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Two oxetanocin A derivatives have been synthesized stereospecifically. The crystal structures of both derivatives and a synthetic inter­mediate are reported on herein.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019004432/zp2033sup1.cif
Contains datablocks global, I, II, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019004432/zp2033Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019004432/zp2033IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019004432/zp2033IIsup5.cml
Supplementary material

CCDC references: 1907200; 1907199; 1907198

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.111
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.15 Report PLAT480_ALERT_4_C Long H...A H-Bond Reported H4' ..CL1 . 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6'B ..N1 . 2.68 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.801 Check
Alert level G PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 6 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: II
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low . 0.959 Why? PLAT921_ALERT_1_B R1 in the CIF and FCF Differ by ............... -0.0128 Check PLAT922_ALERT_1_B wR2 in the CIF and FCF Differ by ............... -0.0385 Check PLAT927_ALERT_1_B Reported and Calculated wR2 Differ by ......... -0.0115 Check
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.63 Report PLAT410_ALERT_2_C Short Intra H...H Contact H3'1 ..H4'B . 1.97 Ang. x,y,z = 1_555 Check PLAT410_ALERT_2_C Short Intra H...H Contact H5'2 ..H4'B . 1.96 Ang. x,y,z = 1_555 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.592 74 Report PLAT923_ALERT_1_C S Values in the CIF and FCF Differ by ....... -0.428 Check PLAT928_ALERT_1_C Reported and Calculated S value Differ by . -0.133 Check PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 1 Check
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 2 Note PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 2 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 13% Note PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C2' - C3' . 1.52 Ang. PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C2' - C5' . 1.53 Ang. PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1 ..Cl1 3.37 Ang. -x,1-y,1-z = 2_566 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 11 Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 1 Note PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 83% Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 3 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 3 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 4 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 12 ALERT level G = General information/check it is not something unexpected 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: IV
