organic compounds
15-(4-Chlorophenyl)-6b-hydroxy-17-methyl-6b,7,16,17-tetrahydro-7,14a-methanonaphtho[1′,8′:1,2,3]pyrrolo[3′,2′:8,8a]azuleno[5,6-b]quinolin-14(15H)-one methanol hemisolvate
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the title solvate, C35H25ClN2O3·0.5CH3OH, the conformation of the central 1-methylpyrrolidine ring is best described as an envelope with the N atom as the flap. The cyclopentane ring adopts a twist conformation on the CH—CH2 bond and the cyclohexane ring has an with the CH2 atom as the flap. The pyrrolidine ring makes dihedral angles of 40.87 (12), 67.89 (11), 81.86 (9) and 70.86 (12)° with the mean planes of the cyclopentane, cyclohexane, acenaphthylene and chlorobenzene rings, respectively. The quinoline ring system is inclined to the naphthalene ring system by 54.14 (6)°. There is a short O—H⋯N contact in the molecule making an S(5) ring motif. In the crystal, there is a disordered and partially occupied ethan-1,2-diol solvent molecule present, located about an inversion centre, which links the title molecules via O—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction.
Keywords: crystal structure; pyrrolidine; quinoline; acenaphthylene; hydrogen bonding.
CCDC reference: 1474273
Structure description
The pyrrolidine ring system is found in a vast variety of compounds displaying an impressive range of biological activities (Babu et al., 2012). Optically active pyrrolidines have been used as intermediates, chiral ligands or auxiliaries in controlled (Savithri et al., 2014). Pyrrolidine compounds are reported to exhibit antimicrobial, antifungal (Govind et al.,2003), anti-influenza virus A (Stylianakis et al., 2003), anti-inflammatory and antitumor (Li & Xu, 2004) activities. They also inhibit retroviral [i.e., human immunodeficiency virus type 1 (HIV-1)], cellular DNA polymerases, protein kinases (Bellina & Rossi, 2006). They also act as antidepressant agents (Wróbel et al., 2013), antibiotics (Nirmala et al., 2009), anticonvulsant, sphingosine-1-phosphate (S1P) receptor agonists, malic enzyme inhibitors, ketoamide-based cathepsin K inhibitors and human melanocortin-4 receptor agonists (Babu et al., 2012). Quinoline derivatives have been synthesized and explored for their analgesic activity, anti-allergetic properties and in treating Alzheimer's disease (AD). They are also reported for their anticancer, antitinephritic, antitumor, anti-inflammatory (Shivaraj et al., 2013), antimalarial, anti-bacterial and antifungal activities (Marella et al., 2013).
The molecular structure of the title compound is shown in Fig. 1. In the molecule there is a short intramolecular O—H⋯N contact forming an S(5) ring motif (Fig. 1 and Table 1). The conformation of the central 1-methyl pyrrolidine ring (C12/C14/N2/C26/C27) is best described as an envelope with atom N2 as the flap and displaced by 0.585 (2) Å from the plane through the other four atoms. The cyclopentane ring adopts a twist conformation on the C10—C11 bond and the cyclohexane ring has an with atom C11 as the flap and displaced by 0.854 (2) Å from the mean plane through the other five atoms. The quinoline ring system (C1–C9/N1) and the acenaphthylene ring system (C14–C25) adopt almost planar conformations, with the maximum deviations being 0.069 (2) Å for atom C8 in the quinoline ring system and 0.128 (2) Å for atom C14 in the acenaphthylene ring system. Chlorine atom Cl1 is displaced from the benzene ring (C28–C33) to which it is attached by 0.0164 (8) Å. The mean plane of the pyrrolidine ring makes dihedral angles of 40.87 (12), 67.89 (11), 81.86 (9) and 70.86 (12)° with the mean planes of the cyclopentane, cyclohexane, acenaphthylene and chlorobenzene rings, respectively. The quinoline ring system is inclined to the naphthalene ring system by 54.14 (6)°.
In the crystal, there is a disordered and partially occupied ethan-1,2-diol solvent molecule present, located about an inversion centre, which links the title molecules via O—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction. (Table 1 and Fig. 2).
Synthesis and crystallization
A mixture of (E)-2-(4-chlorobenzylidene)-3,4-dihydroacridin-1(2H)-one (1 mmol), acenaphthoquinone (1 mmol) and sarcosine (1.5 mmol) was heated to reflux in toluene (3 ml) for 10 h. After completion of the reaction as evident from TLC, the reaction mixture was extracted with ethyl acetate (2 × 20 ml), washed with water (2 × 10 ml), dried over anhydrous Na2SO4 and concentrated under reduced pressure. It was then subjected to using petroleum ether–AcOEt (5:1 v/v) as to obtain the title compound as a pure product. Colourless block-like crystals were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.
