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In the title compound, C19H18N2O2, the two phenyl rings are located on the same side of the thymine ring, resembling the two front claws of a crab. The crystal structure involves some weak C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301986X/wn6181sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301986X/wn6181Isup2.hkl
Contains datablock I

CCDC reference: 225720

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.098
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT024_ALERT_4_C Merging of Friedel Data Preferred for Z<=Si .... ! PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C11 = 5.25 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 = 6.81 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 = 5.56 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C4 PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C1 - C6 = 1.37 Ang.
Alert level G REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. From the CIF: _diffrn_reflns_theta_max 27.02 From the CIF: _reflns_number_total 3508 Count of symmetry unique reflns 2030 Completeness (_total/calc) 172.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1478 Fraction of Friedel pairs measured 0.728 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,3-dibenzylthymine top
Crystal data top
C19H18N2O2F(000) = 648
Mr = 306.35Dx = 1.267 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 599 reflections
a = 8.7466 (10) Åθ = 2.3–18.0°
b = 8.8637 (10) ŵ = 0.08 mm1
c = 20.720 (3) ÅT = 273 K
V = 1606.3 (3) Å3Block, colorless
Z = 40.45 × 0.28 × 0.25 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2618 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
φ and ω scansh = 1011
7934 measured reflectionsk = 117
3508 independent reflectionsl = 2026
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0549P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3508 reflectionsΔρmax = 0.12 e Å3
210 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.16
Special details top