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low . 0.954 Why?
Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5875
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 6 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 4 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-[(6-Chloro-7H-purin-7-yl)methyl]cyclobutan-1-one (I) top
Crystal data top
C10H9ClN4OF(000) = 488
Mr = 236.66Dx = 1.555 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.9736 (5) ÅCell parameters from 9903 reflections
b = 6.8854 (4) Åθ = 3.3–32.6°
c = 12.2746 (5) ŵ = 0.36 mm1
β = 92.938 (4)°T = 110 K
V = 1010.63 (8) Å3Plate, pale_yellow
Z = 40.43 × 0.21 × 0.04 mm
Data collection top
Bruker APEXII CCD
diffractometer
2508 independent reflections
Radiation source: sealed X-ray tube2217 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω scansθmax = 28.3°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
h = 1515
Tmin = 0.661, Tmax = 1.000k = 99
35539 measured reflectionsl = 1616
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.9477P]
where P = (Fo2 + 2Fc2)/3
2508 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.70136 (4)0.21385 (7)0.52904 (4)0.02685 (14)
N10.81306 (13)0.2530 (2)0.35301 (12)0.0230 (3)
N30.93051 (12)0.5196 (2)0.30500 (11)0.0219 (3)
N70.84068 (11)0.6388 (2)0.56456 (11)0.0183 (3)
N90.95030 (12)0.7744 (2)0.44062 (12)0.0216 (3)
O1'0.43878 (13)0.6449 (3)0.76126 (16)0.0503 (5)
C2'0.53242 (16)0.6753 (3)0.73657 (17)0.0303 (4)
C3'0.64220 (16)0.7042 (3)0.80129 (15)0.0297 (4)
H3'A0.6705980.5857400.8390750.036*
H3'B0.6424610.8164810.8516950.036*
C4'0.69801 (14)0.7464 (3)0.69174 (14)0.0215 (4)
H4'0.7203280.8858050.6855330.026*
C5'0.58520 (15)0.7032 (3)0.62724 (16)0.0297 (4)
H5'A0.5547630.8148700.5844830.036*
H5'B0.5862950.5841320.5820800.036*
C6'0.79428 (14)0.6106 (3)0.67259 (12)0.0198 (3)
H6'A0.8541600.6321560.7299570.024*
H6'B0.7682620.4747990.6787460.024*
C20.88240 (14)0.3491 (3)0.28787 (13)0.0230 (4)
H20.8983770.2859130.2216490.028*
C40.90857 (13)0.6006 (3)0.40103 (13)0.0183 (3)
C50.83895 (13)0.5123 (2)0.47653 (12)0.0176 (3)
C60.79181 (14)0.3358 (3)0.44645 (13)0.0198 (3)
C80.90917 (14)0.7900 (3)0.53629 (14)0.0205 (3)
H80.9250730.8973560.5831670.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0305 (2)0.0264 (2)0.0241 (2)0.00833 (17)0.00535 (16)0.00170 (17)
N10.0231 (7)0.0246 (8)0.0213 (7)0.0002 (6)0.0002 (6)0.0029 (6)
N30.0215 (7)0.0272 (8)0.0173 (7)0.0026 (6)0.0046 (5)0.0014 (6)
N70.0202 (7)0.0202 (7)0.0146 (6)0.0007 (5)0.0030 (5)0.0009 (5)
N90.0213 (7)0.0210 (7)0.0229 (7)0.0006 (6)0.0036 (5)0.0027 (6)
O1'0.0302 (8)0.0585 (12)0.0639 (11)0.0075 (8)0.0186 (8)0.0010 (9)
C2'0.0257 (9)0.0282 (10)0.0377 (10)0.0011 (7)0.0102 (8)0.0006 (8)
C3'0.0284 (9)0.0409 (12)0.0207 (8)0.0025 (8)0.0091 (7)0.0002 (8)