Refinement
Crystal data, data collection and structure . The partially occupied methanol solvent molecule is disordered and located about an inversion centre (Fig. 1). The solvate molecule shows a high degree of disorder in such a way that the methyl carbon atom assumes four positions. Two are within the each with 0.25 occupancy, and the counterparts occupy symmetry-related positions, each with 0.25 occupancy. Similarly, the hydroxyl group assumes two positions with 0.5 occupancy. The hydrogen atoms could not be fixed on the carbon atom with agreeable geometry.
details are summarized in Table 2
|
Structural data
CCDC reference: 1474273
10.1107/S2414314616006374/su4031sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006374/su4031Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006374/su4031Isup3.cml
A mixture of (E)-2-(4-chlorobenzylidene)-3,4-dihydroacridin-1(2H)-one (1 mmol), acenaphthoquinone (1 mmol) and sarcosine (1.5 mmol) was heated to reflux in toluene (3 ml) for 10 h. After completion of the reaction as evident from TLC, the reaction mixture was extracted with ethyl acetate (2 × 20 ml), washed with water (2 × 10 ml), dried over anhydrous Na2SO4 and concentrated under reduced pressure. It was then subjected to
using petroleum ether–AcOEt (5:1 v/v) as to obtain the title compound as a pure product. Colourless block-like crystals were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.Crystal data, data collection and structure
details are summarized in Table 2. The partially occupied methanol solvent molecule is disordered and located about an inversion centre (Fig. 1). The solvate molecule shows high degree of disorder in such a way that the methyl carbon atom assumes four positions. Two are within the each with 0.25 occupancy and the counterparts occupy symmetry related position with 0.25 occupancy each. Similarly the hydroxyl group assumes two positions with 0.5 occupancy. So hydrogen atoms could not be fixed on carbon atom with agreeable geometry.The pyrrolidine ring system is found in a vast variety of compounds displaying an impressive range of biological activities (Babu et al., 2012). Optically active pyrrolidines have been used as intermediates, chiral ligands or auxiliaries in controlled
(Savithri et al., 2014). Pyrrolidine compounds are reported to exhibit antimicrobial, antifungal (Govind et al.,2003), anti-influenza virus A (Stylianakis et al., 2003), anti-inflammatory and antitumor (Li & Xu, 2004) activities. They also inhibit retroviral [i.e., human immunodeficiency virus type 1 (HIV-1)], cellular DNA polymerases, protein kinases (Bellina & Rossi, 2006). They also act as antidepressant agents (Wróbel et al., 2013), antibiotics (Nirmala et al., 2009), anticonvulsant, sphingosine-1-phosphate (S1P) receptor agonists, malic enzyme inhibitors, ketoamide-based cathepsin K inhibitors and human melanocortin-4 receptor agonists (Babu et al., 2012). Quinoline derivatives have been synthesized and explored for their analgesic activity, anti-allergetic properties and in treating Alzheimer's disease (AD). They are also reported for their anticancer, antitinephritic, antitumor, anti-inflammatory (Shivaraj et al., 2013), antimalarial, anti-bacterial and antifungal activities (Marella et al., 2013).The molecular structure of the title compound is shown in Fig. 1. In the molecule there is a short intramolecular O—H···N contact forming an S(5) ring motif (Fig. 1 and Table 1). The conformation of the central 1-methyl pyrrolidine ring (C12/C14/N2/C26/C27) is best described as an
