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The title compound, C24H26N4O4, was synthesized by the reaction of methyl {2-[(3-phenyl-1,2,4-oxa­diazol-5-yl)­methoxy]­phenyl}acetate and N,N-di­methyl­form­amide di­methyl acetal and crystallizes in the triclinic space group P\overline 1 with two independent mol­ecules in the asymmetric unit. The crystal packing is stabilized mainly by van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021610/cv6361sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021610/cv6361Isup2.hkl
Contains datablock I

CCDC reference: 252976

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.073
  • wR factor = 0.259
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.259 PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C21 .. 5.50 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C21
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXS97.

Methyl 3-dimethylamino-2-{2-[2-(dimethylamino)-1-(3-phenyl-1,2,4-oxadiazol-5- yl)vinyloxy]phenyl}acrylate top
Crystal data top
C24H26N4O4Z = 4
Mr = 434.49F(000) = 920
Triclinic, P1Dx = 1.254 Mg m3
a = 11.220 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.260 (3) ÅCell parameters from 25 reflections
c = 17.762 (4) Åθ = 10–13°
α = 71.06 (3)°µ = 0.09 mm1
β = 86.35 (3)°T = 293 K
γ = 85.19 (3)°Block, colourless
V = 2301.1 (8) Å30.50 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
4761 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 26.0°, θmin = 1.2°
ω/2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 1414
Tmin = 0.961, Tmax = 0.974l = 2121
9501 measured reflections3 standard reflections every 200 reflections
9014 independent reflections intensity decay: none
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)] = 0.073H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.259 w = 1/[σ2(Fo2) + (0.1P)2 + 1.9P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.019
9014 reflectionsΔρmax = 0.32 e Å3
578 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (15)
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
O10.4433 (3)0.7041 (3)0.1043 (2)0.0757 (10)
O20.2919 (2)0.6539 (2)0.01330 (16)0.0579 (8)
O30.1441 (3)0.8162 (3)0.22610 (19)0.0858 (11)
O40.0136 (3)0.7239 (3)0.13038 (19)0.0754 (9)
O50.9365 (3)0.2143 (3)0.55314 (18)0.0703 (9)
O60.7730 (2)0.0645 (2)0.56559 (16)0.0556 (7)
O70.6299 (4)0.1881 (3)0.7743 (2)0.0861 (11)
O80.5084 (3)0.0843 (3)0.6783 (2)0.0744 (9)
N10.5349 (4)0.7096 (4)0.1547 (3)0.0761 (12)
N20.5286 (3)0.5271 (3)0.1533 (2)0.0553 (9)
N30.3170 (4)0.9392 (3)0.0801 (3)0.0720 (11)
N40.2889 (4)0.4044 (3)0.0247 (2)0.0676 (10)
N51.0272 (3)0.2944 (4)0.5324 (2)0.0706 (11)
N61.0133 (3)0.2156 (3)0.4350 (2)0.0537 (9)
N70.8204 (4)0.0864 (4)0.7628 (2)0.0752 (12)
N80.7662 (3)0.0295 (3)0.4299 (2)0.0643 (10)
C10.8137 (5)0.4234 (5)0.3167 (3)0.0768 (15)
H1B0.84400.34680.33460.092*
C20.7243 (4)0.4551 (4)0.2629 (3)0.0660 (12)
H2B0.69480.40050.24410.079*
C30.6783 (4)0.5695 (4)0.2365 (2)0.0547 (11)
C40.7251 (4)0.6498 (4)0.2637 (3)0.0662 (12)