C4'0.0198 (8)0.0263 (9)0.0187 (8)0.0019 (6)0.0046 (6)0.0022 (6)
C5'0.0215 (8)0.0425 (12)0.0251 (9)0.0037 (8)0.0000 (7)0.0010 (8)
C6'0.0228 (8)0.0253 (9)0.0116 (7)0.0016 (7)0.0033 (6)0.0011 (6)
C20.0229 (8)0.0301 (9)0.0162 (7)0.0041 (7)0.0021 (6)0.0038 (7)
C40.0177 (7)0.0204 (8)0.0168 (7)0.0022 (6)0.0003 (6)0.0037 (6)
C50.0179 (7)0.0213 (8)0.0135 (7)0.0035 (6)0.0004 (6)0.0011 (6)
C60.0195 (7)0.0223 (8)0.0175 (7)0.0007 (6)0.0015 (6)0.0039 (6)
C80.0205 (7)0.0176 (8)0.0232 (8)0.0009 (6)0.0014 (6)0.0022 (6)
Geometric parameters (Å, º) top
Cl1—C61.7372 (17)C3'—H3'A0.9900
N1—C61.317 (2)C3'—H3'B0.9900
N1—C21.354 (2)C4'—C6'1.512 (2)
N3—C21.320 (2)C4'—C5'1.559 (2)
N3—C41.342 (2)C4'—H4'1.0000
N7—C81.381 (2)C5'—H5'A0.9900
N7—C51.387 (2)C5'—H5'B0.9900
N7—C6'1.4765 (19)C6'—H6'A0.9900
N9—C81.301 (2)C6'—H6'B0.9900
N9—C41.376 (2)C2—H20.9500
O1'—C2'1.195 (2)C4—C51.415 (2)
C2'—C3'1.514 (3)C5—C61.382 (2)
C2'—C5'1.524 (3)C8—H80.9500
C3'—C4'1.559 (2)
C6—N1—C2117.04 (16)C2'—C5'—H5'B114.0
C2—N3—C4113.96 (15)C4'—C5'—H5'B114.0
C8—N7—C5105.24 (13)H5'A—C5'—H5'B111.2
C8—N7—C6'125.49 (14)N7—C6'—C4'112.54 (14)
C5—N7—C6'128.74 (15)N7—C6'—H6'A109.1
C8—N9—C4104.09 (14)C4'—C6'—H6'A109.1
O1'—C2'—C3'133.7 (2)N7—C6'—H6'B109.1
O1'—C2'—C5'133.0 (2)C4'—C6'—H6'B109.1
C3'—C2'—C5'93.29 (14)H6'A—C6'—H6'B107.8
C2'—C3'—C4'88.33 (14)N3—C2—N1128.03 (16)
C2'—C3'—H3'A113.9N3—C2—H2116.0
C4'—C3'—H3'A113.9N1—C2—H2116.0
C2'—C3'—H3'B113.9N3—C4—N9126.01 (15)
C4'—C3'—H3'B113.9N3—C4—C5123.02 (16)
H3'A—C3'—H3'B111.1N9—C4—C5110.96 (14)
C6'—C4'—C5'116.77 (16)C6—C5—N7138.56 (15)
C6'—C4'—C3'112.49 (15)C6—C5—C4116.68 (15)
C5'—C4'—C3'90.22 (14)N7—C5—C4104.75 (14)
C6'—C4'—H4'111.9N1—C6—C5121.22 (16)
C5'—C4'—H4'111.9N1—C6—Cl1116.95 (14)
C3'—C4'—H4'111.9C5—C6—Cl1121.83 (13)
C2'—C5'—C4'87.96 (14)N9—C8—N7114.95 (15)
C2'—C5'—H5'A114.0N9—C8—H8122.5
C4'—C5'—H5'A114.0N7—C8—H8122.5
O1'—C2'—C3'—C4'175.7 (3)C8—N7—C5—C6179.2 (2)
C5'—C2'—C3'—C4'3.32 (16)C6'—N7—C5—C67.2 (3)
C2'—C3'—C4'—C6'122.53 (16)C8—N7—C5—C40.10 (17)
C2'—C3'—C4'—C5'3.24 (16)C6'—N7—C5—C4171.83 (15)
O1'—C2'—C5'—C4'175.7 (3)N3—C4—C5—C60.8 (2)
C3'—C2'—C5'—C4'3.32 (16)N9—C4—C5—C6179.83 (14)
C6'—C4'—C5'—C2'118.72 (16)N3—C4—C5—N7178.47 (15)
C3'—C4'—C5'—C2'3.22 (15)N9—C4—C5—N70.52 (18)
C8—N7—C6'—C4'76.0 (2)C2—N1—C6—C50.4 (2)
C5—N7—C6'—C4'113.61 (19)C2—N1—C6—Cl1179.16 (13)
C5'—C4'—C6'—N772.5 (2)N7—C5—C6—N1177.58 (18)
C3'—C4'—C6'—N7174.86 (15)C4—C5—C6—N11.4 (2)
C4—N3—C2—N12.1 (3)N7—C5—C6—Cl12.9 (3)
C6—N1—C2—N31.5 (3)C4—C5—C6—Cl1178.08 (12)
C2—N3—C4—N9178.09 (16)C4—N9—C8—N70.70 (19)
C2—N3—C4—C50.8 (2)C5—N7—C8—N90.4 (2)
C8—N9—C4—N3178.22 (16)C6'—N7—C8—N9172.66 (15)
C8—N9—C4—C50.74 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···Cl10.992.663.407 (2)132
C4—H4···Cl1i1.002.973.7889 (19)140
C6—H6B···N1ii0.992.683.343 (2)124
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2.
