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In the title solvated compound, C28H19N2O4·C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the meth­oxy- and chloro­phenyl rings and the ring plane of the 1H-benzo[de]iso­quinoline-1,3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intra­molecular C—H...O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and meth­oxy­benzene rings. In the crystal, the components are linked by C—H...O hydrogen bonds, C—H...π inter­actions and aromatic π–π stacking inter­actions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent mol­ecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015001425/hb7354sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015001425/hb7354Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015001425/hb7354Isup3.cml
Supplementary material

CCDC reference: 1044874

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in solvent or counterion
  • R factor = 0.061
  • wR factor = 0.191
  • Data-to-parameter ratio = 21.6

checkCIF/PLATON results

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Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 23 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 8 Note PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00200 Degree PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage = 100 Note PLAT793_ALERT_4_G The Model has Chirality at C1 (Centro SPGR) S Verify PLAT793_ALERT_4_G The Model has Chirality at C2 (Centro SPGR) S Verify PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 6 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 2 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 80 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 9 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Even more than 70 years after the discovery of penicillin, β-lactam antibiotics remain as one of the most important contributions of science to humanity (Southgate, 1994) and the β-lactam antibiotics have served as a powerful line of defense against bacterial infections (Long, et al., 2002). They have also been used as synthons for the synthesis of various natural and unnatural products (Alcaide & Almendros, 2004). On the other hand, cyclic imides have received special attraction due to their widely potential pharmaceutical applications (Zhang & Zhou, 2011). Isoquinolindione (naphthalimide) derivatives are cyclic imides to be of interest due to their useful photophysical and biological properties that offer promise for medical applications as free radical scavengers (Zhang, et al., 2011), potential photoredox anticancer agents (MacIntyre, et al., 2010), fluorescent labels (Sawa, et al., 2006), photosensitizers (Rogers & Kelly, 1999) and imaging agents (Alcala et al., 2011). Many of these properties are related to 1,8- naphthalimides planar shape and optimal size that makes them efficient DNA intercalating agents with high antitumor activity (Li et al., 2011; Zarei, 2013).

In the title compound (Fig. 1), the β-lactam ring (N1/C1–C3) is nearly planar [r.m.s. deviation = 0.002 Å]. It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy and choloro phenyl rings (C4–C9 and C11–C16) and the ring plane (N2/C17–C28) of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group which is nearly planar [max. deviations = -0.089 (1) Å for N2 and 0.044 (2) Å for C24], respectively.

All bond lengths and bond angles are normal and comparable with those reported for related compounds (Butcher et al., 2011; Atioğlu et al., 2014; Jarrahpour et al., 2012).

Molecular conformation is stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal, molecules are linked by intermolecular C—H···O hydrogen bonds, forming three dimensional network (Table 1, Figs. 2 & 3).

Furthermore, one weak C—H···π interaction (Table 1) and π-π stacking interactions [Cg2···Cg6 (2 - x,1 - y,-z) = 3.6166 (10) Å and Cg5···Cg6(2 - x,1 - y,-z) = 3.7159 (10) Å; where Cg2, Cg5 and Cg6 are centroids of the N2/C17/C18/C23/C24/C28 central pyridine ring and the C18–C23 and C22—C27 benzene rings of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group, respectively] also partially take part in the stabilization of the structure.

Related literature top

For general background to β-lactams, see: Alcaide & Almendros (2004); Alcala et al. (2011); Li et al. (2011); Long & Turos (2002); MacIntyre et al. (2010); Rogers & Kelly (1999); Sawa et al. (2006); Southgate (1994); Zhang & Zhou (2011); Zhang et al. (2011). For related structures, see: Atioğlu et al. (2014); Butcher et al. (2011); Jarrahpour et al. (2012); Zarei (2013).

