organic compounds
1-Benzyl-5-chloroindoline-2,3-dione
aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Iimmouzzer, BP 2202, Fez, Morocco, bLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco, cUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France, and dDépartement de chimie, Faculté des Sciences, Université Ibn Zohr, BP 8106, Cité Dakhla, 80000 Agadir, Morocco
*Correspondence e-mail: haoudi_amal@yahoo.fr
The title compound, C15H10ClNO2, crystallizes with two molecules (A and B) in the which have almost identical conformations (r.m.s. overlay fit = 0.057 Å). In molecule A, the dihedral angle between the indole ring system (r.m.s. deviation = 0.025 Å) and the phenyl group is 71.39 (8)°. Equivalent data for molecule B are 0.023 Å and 71.43 (9)°. In the crystal, the A and B molecules are linked by a C—H⋯O hydrogen bond and aromatic π–π stacking is also observed [shortest centroid–centroid separation = 3.5810 (11) Å].
Keywords: crystal structure; indoline; hydrogen bonding; π–π stacking.
CCDC reference: 1482161
Structure description
5-Chloro-indoline-2,3-dione has been used as a starting material for a variety of chemical reactions such as 1,3-dipolar cycloaddition (Ranjith Kumar et al., 2009) and in the synthesis of several heterocyclic systems (Kharbach et al., 2016). As part of our studies in this area, the synthesis and structure of the title compound, C15H10ClNO2, are now described.
The title compound crystallizes with two molecules (A and B) in the (Fig. 1). In each molecule, the indoline ring system is almost planar, with the largest deviation from the mean plane being 0.0230 (17) Å in molecule A and 0.0418 (18) Å in molecule B. The conformation of the two molecules are almost identical, as indicated by the angles of inclination of the indole moiety with respect to the benzyl ring system, the dihedral angles being 71.43 (9) and 71.39 (8)° in molecules A and B, respectively.
In the crystal, the A and B molecules are linked by a C—H⋯O hydrogen bond (Table 1) and aromatic π–π stacking is also observed [shortest centroid–centroid separation = 3.5810 (11) Å].
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Synthesis and crystallization
