2—F1 | 118.5 (3) | C29—C30—H30 | 120.7 |
C7—C2—C3 | 122.7 (3) | C31—C30—H30 | 120.7 |
F1—C2—C3 | 118.8 (3) | C30—C31—C32 | 121.6 (3) |
C2—C3—C4 | 117.9 (3) | C30—C31—H31 | 119.2 |
C2—C3—H3 | 121.0 | C32—C31—H31 | 119.2 |
C4—C3—H3 | 121.0 | C33—C32—C31 | 116.6 (3) |
C3—C4—C5 | 122.3 (3) | C33—C32—C35 | 121.6 (3) |
C3—C4—H4 | 118.9 | C31—C32—C35 | 121.8 (3) |
C5—C4—H4 | 118.9 | C34—C33—C32 | 122.7 (3) |
C4—C5—C6 | 117.0 (3) | C34—C33—H33 | 118.7 |
C4—C5—C8 | 122.0 (3) | C32—C33—H33 | 118.7 |
C6—C5—C8 | 121.0 (3) | C29—C34—C33 | 118.3 (3) |
C7—C6—C5 | 121.1 (3) | C29—C34—H34 | 120.9 |
C7—C6—H6 | 119.4 | C33—C34—H34 | 120.9 |
C5—C6—H6 | 119.4 | C36—C35—C55 | 116.5 (3) |
C2—C7—C6 | 118.9 (3) | C36—C35—C32 | 121.9 (3) |
C2—C7—H7 | 120.5 | C55—C35—C32 | 121.6 (3) |
C6—C7—H7 | 120.5 | C37—C36—C35 | 121.6 (3) |
C28—C8—C9 | 117.1 (3) | C37—C36—H36 | 119.2 |
C28—C8—C5 | 121.4 (3) | C35—C36—H36 | 119.2 |
C9—C8—C5 | 121.5 (3) | C36—C37—C38 | 121.5 (3) |
C10—C9—C8 | 121.1 (3) | C36—C37—H37 | 119.3 |
C10—C9—H9 | 119.5 | C38—C37—H37 | 119.3 |
C8—C9—H9 | 119.5 | C54—C38—C37 | 117.0 (3) |
C9—C10—C11 | 122.1 (3) | C54—C38—C39 | 121.9 (3) |
C9—C10—H10 | 119.0 | C37—C38—C39 | 121.0 (3) |
C11—C10—H10 | 119.0 | N3—C39—C38 | 117.5 (2) |
C10—C11—C27 | 116.6 (3) | N3—C39—H39A | 107.9 |
C10—C11—C12 | 121.2 (3) | C38—C39—H39A | 107.9 |
C27—C11—C12 | 122.2 (3) | N3—C39—H39B | 107.9 |
N1—C12—C11 | 116.8 (2) | C38—C39—H39B | 107.9 |
N1—C12—H12A | 108.1 | H39A—C39—H39B | 107.2 |
C11—C12—H12A | 108.1 | N3—C40—C41 | 110.7 (2) |
N1—C12—H12B | 108.1 | N3—C40—H40A | 109.5 |
C11—C12—H12B | 108.1 | C41—C40—H40A | 109.5 |
H12A—C12—H12B | 107.3 | N3—C40—H40B | 109.5 |
N1—C13—C14 | 110.1 (2) | C41—C40—H40B | 109.5 |
N1—C13—H13A | 109.6 | H40A—C40—H40B | 108.1 |
C14—C13—H13A | 109.6 | C40—C41—C42 | 109.9 (2) |
N1—C13—H13B | 109.6 | C40—C41—H41A | 109.7 |
C14—C13—H13B | 109.6 | C42—C41—H41A | 109.7 |
H13A—C13—H13B | 108.1 | C40—C41—H41B | 109.7 |
C13—C14—C15 | 109.1 (2) | C42—C41—H41B | 109.7 |
C13—C14—H14A | 109.9 | H41A—C41—H41B | 108.2 |
C15—C14—H14A | 109.9 | C43—C42—C41 | 114.7 (2) |
C13—C14—H14B | 109.9 | C43—C42—C52 | 111.6 (2) |
C15—C14—H14B | 109.9 | C41—C42—C52 | 108.1 (2) |
H14A—C14—H14B | 108.3 | C43—C42—H42 | 107.4 |
C16—C15—C14 | 114.7 (2) | C41—C42—H42 | 107.4 |
C16—C15—C25 | 111.9 (2) | C52—C42—H42 | 107.4 |
C14—C15—C25 | 108.0 (2) | C51—C43—C44 | 116.4 (3) |
C16—C15—H15 | 107.3 | C51—C43—C42 | 120.5 (3) |