Experimental top

4-Chlorophenyl-N-(4-methoxyphenyl)methanimine (1 mmol), triethylamine (5 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid (1.50 mmol) and tosyl chloride (1.50 mmol) were added to anhydrous CH2Cl2 (5 ml) and the mixture was stirred at room temperature for 24 h. The mixture was washed with HCl 1 N (2×20 ml), saturated aqueous NaHCO3 solution (50 ml) and brine (20 ml). The organic layer was dried (Na2SO4) and the solvent was removed to give the product as a white solid·It was then purified by recrystallization from DMSO to afford colourless triclinic crystals (Yield 75%); Mp: 528–530 K; IR (KBr, cm-1): 1774 (CO β-lactam),1704 (CO Naph), 1666 (CO Naph); 1H-NMR (250 MHz, DMSO-d6) δ 1.27 (CH3 t, 3H, J = 6.75), 3.95 (CH2 q, 2H, J = 6.75), 5.69 (CH β-lactam d, 1H, J = 2.75), 5.94 (CH β-lactam d, 1H, J = 2.75), 6.91 (aromat d, 2H, J = 9.00), 7.19 (aromat d, 2H, J = 9.00), 7.79–7.89 (ArH, m, 4H), 8.24 (aromat d, 2H, J = 9.00), 8.43–8.50 (ArH, m, 4H); 13C-NMR (62 MHz, DMSO-d6) δ 163.22 (CO β-lactam), 162.13 (CO Naph), 155.04, 147.47, 144.82, 134.88, 131.22, 131.17, 130.50, 128.10, 127.43, 127.30, 123.95, 121.54, 118.29, 115.04, (aromatic carbons), 63.41 (C β-lactam), 63.19 (C β-lactam), 58.08 (CH2—O), 14.56 (CH3); GC—MS m/z = 507 [M+].

