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In the title mol­ecule, C25H21Cl1N4O6, all bond lengths and angles show normal values. Weak inter­molecular C—H...Cl hydrogen bonds link the mol­ecules into chains extending along the crystallographic c axis. The crystal packing is further stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010671/cv2023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010671/cv2023Isup2.hkl
Contains datablock I

CCDC reference: 608408

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.140
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C13 .. 5.40 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.11 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C25H21ClN4O6Z = 2
Mr = 508.91F(000) = 528
Triclinic, P1Dx = 1.392 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 9.524 (4) ÅCell parameters from 8448 reflections
b = 11.064 (4) Åθ = 3.1–27.5°
c = 12.334 (7) ŵ = 0.21 mm1
α = 88.869 (17)°T = 298 K
β = 70.14 (2)°Chunk, yellow
γ = 83.410 (19)°0.32 × 0.20 × 0.18 mm
V = 1214.0 (10) Å3
Data collection top
Rigaku RAXIS-RAPID
diffractometer
5464 independent reflections
Radiation source: fine-focus sealed tube3282 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1012
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
k = 1413
Tmin = 0.928, Tmax = 0.964l = 1515
11829 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0735P)2]
where P = (Fo2 + 2Fc2)/3
5464 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

Experimental. 1H NMR (CDCl3, 500 MHz, δ, p.p.m.): 3.81(s, 6H), 4.35(s, 2H), 5.78(s, 1H), 6.59–8.34(m, 11H). MS-ESI m/z 509 ([M+1]+)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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*/Ueq
C11.0992 (2)0.23648 (15)0.07818 (17)0.0596 (4)
C21.1417 (2)0.32656 (16)0.15749 (18)0.0655 (5)
H21.14040.31800.23200.079*
C31.1859 (2)0.42923 (15)0.12408 (19)0.0664 (5)
C41.1885 (2)0.44413 (16)0.0144 (2)0.0698 (5)
H41.21920.51430.00640.084*
C51.1452 (2)0.35381 (16)0.06409 (19)0.0686 (5)
H51.14460.36360.13900.082*
C61.1024 (2)0.24809 (14)0.03221 (17)0.0589 (4)
C71.0577 (2)0.16140 (14)0.21717 (17)0.0624 (5)
C81.1872 (2)0.13091 (16)0.2439 (2)0.0715 (5)
H81.27850.10890.18570.086*
C91.1799 (2)0.13337 (15)0.3565 (2)0.0708 (6)
H91.26710.11380.37420.085*
C101.0442 (2)0.16461 (13)0.44505 (18)0.0601 (5)
C110.9156 (2)0.19436 (15)0.41560 (18)0.0628 (5)
H110.82370.21600.47330.075*
C120.9230 (2)0.19213 (15)0.30196 (17)0.0627 (5)
H120.83640.21150.28330.075*
C130.8987 (3)0.17673 (17)0.6531 (2)0.0822 (7)
H13A0.91610.13910.71990.099*
H13B0.83010.13070.63290.099*
C140.8237 (3)0.30515 (16)0.68655 (17)0.0662 (5)
C150.8931 (3)0.40759 (17)0.63941 (18)0.0741 (6)
H150.98970.39790.58550.089*
C160.8202 (3)0.52352 (18)0.6718 (2)0.0819 (6)
H160.86830.59070.63920.098*
C170.6788 (3)0.5406 (2)0.7509 (2)0.0872 (7)
H170.63000.61890.77090.105*
C180.6080 (3)0.4407 (2)0.8013 (2)0.0839 (6)
H180.51290.45110.85720.101*
C190.6814 (3)0.32560 (19)0.76692 (18)0.0717 (6)
C200.5342 (2)0.16607 (16)0.76924 (17)0.0638 (5)
C210.4151 (2)0.00458 (16)0.77120 (19)0.0677 (5)
C220.3932 (2)0.03961 (18)0.6709 (2)0.0775 (6)