To a solution of 5-chloro-1H-indole-2,3-dione (0.4 g, 2,20 mmol) in N,N-dimethylformamide (25 ml), were added (0.5 g, 3,3 mmol) K2CO3, tetra-n-butylammonium fluoride (0.1 g, 0.3 mmol), and benzyl chloride (0.27 ml, 2,42 mmol)·The reaction mixture was stirred for 48 h at room temperature. After filtration the solution was evaporated under reduced pressure. The residue obtained was recrystallized from ethanol solution to afford the title compound as red crystals in a yield of 72% (m.p. 413 K)
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1482161
10.1107/S2414314616008543/hb4051sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616008543/hb4051Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616008543/hb4051Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C15H10ClNO2 | F(000) = 1120 |
Mr = 271.69 | Dx = 1.400 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.4576 (2) Å | Cell parameters from 9947 reflections |
b = 27.6646 (11) Å | θ = 2.4–25.1° |
c = 20.9530 (8) Å | µ = 0.29 mm−1 |
β = 93.870 (2)° | T = 296 K |
V = 2577.98 (18) Å3 | Block, red |
Z = 8 | 0.32 × 0.26 × 0.19 mm |
Bruker APEXII CCD diffractometer | 4206 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.034 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 28.3°, θmin = 2.4° |
Tmin = 0.694, Tmax = 0.746 | h = −5→5 |
44717 measured reflections | k = −36→36 |
6252 independent reflections | l = −27→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0466P)2 + 0.6966P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
6252 reflections | Δρmax = 0.22 e Å−3 |
343 parameters | Δρmin = −0.29 e Å−3 |
0 restraints |
Experimental. SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0610 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9304. The λ/2 correction factor is Not present. |
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 | ||
Cl1 | 0.89958 (12) | 0.43330 (2) | 0.48461 (2) | 0.06747 (16) | |
Cl2 | 1.48632 (14) | 0.11968 (2) | 0.42404 (3) | 0.08210 (19) | |
N1 | 0.0180 (3) | 0.46593 (5) | 0.26720 (7) | 0.0491 (3) | |
O1 | 0.1339 (4) | 0.57466 (5) | 0.34834 (7) | 0.0820 (5) | |
O2 | −0.2505 (4) | 0.53491 (6) | 0.24114 (7) | 0.0808 (4) | |
N2 | 0.6629 (4) | 0.22139 (6) | 0.23884 (7) | 0.0589 (4) | |
C1 | 0.2383 (4) | 0.45266 (5) | 0.31566 (8) | 0.0418 (4) | |
C6 | 0.3177 (4) | 0.49196 (5) | 0.35516 (8) | 0.0436 (4) | |
C16 | 0.8647 (4) | 0.19261 (6) | 0.27710 (8) | 0.0464 (4) | |
C10 | 0.0785 (4) | 0.43138 (6) | 0.16009 (8) | 0.0480 (4) | |
C25 | 0.7006 (4) | 0.21277 (6) | 0.12230 (8) | 0.0489 (4) | |
C5 | 0.5237 (4) | 0.48727 (6) | 0.40690 (8) | 0.0468 (4) | |