Refinement top

H atoms were located in calculated positions with C—H = 0.93 - 0.98 Å, and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). The (0 1 0), (10 - 4 3), (9 - 4 5), (0 0 1), (0 3 5), (0 1 6), (2 2 4), (1 - 5 2), (3 1 5), (-3 3 3), (2 1 6), (-2 4 8), (0 - 3 1), (-2 2 7), (1 - 5 1), (-2 3 4), (3 - 6 9), (2 0 5), (6 3 3), (-2 - 5 2), (-3 5 3), (-3 - 10 7), (-1 0 11) and (-2 - 8 4) reflections were omitted owing to bad disagreement. The crystal quality and data was not good enough. All the atoms of the dimethyl sulfoxide (DMSO) solvent molecule are disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Perspective view of the molecular structure of the title compound with displacement ellipsoids for non-H atoms drawn at the 30% probability level. Only the major component of the disordered solvent molecule is displayed.
[Figure 2] Fig. 2. The hydrogen bonding and molecular packing of the title compound along a axis. Only the major component of the disordered solvent molecule is displayed.
[Figure 3] Fig. 3. The hydrogen bonding and molecular packing of the title compound along c axis. Only the major component of the disordered solvent molecule is displayed.
2-[2-(4-Chlorophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate top
Crystal data top
C28H19ClN2O4·C2H6OSZ = 2
Mr = 561.03F(000) = 584
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9925 (3) ÅCell parameters from 9923 reflections
b = 12.1761 (5) Åθ = 2.9–29.9°
c = 14.2313 (6) ŵ = 0.26 mm1
α = 93.549 (2)°T = 296 K
β = 95.520 (2)°Prism, colourless
γ = 101.602 (2)°0.45 × 0.30 × 0.20 mm
V = 1345.67 (9) Å3
Data collection top
Bruker APEXII CCD
diffractometer
5777 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.022
Graphite monochromatorθmax = 30.0°, θmin = 2.2°
ϕ and ω scansh = 1111
29975 measured reflectionsk = 1717
7737 independent reflectionsl = 1919
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.0977P)2 + 0.5061P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
7737 reflectionsΔρmax = 0.68 e Å3
359 parametersΔρmin = 0.52 e Å3
Crystal data top
C28H19ClN2O4·C2H6OSγ = 101.602 (2)°
Mr = 561.03V = 1345.67 (9) Å3
Triclinic, P1Z = 2
a = 7.9925 (3) ÅMo Kα radiation
b = 12.1761 (5) ŵ = 0.26 mm1
c = 14.2313 (6) ÅT = 296 K
α = 93.549 (2)°0.45 × 0.30 × 0.20 mm
β = 95.520 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
5777 reflections with I > 2σ(I)
29975 measured reflectionsRint = 0.022
7737 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0616 restraints
wR(F2) = 0.191H-atom parameters constrained
S = 1.05Δρmax = 0.68 e Å3
7737 reflectionsΔρmin = 0.52 e Å3
359 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.69679 (12)0.13588 (7)0.68363 (4)0.0886 (3)
S1A0.83996 (15)0.62942 (10)0.36822 (7)0.0884 (4)0.847 (2)
S1B0.7471 (8)0.6453 (5)0.4182 (4)0.0884 (4)0.153 (2)
O10.5935 (2)0.15324 (13)0.07604 (10)0.0572 (5)
O20.20212 (18)0.02113 (14)0.22243 (12)0.0620 (5)
O31.06205 (19)0.37028 (13)0.29270 (12)0.0603 (5)
O40.58077 (15)0.40773 (12)0.11511 (10)0.0467 (4)
