




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015001425/hb7354sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015001425/hb7354Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015001425/hb7354Isup3.cml |
CCDC reference: 1044874
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(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
No syntax errors found
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
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+].
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.
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).
C28H19ClN2O4·C2H6OS | Z = 2 |
Mr = 561.03 | F(000) = 584 |
Triclinic, P1 | Dx = 1.385 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9925 (3) Å | Cell parameters from 9923 reflections |
b = 12.1761 (5) Å | θ = 2.9–29.9° |
c = 14.2313 (6) Å | µ = 0.26 mm−1 |
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 |
Bruker APEXII CCD diffractometer | 5777 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 30.0°, θmin = 2.2° |
ϕ and ω scans | h = −11→11 |
29975 measured reflections | k = −17→17 |
7737 independent reflections | l = −19→19 |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H-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 reflections | Δρmax = 0.68 e Å−3 |
359 parameters | Δρmin = −0.52 e Å−3 |
C28H19ClN2O4·C2H6OS | γ = 101.602 (2)° |
Mr = 561.03 | V = 1345.67 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9925 (3) Å | Mo Kα radiation |
b = 12.1761 (5) Å | µ = 0.26 mm−1 |
c = 14.2313 (6) Å | T = 296 K |
α = 93.549 (2)° | 0.45 × 0.30 × 0.20 mm |
β = 95.520 (2)° |
Bruker APEXII CCD diffractometer | 5777 reflections with I > 2σ(I) |
29975 measured reflections | Rint = 0.022 |
7737 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 6 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.68 e Å−3 |
7737 reflections | Δρmin = −0.52 e Å−3 |
359 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.69679 (12) | 0.13588 (7) | 0.68363 (4) | 0.0886 (3) | |
S1A | 0.83996 (15) | 0.62942 (10) | 0.36822 (7) | 0.0884 (4) | 0.847 (2) |
S1B | 0.7471 (8) | 0.6453 (5) | 0.4182 (4) | 0.0884 (4) | 0.153 (2) |
O1 | 0.5935 (2) | 0.15324 (13) | 0.07604 (10) | 0.0572 (5) | |
O2 | −0.20212 (18) | −0.02113 (14) | 0.22243 (12) | 0.0620 (5) | |