H220.34580.00670.63480.093*
C230.4449 (2)0.14655 (17)0.62657 (18)0.0667 (5)
C240.3696 (3)0.1299 (2)0.9305 (2)0.0972 (8)
H24A0.47210.13900.92800.146*
H24B0.32740.20490.95380.146*
H24C0.31290.06630.98480.146*
C250.4708 (3)0.2997 (2)0.4838 (2)0.0985 (8)
H25A0.42750.36400.54050.148*
H25B0.44170.31780.41740.148*
H25C0.57830.29240.46150.148*
N11.0393 (2)0.16729 (15)0.55853 (17)0.0795 (5)
H11.13410.14100.57100.080*
N20.48542 (17)0.06733 (13)0.82408 (14)0.0640 (4)
N30.51929 (18)0.21190 (13)0.67419 (14)0.0666 (4)
N41.2341 (2)0.52390 (16)0.2084 (2)0.0838 (5)
O11.06171 (17)0.15311 (11)0.10288 (12)0.0730 (4)
O20.61195 (19)0.22477 (14)0.82188 (13)0.0894 (5)
O30.36420 (19)0.09925 (13)0.81816 (16)0.0919 (5)
O40.41850 (19)0.18774 (14)0.53136 (14)0.0895 (5)
O51.2280 (2)0.51091 (15)0.30417 (19)0.1147 (6)
O61.2780 (2)0.61300 (14)0.17832 (18)0.1085 (6)
Cl11.04216 (7)0.10522 (4)0.11542 (5)0.0814 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0570 (11)0.0552 (9)0.0687 (13)0.0102 (7)0.0226 (9)0.0014 (8)
C20.0639 (12)0.0637 (11)0.0687 (13)0.0075 (8)0.0224 (10)0.0069 (8)
C30.0596 (11)0.0540 (10)0.0826 (15)0.0091 (8)0.0199 (10)0.0127 (9)
C40.0702 (13)0.0524 (10)0.0886 (16)0.0161 (8)0.0266 (11)0.0034 (9)
C50.0794 (13)0.0581 (10)0.0713 (13)0.0182 (8)0.0262 (11)0.0009 (8)
C60.0580 (11)0.0507 (9)0.0681 (12)0.0109 (7)0.0200 (9)0.0031 (7)
C70.0770 (13)0.0464 (9)0.0693 (13)0.0180 (8)0.0287 (11)0.0050 (7)
C80.0662 (13)0.0553 (10)0.0935 (17)0.0082 (8)0.0267 (12)0.0056 (9)
C90.0694 (13)0.0538 (10)0.1037 (18)0.0025 (8)0.0494 (13)0.0021 (9)
C100.0743 (13)0.0420 (8)0.0790 (13)0.0100 (7)0.0445 (11)0.0077 (7)
C110.0648 (12)0.0624 (10)0.0665 (13)0.0096 (8)0.0287 (10)0.0089 (8)
C120.0670 (12)0.0607 (10)0.0711 (13)0.0150 (8)0.0355 (11)0.0130 (8)
C130.129 (2)0.0669 (12)0.0717 (15)0.0282 (12)0.0565 (15)0.0199 (10)
C140.0994 (16)0.0611 (10)0.0570 (12)0.0322 (9)0.0443 (12)0.0129 (8)
C150.0965 (15)0.0706 (12)0.0637 (13)0.0352 (10)0.0303 (11)0.0092 (9)
C160.1132 (19)0.0613 (12)0.0820 (16)0.0349 (11)0.0394 (15)0.0062 (10)
C170.1035 (19)0.0741 (13)0.0964 (18)0.0202 (12)0.0467 (16)0.0036 (11)
C180.0817 (15)0.0979 (16)0.0829 (16)0.0247 (12)0.0372 (13)0.0023 (12)
C190.0902 (15)0.0839 (13)0.0625 (13)0.0437 (11)0.0440 (12)0.0186 (10)
C200.0679 (12)0.0736 (11)0.0582 (12)0.0265 (9)0.0268 (10)0.0095 (8)
C210.0670 (12)0.0613 (10)0.0765 (14)0.0181 (8)0.0231 (11)0.0018 (9)
C220.0828 (15)0.0748 (12)0.0860 (16)0.0235 (10)0.0379 (12)0.0076 (10)
C230.0695 (12)0.0758 (12)0.0622 (12)0.0123 (9)0.0307 (10)0.0015 (9)
C240.1037 (19)0.0853 (15)0.101 (2)0.0366 (13)0.0255 (15)0.0284 (13)
C250.116 (2)0.1108 (18)0.0846 (18)0.0181 (15)0.0546 (16)0.0239 (13)
N10.0929 (14)0.0764 (10)0.0887 (14)0.0047 (9)0.0577 (12)0.0054 (9)
N20.0602 (9)0.0685 (9)0.0648 (10)0.0183 (7)0.0200 (8)0.0103 (7)
N30.0732 (11)0.0737 (9)0.0639 (10)0.0228 (8)0.0336 (9)0.0116 (7)
N40.0856 (13)0.0659 (11)0.1002 (17)0.0135 (9)0.0318 (12)0.0224 (10)
O10.1009 (10)0.0590 (7)0.0652 (9)0.0314 (7)0.0293 (8)0.0057 (6)
O20.1214 (12)0.1065 (11)0.0722 (10)0.0697 (9)0.0579 (9)0.0367 (8)
O30.1077 (12)0.0719 (9)0.1047 (13)0.0369 (8)0.0393 (10)0.0131 (8)