with atom N2 as the flap and displaced by 0.585 (2) Å from the plane through the other four atoms. The cyclopentane ring adopts a twist conformation on the C10—C11 bond and the cyclohexane ring has an with atom C11 as the flap and displaced by 0.854 (2) Å from the mean plane through the other five atoms. The quinoline ring system (C1–C9/N1) and the acenaphthylene ring system (C14–C25) adopt almost planar conformations, with the maximum deviations being 0.069 (2) Å for atom C8 in the quinoline ring system and 0.128 (2) Å for atom C14 in the acenaphthylene ring system. Chlorine atom Cl1 is displaced from the benzene ring (C28–C33) to which it is attached by 0.0164 (8) Å. The mean plane of the pyrrolidine ring makes dihedral angles of 40.87 (12), 67.89 (11), 81.86 (9) and 70.86 (12)° with the mean planes of the cyclopentane, cyclohexane, acenaphthylene and chlorobenzene rings, respectively. The quinoline ring system is inclined to the naphthalene ring system by 54.14 (6)°.In the crystal, there is a disordered and partially occupied ethan-1,2-diol solvent molecule present, located about an inversion centre, which links the title molecules via O—H···O and C—H···O hydrogen bonds, forming chains propagating along the a-axis direction. (Table 1 and Fig. 2).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 30% probability level. The N—H···O contact is shown as a thin dashed lines(see Table 1). | |
Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1). For clarity, only one position of the disordered and partially occupied ethan-1,2-diol solvent molecule is shown. |
C34H25ClN2O2·0.5CH4O | Z = 2 |
Mr = 544.53 | F(000) = 569 |
Triclinic, P1 | Dx = 1.337 Mg m−3 |
a = 10.3848 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4306 (3) Å | Cell parameters from 5568 reflections |
c = 14.4513 (4) Å | θ = 1.5–26.5° |
α = 69.394 (1)° | µ = 0.18 mm−1 |
β = 72.388 (1)° | T = 293 K |
γ = 70.871 (1)° | Block, colourless |
V = 1352.92 (7) Å3 | 0.22 × 0.16 × 0.12 mm |
Bruker SMART APEXII area-detector diffractometer | 4425 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
ω and φ scans | θmax = 26.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −13→13 |
Tmin = 0.966, Tmax = 0.978 | k = −13→12 |
20173 measured reflections | l = −18→15 |
5563 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.1116P)2 + 0.2946P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5563 reflections | Δρmax = 0.66 e Å−3 |
386 parameters | Δρmin = −0.44 e Å−3 |
3 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (4) |
C34H25ClN2O2·0.5CH4O | γ = 70.871 (1)° |
Mr = 544.53 | V = 1352.92 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.3848 (3) Å | Mo Kα radiation |
b = 10.4306 (3) Å | µ = 0.18 mm−1 |
c = 14.4513 (4) Å | T = 293 K |
α = 69.394 (1)° | 0.22 × 0.16 × 0.12 mm |
β = 72.388 (1)° |
Bruker SMART APEXII area-detector diffractometer | 5563 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 4425 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.978 | Rint = 0.019 |
20173 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 3 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.66 e Å−3 |
5563 reflections | Δρmin = −0.44 e Å−3 |
386 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.72400 (8) | −0.21816 (7) | 0.66553 (5) | 0.0903 (3) | |
O1 | 0.58561 (15) | 0.35178 (15) | 0.13530 (11) | 0.0563 (4) | |
O2 | 0.67317 (16) | 0.59399 (18) | 0.39571 (11) | 0.0570 (4) | |
H2O | 0.743 (3) | 0.520 (3) | 0.405 (2) | 0.092 (10)* | |
N1 | 0.27834 (16) | 0.70993 (17) | 0.28663 (12) | 0.0470 (4) | |
N2 | 0.84974 (15) | 0.43617 (16) | 0.27419 (13) | 0.0472 (4) | |