O3 | 1.06205 (19) | 0.37028 (13) | 0.29270 (12) | 0.0603 (5) | |
O4 | 0.58077 (15) | 0.40773 (12) | 0.11511 (10) | 0.0467 (4) | |
N1 | 0.48129 (19) | 0.18953 (13) | 0.21909 (10) | 0.0411 (4) | |
N2 | 0.82660 (17) | 0.38087 (12) | 0.19376 (10) | 0.0355 (4) | |
C1 | 0.5863 (2) | 0.27720 (14) | 0.28906 (12) | 0.0368 (5) | |
C2 | 0.7342 (2) | 0.27719 (14) | 0.22466 (12) | 0.0381 (5) | |
C3 | 0.5985 (2) | 0.19748 (15) | 0.15453 (13) | 0.0423 (5) | |
C4 | 0.3093 (2) | 0.13255 (14) | 0.21725 (12) | 0.0372 (5) | |
C5 | 0.2294 (3) | 0.05633 (17) | 0.14244 (13) | 0.0469 (6) | |
O5A | 0.6596 (5) | 0.5604 (2) | 0.3457 (2) | 0.1081 (11) | 0.847 (2) |
C6 | 0.0575 (3) | 0.00331 (17) | 0.14164 (14) | 0.0497 (6) | |
C7 | −0.0327 (2) | 0.02482 (16) | 0.21594 (14) | 0.0450 (5) | |
C8 | 0.0494 (2) | 0.09910 (18) | 0.29171 (15) | 0.0488 (6) | |
C9 | 0.2184 (2) | 0.15335 (16) | 0.29214 (14) | 0.0450 (6) | |
C10 | −0.2998 (3) | −0.0868 (2) | 0.1422 (2) | 0.0750 (9) | |
C11 | 0.6159 (2) | 0.24211 (14) | 0.38776 (12) | 0.0365 (4) | |
C12 | 0.6490 (2) | 0.13637 (15) | 0.40284 (13) | 0.0413 (5) | |
C13 | 0.6763 (3) | 0.10452 (17) | 0.49434 (14) | 0.0477 (6) | |
C14 | 0.6676 (3) | 0.17782 (19) | 0.56949 (14) | 0.0524 (6) | |
C15 | 0.6345 (4) | 0.2827 (2) | 0.55697 (15) | 0.0612 (8) | |
C16 | 0.6094 (3) | 0.31440 (17) | 0.46505 (14) | 0.0500 (6) | |
C17 | 1.0008 (2) | 0.41714 (14) | 0.22957 (12) | 0.0376 (5) | |
C18 | 1.1000 (2) | 0.51167 (13) | 0.18560 (11) | 0.0337 (4) | |
C19 | 1.2760 (2) | 0.54014 (16) | 0.20663 (13) | 0.0428 (5) | |
C20 | 1.3723 (2) | 0.62737 (18) | 0.16236 (15) | 0.0495 (6) | |
C21 | 1.2935 (2) | 0.68586 (17) | 0.09901 (13) | 0.0464 (5) | |
C22 | 1.1127 (2) | 0.66006 (14) | 0.07639 (12) | 0.0372 (5) | |
C23 | 1.01511 (19) | 0.56994 (13) | 0.11954 (10) | 0.0316 (4) | |
C24 | 0.83533 (19) | 0.53926 (13) | 0.09505 (11) | 0.0325 (4) | |
C25 | 0.7550 (2) | 0.59720 (15) | 0.03094 (12) | 0.0393 (5) | |
C26 | 0.8512 (3) | 0.68702 (16) | −0.01091 (13) | 0.0462 (6) | |
C27 | 1.0259 (3) | 0.71740 (15) | 0.01086 (13) | 0.0438 (5) | |
C28 | 0.7350 (2) | 0.44063 (14) | 0.13389 (11) | 0.0341 (4) | |
O5B | 0.688 (3) | 0.6029 (15) | 0.3255 (13) | 0.1081 (11) | 0.153 (2) |
C29A | 0.8342 (10) | 0.7606 (7) | 0.3416 (6) | 0.183 (3) | 0.847 (2) |