3-[(6-Chloro-8,9-dihydro-7H-purin-7-yl)methyl]cyclobutan-1-ol (II) top
Crystal data top
C10H13ClN4OZ = 2
Mr = 240.69F(000) = 252
Triclinic, P1Dx = 1.488 Mg m3
a = 6.1101 (4) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.6075 (5) ÅCell parameters from 8605 reflections
c = 11.0083 (7) Åθ = 4.3–65.4°
α = 68.957 (6)°µ = 3.03 mm1
β = 83.799 (5)°T = 110 K
γ = 87.189 (5)°Plate, colorless
V = 537.15 (6) Å30.44 × 0.30 × 0.12 mm
Data collection top
Bruker–Nonius Kappa CCD
diffractometer
1793 independent reflections
Radiation source: sealed X-ray tube, Enhance (Cu) X-ray Source1681 reflections with I > 2σ(I)
Detector resolution: 7.9 pixels mm-1Rint = 0.028
ω scansθmax = 66.0°, θmin = 4.3°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
h = 75
Tmin = 0.771, Tmax = 1.000k = 1010
9261 measured reflectionsl = 1312
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)] = 0.037Hydrogen site location: mixed
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.5464P]
where P = (Fo2 + 2Fc2)/3
1793 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.71 e Å3
1 restraintΔρmin = 0.27 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.16834 (8)0.41808 (6)0.40624 (5)0.02598 (19)
N10.4817 (3)0.2850 (2)0.28999 (16)0.0208 (4)
C20.6669 (3)0.2012 (3)0.28642 (19)0.0208 (4)
H20.7190700.1937950.2041610.025*
N30.7920 (3)0.1241 (2)0.38609 (16)0.0201 (4)
C40.7122 (3)0.1387 (2)0.49898 (19)0.0181 (4)
C50.5139 (3)0.2254 (2)0.51675 (19)0.0175 (4)
C60.4064 (3)0.2984 (2)0.40720 (19)0.0185 (4)
N70.4843 (3)0.2163 (2)0.64573 (16)0.0195 (4)
C80.6671 (3)0.1184 (3)0.71453 (19)0.0217 (4)
H8A0.7502750.1847680.7508300.026*
H8B0.6127780.0164170.7863890.026*
N90.8027 (3)0.0776 (2)0.61286 (16)0.0212 (4)
H90.916 (3)0.018 (3)0.627 (2)0.021 (6)*
O1'0.1576 (3)0.2578 (2)1.12373 (14)0.0278 (4)
H1'0.256 (5)0.284 (4)1.161 (3)0.045 (8)*
C2'0.2169 (4)0.3455 (3)0.9900 (2)0.0273 (5)
H2'0.2304290.4668330.9736320.033*
C3'0.4091 (4)0.2873 (3)0.9160 (2)0.0346 (6)
H3'10.4464030.1676410.9564020.041*
H3'20.5419330.3569320.8957490.041*
C5'0.0629 (4)0.3203 (3)0.8985 (2)0.0277 (5)
H5'10.0442860.4125240.8668790.033*
H5'20.0112590.2112150.9333260.033*
C4'0.2642 (4)0.3281 (3)0.7998 (2)0.0240 (6)0.858 (4)
H4'0.2886180.4458760.7395040.029*0.858 (4)
C6'0.2716 (4)0.2157 (3)0.7213 (2)0.0229 (6)0.858 (4)
H6'10.2391120.1005180.7815650.027*0.858 (4)
H6'20.1551810.2511060.6606800.027*0.858 (4)
C4'B0.246 (3)0.216 (2)0.8417 (15)0.0240 (6)0.142 (4)