C14—C15—H15 | 107.3 | C44—C43—C42 | 123.1 (3) |
C25—C15—H15 | 107.3 | C48—C44—C43 | 121.9 (3) |
C24—C16—C17 | 116.7 (3) | C48—C44—N4 | 117.2 (3) |
C24—C16—C15 | 120.5 (3) | C43—C44—N4 | 120.8 (3) |
C17—C16—C15 | 122.8 (3) | O2—C45—N4 | 120.0 (3) |
C21—C17—C16 | 122.0 (3) | O2—C45—C46 | 123.0 (3) |
C21—C17—N2 | 116.8 (3) | N4—C45—C46 | 117.0 (3) |
C16—C17—N2 | 121.1 (3) | C45—C46—C47 | 111.3 (3) |
O1—C18—N2 | 120.9 (3) | C45—C46—H46A | 109.4 |
O1—C18—C19 | 122.0 (3) | C47—C46—H46A | 109.4 |
N2—C18—C19 | 117.0 (3) | C45—C46—H46B | 109.4 |
C18—C19—C20 | 110.5 (3) | C47—C46—H46B | 109.4 |
C18—C19—H19A | 109.5 | H46A—C46—H46B | 108.0 |
C20—C19—H19A | 109.5 | C48—C47—C46 | 110.7 (2) |
C18—C19—H19B | 109.5 | C48—C47—H47A | 109.5 |
C20—C19—H19B | 109.5 | C46—C47—H47A | 109.5 |
H19A—C19—H19B | 108.1 | C48—C47—H47B | 109.5 |
C21—C20—C19 | 111.1 (2) | C46—C47—H47B | 109.5 |
C21—C20—H20A | 109.4 | H47A—C47—H47B | 108.1 |
C19—C20—H20A | 109.4 | C49—C48—C44 | 119.6 (3) |
C21—C20—H20B | 109.4 | C49—C48—C47 | 122.0 (3) |
C19—C20—H20B | 109.4 | C44—C48—C47 | 118.3 (3) |
H20A—C20—H20B | 108.0 | C48—C49—C50 | 119.8 (3) |
C22—C21—C17 | 118.8 (3) | C48—C49—H49 | 120.1 |
C22—C21—C20 | 123.2 (3) | C50—C49—H49 | 120.1 |
C17—C21—C20 | 118.0 (3) | C51—C50—C49 | 119.8 (3) |
C23—C22—C21 | 120.6 (3) | C51—C50—H50 | 120.1 |
C23—C22—H22 | 119.7 | C49—C50—H50 | 120.1 |
C21—C22—H22 | 119.7 | C50—C51—C43 | 122.5 (3) |
C22—C23—C24 | 119.6 (3) | C50—C51—H51 | 118.7 |
C22—C23—H23 | 120.2 | C43—C51—H51 | 118.7 |
C24—C23—H23 | 120.2 | C53—C52—C42 | 110.9 (2) |
C16—C24—C23 | 122.3 (3) | C53—C52—H52A | 109.5 |
C16—C24—H24 | 118.8 | C42—C52—H52A | 109.5 |
C23—C24—H24 | 118.8 | C53—C52—H52B | 109.5 |
C26—C25—C15 | 111.4 (2) | C42—C52—H52B | 109.5 |
C26—C25—H25A | 109.3 | H52A—C52—H52B | 108.1 |
C15—C25—H25A | 109.3 | N3—C53—C52 | 111.1 (3) |
C26—C25—H25B | 109.3 | N3—C53—H53A | 109.4 |
C15—C25—H25B | 109.3 | C52—C53—H53A | 109.4 |
H25A—C25—H25B | 108.0 | N3—C53—H53B | 109.4 |
N1—C26—C25 | 110.8 (2) | C52—C53—H53B | 109.4 |
N1—C26—H26A | 109.5 | H53A—C53—H53B | 108.0 |
C25—C26—H26A | 109.5 | C55—C54—C38 | 121.4 (3) |
N1—C26—H26B | 109.5 | C55—C54—H54 | 119.3 |
C25—C26—H26B | 109.5 | C38—C54—H54 | 119.3 |
H26A—C26—H26B | 108.1 | C54—C55—C35 | 121.9 (3) |
C28—C27—C11 | 121.9 (3) | C54—C55—H55 | 119.1 |
C28—C27—H27 | 119.1 | C35—C55—H55 | 119.1 |
C11—C27—H27 | 119.1 | C61i—Cl1—C61 | 69.6 (5) |