C30A | 0.8821 (12) | 0.6486 (7) | 0.4874 (7) | 0.183 (3) | 0.847 (2) |
C29B | 0.821 (6) | 0.786 (2) | 0.413 (4) | 0.183 (3) | 0.153 (2) |
C30B | 0.904 (5) | 0.593 (4) | 0.479 (5) | 0.183 (3) | 0.153 (2) |
H1 | 0.54490 | 0.34770 | 0.28880 | 0.0440* | |
H2 | 0.81630 | 0.23530 | 0.25290 | 0.0460* | |
H5 | 0.29030 | 0.04040 | 0.09260 | 0.0560* | |
H6 | 0.00350 | −0.04690 | 0.09060 | 0.0600* | |
H8 | −0.01000 | 0.11250 | 0.34290 | 0.0580* | |
H9 | 0.27160 | 0.20410 | 0.34290 | 0.0540* | |
H10A | −0.41530 | −0.11360 | 0.15630 | 0.1130* | |
H10B | −0.30120 | −0.04140 | 0.08940 | 0.1130* | |
H10C | −0.24890 | −0.14960 | 0.12670 | 0.1130* | |
H12 | 0.65280 | 0.08650 | 0.35130 | 0.0500* | |
H13 | 0.70030 | 0.03420 | 0.50420 | 0.0570* | |
H15 | 0.62890 | 0.33170 | 0.60890 | 0.0730* | |
H16 | 0.58800 | 0.38550 | 0.45580 | 0.0600* | |
H19 | 1.33080 | 0.50150 | 0.25020 | 0.0510* | |
H20 | 1.49120 | 0.64560 | 0.17630 | 0.0590* | |
H21 | 1.35960 | 0.74340 | 0.07030 | 0.0560* | |
H25 | 0.63660 | 0.57680 | 0.01530 | 0.0470* | |
H26 | 0.79580 | 0.72620 | −0.05380 | 0.0550* | |
H27 | 1.08800 | 0.77660 | −0.01790 | 0.0530* | |
H29A | 0.94730 | 0.80710 | 0.35510 | 0.2740* | 0.847 (2) |
H29B | 0.79540 | 0.76000 | 0.27560 | 0.2740* | 0.847 (2) |
H29C | 0.75680 | 0.78990 | 0.37900 | 0.2740* | 0.847 (2) |
H30A | 0.99640 | 0.69240 | 0.50420 | 0.2740* | 0.847 (2) |
H30B | 0.80100 | 0.68750 | 0.51270 | 0.2740* | 0.847 (2) |
H30C | 0.87290 | 0.57690 | 0.51320 | 0.2740* | 0.847 (2) |
H29D | 0.86430 | 0.82040 | 0.47590 | 0.2740* | 0.153 (2) |
H29E | 0.91190 | 0.79800 | 0.37310 | 0.2740* | 0.153 (2) |
H29F | 0.72910 | 0.81960 | 0.38830 | 0.2740* | 0.153 (2) |
H30D | 0.93010 | 0.63100 | 0.54170 | 0.2740* | 0.153 (2) |
H30E | 0.86390 | 0.51410 | 0.48360 | 0.2740* | 0.153 (2) |
H30F | 1.00470 | 0.60530 | 0.44680 | 0.2740* | 0.153 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1404 (7) | 0.0971 (5) | 0.0389 (3) | 0.0438 (5) | 0.0117 (3) | 0.0232 (3) |
S1A | 0.0995 (7) | 0.1062 (7) | 0.0621 (5) | 0.0320 (6) | 0.0056 (4) | −0.0015 (5) |
S1B | 0.0995 (7) | 0.1062 (7) | 0.0621 (5) | 0.0320 (6) | 0.0056 (4) | −0.0015 (5) |
O1 | 0.0713 (10) | 0.0540 (8) | 0.0402 (7) | −0.0060 (7) | 0.0177 (7) | 0.0018 (6) |
O2 | 0.0407 (7) | 0.0676 (10) | 0.0676 (10) | −0.0074 (7) | 0.0065 (7) | −0.0120 (8) |