C1 | 0.19626 (18) | 0.75391 (19) | 0.21738 (14) | 0.0463 (4) | |
C2 | 0.0684 (2) | 0.8558 (2) | 0.23152 (19) | 0.0626 (6) | |
H2 | 0.0427 | 0.8932 | 0.2860 | 0.075* | |
C3 | −0.0175 (2) | 0.8992 (3) | 0.1653 (2) | 0.0702 (6) | |
H3 | −0.1023 | 0.9648 | 0.1760 | 0.084* | |
C4 | 0.0197 (2) | 0.8469 (2) | 0.08168 (19) | 0.0634 (6) | |
H4 | −0.0402 | 0.8778 | 0.0374 | 0.076* | |
C5 | 0.1428 (2) | 0.7514 (2) | 0.06473 (17) | 0.0549 (5) | |
H5 | 0.1686 | 0.7199 | 0.0074 | 0.066* | |
C6 | 0.23238 (19) | 0.69925 (19) | 0.13379 (14) | 0.0447 (4) | |
C7 | 0.35429 (19) | 0.58980 (19) | 0.12598 (14) | 0.0440 (4) | |
H7 | 0.3811 | 0.5501 | 0.0725 | 0.053* | |
C8 | 0.43319 (17) | 0.54205 (18) | 0.19758 (13) | 0.0391 (4) | |
C9 | 0.39312 (17) | 0.60925 (18) | 0.27596 (13) | 0.0401 (4) | |
C10 | 0.48274 (18) | 0.55891 (19) | 0.35269 (13) | 0.0423 (4) | |
H10 | 0.4294 | 0.5842 | 0.4151 | 0.051* | |
C11 | 0.54119 (19) | 0.39953 (19) | 0.37358 (13) | 0.0448 (4) | |
H11A | 0.4683 | 0.3517 | 0.3885 | 0.054* | |
H11B | 0.5893 | 0.3612 | 0.4292 | 0.054* | |
C12 | 0.64345 (17) | 0.38709 (17) | 0.27249 (13) | 0.0393 (4) | |
C13 | 0.55758 (18) | 0.41925 (18) | 0.19547 (13) | 0.0402 (4) | |
C14 | 0.71568 (17) | 0.51111 (17) | 0.24384 (13) | 0.0388 (4) | |
C15 | 0.61918 (18) | 0.61159 (19) | 0.31166 (13) | 0.0414 (4) | |
C16 | 0.60670 (18) | 0.75928 (19) | 0.24087 (14) | 0.0434 (4) | |
C17 | 0.5485 (2) | 0.8893 (2) | 0.25675 (18) | 0.0569 (5) | |
H17 | 0.5065 | 0.8983 | 0.3216 | 0.068* | |
C18 | 0.5533 (3) | 1.0098 (2) | 0.1728 (2) | 0.0694 (7) | |
H18 | 0.5162 | 1.0987 | 0.1837 | 0.083* | |
C19 | 0.6103 (2) | 1.0011 (2) | 0.0763 (2) | 0.0663 (6) | |
H19 | 0.6108 | 1.0833 | 0.0230 | 0.080* | |
C20 | 0.66844 (19) | 0.8680 (2) | 0.05661 (16) | 0.0525 (5) | |
C21 | 0.66716 (17) | 0.74950 (18) | 0.14204 (14) | 0.0412 (4) | |
C22 | 0.72521 (17) | 0.60975 (18) | 0.13645 (13) | 0.0410 (4) | |
C23 | 0.7808 (2) | 0.5866 (2) | 0.04288 (15) | 0.0538 (5) | |
H23 | 0.8193 | 0.4952 | 0.0367 | 0.065* | |
C24 | 0.7782 (2) | 0.7046 (3) | −0.04387 (16) | 0.0638 (6) | |
H24 | 0.8132 | 0.6890 | −0.1074 | 0.077* | |
C25 | 0.7264 (2) | 0.8401 (3) | −0.03804 (17) | 0.0638 (6) | |
H25 | 0.7294 | 0.9148 | −0.0969 | 0.077* | |
C26 | 0.8953 (2) | 0.3053 (2) | 0.24478 (17) | 0.0559 (5) | |
H26A | 0.9666 | 0.2373 | 0.2800 | 0.067* | |
H26B | 0.9325 | 0.3234 | 0.1725 | 0.067* | |
C27 | 0.76447 (19) | 0.25010 (19) | 0.27486 (15) | 0.0463 (4) | |
H27 | 0.7655 | 0.2117 | 0.2217 | 0.056* | |
C28 | 0.75497 (19) | 0.13475 (19) | 0.37432 (15) | 0.0458 (4) | |
C29 | 0.7023 (2) | 0.0238 (2) | 0.38486 (16) | 0.0543 (5) | |
H29 | 0.6719 | 0.0224 | 0.3310 | 0.065* | |
C30 | 0.6933 (2) | −0.0857 (2) | 0.47347 (18) | 0.0632 (6) | |
H30 | 0.6583 | −0.1601 | 0.4788 | 0.076* | |
C31 | 0.7367 (2) | −0.0827 (2) | 0.55281 (17) | 0.0589 (5) | |
C32 | 0.7896 (3) | 0.0258 (3) | 0.5450 (2) | 0.0720 (7) | |
H32 | 0.8186 | 0.0273 | 0.5994 | 0.086* | |
C33 | 0.7997 (3) | 0.1334 (2) | 0.45517 (19) | 0.0653 (6) | |
H33 | 0.8373 | 0.2060 | 0.4495 | 0.078* | |
C34 | 0.9561 (2) | 0.5167 (2) | 0.23428 (18) | 0.0600 (5) | |
H34A | 0.9804 | 0.5378 | 0.1619 | 0.090* | |
H34B | 1.0375 | 0.4619 | 0.2615 | 0.090* | |
H34C | 0.9203 | 0.6033 | 0.2533 | 0.090* | |
O3 | 0.1064 (5) | 0.6190 (5) | 0.4934 (3) | 0.0885 (11) | 0.5 |
H3O | 0.1791 | 0.6313 | 0.4529 | 0.133* | 0.5 |
C35A | 0.0517 (15) | 0.5293 (19) | 0.4674 (10) | 0.067 (3) | 0.25 |
H35A | 0.0192 | 0.5837 | 0.4053 | 0.080* | 0.25 |
H35B | 0.1295 | 0.4524 | 0.4515 | 0.080* | 0.25 |
C35B | −0.0043 (14) | 0.5733 (13) | 0.4846 (11) | 0.058 (3) | 0.25 |