N10.48129 (19)0.18953 (13)0.21909 (10)0.0411 (4)
N20.82660 (17)0.38087 (12)0.19376 (10)0.0355 (4)
C10.5863 (2)0.27720 (14)0.28906 (12)0.0368 (5)
C20.7342 (2)0.27719 (14)0.22466 (12)0.0381 (5)
C30.5985 (2)0.19748 (15)0.15453 (13)0.0423 (5)
C40.3093 (2)0.13255 (14)0.21725 (12)0.0372 (5)
C50.2294 (3)0.05633 (17)0.14244 (13)0.0469 (6)
O5A0.6596 (5)0.5604 (2)0.3457 (2)0.1081 (11)0.847 (2)
C60.0575 (3)0.00331 (17)0.14164 (14)0.0497 (6)
C70.0327 (2)0.02482 (16)0.21594 (14)0.0450 (5)
C80.0494 (2)0.09910 (18)0.29171 (15)0.0488 (6)
C90.2184 (2)0.15335 (16)0.29214 (14)0.0450 (6)
C100.2998 (3)0.0868 (2)0.1422 (2)0.0750 (9)
C110.6159 (2)0.24211 (14)0.38776 (12)0.0365 (4)
C120.6490 (2)0.13637 (15)0.40284 (13)0.0413 (5)
C130.6763 (3)0.10452 (17)0.49434 (14)0.0477 (6)
C140.6676 (3)0.17782 (19)0.56949 (14)0.0524 (6)
C150.6345 (4)0.2827 (2)0.55697 (15)0.0612 (8)
C160.6094 (3)0.31440 (17)0.46505 (14)0.0500 (6)
C171.0008 (2)0.41714 (14)0.22957 (12)0.0376 (5)
C181.1000 (2)0.51167 (13)0.18560 (11)0.0337 (4)
C191.2760 (2)0.54014 (16)0.20663 (13)0.0428 (5)
C201.3723 (2)0.62737 (18)0.16236 (15)0.0495 (6)
C211.2935 (2)0.68586 (17)0.09901 (13)0.0464 (5)
C221.1127 (2)0.66006 (14)0.07639 (12)0.0372 (5)
C231.01511 (19)0.56994 (13)0.11954 (10)0.0316 (4)
C240.83533 (19)0.53926 (13)0.09505 (11)0.0325 (4)
C250.7550 (2)0.59720 (15)0.03094 (12)0.0393 (5)
C260.8512 (3)0.68702 (16)0.01091 (13)0.0462 (6)
C271.0259 (3)0.71740 (15)0.01086 (13)0.0438 (5)
C280.7350 (2)0.44063 (14)0.13389 (11)0.0341 (4)
O5B0.688 (3)0.6029 (15)0.3255 (13)0.1081 (11)0.153 (2)
C29A0.8342 (10)0.7606 (7)0.3416 (6)0.183 (3)0.847 (2)
C30A0.8821 (12)0.6486 (7)0.4874 (7)0.183 (3)0.847 (2)
C29B0.821 (6)0.786 (2)0.413 (4)0.183 (3)0.153 (2)
C30B0.904 (5)0.593 (4)0.479 (5)0.183 (3)0.153 (2)
H10.544900.347700.288800.0440*
H20.816300.235300.252900.0460*
H50.290300.040400.092600.0560*
H60.003500.046900.090600.0600*
H80.010000.112500.342900.0580*
H90.271600.204100.342900.0540*
H10A0.415300.113600.156300.1130*
H10B0.301200.041400.089400.1130*
H10C0.248900.149600.126700.1130*
H120.652800.086500.351300.0500*
H130.700300.034200.504200.0570*
H150.628900.331700.608900.0730*
H160.588000.385500.455800.0600*
H191.330800.501500.250200.0510*
H201.491200.645600.176300.0590*
H211.359600.743400.070300.0560*
H250.636600.576800.015300.0470*
H260.795800.726200.053800.0550*
H271.088000.776600.017900.0530*
H29A0.947300.807100.355100.2740*0.847 (2)
H29B0.795400.760000.275600.2740*0.847 (2)
H29C0.756800.789900.379000.2740*0.847 (2)
H30A0.996400.692400.504200.2740*0.847 (2)
H30B0.801000.687500.512700.2740*0.847 (2)
H30C0.872900.576900.513200.2740*0.847 (2)
H29D0.864300.820400.475900.2740*0.153 (2)
H29E0.911900.798000.373100.2740*0.153 (2)
H29F0.729100.819600.388300.2740*0.153 (2)
H30D0.930100.631000.541700.2740*0.153 (2)
H30E0.863900.514100.483600.2740*0.153 (2)
H30F1.004700.605300.446800.2740*0.153 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1404 (7)0.0971 (5)0.0389 (3)0.0438 (5)0.0117 (3)0.0232 (3)
S1A0.0995 (7)0.1062 (7)0.0621 (5)0.0320 (6)0.0056 (4)0.0015 (5)