O3 | 0.0527 (8) | 0.0609 (9) | 0.0618 (9) | 0.0030 (7) | −0.0159 (7) | 0.0261 (7) |
O4 | 0.0309 (6) | 0.0547 (8) | 0.0505 (7) | −0.0006 (5) | −0.0019 (5) | 0.0152 (6) |
N1 | 0.0403 (7) | 0.0450 (8) | 0.0327 (7) | −0.0041 (6) | 0.0042 (5) | 0.0040 (6) |
N2 | 0.0317 (6) | 0.0381 (7) | 0.0354 (7) | 0.0019 (5) | 0.0032 (5) | 0.0111 (5) |
C1 | 0.0355 (8) | 0.0394 (8) | 0.0328 (8) | 0.0009 (6) | 0.0036 (6) | 0.0058 (6) |
C2 | 0.0381 (8) | 0.0385 (8) | 0.0369 (8) | 0.0030 (6) | 0.0065 (6) | 0.0104 (6) |
C3 | 0.0478 (9) | 0.0399 (8) | 0.0368 (9) | 0.0002 (7) | 0.0085 (7) | 0.0083 (7) |
C4 | 0.0378 (8) | 0.0368 (8) | 0.0353 (8) | 0.0027 (6) | 0.0020 (6) | 0.0091 (6) |
C5 | 0.0503 (10) | 0.0490 (10) | 0.0361 (9) | −0.0030 (8) | 0.0077 (7) | 0.0025 (7) |
O5A | 0.128 (2) | 0.0609 (17) | 0.112 (2) | −0.0059 (18) | −0.0486 (19) | 0.0060 (15) |
C6 | 0.0515 (10) | 0.0459 (10) | 0.0431 (10) | −0.0064 (8) | 0.0025 (8) | −0.0035 (8) |
C7 | 0.0393 (9) | 0.0410 (9) | 0.0508 (10) | 0.0012 (7) | 0.0023 (7) | 0.0009 (7) |
C8 | 0.0377 (9) | 0.0554 (11) | 0.0507 (11) | 0.0063 (8) | 0.0067 (7) | −0.0065 (8) |
C9 | 0.0383 (9) | 0.0486 (10) | 0.0440 (10) | 0.0051 (7) | −0.0001 (7) | −0.0077 (8) |
C10 | 0.0529 (13) | 0.0739 (16) | 0.0820 (18) | −0.0143 (11) | 0.0018 (12) | −0.0205 (13) |
C11 | 0.0332 (7) | 0.0404 (8) | 0.0335 (8) | 0.0008 (6) | 0.0045 (6) | 0.0061 (6) |
C12 | 0.0458 (9) | 0.0401 (8) | 0.0376 (9) | 0.0059 (7) | 0.0084 (7) | 0.0044 (7) |
C13 | 0.0555 (11) | 0.0449 (9) | 0.0448 (10) | 0.0109 (8) | 0.0092 (8) | 0.0122 (8) |
C14 | 0.0626 (12) | 0.0604 (12) | 0.0352 (9) | 0.0123 (9) | 0.0059 (8) | 0.0120 (8) |
C15 | 0.0901 (17) | 0.0599 (13) | 0.0355 (10) | 0.0227 (12) | 0.0047 (10) | −0.0008 (9) |
C16 | 0.0686 (13) | 0.0423 (9) | 0.0395 (10) | 0.0142 (9) | 0.0025 (8) | 0.0031 (7) |
C17 | 0.0347 (8) | 0.0404 (8) | 0.0358 (8) | 0.0052 (6) | −0.0021 (6) | 0.0056 (6) |
C18 | 0.0310 (7) | 0.0361 (7) | 0.0313 (7) | 0.0025 (6) | 0.0011 (5) | −0.0008 (6) |
C19 | 0.0334 (8) | 0.0491 (9) | 0.0418 (9) | 0.0044 (7) | −0.0029 (6) | −0.0031 (7) |
C20 | 0.0315 (8) | 0.0594 (11) | 0.0495 (10) | −0.0059 (7) | 0.0027 (7) | −0.0061 (8) |
C21 | 0.0417 (9) | 0.0475 (9) | 0.0417 (9) | −0.0108 (7) | 0.0095 (7) | −0.0029 (7) |