H35C | −0.0904 | 0.6180 | 0.5235 | 0.069* | 0.25 |
H35D | −0.0121 | 0.6094 | 0.4143 | 0.069* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1073 (6) | 0.0674 (4) | 0.0697 (4) | −0.0169 (4) | −0.0261 (4) | 0.0138 (3) |
O1 | 0.0633 (8) | 0.0546 (8) | 0.0575 (8) | −0.0072 (6) | −0.0138 (7) | −0.0295 (7) |
O2 | 0.0588 (8) | 0.0722 (10) | 0.0482 (8) | −0.0098 (8) | −0.0204 (6) | −0.0250 (7) |
N1 | 0.0430 (8) | 0.0512 (9) | 0.0457 (9) | −0.0099 (7) | −0.0042 (6) | −0.0181 (7) |
N2 | 0.0390 (7) | 0.0422 (8) | 0.0555 (9) | −0.0108 (6) | −0.0091 (6) | −0.0082 (7) |
C1 | 0.0415 (9) | 0.0444 (10) | 0.0504 (10) | −0.0140 (7) | −0.0059 (8) | −0.0103 (8) |
C2 | 0.0523 (11) | 0.0584 (13) | 0.0701 (14) | −0.0041 (9) | −0.0108 (10) | −0.0203 (11) |
C3 | 0.0510 (11) | 0.0571 (13) | 0.0899 (18) | −0.0011 (10) | −0.0205 (11) | −0.0124 (12) |
C4 | 0.0590 (12) | 0.0553 (12) | 0.0738 (15) | −0.0175 (10) | −0.0283 (11) | −0.0005 (11) |
C5 | 0.0596 (11) | 0.0518 (11) | 0.0570 (12) | −0.0212 (9) | −0.0208 (9) | −0.0056 (9) |
C6 | 0.0456 (9) | 0.0437 (9) | 0.0459 (10) | −0.0189 (7) | −0.0098 (7) | −0.0066 (7) |
C7 | 0.0478 (9) | 0.0475 (10) | 0.0411 (9) | −0.0172 (8) | −0.0078 (7) | −0.0142 (8) |
C8 | 0.0394 (8) | 0.0415 (9) | 0.0371 (9) | −0.0151 (7) | −0.0025 (7) | −0.0119 (7) |
C9 | 0.0389 (8) | 0.0440 (9) | 0.0370 (8) | −0.0149 (7) | −0.0007 (7) | −0.0129 (7) |
C10 | 0.0433 (9) | 0.0513 (10) | 0.0318 (8) | −0.0129 (7) | −0.0017 (7) | −0.0152 (7) |
C11 | 0.0482 (9) | 0.0481 (10) | 0.0351 (9) | −0.0165 (8) | −0.0033 (7) | −0.0084 (7) |
C12 | 0.0410 (8) | 0.0356 (8) | 0.0389 (9) | −0.0117 (7) | −0.0038 (7) | −0.0098 (7) |
C13 | 0.0445 (9) | 0.0410 (9) | 0.0362 (8) | −0.0172 (7) | −0.0010 (7) | −0.0124 (7) |
C14 | 0.0397 (8) | 0.0374 (9) | 0.0382 (9) | −0.0111 (7) | −0.0056 (7) | −0.0103 (7) |
C15 | 0.0450 (9) | 0.0469 (10) | 0.0377 (9) | −0.0126 (7) | −0.0100 (7) | −0.0161 (7) |
C16 | 0.0414 (9) | 0.0432 (9) | 0.0534 (10) | −0.0119 (7) | −0.0157 (7) | −0.0166 (8) |
C17 | 0.0564 (11) | 0.0514 (11) | 0.0766 (14) | −0.0086 (9) | −0.0226 (10) | −0.0311 (10) |
C18 | 0.0670 (13) | 0.0395 (11) | 0.111 (2) | −0.0067 (9) | −0.0369 (14) | −0.0227 (12) |
C19 | 0.0595 (12) | 0.0427 (11) | 0.0920 (18) | −0.0165 (9) | −0.0333 (12) | 0.0046 (11) |
C20 | 0.0419 (9) | 0.0486 (10) | 0.0616 (12) | −0.0155 (8) | −0.0189 (8) | 0.0015 (9) |
C21 | 0.0379 (8) | 0.0404 (9) | 0.0475 (10) | −0.0138 (7) | −0.0127 (7) | −0.0080 (7) |
C22 | 0.0396 (8) | 0.0430 (9) | 0.0384 (9) | −0.0147 (7) | −0.0039 (7) | −0.0087 (7) |
C23 | 0.0514 (10) | 0.0591 (12) | 0.0447 (10) | −0.0176 (9) | 0.0028 (8) | −0.0147 (9) |
C24 | 0.0538 (11) | 0.0867 (17) | 0.0384 (10) | −0.0223 (11) | 0.0010 (8) | −0.0075 (10) |
C25 | 0.0507 (11) | 0.0717 (15) | 0.0512 (12) | −0.0220 (10) | −0.0124 (9) | 0.0112 (10) |
C26 | 0.0446 (10) | 0.0438 (10) | 0.0668 (13) | −0.0077 (8) | −0.0038 (9) | −0.0108 (9) |
C27 | 0.0471 (9) | 0.0386 (9) | 0.0506 (10) | −0.0090 (7) | −0.0086 (8) | −0.0123 (8) |
C28 | 0.0450 (9) | 0.0375 (9) | 0.0540 (10) | −0.0081 (7) | −0.0149 (8) | −0.0102 (8) |
C29 | 0.0618 (11) | 0.0492 (11) | 0.0576 (12) | −0.0204 (9) | −0.0198 (9) | −0.0096 (9) |
C30 | 0.0726 (14) | 0.0496 (11) | 0.0693 (14) | −0.0265 (10) | −0.0207 (11) | −0.0036 (10) |
C31 | 0.0583 (12) | 0.0464 (11) | 0.0597 (12) | −0.0074 (9) | −0.0179 (10) | −0.0012 (9) |
C32 | 0.0918 (17) | 0.0656 (14) | 0.0678 (15) | −0.0188 (13) | −0.0444 (13) | −0.0069 (11) |
C33 | 0.0827 (15) | 0.0525 (12) | 0.0742 (15) | −0.0258 (11) | −0.0381 (12) | −0.0072 (10) |
C34 | 0.0461 (10) | 0.0555 (12) | 0.0762 (15) | −0.0183 (9) | −0.0143 (10) | −0.0096 (10) |