H4'B0.2287330.0922430.8702060.029*0.142 (4)
C6'B0.332 (3)0.308 (2)0.7043 (15)0.0229 (6)0.142 (4)
H6'30.2062240.3450770.6508240.027*0.142 (4)
H6'40.4065210.4095220.7013600.027*0.142 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0222 (3)0.0321 (3)0.0240 (3)0.0101 (2)0.0049 (2)0.0110 (2)
N10.0227 (9)0.0239 (9)0.0162 (8)0.0000 (7)0.0018 (7)0.0078 (7)
C20.0227 (11)0.0255 (10)0.0158 (10)0.0004 (8)0.0012 (8)0.0104 (8)
N30.0198 (9)0.0244 (9)0.0173 (8)0.0013 (7)0.0010 (7)0.0100 (7)
C40.0171 (10)0.0192 (10)0.0186 (10)0.0008 (8)0.0003 (8)0.0080 (8)
C50.0181 (10)0.0193 (9)0.0166 (10)0.0025 (8)0.0006 (8)0.0087 (8)
C60.0168 (10)0.0204 (10)0.0192 (10)0.0014 (8)0.0004 (8)0.0087 (8)
N70.0173 (9)0.0277 (9)0.0155 (8)0.0057 (7)0.0014 (7)0.0109 (7)
C80.0212 (11)0.0293 (11)0.0176 (10)0.0059 (8)0.0036 (8)0.0121 (8)
N90.0181 (9)0.0294 (10)0.0181 (9)0.0094 (7)0.0038 (7)0.0114 (7)
O1'0.0275 (9)0.0394 (9)0.0177 (7)0.0028 (7)0.0043 (6)0.0115 (7)
C2'0.0286 (12)0.0371 (12)0.0179 (10)0.0017 (9)0.0008 (9)0.0119 (9)
C3'0.0257 (12)0.0522 (15)0.0340 (13)0.0000 (11)0.0030 (10)0.0253 (12)
C5'0.0250 (11)0.0400 (13)0.0215 (11)0.0119 (9)0.0052 (9)0.0157 (10)
C4'0.0258 (13)0.0263 (14)0.0205 (12)0.0035 (11)0.0002 (10)0.0104 (11)
C6'0.0164 (12)0.0341 (16)0.0216 (12)0.0011 (11)0.0000 (10)0.0147 (11)
C4'B0.0258 (13)0.0263 (14)0.0205 (12)0.0035 (11)0.0002 (10)0.0104 (11)
C6'B0.0164 (12)0.0341 (16)0.0216 (12)0.0011 (11)0.0000 (10)0.0147 (11)
Geometric parameters (Å, º) top
Cl1—C61.739 (2)C2'—C3'1.524 (3)
N1—C21.317 (3)C2'—C5'1.527 (3)
N1—C61.365 (3)C2'—H2'1.0000
C2—N31.355 (3)C3'—C4'1.561 (3)
C2—H20.9500C3'—C4'B1.626 (16)
N3—C41.332 (3)C3'—H3'10.9900
C4—N91.342 (3)C3'—H3'20.9900
C4—C51.424 (3)C5'—C4'1.537 (3)
C5—C61.366 (3)C5'—C4'B1.616 (15)
C5—N71.386 (2)C5'—H5'10.9900
N7—C6'B1.440 (15)C5'—H5'20.9900
N7—C6'1.465 (3)C4'—C6'1.508 (3)
N7—C81.471 (3)C4'—H4'1.0000
C8—N91.455 (3)C6'—H6'10.9900
C8—H8A0.9900C6'—H6'20.9900
C8—H8B0.9900C4'B—C6'B1.48 (2)
N9—H90.833 (17)C4'B—H4'B1.0000
O1'—C2'1.407 (3)C6'B—H6'30.9900
O1'—H1'0.84 (3)C6'B—H6'40.9900
C2—N1—C6116.73 (17)C2'—C3'—H3'1114.0
N1—C2—N3127.76 (18)C4'—C3'—H3'1114.0
N1—C2—H2116.1C2'—C3'—H3'2114.0
N3—C2—H2116.1C4'—C3'—H3'2114.0
C4—N3—C2113.74 (17)H3'1—C3'—H3'2111.2
N3—C4—N9126.70 (19)C2'—C5'—C4'88.64 (17)
N3—C4—C5124.39 (18)C2'—C5'—C4'B92.8 (6)
N9—C4—C5108.91 (17)C2'—C5'—H5'1113.9
C6—C5—N7136.29 (19)C4'—C5'—H5'1113.9
C6—C5—C4115.33 (18)C2'—C5'—H5'2113.9
N7—C5—C4108.35 (17)C4'—C5'—H5'2113.9