H5 | 0.5764 | 0.5135 | 0.4330 | 0.056* | |
C4 | 0.6490 (4) | 0.44222 (6) | 0.41863 (8) | 0.0465 (4) | |
C3 | 0.5724 (4) | 0.40332 (6) | 0.37927 (8) | 0.0505 (4) | |
H3 | 0.6612 | 0.3734 | 0.3881 | 0.061* | |
C2 | 0.3667 (4) | 0.40793 (6) | 0.32713 (8) | 0.0486 (4) | |
H2 | 0.3168 | 0.3817 | 0.3007 | 0.058* | |
O4 | 0.4619 (6) | 0.29741 (7) | 0.24693 (8) | 0.1259 (8) | |
C21 | 0.9722 (5) | 0.21743 (6) | 0.33183 (8) | 0.0556 (5) | |
C20 | 1.1657 (5) | 0.19600 (7) | 0.37758 (9) | 0.0599 (5) | |
H20 | 1.2362 | 0.2126 | 0.4141 | 0.072* | |
C17 | 0.9515 (4) | 0.14584 (6) | 0.26680 (9) | 0.0520 (4) | |
H17 | 0.8824 | 0.1291 | 0.2303 | 0.062* | |
C11 | 0.2055 (4) | 0.38866 (7) | 0.14143 (10) | 0.0600 (5) | |
H11 | 0.1789 | 0.3606 | 0.1648 | 0.072* | |
C9 | −0.1098 (4) | 0.43402 (7) | 0.21675 (9) | 0.0561 (5) | |
H9A | −0.3091 | 0.4455 | 0.2027 | 0.067* | |
H9B | −0.1308 | 0.4018 | 0.2342 | 0.067* | |
C19 | 1.2502 (4) | 0.14898 (7) | 0.36694 (8) | 0.0534 (4) | |
C7 | 0.1390 (5) | 0.53319 (6) | 0.33089 (9) | 0.0551 (4) | |
C30 | 0.7950 (5) | 0.25819 (7) | 0.10518 (9) | 0.0608 (5) | |
H30 | 0.7444 | 0.2849 | 0.1291 | 0.073* | |
C8 | −0.0624 (4) | 0.51317 (7) | 0.27356 (9) | 0.0567 (5) | |
C18 | 1.1458 (4) | 0.12459 (6) | 0.31285 (9) | 0.0565 (5) | |
H18 | 1.2075 | 0.0929 | 0.3070 | 0.068* | |
C15 | 0.1231 (5) | 0.47248 (7) | 0.12408 (9) | 0.0637 (5) | |
H15 | 0.0395 | 0.5017 | 0.1357 | 0.076* | |
O3 | 0.8623 (7) | 0.29835 (6) | 0.36596 (9) | 0.1378 (10) | |
C12 | 0.3732 (5) | 0.38726 (9) | 0.08782 (11) | 0.0717 (6) | |
H12 | 0.4579 | 0.3583 | 0.0756 | 0.086* | |
C24 | 0.5105 (4) | 0.20621 (8) | 0.17810 (9) | 0.0644 (5) | |
H24A | 0.3268 | 0.2248 | 0.1706 | 0.077* | |
H24B | 0.4553 | 0.1724 | 0.1811 | 0.077* | |
C26 | 0.7800 (5) | 0.17377 (8) | 0.08660 (11) | 0.0725 (6) | |
H26 | 0.7196 | 0.1429 | 0.0976 | 0.087* | |
C29 | 0.9621 (5) | 0.26426 (9) | 0.05342 (10) | 0.0757 (6) | |
H29 | 1.0230 | 0.2951 | 0.0421 | 0.091* | |
C13 | 0.4138 (5) | 0.42790 (10) | 0.05335 (11) | 0.0769 (6) | |
H13 | 0.5260 | 0.4268 | 0.0175 | 0.092* | |
C23 | 0.6255 (6) | 0.26494 (8) | 0.26680 (10) | 0.0837 (7) | |
C14 | 0.2892 (6) | 0.47045 (9) | 0.07147 (11) | 0.0806 (7) | |
H14 | 0.3175 | 0.4983 | 0.0478 | 0.097* | |
C28 | 1.0399 (6) | 0.22532 (12) | 0.01830 (11) | 0.0878 (8) | |
H28 | 1.1549 | 0.2294 | −0.0167 | 0.105* | |
C22 | 0.8338 (7) | 0.26512 (8) | 0.32918 (10) | 0.0838 (7) | |