S1B0.0995 (7)0.1062 (7)0.0621 (5)0.0320 (6)0.0056 (4)0.0015 (5)
O10.0713 (10)0.0540 (8)0.0402 (7)0.0060 (7)0.0177 (7)0.0018 (6)
O20.0407 (7)0.0676 (10)0.0676 (10)0.0074 (7)0.0065 (7)0.0120 (8)
O30.0527 (8)0.0609 (9)0.0618 (9)0.0030 (7)0.0159 (7)0.0261 (7)
O40.0309 (6)0.0547 (8)0.0505 (7)0.0006 (5)0.0019 (5)0.0152 (6)
N10.0403 (7)0.0450 (8)0.0327 (7)0.0041 (6)0.0042 (5)0.0040 (6)
N20.0317 (6)0.0381 (7)0.0354 (7)0.0019 (5)0.0032 (5)0.0111 (5)
C10.0355 (8)0.0394 (8)0.0328 (8)0.0009 (6)0.0036 (6)0.0058 (6)
C20.0381 (8)0.0385 (8)0.0369 (8)0.0030 (6)0.0065 (6)0.0104 (6)
C30.0478 (9)0.0399 (8)0.0368 (9)0.0002 (7)0.0085 (7)0.0083 (7)
C40.0378 (8)0.0368 (8)0.0353 (8)0.0027 (6)0.0020 (6)0.0091 (6)
C50.0503 (10)0.0490 (10)0.0361 (9)0.0030 (8)0.0077 (7)0.0025 (7)
O5A0.128 (2)0.0609 (17)0.112 (2)0.0059 (18)0.0486 (19)0.0060 (15)
C60.0515 (10)0.0459 (10)0.0431 (10)0.0064 (8)0.0025 (8)0.0035 (8)
C70.0393 (9)0.0410 (9)0.0508 (10)0.0012 (7)0.0023 (7)0.0009 (7)
C80.0377 (9)0.0554 (11)0.0507 (11)0.0063 (8)0.0067 (7)0.0065 (8)
C90.0383 (9)0.0486 (10)0.0440 (10)0.0051 (7)0.0001 (7)0.0077 (8)
C100.0529 (13)0.0739 (16)0.0820 (18)0.0143 (11)0.0018 (12)0.0205 (13)
C110.0332 (7)0.0404 (8)0.0335 (8)0.0008 (6)0.0045 (6)0.0061 (6)
C120.0458 (9)0.0401 (8)0.0376 (9)0.0059 (7)0.0084 (7)0.0044 (7)
C130.0555 (11)0.0449 (9)0.0448 (10)0.0109 (8)0.0092 (8)0.0122 (8)
C140.0626 (12)0.0604 (12)0.0352 (9)0.0123 (9)0.0059 (8)0.0120 (8)
C150.0901 (17)0.0599 (13)0.0355 (10)0.0227 (12)0.0047 (10)0.0008 (9)
C160.0686 (13)0.0423 (9)0.0395 (10)0.0142 (9)0.0025 (8)0.0031 (7)
C170.0347 (8)0.0404 (8)0.0358 (8)0.0052 (6)0.0021 (6)0.0056 (6)
C180.0310 (7)0.0361 (7)0.0313 (7)0.0025 (6)0.0011 (5)0.0008 (6)
C190.0334 (8)0.0491 (9)0.0418 (9)0.0044 (7)0.0029 (6)0.0031 (7)
C200.0315 (8)0.0594 (11)0.0495 (10)0.0059 (7)0.0027 (7)0.0061 (8)
C210.0417 (9)0.0475 (9)0.0417 (9)0.0108 (7)0.0095 (7)0.0029 (7)
C220.0416 (8)0.0344 (8)0.0316 (8)0.0019 (6)0.0076 (6)0.0016 (6)
C230.0324 (7)0.0323 (7)0.0276 (7)0.0017 (5)0.0037 (5)0.0009 (5)
C240.0326 (7)0.0341 (7)0.0296 (7)0.0037 (6)0.0029 (5)0.0039 (6)
C250.0399 (8)0.0411 (8)0.0361 (8)0.0083 (7)0.0003 (6)0.0057 (7)
C260.0590 (11)0.0409 (9)0.0401 (9)0.0130 (8)0.0031 (8)0.0106 (7)
C270.0561 (10)0.0345 (8)0.0382 (9)0.0002 (7)0.0105 (7)0.0060 (7)
C280.0310 (7)0.0389 (8)0.0312 (7)0.0040 (6)0.0020 (5)0.0069 (6)
O5B0.128 (2)0.0609 (17)0.112 (2)0.0059 (18)0.0486 (19)0.0060 (15)
C29A0.140 (4)0.184 (6)0.187 (5)0.034 (4)0.060 (4)0.058 (5)
C30A0.140 (4)0.184 (6)0.187 (5)0.034 (4)0.060 (4)0.058 (5)
C29B0.140 (4)0.184 (6)0.187 (5)0.034 (4)0.060 (4)0.058 (5)
C30B0.140 (4)0.184 (6)0.187 (5)0.034 (4)0.060 (4)0.058 (5)
Geometric parameters (Å, º) top
Cl1—C141.741 (2)C22—C231.422 (2)
S1A—C30A1.689 (10)C22—C271.411 (3)
S1A—O5A1.509 (4)C23—C241.413 (2)
S1A—C29A1.673 (8)C24—C251.375 (2)
S1B—O5B1.388 (19)C24—C281.473 (2)
S1B—C30B1.71 (5)C25—C261.405 (3)
S1B—C29B1.71 (3)C26—C271.370 (3)
O1—C31.203 (2)C1—H10.9800
O2—C101.420 (3)C2—H20.9800
O2—C71.371 (2)C5—H50.9300
O3—C171.210 (2)C6—H60.9300
O4—C281.215 (2)C8—H80.9300