O40.1102 (12)0.1000 (11)0.0813 (11)0.0241 (9)0.0588 (10)0.0091 (8)
O50.1576 (18)0.0922 (12)0.0941 (14)0.0329 (11)0.0382 (13)0.0317 (10)
O60.1274 (15)0.0717 (10)0.1431 (17)0.0399 (9)0.0606 (13)0.0381 (9)
Cl10.1067 (4)0.0724 (3)0.0800 (4)0.0357 (3)0.0431 (3)0.0052 (2)
Geometric parameters (Å, º) top
C1—C21.378 (3)C15—C161.384 (3)
C1—C61.381 (3)C15—H150.9300
C1—Cl11.7297 (18)C16—C171.363 (3)
C2—C31.373 (3)C16—H160.9300
C2—H20.9300C17—C181.386 (3)
C3—C41.375 (3)C17—H170.9300
C3—N41.460 (3)C18—C191.381 (3)
C4—C51.375 (3)C18—H180.9300
C4—H40.9300C19—O21.406 (2)
C5—C61.388 (2)C20—N31.313 (2)
C5—H50.9300C20—N21.319 (2)
C6—O11.357 (2)C20—O21.358 (2)
C7—C121.363 (3)C21—N21.333 (2)
C7—C81.385 (3)C21—O31.342 (2)
C7—O11.402 (2)C21—C221.365 (3)
C8—C91.367 (3)C22—C231.366 (3)
C8—H80.9300C22—H220.9300
C9—C101.391 (3)C23—N31.337 (2)
C9—H90.9300C23—O41.343 (2)
C10—N11.385 (3)C24—O31.437 (3)
C10—C111.395 (3)C24—H24A0.9600
C11—C121.380 (3)C24—H24B0.9600
C11—H110.9300C24—H24C0.9600
C12—H120.9300C25—O41.428 (3)
C13—N11.441 (3)C25—H25A0.9600
C13—C141.513 (3)C25—H25B0.9600
C13—H13A0.9700C25—H25C0.9600
C13—H13B0.9700N1—H10.9777
C14—C191.377 (3)N4—O51.215 (3)
C14—C151.394 (2)N4—O61.224 (2)
C2—C1—C6121.02 (16)C17—C16—C15120.87 (19)
C2—C1—Cl1120.53 (16)C17—C16—H16119.6
C6—C1—Cl1118.45 (13)C15—C16—H16119.6
C3—C2—C1118.5 (2)C16—C17—C18119.7 (2)
C3—C2—H2120.7C16—C17—H17120.2
C1—C2—H2120.7C18—C17—H17120.2
C2—C3—C4121.83 (17)C19—C18—C17118.8 (2)
C2—C3—N4118.8 (2)C19—C18—H18120.6
C4—C3—N4119.35 (18)C17—C18—H18120.6
C3—C4—C5119.09 (17)C14—C19—C18123.00 (17)
C3—C4—H4120.5C14—C19—O2118.32 (19)
C5—C4—H4120.5C18—C19—O2118.5 (2)
C4—C5—C6120.4 (2)N3—C20—N2129.63 (16)
C4—C5—H5119.8N3—C20—O2118.07 (15)
C6—C5—H5119.8N2—C20—O2112.29 (16)
O1—C6—C1116.43 (14)N2—C21—O3118.52 (19)
O1—C6—C5124.42 (18)N2—C21—C22123.49 (17)
C1—C6—C5119.15 (17)O3—C21—C22117.99 (17)
C12—C7—C8120.7 (2)C21—C22—C23116.27 (17)
C12—C7—O1118.86 (17)C21—C22—H22121.9
C8—C7—O1120.27 (19)C23—C22—H22121.9
C9—C8—C7119.5 (2)N3—C23—O4118.86 (17)
C9—C8—H8120.2N3—C23—C22122.91 (18)
C7—C8—H8120.2O4—C23—C22118.23 (17)
C8—C9—C10121.18 (18)O3—C24—H24A109.5
C8—C9—H9119.4O3—C24—H24B109.5
C10—C9—H9119.4H24A—C24—H24B109.5
N1—C10—C9120.27 (18)O3—C24—H24C109.5
N1—C10—C11121.7 (2)H24A—C24—H24C109.5
C9—C10—C11118.01 (19)H24B—C24—H24C109.5
C12—C11—C10120.8 (2)O4—C25—H25A109.5
C12—C11—H11119.6O4—C25—H25B109.5
C10—C11—H11119.6H25A—C25—H25B109.5
C7—C12—C11119.71 (18)O4—C25—H25C109.5
C7—C12—H12120.1H25A—C25—H25C109.5
C11—C12—H12120.1H25B—C25—H25C109.5
N1—C13—C14115.01 (16)C10—N1—C13121.44 (17)
N1—C13—H13A108.5C10—N1—H1115.8
C14—C13—H13A108.5C13—N1—H1120.8
N1—C13—H13B108.5C20—N2—C21113.58 (17)
C14—C13—H13B108.5C20—N3—C23114.03 (16)
H13A—C13—H13B107.5O5—N4—O6123.31 (19)
C19—C14—C15116.78 (19)O5—N4—C3118.70 (19)
C19—C14—C13120.52 (17)O6—N4—C3118.0 (2)
C15—C14—C13122.7 (2)C6—O1—C7119.02 (13)
C16—C15—C14120.9 (2)C20—O2—C19118.09 (14)
C16—C15—H15119.6C21—O3—C24118.69 (17)
C14—C15—H15119.6C23—O4—C25119.23 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···Cl1i0.972.693.600 (3)156
Symmetry code: (i) x, y, z+1.
 

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