C27 | 0.9474 (7) | 0.18010 (11) | 0.03494 (12) | 0.0937 (8) | |
H27 | 0.9990 | 0.1535 | 0.0109 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0701 (3) | 0.0689 (3) | 0.0622 (3) | 0.0014 (2) | −0.0044 (2) | 0.0077 (2) |
Cl2 | 0.0794 (4) | 0.0920 (4) | 0.0726 (3) | 0.0125 (3) | −0.0121 (3) | 0.0205 (3) |
N1 | 0.0558 (9) | 0.0433 (8) | 0.0488 (8) | −0.0013 (6) | 0.0066 (7) | 0.0031 (6) |
O1 | 0.1337 (14) | 0.0374 (7) | 0.0748 (10) | 0.0197 (8) | 0.0069 (9) | −0.0047 (6) |
O2 | 0.0923 (11) | 0.0728 (10) | 0.0758 (10) | 0.0292 (9) | −0.0041 (8) | 0.0133 (8) |
N2 | 0.0693 (10) | 0.0558 (9) | 0.0523 (9) | 0.0217 (8) | 0.0098 (8) | 0.0083 (7) |
C1 | 0.0463 (9) | 0.0358 (8) | 0.0447 (8) | −0.0021 (7) | 0.0129 (7) | 0.0010 (6) |
C6 | 0.0553 (10) | 0.0308 (8) | 0.0465 (9) | 0.0000 (7) | 0.0166 (7) | 0.0006 (6) |
C16 | 0.0516 (10) | 0.0430 (9) | 0.0457 (9) | 0.0047 (7) | 0.0105 (7) | 0.0037 (7) |
C10 | 0.0464 (9) | 0.0504 (10) | 0.0459 (9) | −0.0078 (8) | −0.0066 (7) | −0.0006 (7) |
C25 | 0.0444 (9) | 0.0526 (10) | 0.0481 (9) | 0.0034 (7) | −0.0097 (7) | 0.0061 (7) |
C5 | 0.0578 (10) | 0.0369 (8) | 0.0468 (9) | −0.0062 (7) | 0.0119 (8) | −0.0029 (7) |
C4 | 0.0488 (9) | 0.0451 (9) | 0.0469 (9) | −0.0004 (7) | 0.0118 (7) | 0.0031 (7) |
C3 | 0.0595 (11) | 0.0357 (9) | 0.0577 (10) | 0.0078 (8) | 0.0152 (8) | 0.0035 (7) |
C2 | 0.0618 (11) | 0.0334 (8) | 0.0518 (9) | −0.0009 (7) | 0.0117 (8) | −0.0048 (7) |
O4 | 0.197 (2) | 0.0971 (13) | 0.0846 (12) | 0.0978 (15) | 0.0187 (13) | 0.0159 (10) |
C21 | 0.0792 (13) | 0.0421 (9) | 0.0467 (9) | 0.0079 (9) | 0.0128 (9) | −0.0020 (7) |
C20 | 0.0810 (14) | 0.0544 (11) | 0.0443 (9) | −0.0040 (10) | 0.0030 (9) | −0.0040 (8) |
C17 | 0.0619 (11) | 0.0399 (9) | 0.0538 (10) | 0.0006 (8) | 0.0006 (8) | −0.0041 (7) |
C11 | 0.0643 (12) | 0.0506 (11) | 0.0629 (12) | −0.0039 (9) | −0.0119 (10) | −0.0024 (9) |
C9 | 0.0557 (11) | 0.0571 (11) | 0.0549 (10) | −0.0132 (9) | 0.0003 (8) | 0.0017 (8) |
C19 | 0.0537 (10) | 0.0527 (11) | 0.0538 (10) | 0.0008 (8) | 0.0036 (8) | 0.0092 (8) |
C7 | 0.0757 (12) | 0.0393 (9) | 0.0521 (10) | 0.0073 (9) | 0.0182 (9) | 0.0036 (8) |
C30 | 0.0744 (13) | 0.0535 (11) | 0.0532 (11) | 0.0010 (9) | −0.0055 (10) | 0.0050 (8) |
C8 | 0.0664 (12) | 0.0484 (10) | 0.0567 (10) | 0.0107 (9) | 0.0136 (9) | 0.0080 (8) |
C18 | 0.0651 (12) | 0.0414 (9) | 0.0628 (11) | 0.0081 (8) | 0.0020 (9) | −0.0004 (8) |