N1—C31.368 (2)C9—H90.9300
N1—C11.477 (2)C10—H10C0.9600
N1—C41.407 (2)C10—H10B0.9600
N2—C281.401 (2)C10—H10A0.9600
N2—C21.445 (2)C12—H120.9300
N2—C171.408 (2)C13—H130.9300
C1—C21.564 (2)C15—H150.9300
C1—C111.504 (2)C16—H160.9300
C2—C31.537 (2)C19—H190.9300
C4—C51.382 (3)C20—H200.9300
C4—C91.385 (2)C21—H210.9300
C5—C61.394 (3)C25—H250.9300
C6—C71.377 (3)C26—H260.9300
C7—C81.384 (3)C27—H270.9300
C8—C91.378 (2)C29A—H29C0.9600
C11—C121.391 (2)C29A—H29A0.9600
C11—C161.377 (3)C29A—H29B0.9600
C12—C131.391 (3)C30A—H30A0.9600
C13—C141.366 (3)C30A—H30B0.9600
C14—C151.374 (3)C30A—H30C0.9600
C15—C161.394 (3)C29B—H29D0.9700
C17—C181.471 (2)C29B—H29E0.9600
C18—C231.415 (2)C29B—H29F0.9600
C18—C191.378 (2)C30B—H30D0.9600
C19—C201.402 (3)C30B—H30E0.9600
C20—C211.367 (3)C30B—H30F0.9500
C21—C221.416 (2)
O5A—S1A—C30A107.4 (3)O4—C28—N2119.23 (15)
C29A—S1A—C30A100.9 (4)N1—C1—H1112.00
O5A—S1A—C29A107.1 (3)C11—C1—H1112.00
C29B—S1B—C30B108 (2)C2—C1—H1112.00
O5B—S1B—C29B106 (2)C3—C2—H2110.00
O5B—S1B—C30B119 (2)N2—C2—H2109.00
C7—O2—C10118.08 (18)C1—C2—H2109.00
C3—N1—C4133.80 (15)C6—C5—H5120.00
C1—N1—C4129.79 (14)C4—C5—H5120.00
C1—N1—C395.78 (14)C7—C6—H6120.00
C2—N2—C17117.44 (14)C5—C6—H6120.00
C17—N2—C28124.63 (14)C7—C8—H8120.00
C2—N2—C28117.87 (14)C9—C8—H8120.00
N1—C1—C11115.59 (14)C4—C9—H9120.00
N1—C1—C286.20 (12)C8—C9—H9120.00
C2—C1—C11117.03 (14)O2—C10—H10C109.00
C1—C2—C385.86 (12)O2—C10—H10B109.00
N2—C2—C1120.95 (14)H10A—C10—H10C110.00
N2—C2—C3119.42 (14)O2—C10—H10A109.00
O1—C3—N1132.51 (17)H10A—C10—H10B109.00
N1—C3—C291.20 (14)H10B—C10—H10C109.00
O1—C3—C2136.20 (17)C11—C12—H12120.00
N1—C4—C9119.16 (15)C13—C12—H12120.00
C5—C4—C9119.41 (17)C14—C13—H13120.00
N1—C4—C5121.44 (16)C12—C13—H13120.00
C4—C5—C6120.03 (19)C14—C15—H15121.00
C5—C6—C7120.34 (18)C16—C15—H15121.00
O2—C7—C8115.19 (17)C11—C16—H16120.00
C6—C7—C8119.29 (17)C15—C16—H16119.00
O2—C7—C6125.52 (18)C20—C19—H19120.00
C7—C8—C9120.65 (18)C18—C19—H19120.00
C4—C9—C8120.25 (18)C21—C20—H20120.00
C12—C11—C16118.78 (17)C19—C20—H20120.00
C1—C11—C16120.29 (16)C22—C21—H21120.00
C1—C11—C12120.93 (15)C20—C21—H21120.00
C11—C12—C13120.60 (17)C26—C25—H25120.00
C12—C13—C14119.18 (19)C24—C25—H25120.00
C13—C14—C15121.63 (19)C27—C26—H26120.00
Cl1—C14—C13118.83 (17)C25—C26—H26120.00
Cl1—C14—C15119.53 (16)C22—C27—H27120.00
C14—C15—C16118.8 (2)C26—C27—H27120.00
C11—C16—C15121.02 (19)S1A—C29A—H29B109.00
O3—C17—C18123.36 (16)H29A—C29A—H29C109.00
O3—C17—N2120.05 (16)S1A—C29A—H29C109.00
N2—C17—C18116.58 (14)H29A—C29A—H29B110.00
C17—C18—C19119.58 (15)S1A—C29A—H29A109.00
C17—C18—C23119.88 (14)H29B—C29A—H29C110.00
C19—C18—C23120.51 (15)S1A—C30A—H30C110.00
C18—C19—C20119.98 (16)H30A—C30A—H30C109.00
C19—C20—C21120.76 (16)H30B—C30A—H30C109.00
C20—C21—C22120.96 (17)H30A—C30A—H30B109.00
C21—C22—C27122.97 (17)S1A—C30A—H30A110.00
C23—C22—C27118.61 (16)S1A—C30A—H30B109.00
C21—C22—C23118.39 (15)S1B—C29B—H29D109.00
C22—C23—C24119.53 (14)S1B—C29B—H29E110.00
C18—C23—C24121.09 (14)S1B—C29B—H29F110.00
C18—C23—C22119.37 (14)H29D—C29B—H29E109.00
C23—C24—C25120.25 (15)H29D—C29B—H29F109.00