C27—C28—C8 | 121.2 (3) | Cl1i—C61—Cl2 | 112.9 (5) |
C27—C28—H28 | 119.4 | Cl1i—C61—Cl1 | 110.4 (5) |
C8—C28—H28 | 119.4 | Cl2—C61—Cl1 | 101.8 (3) |
C40—N3—C39 | 113.9 (2) | Cl1i—C61—H61 | 110.5 |
C40—N3—C53 | 110.8 (2) | Cl2—C61—H61 | 110.5 |
C39—N3—C53 | 112.0 (2) | Cl1—C61—H61 | 110.5 |
C45—N4—C44 | 124.0 (3) | ||
C7—C2—C3—C4 | 0.3 (5) | F2—C29—C30—C31 | 177.6 (3) |
F1—C2—C3—C4 | −179.4 (3) | C34—C29—C30—C31 | −1.3 (5) |
C2—C3—C4—C5 | −0.1 (5) | C29—C30—C31—C32 | 0.0 (5) |
C3—C4—C5—C6 | 0.2 (5) | C30—C31—C32—C33 | 1.4 (5) |
C3—C4—C5—C8 | −179.3 (3) | C30—C31—C32—C35 | −177.9 (3) |
C4—C5—C6—C7 | −0.5 (4) | C31—C32—C33—C34 | −1.7 (5) |
C8—C5—C6—C7 | 179.0 (3) | C35—C32—C33—C34 | 177.7 (3) |
F1—C2—C7—C6 | 179.2 (3) | F2—C29—C34—C33 | −177.9 (3) |
C3—C2—C7—C6 | −0.6 (5) | C30—C29—C34—C33 | 1.1 (5) |
C5—C6—C7—C2 | 0.7 (5) | C32—C33—C34—C29 | 0.5 (5) |
C4—C5—C8—C28 | 152.9 (3) | C33—C32—C35—C36 | −155.2 (3) |
C6—C5—C8—C28 | −26.6 (4) | C31—C32—C35—C36 | 24.1 (4) |
C4—C5—C8—C9 | −26.8 (4) | C33—C32—C35—C55 | 23.0 (4) |
C6—C5—C8—C9 | 153.7 (3) | C31—C32—C35—C55 | −157.7 (3) |
C28—C8—C9—C10 | 0.4 (4) | C55—C35—C36—C37 | −0.2 (4) |
C5—C8—C9—C10 | −179.9 (3) | C32—C35—C36—C37 | 178.0 (3) |
C8—C9—C10—C11 | 1.3 (5) | C35—C36—C37—C38 | −0.9 (5) |
C9—C10—C11—C27 | −1.7 (4) | C36—C37—C38—C54 | 1.2 (4) |
C9—C10—C11—C12 | 177.7 (3) | C36—C37—C38—C39 | −177.8 (3) |
C13—N1—C12—C11 | 75.3 (3) | C40—N3—C39—C38 | −70.1 (3) |
C26—N1—C12—C11 | −53.1 (3) | C53—N3—C39—C38 | 56.6 (3) |
C10—C11—C12—N1 | 100.2 (3) | C54—C38—C39—N3 | 86.9 (4) |
C27—C11—C12—N1 | −80.3 (4) | C37—C38—C39—N3 | −94.1 (3) |
C26—N1—C13—C14 | −60.6 (3) | C39—N3—C40—C41 | −172.4 (2) |
C12—N1—C13—C14 | 170.9 (2) | C53—N3—C40—C41 | 60.3 (3) |
N1—C13—C14—C15 | 61.2 (3) | N3—C40—C41—C42 | −60.4 (3) |
C13—C14—C15—C16 | 176.2 (2) | C40—C41—C42—C43 | −177.6 (3) |
C13—C14—C15—C25 | −58.2 (3) | C40—C41—C42—C52 | 57.1 (3) |
C14—C15—C16—C24 | 50.7 (4) | C41—C42—C43—C51 | −54.7 (4) |
C25—C15—C16—C24 | −72.8 (3) | C52—C42—C43—C51 | 68.7 (4) |
C14—C15—C16—C17 | −131.7 (3) | C41—C42—C43—C44 | 127.7 (3) |
C25—C15—C16—C17 | 104.8 (3) | C52—C42—C43—C44 | −108.9 (3) |
C24—C16—C17—C21 | 0.5 (4) | C51—C43—C44—C48 | 0.1 (4) |
C15—C16—C17—C21 | −177.2 (3) | C42—C43—C44—C48 | 177.8 (3) |
C24—C16—C17—N2 | 179.3 (3) | C51—C43—C44—N4 | −178.9 (3) |
C15—C16—C17—N2 | 1.6 (4) | C42—C43—C44—N4 | −1.2 (4) |
C18—N2—C17—C21 | −23.1 (4) | C45—N4—C44—C48 | 23.1 (4) |