C22 | 0.0416 (8) | 0.0344 (8) | 0.0316 (8) | −0.0019 (6) | 0.0076 (6) | −0.0016 (6) |
C23 | 0.0324 (7) | 0.0323 (7) | 0.0276 (7) | 0.0017 (5) | 0.0037 (5) | −0.0009 (5) |
C24 | 0.0326 (7) | 0.0341 (7) | 0.0296 (7) | 0.0037 (6) | 0.0029 (5) | 0.0039 (6) |
C25 | 0.0399 (8) | 0.0411 (8) | 0.0361 (8) | 0.0083 (7) | −0.0003 (6) | 0.0057 (7) |
C26 | 0.0590 (11) | 0.0409 (9) | 0.0401 (9) | 0.0130 (8) | 0.0031 (8) | 0.0106 (7) |
C27 | 0.0561 (10) | 0.0345 (8) | 0.0382 (9) | −0.0002 (7) | 0.0105 (7) | 0.0060 (7) |
C28 | 0.0310 (7) | 0.0389 (8) | 0.0312 (7) | 0.0040 (6) | 0.0020 (5) | 0.0069 (6) |
O5B | 0.128 (2) | 0.0609 (17) | 0.112 (2) | −0.0059 (18) | −0.0486 (19) | 0.0060 (15) |
C29A | 0.140 (4) | 0.184 (6) | 0.187 (5) | −0.034 (4) | −0.060 (4) | 0.058 (5) |
C30A | 0.140 (4) | 0.184 (6) | 0.187 (5) | −0.034 (4) | −0.060 (4) | 0.058 (5) |
C29B | 0.140 (4) | 0.184 (6) | 0.187 (5) | −0.034 (4) | −0.060 (4) | 0.058 (5) |
C30B | 0.140 (4) | 0.184 (6) | 0.187 (5) | −0.034 (4) | −0.060 (4) | 0.058 (5) |
Cl1—C14 | 1.741 (2) | C22—C23 | 1.422 (2) |
S1A—C30A | 1.689 (10) | C22—C27 | 1.411 (3) |
S1A—O5A | 1.509 (4) | C23—C24 | 1.413 (2) |
S1A—C29A | 1.673 (8) | C24—C25 | 1.375 (2) |
S1B—O5B | 1.388 (19) | C24—C28 | 1.473 (2) |
S1B—C30B | 1.71 (5) | C25—C26 | 1.405 (3) |
S1B—C29B | 1.71 (3) | C26—C27 | 1.370 (3) |
O1—C3 | 1.203 (2) | C1—H1 | 0.9800 |
O2—C10 | 1.420 (3) | C2—H2 | 0.9800 |
O2—C7 | 1.371 (2) | C5—H5 | 0.9300 |
O3—C17 | 1.210 (2) | C6—H6 | 0.9300 |
O4—C28 | 1.215 (2) | C8—H8 | 0.9300 |
N1—C3 | 1.368 (2) | C9—H9 | 0.9300 |
N1—C1 | 1.477 (2) | C10—H10C | 0.9600 |
N1—C4 | 1.407 (2) | C10—H10B | 0.9600 |
N2—C28 | 1.401 (2) | C10—H10A | 0.9600 |
N2—C2 | 1.445 (2) | C12—H12 | 0.9300 |
N2—C17 | 1.408 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.564 (2) | C15—H15 | 0.9300 |
C1—C11 | 1.504 (2) | C16—H16 | 0.9300 |
C2—C3 | 1.537 (2) | C19—H19 | 0.9300 |
C4—C5 | 1.382 (3) | C20—H20 | 0.9300 |
C4—C9 | 1.385 (2) | C21—H21 | 0.9300 |
C5—C6 | 1.394 (3) | C25—H25 | 0.9300 |
C6—C7 | 1.377 (3) | C26—H26 | 0.9300 |
C7—C8 | 1.384 (3) | C27—H27 | 0.9300 |
C8—C9 | 1.378 (2) | C29A—H29C | 0.9600 |
C11—C12 | 1.391 (2) | C29A—H29A | 0.9600 |
C11—C16 | 1.377 (3) | C29A—H29B | 0.9600 |
C12—C13 | 1.391 (3) | C30A—H30A | 0.9600 |
C13—C14 | 1.366 (3) | C30A—H30B | 0.9600 |