C25—C24—C28119.77 (14)H29E—C29B—H29F110.00
C23—C24—C28119.88 (14)S1B—C30B—H30D109.00
C24—C25—C26120.21 (16)S1B—C30B—H30E109.00
C25—C26—C27120.58 (18)S1B—C30B—H30F110.00
C22—C27—C26120.81 (17)H30D—C30B—H30E109.00
N2—C28—C24116.85 (14)H30D—C30B—H30F110.00
O4—C28—C24123.89 (15)H30E—C30B—H30F110.00
C10—O2—C7—C67.4 (3)C6—C7—C8—C91.6 (3)
C10—O2—C7—C8172.23 (19)O2—C7—C8—C9178.04 (18)
C3—N1—C1—C27.68 (13)C7—C8—C9—C41.2 (3)
C4—N1—C1—C1162.4 (2)C1—C11—C12—C13180.00 (18)
C4—N1—C1—C2179.39 (17)C16—C11—C12—C130.5 (3)
C3—N1—C1—C11125.92 (15)C12—C11—C16—C150.3 (3)
C4—N1—C3—O14.1 (4)C1—C11—C16—C15179.2 (2)
C1—N1—C3—C27.80 (14)C11—C12—C13—C141.0 (3)
C4—N1—C3—C2178.97 (19)C12—C13—C14—C150.8 (4)
C1—N1—C4—C5176.58 (17)C12—C13—C14—Cl1178.46 (17)
C3—N1—C4—C58.0 (3)Cl1—C14—C15—C16179.2 (2)
C1—N1—C4—C93.5 (3)C13—C14—C15—C160.0 (4)
C3—N1—C4—C9172.02 (19)C14—C15—C16—C110.6 (4)
C1—N1—C3—O1175.3 (2)O3—C17—C18—C199.3 (3)
C17—N2—C2—C3143.50 (15)N2—C17—C18—C237.7 (2)
C28—N2—C2—C339.3 (2)O3—C17—C18—C23173.05 (17)
C28—N2—C17—C1813.0 (2)N2—C17—C18—C19169.99 (15)
C28—N2—C2—C164.7 (2)C17—C18—C23—C22179.03 (15)
C2—N2—C28—O44.7 (2)C19—C18—C23—C24177.96 (15)
C2—N2—C17—O39.2 (2)C17—C18—C23—C240.3 (2)
C17—N2—C28—O4172.28 (16)C19—C18—C23—C221.4 (2)
C28—N2—C17—O3167.75 (17)C23—C18—C19—C200.1 (3)
C2—N2—C17—C18170.06 (14)C17—C18—C19—C20177.60 (17)
C2—N2—C28—C24173.56 (14)C18—C19—C20—C210.8 (3)
C17—N2—C2—C1112.52 (17)C19—C20—C21—C220.0 (3)
C17—N2—C28—C249.5 (2)C20—C21—C22—C231.5 (3)
N1—C1—C11—C16139.21 (18)C20—C21—C22—C27179.41 (18)
N1—C1—C11—C1240.3 (2)C21—C22—C23—C24177.24 (15)
C2—C1—C11—C16121.47 (19)C27—C22—C23—C18179.85 (15)
C11—C1—C2—C3123.69 (15)C21—C22—C23—C182.1 (2)
N1—C1—C2—C36.81 (12)C23—C22—C27—C260.0 (3)
C11—C1—C2—N2114.25 (17)C27—C22—C23—C240.8 (2)
C2—C1—C11—C1259.0 (2)C21—C22—C27—C26177.94 (18)
N1—C1—C2—N2128.87 (15)C18—C23—C24—C283.9 (2)
C1—C2—C3—O1175.9 (2)C22—C23—C24—C250.9 (2)
N2—C2—C3—N1130.79 (15)C22—C23—C24—C28175.38 (14)
N2—C2—C3—O152.5 (3)C18—C23—C24—C25179.75 (15)
C1—C2—C3—N17.35 (13)C23—C24—C25—C260.2 (2)
C5—C4—C9—C80.5 (3)C25—C24—C28—N2175.73 (15)
N1—C4—C9—C8179.60 (17)C23—C24—C28—O4178.75 (16)
C9—C4—C5—C61.6 (3)C23—C24—C28—N20.6 (2)
N1—C4—C5—C6178.42 (18)C28—C24—C25—C26176.07 (16)
C4—C5—C6—C71.2 (3)C25—C24—C28—O42.4 (3)
C5—C6—C7—O2179.20 (19)C24—C25—C26—C270.6 (3)
C5—C6—C7—C80.4 (3)C25—C26—C27—C220.7 (3)
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C11–C16 benzene ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O10.932.573.169 (3)122
C21—H21···O1i0.932.523.344 (2)148
C25—H25···O4ii0.932.463.221 (2)139
C30A—H30A···Cg4iii0.962.883.818 (10)167
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z; (iii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C11–C16 benzene ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O10.932.573.169 (3)122
C21—H21···O1i0.932.523.344 (2)148
C25—H25···O4ii0.932.463.221 (2)139
C30A—H30A···Cg4iii0.962.883.818 (10)167
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z; (iii) x+2, y+1, z+1.
 

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