C18—N2—C17—C16 | 158.0 (3) | C45—N4—C44—C43 | −157.8 (3) |
C17—N2—C18—O1 | −174.4 (3) | C44—N4—C45—O2 | 174.1 (3) |
C17—N2—C18—C19 | 6.1 (4) | C44—N4—C45—C46 | −6.3 (4) |
O1—C18—C19—C20 | −147.6 (3) | O2—C45—C46—C47 | 148.1 (3) |
N2—C18—C19—C20 | 31.9 (4) | N4—C45—C46—C47 | −31.5 (4) |
C18—C19—C20—C21 | −52.3 (3) | C45—C46—C47—C48 | 51.3 (3) |
C16—C17—C21—C22 | −1.3 (4) | C43—C44—C48—C49 | 1.2 (4) |
N2—C17—C21—C22 | 179.8 (3) | N4—C44—C48—C49 | −179.7 (3) |
C16—C17—C21—C20 | 177.6 (3) | C43—C44—C48—C47 | −178.2 (3) |
N2—C17—C21—C20 | −1.3 (4) | N4—C44—C48—C47 | 0.9 (4) |
C19—C20—C21—C22 | −143.2 (3) | C46—C47—C48—C49 | 143.6 (3) |
C19—C20—C21—C17 | 38.0 (4) | C46—C47—C48—C44 | −37.0 (4) |
C17—C21—C22—C23 | 1.3 (4) | C44—C48—C49—C50 | −2.1 (5) |
C20—C21—C22—C23 | −177.5 (3) | C47—C48—C49—C50 | 177.2 (3) |
C21—C22—C23—C24 | −0.6 (5) | C48—C49—C50—C51 | 1.8 (5) |
C17—C16—C24—C23 | 0.3 (4) | C49—C50—C51—C43 | −0.5 (5) |
C15—C16—C24—C23 | 178.0 (3) | C44—C43—C51—C50 | −0.5 (5) |
C22—C23—C24—C16 | −0.3 (5) | C42—C43—C51—C50 | −178.3 (3) |
C16—C15—C25—C26 | −176.8 (3) | C43—C42—C52—C53 | 177.4 (2) |
C14—C15—C25—C26 | 55.9 (3) | C41—C42—C52—C53 | −55.5 (3) |
C13—N1—C26—C25 | 57.2 (3) | C40—N3—C53—C52 | −58.3 (3) |
C12—N1—C26—C25 | −173.5 (2) | C39—N3—C53—C52 | 173.4 (3) |
C15—C25—C26—N1 | −55.2 (3) | C42—C52—C53—N3 | 56.6 (3) |
C10—C11—C27—C28 | 0.7 (4) | C37—C38—C54—C55 | −0.4 (4) |
C12—C11—C27—C28 | −178.8 (3) | C39—C38—C54—C55 | 178.6 (3) |
C11—C27—C28—C8 | 0.9 (5) | C38—C54—C55—C35 | −0.7 (5) |
C9—C8—C28—C27 | −1.4 (4) | C36—C35—C55—C54 | 1.0 (4) |
C5—C8—C28—C27 | 178.8 (3) | C32—C35—C55—C54 | −177.2 (3) |
Symmetry code: (i) −x, −y, −z. |
Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of rings C2–C7, C8–C11/C27/C28, C16/C17/C21–C24, C29–C34, C35–C38/C54/C55 and C43/C44/C48–C51, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1ii | 0.88 (3) | 1.99 (3) | 2.869 (3) | 173 (3) |
N4—H4N···O2iii | 0.85 (3) | 2.01 (3) | 2.854 (3) | 169 (3) |
C15—H15···O1ii | 1.00 | 2.42 | 3.286 (4) | 145 |
C34—H34···F1iv | 0.95 | 2.53 | 3.406 (4) | 154 |
C42—H42···O2iii | 1.00 | 2.34 | 3.233 (4) | 148 |
C61—H61···N3v | 1.00 | 2.00 | 2.978 (9) | 164 |
C3—H3···Cg3vi | 0.95 | 2.65 | 3.483 (3) | 147 |
C7—H7···Cg4v | 0.95 | 2.82 | 3.366 (3) | 117 |
C19—H19B···Cg2ii | 0.99 | 2.84 | 3.779 (3) | 159 |
C26—H26B···Cg5vii | 0.99 | 2.94 | 3.903 (3) | 165 |
C28—H28···Cg5v | 0.95 | 2.71 | 3.567 (3) | 150 |