C15 | 0.0784 (14) | 0.0528 (11) | 0.0606 (12) | −0.0021 (10) | 0.0098 (10) | 0.0044 (9) |
O3 | 0.262 (3) | 0.0681 (11) | 0.0817 (12) | 0.0613 (14) | 0.0030 (15) | −0.0282 (9) |
C12 | 0.0679 (13) | 0.0734 (15) | 0.0726 (14) | 0.0055 (11) | −0.0049 (11) | −0.0232 (12) |
C24 | 0.0523 (11) | 0.0772 (14) | 0.0630 (12) | 0.0059 (10) | −0.0022 (9) | 0.0143 (10) |
C26 | 0.0907 (16) | 0.0543 (12) | 0.0715 (14) | 0.0025 (11) | −0.0026 (12) | −0.0034 (10) |
C29 | 0.0802 (15) | 0.0833 (16) | 0.0622 (13) | −0.0167 (12) | −0.0043 (11) | 0.0214 (12) |
C13 | 0.0771 (15) | 0.0949 (18) | 0.0600 (12) | −0.0107 (13) | 0.0141 (11) | −0.0138 (12) |
C23 | 0.125 (2) | 0.0678 (14) | 0.0607 (12) | 0.0473 (14) | 0.0264 (13) | 0.0102 (11) |
C14 | 0.1027 (18) | 0.0774 (16) | 0.0638 (13) | −0.0130 (13) | 0.0205 (13) | 0.0109 (11) |
C28 | 0.0759 (16) | 0.137 (3) | 0.0511 (12) | 0.0076 (16) | 0.0073 (11) | 0.0098 (14) |
C22 | 0.144 (2) | 0.0541 (12) | 0.0549 (12) | 0.0337 (13) | 0.0206 (13) | −0.0019 (10) |
C27 | 0.117 (2) | 0.0932 (19) | 0.0712 (16) | 0.0253 (17) | 0.0095 (15) | −0.0180 (14) |
Cl1—C4 | 1.7355 (18) | C20—H20 | 0.9300 |
Cl2—C19 | 1.7399 (18) | C20—C19 | 1.376 (3) |
N1—C1 | 1.413 (2) | C17—H17 | 0.9300 |
N1—C9 | 1.463 (2) | C17—C18 | 1.384 (2) |
N1—C8 | 1.364 (2) | C11—H11 | 0.9300 |
O1—C7 | 1.205 (2) | C11—C12 | 1.391 (3) |
O2—C8 | 1.204 (2) | C9—H9A | 0.9700 |
N2—C16 | 1.410 (2) | C9—H9B | 0.9700 |
N2—C24 | 1.463 (2) | C19—C18 | 1.373 (3) |
N2—C23 | 1.355 (3) | C7—C8 | 1.553 (3) |
C1—C6 | 1.397 (2) | C30—H30 | 0.9300 |
C1—C2 | 1.377 (2) | C30—C29 | 1.367 (3) |
C6—C5 | 1.379 (2) | C18—H18 | 0.9300 |
C6—C7 | 1.463 (2) | C15—H15 | 0.9300 |
C16—C21 | 1.394 (2) | C15—C14 | 1.370 (3) |
C16—C17 | 1.372 (2) | O3—C22 | 1.201 (3) |
C10—C11 | 1.378 (3) | C12—H12 | 0.9300 |
C10—C9 | 1.501 (3) | C12—C13 | 1.355 (3) |
C10—C15 | 1.386 (2) | C24—H24A | 0.9700 |
C25—C30 | 1.380 (3) | C24—H24B | 0.9700 |
C25—C24 | 1.501 (3) | C26—H26 | 0.9300 |
C25—C26 | 1.373 (3) | C26—C27 | 1.367 (3) |
C5—H5 | 0.9300 | C29—H29 | 0.9300 |
C5—C4 | 1.381 (2) | C29—C28 | 1.362 (4) |
C4—C3 | 1.385 (2) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.366 (3) |
C3—C2 | 1.384 (3) | C23—C22 | 1.551 (4) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
O4—C23 | 1.213 (3) | C28—H28 | 0.9300 |
C21—C20 | 1.379 (3) | C28—C27 | 1.370 (4) |
C21—C22 | 1.456 (3) | C27—H27 | 0.9300 |
C1—N1—C9 | 125.50 (14) | C20—C19—Cl2 | 119.23 (14) |