C14—C15 | 1.374 (3) | C30A—H30C | 0.9600 |
C15—C16 | 1.394 (3) | C29B—H29D | 0.9700 |
C17—C18 | 1.471 (2) | C29B—H29E | 0.9600 |
C18—C23 | 1.415 (2) | C29B—H29F | 0.9600 |
C18—C19 | 1.378 (2) | C30B—H30D | 0.9600 |
C19—C20 | 1.402 (3) | C30B—H30E | 0.9600 |
C20—C21 | 1.367 (3) | C30B—H30F | 0.9500 |
C21—C22 | 1.416 (2) | ||
O5A—S1A—C30A | 107.4 (3) | O4—C28—N2 | 119.23 (15) |
C29A—S1A—C30A | 100.9 (4) | N1—C1—H1 | 112.00 |
O5A—S1A—C29A | 107.1 (3) | C11—C1—H1 | 112.00 |
C29B—S1B—C30B | 108 (2) | C2—C1—H1 | 112.00 |
O5B—S1B—C29B | 106 (2) | C3—C2—H2 | 110.00 |
O5B—S1B—C30B | 119 (2) | N2—C2—H2 | 109.00 |
C7—O2—C10 | 118.08 (18) | C1—C2—H2 | 109.00 |
C3—N1—C4 | 133.80 (15) | C6—C5—H5 | 120.00 |
C1—N1—C4 | 129.79 (14) | C4—C5—H5 | 120.00 |
C1—N1—C3 | 95.78 (14) | C7—C6—H6 | 120.00 |
C2—N2—C17 | 117.44 (14) | C5—C6—H6 | 120.00 |
C17—N2—C28 | 124.63 (14) | C7—C8—H8 | 120.00 |
C2—N2—C28 | 117.87 (14) | C9—C8—H8 | 120.00 |
N1—C1—C11 | 115.59 (14) | C4—C9—H9 | 120.00 |
N1—C1—C2 | 86.20 (12) | C8—C9—H9 | 120.00 |
C2—C1—C11 | 117.03 (14) | O2—C10—H10C | 109.00 |
C1—C2—C3 | 85.86 (12) | O2—C10—H10B | 109.00 |
N2—C2—C1 | 120.95 (14) | H10A—C10—H10C | 110.00 |
N2—C2—C3 | 119.42 (14) | O2—C10—H10A | 109.00 |
O1—C3—N1 | 132.51 (17) | H10A—C10—H10B | 109.00 |
N1—C3—C2 | 91.20 (14) | H10B—C10—H10C | 109.00 |
O1—C3—C2 | 136.20 (17) | C11—C12—H12 | 120.00 |
N1—C4—C9 | 119.16 (15) | C13—C12—H12 | 120.00 |
C5—C4—C9 | 119.41 (17) | C14—C13—H13 | 120.00 |
N1—C4—C5 | 121.44 (16) | C12—C13—H13 | 120.00 |
C4—C5—C6 | 120.03 (19) | C14—C15—H15 | 121.00 |
C5—C6—C7 | 120.34 (18) | C16—C15—H15 | 121.00 |
O2—C7—C8 | 115.19 (17) | C11—C16—H16 | 120.00 |
C6—C7—C8 | 119.29 (17) | C15—C16—H16 | 119.00 |
O2—C7—C6 | 125.52 (18) | C20—C19—H19 | 120.00 |
C7—C8—C9 | 120.65 (18) | C18—C19—H19 | 120.00 |
C4—C9—C8 | 120.25 (18) | C21—C20—H20 | 120.00 |
C12—C11—C16 | 118.78 (17) | C19—C20—H20 | 120.00 |
C1—C11—C16 | 120.29 (16) | C22—C21—H21 | 120.00 |
C1—C11—C12 | 120.93 (15) | C20—C21—H21 | 120.00 |
C11—C12—C13 | 120.60 (17) | C26—C25—H25 | 120.00 |
C12—C13—C14 | 119.18 (19) | C24—C25—H25 | 120.00 |
C13—C14—C15 | 121.63 (19) | C27—C26—H26 | 120.00 |
Cl1—C14—C13 | 118.83 (17) | C25—C26—H26 | 120.00 |
Cl1—C14—C15 | 119.53 (16) | C22—C27—H27 | 120.00 |
C14—C15—C16 | 118.8 (2) | C26—C27—H27 | 120.00 |