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
O10.40423 (13)1.19121 (14)0.07784 (6)0.0749 (4)
O20.06716 (14)0.81307 (15)0.12073 (6)0.0734 (4)
N10.22761 (14)1.13075 (15)0.00165 (7)0.0567 (3)
N20.23650 (13)1.00069 (16)0.09917 (6)0.0541 (3)
C10.5975 (3)1.1347 (2)0.18855 (11)0.0841 (6)
H10.66701.10900.22070.101*
C20.5984 (3)1.0608 (3)0.13095 (11)0.0951 (7)
H20.67020.98540.12350.114*
C30.4940 (2)1.0965 (2)0.08357 (10)0.0768 (5)
H30.49511.04350.04480.092*
C40.38888 (17)1.20868 (17)0.09264 (8)0.0544 (4)
C50.3904 (2)1.2829 (2)0.15068 (9)0.0788 (6)
H50.32021.35980.15800.095*
C60.4940 (2)1.2461 (3)0.19847 (9)0.0873 (6)
H60.49271.29790.23750.105*
C70.27772 (18)1.2545 (2)0.04062 (8)0.0624 (4)
H7A0.32501.33190.01420.075*
H7B0.18831.29860.06090.075*
C80.11132 (18)1.03707 (18)0.01822 (8)0.0549 (4)
H80.07091.05130.05930.066*
C90.05374 (17)0.92755 (18)0.01805 (7)0.0543 (4)
C100.0742 (2)0.8272 (2)0.00439 (10)0.0770 (5)
H10A0.16520.84980.01970.115*
H10B0.04650.72360.00230.115*
H10C0.09270.84420.04950.115*
C110.11435 (17)0.90589 (18)0.08204 (8)0.0543 (4)
C120.29712 (18)1.11346 (19)0.06058 (8)0.0563 (4)
C130.30099 (19)0.9825 (2)0.16485 (7)0.0638 (5)
H13A0.21890.95880.19460.077*
H13B0.34611.07740.17840.077*
C140.42074 (17)0.8601 (2)0.16851 (7)0.0572 (4)
C150.3854 (2)0.7192 (2)0.19221 (8)0.0690 (5)
H150.28640.69950.20630.083*
C160.4938 (2)0.6071 (3)0.19541 (10)0.0835 (6)
H160.46700.51200.21060.100*
C170.6406 (2)0.6348 (3)0.17636 (9)0.0826 (6)
H170.71410.55920.17900.099*
C180.6787 (2)0.7746 (3)0.15341 (9)0.0847 (6)
H180.77850.79440.14050.102*
C190.56917 (19)0.8862 (2)0.14937 (9)0.0722 (5)
H190.59600.98070.13350.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0592 (7)0.0808 (8)0.0849 (9)0.0192 (7)0.0082 (6)0.0006 (7)
O20.0626 (7)0.0884 (9)0.0692 (8)0.0146 (7)0.0023 (6)0.0170 (6)
N10.0488 (7)0.0600 (8)0.0614 (8)0.0021 (6)0.0022 (6)0.0036 (6)
N20.0460 (7)0.0658 (8)0.0505 (7)0.0039 (6)0.0008 (6)0.0022 (6)
C10.0851 (13)0.0910 (14)0.0761 (13)0.0019 (13)0.0188 (11)0.0025 (11)
C20.0985 (16)0.0872 (14)0.0998 (17)0.0318 (13)0.0265 (14)0.0129 (12)
C30.0836 (12)0.0690 (11)0.0778 (13)0.0193 (10)0.0164 (10)0.0191 (9)
C40.0469 (8)0.0532 (9)0.0632 (10)0.0047 (7)0.0042 (7)0.0055 (8)
C50.0654 (10)0.0919 (13)0.0791 (13)0.0156 (11)0.0026 (10)0.0261 (11)
C60.0792 (13)0.1188 (17)0.0638 (12)0.0002 (14)0.0010 (10)0.0235 (12)
C70.0558 (9)0.0571 (10)0.0743 (11)0.0024 (8)0.0011 (8)0.0107 (9)
C80.0485 (8)0.0641 (9)0.0521 (9)0.0055 (8)0.0026 (7)0.0028 (8)
C90.0481 (8)0.0612 (10)0.0537 (9)0.0011 (7)0.0000 (7)0.0033 (8)
C100.0733 (11)0.0854 (12)0.0724 (12)0.0198 (10)0.0133 (10)0.0014 (10)
C110.0437 (7)0.0601 (9)0.0592 (10)0.0009 (7)0.0036 (7)0.0025 (8)
C120.0460 (8)0.0625 (10)0.0605 (10)0.0001 (8)0.0008 (7)0.0036 (8)
C130.0589 (9)0.0817 (12)0.0508 (9)0.0054 (9)0.0030 (8)0.0071 (8)
C140.0514 (9)0.0812 (11)0.0389 (8)0.0110 (9)0.0031 (7)0.0012 (7)
C150.0567 (9)0.0964 (14)0.0538 (9)0.0101 (10)0.0041 (8)0.0159 (10)
C160.0820 (14)0.0949 (15)0.0736 (13)0.0004 (12)0.0157 (11)0.0245 (11)
C170.0782 (14)0.1089 (17)0.0607 (11)0.0217 (13)0.0155 (10)0.0053 (11)
C180.0510 (9)0.141 (2)0.0624 (12)0.0013 (12)0.0001 (9)0.0048 (13)
C190.0536 (10)0.0939 (13)0.0691 (11)0.0123 (10)0.0005 (8)0.0125 (10)
Geometric parameters (Å, º) top
O1—C121.2168 (18)C8—C91.327 (2)
O2—C111.2206 (19)C8—H80.9300
N1—C121.373 (2)C9—C111.441 (2)
N1—C81.376 (2)C9—C101.503 (2)
N1—C71.470 (2)C10—H10A0.9600
N2—C121.385 (2)C10—H10B0.9600
N2—C111.4047 (19)C10—H10C0.9600
N2—C131.4819 (19)C13—C141.510 (3)
C1—C61.356 (3)C13—H13A0.9700
C1—C21.361 (3)C13—H13B0.9700
C1—H10.9300C14—C191.377 (2)
C2—C31.377 (3)C14—C151.377 (3)
C2—H20.9300C15—C161.375 (3)
C3—C41.367 (2)C15—H150.9300
C3—H30.9300C16—C171.366 (3)
C4—C51.371 (2)C16—H160.9300
C4—C71.507 (2)C17—C181.368 (3)
C5—C61.381 (3)C17—H170.9300
C5—H50.9300C18—C191.380 (3)
C6—H60.9300C18—H180.9300
C7—H7A0.9700C19—H190.9300
C7—H7B0.9700
C12—N1—C8121.75 (14)C9—C10—H10A109.5
C12—N1—C7118.76 (14)C9—C10—H10B109.5
C8—N1—C7119.48 (14)H10A—C10—H10B109.5
C12—N2—C11125.23 (13)C9—C10—H10C109.5
C12—N2—C13117.55 (13)H10A—C10—H10C109.5
C11—N2—C13117.16 (13)H10B—C10—H10C109.5
C6—C1—C2119.16 (19)O2—C11—N2119.63 (15)
C6—C1—H1120.4O2—C11—C9124.73 (15)
C2—C1—H1120.4N2—C11—C9115.63 (14)
C1—C2—C3120.7 (2)O1—C12—N1122.63 (15)
C1—C2—H2119.6O1—C12—N2122.26 (15)
C3—C2—H2119.6N1—C12—N2115.11 (14)
C4—C3—C2120.99 (18)N2—C13—C14112.84 (13)
C4—C3—H3119.5N2—C13—H13A109.0
C2—C3—H3119.5C14—C13—H13A109.0
C3—C4—C5117.57 (16)N2—C13—H13B109.0
C3—C4—C7122.10 (15)C14—C13—H13B109.0
C5—C4—C7120.30 (15)H13A—C13—H13B107.8
C4—C5—C6121.48 (17)C19—C14—C15117.81 (18)
C4—C5—H5119.3C19—C14—C13121.25 (17)
C6—C5—H5119.3C15—C14—C13120.93 (15)
C1—C6—C5120.08 (18)C16—C15—C14121.19 (17)
C1—C6—H6120.0C16—C15—H15119.4
C5—C6—H6120.0C14—C15—H15119.4
N1—C7—C4114.68 (13)C17—C16—C15120.3 (2)
N1—C7—H7A108.6C17—C16—H16119.9
C4—C7—H7A108.6C15—C16—H16119.9
N1—C7—H7B108.6C16—C17—C18119.5 (2)
C4—C7—H7B108.6C16—C17—H17120.3
H7A—C7—H7B107.6C18—C17—H17120.3
C9—C8—N1123.54 (16)C17—C18—C19120.10 (18)
C9—C8—H8118.2C17—C18—H18120.0
N1—C8—H8118.2C19—C18—H18120.0
C8—C9—C11118.62 (15)C14—C19—C18121.11 (19)
C8—C9—C10122.70 (15)C14—C19—H19119.4
C11—C9—C10118.67 (14)C18—C19—H19119.4
 

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