C8—N1—C1 | 110.68 (14) | C18—C19—Cl2 | 119.61 (14) |
C8—N1—C9 | 123.82 (16) | C18—C19—C20 | 121.14 (17) |
C16—N2—C24 | 124.99 (15) | O1—C7—C6 | 131.16 (19) |
C23—N2—C16 | 110.41 (16) | O1—C7—C8 | 123.55 (17) |
C23—N2—C24 | 124.59 (17) | C6—C7—C8 | 105.29 (14) |
C6—C1—N1 | 111.08 (14) | C25—C30—H30 | 119.7 |
C2—C1—N1 | 128.26 (15) | C29—C30—C25 | 120.7 (2) |
C2—C1—C6 | 120.66 (16) | C29—C30—H30 | 119.7 |
C1—C6—C7 | 106.90 (15) | N1—C8—C7 | 105.98 (15) |
C5—C6—C1 | 121.40 (15) | O2—C8—N1 | 126.95 (19) |
C5—C6—C7 | 131.67 (15) | O2—C8—C7 | 127.06 (17) |
C21—C16—N2 | 111.13 (15) | C17—C18—H18 | 119.1 |
C17—C16—N2 | 128.25 (16) | C19—C18—C17 | 121.86 (17) |
C17—C16—C21 | 120.60 (16) | C19—C18—H18 | 119.1 |
C11—C10—C9 | 121.88 (17) | C10—C15—H15 | 119.7 |
C11—C10—C15 | 118.18 (18) | C14—C15—C10 | 120.6 (2) |
C15—C10—C9 | 119.93 (17) | C14—C15—H15 | 119.7 |
C30—C25—C24 | 120.71 (18) | C11—C12—H12 | 119.8 |
C26—C25—C30 | 118.66 (19) | C13—C12—C11 | 120.4 (2) |
C26—C25—C24 | 120.63 (18) | C13—C12—H12 | 119.8 |
C6—C5—H5 | 121.1 | N2—C24—C25 | 112.91 (16) |
C6—C5—C4 | 117.70 (15) | N2—C24—H24A | 109.0 |
C4—C5—H5 | 121.1 | N2—C24—H24B | 109.0 |
C5—C4—Cl1 | 120.08 (13) | C25—C24—H24A | 109.0 |
C5—C4—C3 | 121.00 (16) | C25—C24—H24B | 109.0 |
C3—C4—Cl1 | 118.91 (13) | H24A—C24—H24B | 107.8 |
C4—C3—H3 | 119.3 | C25—C26—H26 | 119.8 |
C2—C3—C4 | 121.47 (16) | C27—C26—C25 | 120.4 (2) |
C2—C3—H3 | 119.3 | C27—C26—H26 | 119.8 |
C1—C2—C3 | 117.76 (15) | C30—C29—H29 | 119.9 |
C1—C2—H2 | 121.1 | C28—C29—C30 | 120.2 (2) |
C3—C2—H2 | 121.1 | C28—C29—H29 | 119.9 |
C16—C21—C22 | 107.07 (17) | C12—C13—H13 | 120.2 |
C20—C21—C16 | 121.61 (16) | C12—C13—C14 | 119.7 (2) |
C20—C21—C22 | 131.28 (18) | C14—C13—H13 | 120.2 |
C21—C20—H20 | 121.3 | N2—C23—C22 | 106.44 (17) |
C19—C20—C21 | 117.31 (17) | O4—C23—N2 | 126.8 (2) |
C19—C20—H20 | 121.3 | O4—C23—C22 | 126.8 (2) |
C16—C17—H17 | 121.3 | C15—C14—H14 | 119.6 |
C16—C17—C18 | 117.47 (16) | C13—C14—C15 | 120.7 (2) |
C18—C17—H17 | 121.3 | C13—C14—H14 | 119.6 |
C10—C11—H11 | 119.8 | C29—C28—H28 | 120.2 |
C10—C11—C12 | 120.40 (19) | C29—C28—C27 | 119.5 (2) |
C12—C11—H11 | 119.8 | C27—C28—H28 | 120.2 |
N1—C9—C10 | 112.91 (14) | C21—C22—C23 | 104.91 (17) |
N1—C9—H9A | 109.0 | O3—C22—C21 | 130.0 (2) |
N1—C9—H9B | 109.0 | O3—C22—C23 | 125.1 (2) |
C10—C9—H9A | 109.0 | C26—C27—C28 | 120.5 (2) |
C10—C9—H9B | 109.0 | C26—C27—H27 | 119.7 |