C11—C16—C15 | 121.02 (19) | S1A—C29A—H29B | 109.00 |
O3—C17—C18 | 123.36 (16) | H29A—C29A—H29C | 109.00 |
O3—C17—N2 | 120.05 (16) | S1A—C29A—H29C | 109.00 |
N2—C17—C18 | 116.58 (14) | H29A—C29A—H29B | 110.00 |
C17—C18—C19 | 119.58 (15) | S1A—C29A—H29A | 109.00 |
C17—C18—C23 | 119.88 (14) | H29B—C29A—H29C | 110.00 |
C19—C18—C23 | 120.51 (15) | S1A—C30A—H30C | 110.00 |
C18—C19—C20 | 119.98 (16) | H30A—C30A—H30C | 109.00 |
C19—C20—C21 | 120.76 (16) | H30B—C30A—H30C | 109.00 |
C20—C21—C22 | 120.96 (17) | H30A—C30A—H30B | 109.00 |
C21—C22—C27 | 122.97 (17) | S1A—C30A—H30A | 110.00 |
C23—C22—C27 | 118.61 (16) | S1A—C30A—H30B | 109.00 |
C21—C22—C23 | 118.39 (15) | S1B—C29B—H29D | 109.00 |
C22—C23—C24 | 119.53 (14) | S1B—C29B—H29E | 110.00 |
C18—C23—C24 | 121.09 (14) | S1B—C29B—H29F | 110.00 |
C18—C23—C22 | 119.37 (14) | H29D—C29B—H29E | 109.00 |
C23—C24—C25 | 120.25 (15) | H29D—C29B—H29F | 109.00 |
C25—C24—C28 | 119.77 (14) | H29E—C29B—H29F | 110.00 |
C23—C24—C28 | 119.88 (14) | S1B—C30B—H30D | 109.00 |
C24—C25—C26 | 120.21 (16) | S1B—C30B—H30E | 109.00 |
C25—C26—C27 | 120.58 (18) | S1B—C30B—H30F | 110.00 |
C22—C27—C26 | 120.81 (17) | H30D—C30B—H30E | 109.00 |
N2—C28—C24 | 116.85 (14) | H30D—C30B—H30F | 110.00 |
O4—C28—C24 | 123.89 (15) | H30E—C30B—H30F | 110.00 |
C10—O2—C7—C6 | −7.4 (3) | C6—C7—C8—C9 | 1.6 (3) |
C10—O2—C7—C8 | 172.23 (19) | O2—C7—C8—C9 | −178.04 (18) |
C3—N1—C1—C2 | −7.68 (13) | C7—C8—C9—C4 | −1.2 (3) |
C4—N1—C1—C11 | 62.4 (2) | C1—C11—C12—C13 | 180.00 (18) |
C4—N1—C1—C2 | −179.39 (17) | C16—C11—C12—C13 | −0.5 (3) |
C3—N1—C1—C11 | −125.92 (15) | C12—C11—C16—C15 | −0.3 (3) |
C4—N1—C3—O1 | −4.1 (4) | C1—C11—C16—C15 | 179.2 (2) |
C1—N1—C3—C2 | 7.80 (14) | C11—C12—C13—C14 | 1.0 (3) |
C4—N1—C3—C2 | 178.97 (19) | C12—C13—C14—C15 | −0.8 (4) |
C1—N1—C4—C5 | 176.58 (17) | C12—C13—C14—Cl1 | 178.46 (17) |
C3—N1—C4—C5 | 8.0 (3) | Cl1—C14—C15—C16 | −179.2 (2) |
C1—N1—C4—C9 | −3.5 (3) | C13—C14—C15—C16 | 0.0 (4) |
C3—N1—C4—C9 | −172.02 (19) | C14—C15—C16—C11 | 0.6 (4) |
C1—N1—C3—O1 | −175.3 (2) | O3—C17—C18—C19 | 9.3 (3) |
C17—N2—C2—C3 | −143.50 (15) | N2—C17—C18—C23 | 7.7 (2) |
C28—N2—C2—C3 | 39.3 (2) | O3—C17—C18—C23 | −173.05 (17) |
C28—N2—C17—C18 | −13.0 (2) | N2—C17—C18—C19 | −169.99 (15) |
C28—N2—C2—C1 | −64.7 (2) | C17—C18—C23—C22 | −179.03 (15) |