N1—C6—C5122.04 (18)H5'1—C5'—H5'2111.1
N1—C6—Cl1115.38 (15)C6'—C4'—C5'118.5 (2)
C5—C6—Cl1122.56 (15)C6'—C4'—C3'120.1 (2)
C5—N7—C6'B128.7 (6)C5'—C4'—C3'87.40 (17)
C5—N7—C6'125.55 (17)C6'—C4'—H4'109.7
C5—N7—C8108.55 (16)C5'—C4'—H4'109.7
C6'B—N7—C8121.7 (6)C3'—C4'—H4'109.7
C6'—N7—C8118.33 (17)N7—C6'—C4'113.3 (2)
N9—C8—N7103.41 (15)N7—C6'—H6'1108.9
N9—C8—H8A111.1C4'—C6'—H6'1108.9
N7—C8—H8A111.1N7—C6'—H6'2108.9
N9—C8—H8B111.1C4'—C6'—H6'2108.9
N7—C8—H8B111.1H6'1—C6'—H6'2107.7
H8A—C8—H8B109.0C6'B—C4'B—C5'112.7 (13)
C4—N9—C8110.76 (17)C6'B—C4'B—C3'99.0 (12)
C4—N9—H9125.9 (17)C5'—C4'B—C3'82.6 (7)
C8—N9—H9123.2 (17)C6'B—C4'B—H4'B118.5
C2'—O1'—H1'103 (2)C5'—C4'B—H4'B118.5
O1'—C2'—C3'121.1 (2)C3'—C4'B—H4'B118.5
O1'—C2'—C5'114.52 (18)N7—C6'B—C4'B115.0 (14)
C3'—C2'—C5'89.12 (16)N7—C6'B—H6'3108.5
O1'—C2'—H2'110.1C4'B—C6'B—H6'3108.5
C3'—C2'—H2'110.1N7—C6'B—H6'4108.5
C5'—C2'—H2'110.1C4'B—C6'B—H6'4108.5
C2'—C3'—C4'87.87 (18)H6'3—C6'B—H6'4107.5
C2'—C3'—C4'B92.5 (5)
C6—N1—C2—N30.8 (3)N7—C8—N9—C41.3 (2)
N1—C2—N3—C40.3 (3)O1'—C2'—C3'—C4'138.2 (2)
C2—N3—C4—N9178.94 (19)C5'—C2'—C3'—C4'19.78 (18)
C2—N3—C4—C50.4 (3)O1'—C2'—C3'—C4'B105.1 (6)
N3—C4—C5—C61.1 (3)C5'—C2'—C3'—C4'B13.3 (6)
N9—C4—C5—C6178.36 (17)O1'—C2'—C5'—C4'144.2 (2)
N3—C4—C5—N7179.35 (17)C3'—C2'—C5'—C4'20.09 (19)
N9—C4—C5—N70.1 (2)O1'—C2'—C5'—C4'B110.7 (6)
C2—N1—C6—C51.6 (3)C3'—C2'—C5'—C4'B13.4 (6)
C2—N1—C6—Cl1177.14 (14)C2'—C5'—C4'—C6'142.7 (2)
N7—C5—C6—N1179.3 (2)C2'—C5'—C4'—C3'19.62 (18)
C4—C5—C6—N11.6 (3)C2'—C3'—C4'—C6'141.4 (2)
N7—C5—C6—Cl10.7 (3)C2'—C3'—C4'—C5'19.66 (18)
C4—C5—C6—Cl1176.96 (14)C5—N7—C6'—C4'135.6 (2)
C6—C5—N7—C6'B10.1 (10)C8—N7—C6'—C4'78.4 (3)
C4—C5—N7—C6'B167.6 (10)C5'—C4'—C6'—N7171.4 (2)
C6—C5—N7—C6'32.6 (4)C3'—C4'—C6'—N766.6 (3)
C4—C5—N7—C6'149.7 (2)C2'—C5'—C4'B—C6'B109.4 (12)
C6—C5—N7—C8178.7 (2)C2'—C5'—C4'B—C3'12.7 (6)
C4—C5—N7—C80.9 (2)C2'—C3'—C4'B—C6'B124.6 (10)
C5—N7—C8—N91.3 (2)C2'—C3'—C4'B—C5'12.7 (6)
C6'B—N7—C8—N9168.2 (9)C5—N7—C6'B—C4'B146.2 (9)
C6'—N7—C8—N9152.69 (18)C8—N7—C6'B—C4'B46.6 (16)
N3—C4—N9—C8179.79 (18)C5'—C4'B—C6'B—N7175.7 (10)
C5—C4—N9—C80.8 (2)C3'—C4'B—C6'B—N798.5 (13)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of ring N1/C2/N3/C4/C5/C6.
D—H···AD—HH···AD···AD—H···A
C6—H62···Cl10.992.643.390 (3)132
N9—H9···N3i0.83 (2)2.14 (2)2.952 (2)166 (2)
O1—H1···N1ii0.84 (3)2.09 (3)2.909 (2)164 (3)
C4—H4···Cg1iii0.992.873.857 (3)170
Symmetry codes: (i) x+2, y, z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1.