O3 | 0.105 (3) | 0.113 (3) | 0.058 (2) | −0.045 (3) | −0.0189 (19) | −0.018 (2) |
C35A | 0.076 (8) | 0.089 (11) | 0.057 (6) | −0.049 (8) | 0.009 (7) | −0.039 (7) |
C35B | 0.061 (7) | 0.045 (7) | 0.060 (8) | 0.005 (5) | −0.026 (6) | −0.012 (5) |
Cl1—C31 | 1.743 (2) | C18—C19 | 1.364 (4) |
O1—C13 | 1.216 (2) | C18—H18 | 0.9300 |
O2—C15 | 1.418 (2) | C19—C20 | 1.413 (3) |
O2—H2O | 0.87 (3) | C19—H19 | 0.9300 |
N1—C9 | 1.315 (2) | C20—C21 | 1.407 (3) |
N1—C1 | 1.369 (2) | C20—C25 | 1.409 (3) |
N2—C26 | 1.460 (3) | C21—C22 | 1.404 (2) |
N2—C34 | 1.463 (2) | C22—C23 | 1.373 (3) |
N2—C14 | 1.469 (2) | C23—C24 | 1.414 (3) |
C1—C6 | 1.413 (3) | C23—H23 | 0.9300 |
C1—C2 | 1.414 (3) | C24—C25 | 1.361 (4) |
C2—C3 | 1.365 (3) | C24—H24 | 0.9300 |
C2—H2 | 0.9300 | C25—H25 | 0.9300 |
C3—C4 | 1.396 (4) | C26—C27 | 1.531 (3) |
C3—H3 | 0.9300 | C26—H26A | 0.9700 |
C4—C5 | 1.354 (3) | C26—H26B | 0.9700 |
C4—H4 | 0.9300 | C27—C28 | 1.516 (3) |
C5—C6 | 1.416 (3) | C27—H27 | 0.9800 |
C5—H5 | 0.9300 | C28—C33 | 1.376 (3) |
C6—C7 | 1.406 (3) | C28—C29 | 1.379 (3) |
C7—C8 | 1.369 (3) | C29—C30 | 1.386 (3) |
C7—H7 | 0.9300 | C29—H29 | 0.9300 |
C8—C9 | 1.425 (2) | C30—C31 | 1.366 (3) |
C8—C13 | 1.493 (2) | C30—H30 | 0.9300 |
C9—C10 | 1.505 (2) | C31—C32 | 1.370 (3) |
C10—C11 | 1.523 (3) | C32—C33 | 1.387 (3) |
C10—C15 | 1.560 (2) | C32—H32 | 0.9300 |
C10—H10 | 0.9800 | C33—H33 | 0.9300 |
C11—C12 | 1.544 (2) | C34—H34A | 0.9600 |
C11—H11A | 0.9700 | C34—H34B | 0.9600 |
C11—H11B | 0.9700 | C34—H34C | 0.9600 |
C12—C13 | 1.513 (2) | O3—C35B | 1.434 (15) |
C12—C27 | 1.561 (2) | O3—C35A | 1.437 (13) |
C12—C14 | 1.574 (2) | O3—H3O | 0.8200 |
C14—C22 | 1.525 (2) | C35A—C35Ai | 1.35 (3) |
C14—C15 | 1.582 (2) | C35A—H35A | 0.9700 |
C15—C16 | 1.509 (2) | C35A—H35B | 0.9700 |
C16—C17 | 1.362 (3) | C35B—C35Bi | 1.41 (3) |
C16—C21 | 1.401 (3) | C35B—H35C | 0.9700 |
C17—C18 | 1.409 (3) | C35B—H35D | 0.9700 |
C17—H17 | 0.9300 | ||
C15—O2—H2O | 112 (2) | C19—C18—H18 | 118.8 |
C9—N1—C1 | 118.06 (15) | C17—C18—H18 | 118.8 |
C26—N2—C34 | 112.47 (16) | C18—C19—C20 | 120.5 (2) |
C26—N2—C14 | 105.83 (15) | C18—C19—H19 | 119.7 |
C34—N2—C14 | 115.37 (15) | C20—C19—H19 | 119.7 |
N1—C1—C6 | 122.77 (17) | C21—C20—C25 | 116.39 (19) |
N1—C1—C2 | 118.60 (18) | C21—C20—C19 | 115.8 (2) |
C6—C1—C2 | 118.62 (19) | C25—C20—C19 | 127.8 (2) |
C3—C2—C1 | 120.1 (2) | C16—C21—C22 | 113.43 (16) |
C3—C2—H2 | 120.0 | C16—C21—C20 | 123.31 (17) |
C1—C2—H2 | 120.0 | C22—C21—C20 | 123.25 (18) |
C2—C3—C4 | 121.2 (2) | C23—C22—C21 | 118.69 (17) |
C2—C3—H3 | 119.4 | C23—C22—C14 | 132.84 (17) |
C4—C3—H3 | 119.4 | C21—C22—C14 | 108.43 (15) |
C5—C4—C3 | 120.3 (2) | C22—C23—C24 | 118.6 (2) |
C5—C4—H4 | 119.9 | C22—C23—H23 | 120.7 |
C3—C4—H4 | 119.9 | C24—C23—H23 | 120.7 |
C4—C5—C6 | 120.3 (2) | C25—C24—C23 | 122.5 (2) |
C4—C5—H5 | 119.8 | C25—C24—H24 | 118.7 |
C6—C5—H5 | 119.8 | C23—C24—H24 | 118.7 |
C7—C6—C1 | 117.53 (17) | C24—C25—C20 | 120.43 (19) |
C7—C6—C5 | 122.98 (18) | C24—C25—H25 | 119.8 |
C1—C6—C5 | 119.43 (18) | C20—C25—H25 | 119.8 |
C8—C7—C6 | 119.54 (17) | N2—C26—C27 | 105.35 (15) |
C8—C7—H7 | 120.2 | N2—C26—H26A | 110.7 |
C6—C7—H7 | 120.2 | C27—C26—H26A | 110.7 |
C7—C8—C9 | 119.00 (16) | N2—C26—H26B | 110.7 |
C7—C8—C13 | 120.79 (16) | C27—C26—H26B | 110.7 |
C9—C8—C13 | 120.20 (15) | H26A—C26—H26B | 108.8 |
N1—C9—C8 | 122.92 (16) | C28—C27—C26 | 113.54 (16) |
N1—C9—C10 | 118.33 (15) | C28—C27—C12 | 115.08 (15) |
C8—C9—C10 | 118.69 (15) | C26—C27—C12 | 103.16 (14) |
C9—C10—C11 | 108.97 (14) | C28—C27—H27 | 108.2 |
C9—C10—C15 | 113.30 (14) | C26—C27—H27 | 108.2 |