C2—N2—C28—O4 | 4.7 (2) | C19—C18—C23—C24 | 177.96 (15) |
C2—N2—C17—O3 | −9.2 (2) | C17—C18—C23—C24 | 0.3 (2) |
C17—N2—C28—O4 | −172.28 (16) | C19—C18—C23—C22 | −1.4 (2) |
C28—N2—C17—O3 | 167.75 (17) | C23—C18—C19—C20 | −0.1 (3) |
C2—N2—C17—C18 | 170.06 (14) | C17—C18—C19—C20 | 177.60 (17) |
C2—N2—C28—C24 | −173.56 (14) | C18—C19—C20—C21 | 0.8 (3) |
C17—N2—C2—C1 | 112.52 (17) | C19—C20—C21—C22 | 0.0 (3) |
C17—N2—C28—C24 | 9.5 (2) | C20—C21—C22—C23 | −1.5 (3) |
N1—C1—C11—C16 | −139.21 (18) | C20—C21—C22—C27 | −179.41 (18) |
N1—C1—C11—C12 | 40.3 (2) | C21—C22—C23—C24 | −177.24 (15) |
C2—C1—C11—C16 | 121.47 (19) | C27—C22—C23—C18 | −179.85 (15) |
C11—C1—C2—C3 | 123.69 (15) | C21—C22—C23—C18 | 2.1 (2) |
N1—C1—C2—C3 | 6.81 (12) | C23—C22—C27—C26 | 0.0 (3) |
C11—C1—C2—N2 | −114.25 (17) | C27—C22—C23—C24 | 0.8 (2) |
C2—C1—C11—C12 | −59.0 (2) | C21—C22—C27—C26 | 177.94 (18) |
N1—C1—C2—N2 | 128.87 (15) | C18—C23—C24—C28 | −3.9 (2) |
C1—C2—C3—O1 | 175.9 (2) | C22—C23—C24—C25 | −0.9 (2) |
N2—C2—C3—N1 | −130.79 (15) | C22—C23—C24—C28 | 175.38 (14) |
N2—C2—C3—O1 | 52.5 (3) | C18—C23—C24—C25 | 179.75 (15) |
C1—C2—C3—N1 | −7.35 (13) | C23—C24—C25—C26 | 0.2 (2) |
C5—C4—C9—C8 | −0.5 (3) | C25—C24—C28—N2 | 175.73 (15) |
N1—C4—C9—C8 | 179.60 (17) | C23—C24—C28—O4 | −178.75 (16) |
C9—C4—C5—C6 | 1.6 (3) | C23—C24—C28—N2 | −0.6 (2) |
N1—C4—C5—C6 | −178.42 (18) | C28—C24—C25—C26 | −176.07 (16) |
C4—C5—C6—C7 | −1.2 (3) | C25—C24—C28—O4 | −2.4 (3) |
C5—C6—C7—O2 | 179.20 (19) | C24—C25—C26—C27 | 0.6 (3) |
C5—C6—C7—C8 | −0.4 (3) | C25—C26—C27—C22 | −0.7 (3) |
Cg4 is the centroid of the C11–C16 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.57 | 3.169 (3) | 122 |
C21—H21···O1i | 0.93 | 2.52 | 3.344 (2) | 148 |
C25—H25···O4ii | 0.93 | 2.46 | 3.221 (2) | 139 |
C30A—H30A···Cg4iii | 0.96 | 2.88 | 3.818 (10) | 167 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1. |
Cg4 is the centroid of the C11–C16 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.57 | 3.169 (3) | 122 |
C21—H21···O1i | 0.93 | 2.52 | 3.344 (2) | 148 |
C25—H25···O4ii | 0.93 | 2.46 | 3.221 (2) | 139 |
C30A—H30A···Cg4iii | 0.96 | 2.88 | 3.818 (10) | 167 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1. |
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.