3-[(6-Chloro-9H-purin-9-yl)methyl]cyclobutan-1-ol (IV) top
Crystal data top
C10H11ClN4OF(000) = 496
Mr = 238.68Dx = 1.482 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 12.7276 (8) ÅCell parameters from 4964 reflections
b = 5.9725 (4) Åθ = 4.0–64.9°
c = 14.819 (1) ŵ = 3.04 mm1
β = 108.250 (3)°T = 110 K
V = 1069.81 (12) Å3Plate, colourless
Z = 40.50 × 0.21 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
1732 independent reflections
Radiation source: sealed X-ray tube1569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 7.9 pixels mm-1θmax = 64.9°, θmin = 4.0°
ω scansh = 1414
Absorption correction: numerical
(CrysAlisPro; Rigaku OD, 2018)
k = 47
Tmin = 0.043, Tmax = 0.741l = 1717
7078 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0599P)2 + 1.4189P]
where P = (Fo2 + 2Fc2)/3
1732 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.65978 (4)0.22748 (10)0.21719 (4)0.0258 (2)
O1'0.06577 (11)0.5696 (3)0.19248 (10)0.0233 (4)
H1'0.0671870.4569860.2267980.035*
N30.44729 (14)0.7995 (3)0.06539 (12)0.0218 (4)
N10.61729 (14)0.5895 (3)0.11346 (12)0.0196 (4)
N70.39848 (13)0.3289 (3)0.19580 (12)0.0199 (4)
N90.30402 (13)0.6280 (3)0.11873 (11)0.0186 (4)
C40.40817 (16)0.6422 (4)0.11001 (13)0.0178 (5)
C50.46564 (16)0.4569 (4)0.15808 (13)0.0168 (5)
C3'0.12604 (16)0.5194 (4)0.07173 (14)0.0201 (5)
H3'A0.0904060.4360470.0314310.024*
H3'B0.1792300.4240100.0906140.024*
C60.57424 (16)0.4399 (4)0.15774 (13)0.0180 (5)
C80.30351 (16)0.4385 (4)0.16970 (14)0.0192 (5)
H80.2402640.3893010.1851650.023*
C20.55210 (18)0.7598 (4)0.07007 (15)0.0223 (5)
H20.5846090.8652500.0388010.027*
C2'0.04431 (16)0.6477 (4)0.15487 (14)0.0177 (5)
H2'0.0773860.6735880.2069460.021*
C4'0.17237 (18)0.7495 (4)0.03173 (15)0.0216 (5)
H4'0.2319500.7962870.0585470.026*
C6'0.21115 (17)0.7800 (4)0.07552 (15)0.0208 (5)
H6'A0.2348060.9369280.0914630.025*
H6'B0.1495390.7475120.1009680.025*
C5'0.05979 (17)0.8537 (4)0.09087 (15)0.0217 (5)
H5'A0.0051700.8662250.0560360.026*
H5'B0.0665930.9961600.1227170.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0169 (3)0.0313 (4)0.0291 (3)0.0052 (2)0.0069 (2)0.0101 (2)
O1'0.0144 (7)0.0311 (10)0.0231 (8)0.0006 (6)0.0037 (6)0.0095 (7)
N30.0217 (9)0.0229 (11)0.0184 (9)0.0037 (8)0.0027 (7)0.0013 (8)
N10.0194 (9)0.0206 (10)0.0183 (8)0.0042 (8)0.0051 (7)0.0005 (8)
N70.0155 (9)0.0260 (11)0.0177 (8)0.0011 (8)0.0045 (7)0.0024 (8)
N90.0142 (8)0.0232 (11)0.0160 (8)0.0021 (8)0.0013 (7)0.0017 (8)
C40.0169 (10)0.0206 (12)0.0129 (9)0.0030 (9)0.0004 (8)0.0016 (8)
C50.0156 (9)0.0207 (12)0.0121 (9)0.0022 (8)0.0014 (7)0.0014 (8)