C11—C10—C15 | 101.39 (14) | C12—C27—H27 | 108.2 |
C9—C10—H10 | 110.9 | C33—C28—C29 | 117.68 (18) |
C11—C10—H10 | 110.9 | C33—C28—C27 | 122.91 (17) |
C15—C10—H10 | 110.9 | C29—C28—C27 | 119.39 (17) |
C10—C11—C12 | 101.90 (13) | C28—C29—C30 | 121.9 (2) |
C10—C11—H11A | 111.4 | C28—C29—H29 | 119.1 |
C12—C11—H11A | 111.4 | C30—C29—H29 | 119.1 |
C10—C11—H11B | 111.4 | C31—C30—C29 | 118.96 (19) |
C12—C11—H11B | 111.4 | C31—C30—H30 | 120.5 |
H11A—C11—H11B | 109.3 | C29—C30—H30 | 120.5 |
C13—C12—C11 | 107.57 (14) | C30—C31—C32 | 120.8 (2) |
C13—C12—C27 | 113.75 (15) | C30—C31—Cl1 | 119.69 (17) |
C11—C12—C27 | 117.37 (15) | C32—C31—Cl1 | 119.56 (18) |
C13—C12—C14 | 108.77 (13) | C31—C32—C33 | 119.4 (2) |
C11—C12—C14 | 102.87 (13) | C31—C32—H32 | 120.3 |
C27—C12—C14 | 105.68 (13) | C33—C32—H32 | 120.3 |
O1—C13—C8 | 121.20 (16) | C28—C33—C32 | 121.3 (2) |
O1—C13—C12 | 123.65 (16) | C28—C33—H33 | 119.4 |
C8—C13—C12 | 115.15 (14) | C32—C33—H33 | 119.4 |
N2—C14—C22 | 115.32 (13) | N2—C34—H34A | 109.5 |
N2—C14—C12 | 102.19 (13) | N2—C34—H34B | 109.5 |
C22—C14—C12 | 117.84 (14) | H34A—C34—H34B | 109.5 |
N2—C14—C15 | 112.19 (14) | N2—C34—H34C | 109.5 |
C22—C14—C15 | 103.50 (13) | H34A—C34—H34C | 109.5 |
C12—C14—C15 | 105.66 (13) | H34B—C34—H34C | 109.5 |
O2—C15—C16 | 112.06 (14) | C35A—O3—H3O | 109.5 |
O2—C15—C10 | 107.96 (14) | C35Ai—C35A—O3 | 121.1 (13) |
C16—C15—C10 | 115.87 (14) | C35Ai—C35A—H35A | 107.1 |
O2—C15—C14 | 112.86 (14) | O3—C35A—H35A | 107.1 |
C16—C15—C14 | 104.98 (13) | C35Ai—C35A—H35B | 107.1 |
C10—C15—C14 | 102.84 (13) | O3—C35A—H35B | 107.1 |
C17—C16—C21 | 119.23 (18) | H35A—C35A—H35B | 106.8 |
C17—C16—C15 | 132.34 (19) | C35Bi—C35B—O3 | 118.6 (12) |
C21—C16—C15 | 108.42 (15) | C35Bi—C35B—H35C | 107.7 |
C16—C17—C18 | 118.6 (2) | O3—C35B—H35C | 107.7 |
C16—C17—H17 | 120.7 | C35Bi—C35B—H35D | 107.7 |
C18—C17—H17 | 120.7 | O3—C35B—H35D | 107.7 |
C19—C18—C17 | 122.5 (2) | H35C—C35B—H35D | 107.1 |
C9—N1—C1—C6 | −2.3 (3) | N2—C14—C15—C16 | 114.11 (14) |
C9—N1—C1—C2 | 176.14 (17) | C22—C14—C15—C16 | −10.84 (16) |
N1—C1—C2—C3 | −178.35 (19) | C12—C14—C15—C16 | −135.32 (13) |
C6—C1—C2—C3 | 0.1 (3) | N2—C14—C15—C10 | −124.27 (14) |
C1—C2—C3—C4 | −1.4 (4) | C22—C14—C15—C10 | 110.77 (14) |
C2—C3—C4—C5 | 0.0 (3) | C12—C14—C15—C10 | −13.71 (17) |
C3—C4—C5—C6 | 2.6 (3) | O2—C15—C16—C17 | −50.2 (3) |
N1—C1—C6—C7 | 3.5 (3) | C10—C15—C16—C17 | 74.3 (2) |
C2—C1—C6—C7 | −174.87 (17) | C14—C15—C16—C17 | −173.05 (19) |
N1—C1—C6—C5 | −179.23 (16) | O2—C15—C16—C21 | 131.07 (15) |
C2—C1—C6—C5 | 2.4 (3) | C10—C15—C16—C21 | −104.43 (16) |
C4—C5—C6—C7 | 173.33 (18) | C14—C15—C16—C21 | 8.23 (17) |
C4—C5—C6—C1 | −3.7 (3) | C21—C16—C17—C18 | −1.0 (3) |
C1—C6—C7—C8 | −0.8 (2) | C15—C16—C17—C18 | −179.61 (18) |
C5—C6—C7—C8 | −177.90 (16) | C16—C17—C18—C19 | 2.0 (3) |
C6—C7—C8—C9 | −2.9 (2) | C17—C18—C19—C20 | −0.3 (3) |
C6—C7—C8—C13 | 175.65 (15) | C18—C19—C20—C21 | −2.1 (3) |
C1—N1—C9—C8 | −1.7 (2) | C18—C19—C20—C25 | 177.5 (2) |
C1—N1—C9—C10 | −179.11 (15) | C17—C16—C21—C22 | 179.04 (16) |
C7—C8—C9—N1 | 4.4 (2) | C15—C16—C21—C22 | −2.0 (2) |
C13—C8—C9—N1 | −174.18 (15) | C17—C16—C21—C20 | −1.5 (3) |
C7—C8—C9—C10 | −178.25 (15) | C15—C16—C21—C20 | 177.38 (15) |
C13—C8—C9—C10 | 3.2 (2) | C25—C20—C21—C16 | −176.57 (16) |
N1—C9—C10—C11 | 142.05 (15) | C19—C20—C21—C16 | 3.0 (3) |
C8—C9—C10—C11 | −35.4 (2) | C25—C20—C21—C22 | 2.8 (3) |
N1—C9—C10—C15 | −105.91 (17) | C19—C20—C21—C22 | −177.60 (17) |
C8—C9—C10—C15 | 76.61 (19) | C16—C21—C22—C23 | 176.50 (16) |
C9—C10—C11—C12 | 68.81 (16) | C20—C21—C22—C23 | −2.9 (3) |
C15—C10—C11—C12 | −50.91 (16) | C16—C21—C22—C14 | −5.43 (19) |