H9A—C9—H9B | 107.8 | C28—C27—H27 | 119.7 |
Cl1—C4—C3—C2 | 177.96 (13) | O4—C23—C22—O3 | −1.0 (5) |
Cl2—C19—C18—C17 | 178.32 (15) | C21—C16—C17—C18 | 0.6 (3) |
N1—C1—C6—C5 | 178.31 (14) | C21—C20—C19—Cl2 | −178.39 (15) |
N1—C1—C6—C7 | −0.09 (18) | C21—C20—C19—C18 | 0.1 (3) |
N1—C1—C2—C3 | −177.86 (15) | C20—C21—C22—O3 | 2.5 (5) |
O1—C7—C8—N1 | 177.33 (18) | C20—C21—C22—C23 | −176.5 (2) |
O1—C7—C8—O2 | −2.4 (3) | C20—C19—C18—C17 | −0.2 (3) |
N2—C16—C21—C20 | 177.89 (17) | C17—C16—C21—C20 | −0.7 (3) |
N2—C16—C21—C22 | −0.1 (2) | C17—C16—C21—C22 | −178.68 (18) |
N2—C16—C17—C18 | −177.71 (17) | C11—C10—C9—N1 | 118.18 (18) |
N2—C23—C22—C21 | −2.0 (3) | C11—C10—C15—C14 | 0.0 (3) |
N2—C23—C22—O3 | 178.9 (3) | C11—C12—C13—C14 | 0.0 (3) |
C1—N1—C9—C10 | −84.7 (2) | C9—N1—C1—C6 | 178.35 (15) |
C1—N1—C8—O2 | −177.55 (19) | C9—N1—C1—C2 | −2.9 (3) |
C1—N1—C8—C7 | 2.67 (18) | C9—N1—C8—O2 | 2.4 (3) |
C1—C6—C5—C4 | −0.2 (2) | C9—N1—C8—C7 | −177.42 (15) |
C1—C6—C7—O1 | −178.3 (2) | C9—C10—C11—C12 | 178.53 (16) |
C1—C6—C7—C8 | 1.63 (18) | C9—C10—C15—C14 | −178.65 (19) |
C6—C1—C2—C3 | 0.8 (2) | C7—C6—C5—C4 | 177.75 (17) |
C6—C5—C4—Cl1 | −177.70 (12) | C30—C25—C24—N2 | −62.5 (2) |
C6—C5—C4—C3 | 0.7 (2) | C30—C25—C26—C27 | −0.4 (3) |
C6—C7—C8—N1 | −2.65 (19) | C30—C29—C28—C27 | 0.5 (4) |
C6—C7—C8—O2 | 177.57 (19) | C8—N1—C1—C6 | −1.75 (19) |
C16—N2—C24—C25 | −83.6 (2) | C8—N1—C1—C2 | 177.04 (17) |
C16—N2—C23—O4 | −178.2 (3) | C8—N1—C9—C10 | 95.4 (2) |
C16—N2—C23—C22 | 1.9 (2) | C15—C10—C11—C12 | 0.0 (3) |
C16—C21—C20—C19 | 0.3 (3) | C15—C10—C9—N1 | −63.3 (2) |
C16—C21—C22—O3 | −179.7 (3) | C12—C13—C14—C15 | −0.1 (4) |
C16—C21—C22—C23 | 1.2 (2) | C24—N2—C16—C21 | 179.86 (17) |
C16—C17—C18—C19 | −0.2 (3) | C24—N2—C16—C17 | −1.7 (3) |
C10—C11—C12—C13 | 0.1 (3) | C24—N2—C23—O4 | 0.7 (4) |
C10—C15—C14—C13 | 0.1 (3) | C24—N2—C23—C22 | −179.14 (19) |
C25—C30—C29—C28 | −0.6 (3) | C24—C25—C30—C29 | −178.42 (17) |
C25—C26—C27—C28 | 0.4 (4) | C24—C25—C26—C27 | 178.5 (2) |
C5—C6—C7—O1 | 3.5 (3) | C26—C25—C30—C29 | 0.5 (3) |
C5—C6—C7—C8 | −176.54 (17) | C26—C25—C24—N2 | 118.6 (2) |
C5—C4—C3—C2 | −0.5 (3) | C29—C28—C27—C26 | −0.4 (4) |
C4—C3—C2—C1 | −0.3 (3) | C23—N2—C16—C21 | −1.2 (2) |
C2—C1—C6—C5 | −0.6 (2) | C23—N2—C16—C17 | 177.2 (2) |
C2—C1—C6—C7 | −178.99 (15) | C23—N2—C24—C25 | 97.6 (2) |
O4—C23—C22—C21 | 178.2 (3) | C22—C21—C20—C19 | 177.8 (2) |
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