C3'0.0188 (10)0.0231 (12)0.0177 (10)0.0034 (9)0.0045 (8)0.0013 (9)
C60.0160 (10)0.0219 (12)0.0134 (9)0.0010 (9)0.0006 (8)0.0002 (9)
C80.0159 (10)0.0234 (13)0.0177 (9)0.0013 (9)0.0045 (8)0.0003 (9)
C20.0230 (11)0.0232 (13)0.0193 (10)0.0064 (9)0.0047 (9)0.0015 (9)
C2'0.0134 (9)0.0220 (12)0.0165 (10)0.0005 (9)0.0031 (8)0.0007 (9)
C4'0.0186 (11)0.0249 (13)0.0194 (11)0.0010 (9)0.0035 (9)0.0009 (9)
C6'0.0193 (11)0.0209 (12)0.0194 (10)0.0043 (9)0.0021 (8)0.0000 (9)
C5'0.0206 (10)0.0223 (13)0.0185 (10)0.0032 (9)0.0011 (8)0.0001 (9)
Geometric parameters (Å, º) top
Cl1—C61.723 (2)C3'—C2'1.544 (3)
O1'—C2'1.415 (2)C3'—H3'A0.9900
O1'—H1'0.8400C3'—H3'B0.9900
N3—C41.332 (3)C8—H80.9500
N3—C21.335 (3)C2—H20.9500
N1—C61.325 (3)C2'—C5'1.528 (3)
N1—C21.342 (3)C2'—H2'1.0000
N7—C81.321 (3)C4'—C6'1.520 (3)
N7—C51.388 (3)C4'—C5'1.556 (3)
N9—C81.362 (3)C4'—H4'1.0000
N9—C41.374 (3)C6'—H6'A0.9900
N9—C6'1.469 (3)C6'—H6'B0.9900
C4—C51.393 (3)C5'—H5'A0.9900
C5—C61.388 (3)C5'—H5'B0.9900
C3'—C4'1.539 (3)
C2'—O1'—H1'109.5N3—C2—H2116.0
C4—N3—C2111.81 (19)N1—C2—H2116.0
C6—N1—C2117.32 (17)O1'—C2'—C5'115.42 (17)
C8—N7—C5103.39 (18)O1'—C2'—C3'119.16 (18)
C8—N9—C4106.00 (17)C5'—C2'—C3'88.88 (16)
C8—N9—C6'127.78 (17)O1'—C2'—H2'110.6
C4—N9—C6'126.10 (18)C5'—C2'—H2'110.6
N3—C4—N9127.7 (2)C3'—C2'—H2'110.6
N3—C4—C5126.60 (19)C6'—C4'—C3'118.02 (19)
N9—C4—C5105.69 (18)C6'—C4'—C5'118.75 (18)
C6—C5—N7134.5 (2)C3'—C4'—C5'88.05 (16)
C6—C5—C4114.87 (19)C6'—C4'—H4'110.1
N7—C5—C4110.64 (17)C3'—C4'—H4'110.1
C4'—C3'—C2'86.87 (17)C5'—C4'—H4'110.1
C4'—C3'—H3'A114.2N9—C6'—C4'109.58 (17)
C2'—C3'—H3'A114.2N9—C6'—H6'A109.8
C4'—C3'—H3'B114.2C4'—C6'—H6'A109.8
C2'—C3'—H3'B114.2N9—C6'—H6'B109.8
H3'A—C3'—H3'B111.3C4'—C6'—H6'B109.8
N1—C6—C5121.3 (2)H6'A—C6'—H6'B108.2
N1—C6—Cl1117.18 (15)C2'—C5'—C4'86.82 (16)
C5—C6—Cl1121.52 (16)C2'—C5'—H5'A114.2
N7—C8—N9114.28 (18)C4'—C5'—H5'A114.2
N7—C8—H8122.9C2'—C5'—H5'B114.2
N9—C8—H8122.9C4'—C5'—H5'B114.2
N3—C2—N1128.1 (2)H5'A—C5'—H5'B111.3
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of ring N1/C2/N3/C4/C5/C6.
D—H···AD—HH···AD···AD—H···A
O1—H1···N7i0.842.032.853 (3)168
C8—H8···O1ii0.952.273.148 (2)153
C2—H2···N3iii0.952.483.311 (3)146
C2—H2···Cg1iv0.992.843.628 (2)136
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y+1, z; (iii) x+1, y+2, z; (iv) x3/2, y+1/2, z3/2.
Geometric parameters (Å, °) about atom C8 for compounds (I), (II) and (IV) top
Bond/angle(I)(II)(IV)
C8—N71.381 (2)1.471 (3)1.362 (3)
C8—N91.301 (2)1.455 (3)1.321 (3)
N7—C8—N9114.95 (15)103.41 (15)114.28 (18)
 

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