C10—C11—C12—C13 | −73.10 (16) | C20—C21—C22—C14 | 175.16 (15) |
C10—C11—C12—C27 | 157.13 (15) | N2—C14—C22—C23 | 64.8 (3) |
C10—C11—C12—C14 | 41.64 (17) | C12—C14—C22—C23 | −56.1 (3) |
C7—C8—C13—O1 | −5.8 (2) | C15—C14—C22—C23 | −172.29 (19) |
C9—C8—C13—O1 | 172.71 (16) | N2—C14—C22—C21 | −112.90 (16) |
C7—C8—C13—C12 | 174.08 (14) | C12—C14—C22—C21 | 126.16 (15) |
C9—C8—C13—C12 | −7.4 (2) | C15—C14—C22—C21 | 10.01 (17) |
C11—C12—C13—O1 | −137.17 (17) | C21—C22—C23—C24 | 0.5 (3) |
C27—C12—C13—O1 | −5.4 (2) | C14—C22—C23—C24 | −176.98 (18) |
C14—C12—C13—O1 | 112.08 (18) | C22—C23—C24—C25 | 1.9 (3) |
C11—C12—C13—C8 | 42.91 (18) | C23—C24—C25—C20 | −2.0 (3) |
C27—C12—C13—C8 | 174.68 (13) | C21—C20—C25—C24 | −0.3 (3) |
C14—C12—C13—C8 | −67.84 (17) | C19—C20—C25—C24 | −179.9 (2) |
C26—N2—C14—C22 | −89.00 (17) | C34—N2—C26—C27 | −169.53 (17) |
C34—N2—C14—C22 | 36.0 (2) | C14—N2—C26—C27 | −42.71 (19) |
C26—N2—C14—C12 | 40.12 (17) | N2—C26—C27—C28 | −99.30 (18) |
C34—N2—C14—C12 | 165.16 (16) | N2—C26—C27—C12 | 25.9 (2) |
C26—N2—C14—C15 | 152.85 (15) | C13—C12—C27—C28 | −118.14 (16) |
C34—N2—C14—C15 | −82.11 (19) | C11—C12—C27—C28 | 8.7 (2) |
C13—C12—C14—N2 | −145.22 (14) | C14—C12—C27—C28 | 122.61 (16) |
C11—C12—C14—N2 | 100.90 (15) | C13—C12—C27—C26 | 117.64 (17) |
C27—C12—C14—N2 | −22.73 (17) | C11—C12—C27—C26 | −115.54 (18) |
C13—C12—C14—C22 | −17.71 (19) | C14—C12—C27—C26 | −1.61 (19) |
C11—C12—C14—C22 | −131.58 (15) | C26—C27—C28—C33 | 36.1 (3) |
C27—C12—C14—C22 | 104.78 (17) | C12—C27—C28—C33 | −82.5 (2) |
C13—C12—C14—C15 | 97.27 (15) | C26—C27—C28—C29 | −142.47 (19) |
C11—C12—C14—C15 | −16.61 (17) | C12—C27—C28—C29 | 99.0 (2) |
C27—C12—C14—C15 | −140.24 (14) | C33—C28—C29—C30 | 0.3 (3) |
C9—C10—C15—O2 | 163.29 (14) | C27—C28—C29—C30 | 178.93 (19) |
C11—C10—C15—O2 | −80.11 (16) | C28—C29—C30—C31 | 0.6 (3) |
C9—C10—C15—C16 | 36.7 (2) | C29—C30—C31—C32 | −0.7 (4) |
C11—C10—C15—C16 | 153.30 (15) | C29—C30—C31—Cl1 | 179.10 (17) |
C9—C10—C15—C14 | −77.19 (17) | C30—C31—C32—C33 | −0.3 (4) |
C11—C10—C15—C14 | 39.40 (16) | Cl1—C31—C32—C33 | 179.97 (19) |
N2—C14—C15—O2 | −8.21 (19) | C29—C28—C33—C32 | −1.3 (3) |
C22—C14—C15—O2 | −133.17 (15) | C27—C28—C33—C32 | −179.8 (2) |
C12—C14—C15—O2 | 102.35 (16) | C31—C32—C33—C28 | 1.3 (4) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···N2 | 0.87 (3) | 2.20 (3) | 2.695 (2) | 116 (2) |
O3—H3O···N1 | 0.82 | 2.28 | 2.984 (4) | 145 |
O2—H2O···O3ii | 0.87 (3) | 2.26 (3) | 3.021 (5) | 146 (2) |
C33—H33···O3ii | 0.93 | 2.53 | 3.408 (6) | 157 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···N2 | 0.87 (3) | 2.20 (3) | 2.695 (2) | 116 (2) |
O3—H3O···N1 | 0.82 | 2.28 | 2.984 (4) | 145 |
O2—H2O···O3i | 0.87 (3) | 2.26 (3) | 3.021 (5) | 146 (2) |
C33—H33···O3i | 0.93 | 2.53 | 3.408 (6) | 157 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C34H25ClN2O2·0.5CH4O |
Mr | 544.53 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.3848 (3), 10.4306 (3), 14.4513 (4) |
α, β, γ (°) | 69.394 (1), 72.388 (1), 70.871 (1) |
V (Å3) | 1352.92 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.22 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.966, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20173, 5563, 4425 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.629 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.178, 1.05 |
No. of reflections | 5563 |
No. of parameters | 386 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.66, −0.44 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.
References
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