C30—H30···Cg6viii | 0.95 | 2.78 | 3.593 (4) | 144 |
C46—H46A···Cg5iii | 0.99 | 2.93 | 3.871 (3) | 159 |
C53—H53A···Cg6vii | 0.99 | 2.86 | 3.825 (3) | 166 |
C55—H55···Cg1 | 0.95 | 2.72 | 3.580 (3) | 151 |
Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) −x+1, −y, −z+1; (vii) x+1, y, z; (viii) −x+2, −y+1, −z. |
Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of rings C2–C7, C8–C11/C27/C28, C16/C17/C21–C24, C29–C34, C35–C38/C54/C55 and C43/C44/C48–C51, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.88 (3) | 1.99 (3) | 2.869 (3) | 173 (3) |
N4—H4N···O2ii | 0.85 (3) | 2.01 (3) | 2.854 (3) | 169 (3) |
C15—H15···O1i | 1.00 | 2.42 | 3.286 (4) | 145 |
C34—H34···F1iii | 0.95 | 2.53 | 3.406 (4) | 154 |
C42—H42···O2ii | 1.00 | 2.34 | 3.233 (4) | 148 |
C61—H61···N3iv | 1.00 | 2.00 | 2.978 (9) | 164 |
C3—H3···Cg3v | 0.95 | 2.65 | 3.483 (3) | 147 |
C7—H7···Cg4iv | 0.95 | 2.82 | 3.366 (3) | 117 |
C19—H19B···Cg2i | 0.99 | 2.84 | 3.779 (3) | 159 |
C26—H26B···Cg5vi | 0.99 | 2.94 | 3.903 (3) | 165 |
C28—H28···Cg5iv | 0.95 | 2.71 | 3.567 (3) | 150 |
C30—H30···Cg6vii | 0.95 | 2.78 | 3.593 (4) | 144 |
C46—H46A···Cg5ii | 0.99 | 2.93 | 3.871 (3) | 159 |
C53—H53A···Cg6vi | 0.99 | 2.86 | 3.825 (3) | 166 |
C55—H55···Cg1 | 0.95 | 2.72 | 3.580 (3) | 151 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1; (iv) x−1, y, z; (v) −x+1, −y, −z+1; (vi) x+1, y, z; (vii) −x+2, −y+1, −z. |
Acknowledgements
The authors would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science & Technology Unit at King Fahd University of Petroleum & Minerals (KFUPM) for funding this work through project No. 11-BIO2138-04 as part of the National Science, Technology and Innovation Plan. HSE is grateful to the XRD Application Laboratory, CSEM, Neuchâtel, for access to the X-ray diffraction equipment..
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Eastwood, P. R. (2000). Tetrahedron Lett. 41, 3705–3708. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2009). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Ullah, N. (2012). Z. Naturforsch. Teil B, 67b, 75–84. CrossRef Google Scholar
Ullah, N. (2013). J. Enzym. Inhib. Med. Chem. doi:10.3109/14756366.2013.776556. Google Scholar
Ullah, N. & Al-Shaheri, A. A. Q. (2012). Z. Naturforsch. Teil B, 67b, 253–262. CrossRef Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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