H4A0.69540.72650.24590.079*
C50.8179 (4)0.6160 (6)0.3183 (3)0.0810 (16)
H5B0.85060.66990.33620.097*
C60.8584 (5)0.5028 (6)0.3441 (3)0.0787 (15)
H6B0.91790.47900.38130.094*
C70.5799 (4)0.6040 (4)0.1802 (3)0.0551 (10)
C80.4460 (4)0.5908 (4)0.1072 (2)0.0563 (11)
C90.3611 (4)0.5633 (4)0.0619 (2)0.0560 (11)
C100.1806 (3)0.6846 (4)0.0433 (2)0.0487 (10)
C110.1386 (4)0.6305 (4)0.1197 (2)0.0596 (11)
H11A0.18540.57150.15420.072*
C120.0273 (5)0.6640 (5)0.1449 (3)0.0704 (13)
H12A0.00060.62840.19680.084*
C130.0433 (4)0.7505 (5)0.0932 (3)0.0760 (14)
H13A0.11950.77240.10930.091*
C140.0020 (4)0.8034 (4)0.0173 (3)0.0645 (12)
H14A0.04420.86350.01690.077*
C150.1130 (4)0.7713 (4)0.0104 (2)0.0510 (10)
C160.1585 (4)0.8233 (4)0.0936 (2)0.0529 (10)
C170.1079 (4)0.7897 (4)0.1567 (3)0.0609 (11)
C180.0410 (6)0.6898 (6)0.1893 (3)0.0992 (19)
H18A0.10640.64310.16490.149*
H18B0.01710.64610.21190.149*
H18C0.07030.75740.23050.149*
C190.2545 (4)0.8874 (4)0.1181 (3)0.0633 (12)
H19A0.28120.89690.17030.076*
C200.4299 (6)0.9880 (6)0.1153 (4)0.114 (2)
H20A0.44500.97730.16630.171*
H20B0.49390.94980.08090.171*
H20C0.42491.06910.12170.171*
C210.2822 (5)0.9499 (5)0.0030 (4)0.0877 (16)
H21A0.20730.91570.01510.132*
H21B0.27371.03020.00700.132*
H21C0.34250.91100.03430.132*
C220.3581 (4)0.4514 (4)0.0627 (2)0.0593 (11)
H22A0.41360.39940.09510.071*
C230.3036 (6)0.2810 (5)0.0373 (3)0.0869 (16)
H23A0.36180.24600.07690.130*
H23B0.33020.26810.01180.130*
H23C0.22840.24720.05500.130*
C240.2024 (5)0.4682 (5)0.0320 (3)0.0829 (16)
H24A0.19920.54830.03590.124*
H24B0.12510.43870.01490.124*
H24C0.22480.46020.08310.124*
C311.2869 (5)0.5200 (5)0.3992 (3)0.0785 (15)
H31A1.31020.57950.41550.094*
C321.1978 (4)0.4508 (4)0.4425 (3)0.0660 (12)
H32A1.16180.46410.48770.079*
C331.1627 (3)0.3622 (4)0.4183 (2)0.0516 (10)
C341.2171 (4)0.3454 (4)0.3503 (3)0.0623 (12)
H34A1.19360.28720.33270.075*
C351.3059 (4)0.4147 (4)0.3087 (3)0.0696 (13)
H35A1.34280.40200.26360.084*
C361.3402 (5)0.5015 (5)0.3331 (3)0.0771 (14)
H36A1.40000.54800.30460.093*
C371.0681 (4)0.2888 (4)0.4633 (2)0.0544 (10)
C380.9341 (4)0.1725 (4)0.4915 (2)0.0543 (10)
C390.8449 (4)0.0927 (4)0.4963 (2)0.0523 (10)
C400.6763 (3)0.1406 (3)0.5701 (2)0.0463 (9)
C410.6150 (4)0.1170 (3)0.6439 (2)0.0484 (10)
C420.5186 (4)0.1904 (4)0.6499 (3)0.0630 (12)
H42A0.47740.17670.69880.076*
C430.4799 (4)0.2835 (4)0.5867 (3)0.0651 (12)
H43A0.41320.33080.59270.078*
C440.5417 (4)0.3047 (4)0.5154 (3)0.0610 (12)
H44A0.51730.36810.47250.073*
C450.6399 (4)0.2339 (3)0.5055 (2)0.0543 (10)
H45A0.68070.24860.45640.065*
C460.6565 (4)0.0131 (4)0.7111 (2)0.0546 (10)
C470.6013 (4)0.0954 (4)0.7257 (3)0.0596 (11)
C480.4479 (5)0.1877 (4)0.6885 (4)0.0930 (18)
H48A0.38420.17040.65190.140*
H48B0.41550.21610.74210.140*
H48C0.50370.24550.67830.140*
C490.7513 (4)0.0064 (4)0.7561 (3)0.0613 (12)
H49A0.77260.06810.78880.074*
C500.9255 (6)0.0518 (6)0.8096 (4)0.106 (2)
H50A0.93410.03100.83080.159*
H50B0.91770.08360.85260.159*
H50C0.99480.07990.77660.159*
C510.7953 (5)0.2088 (4)0.7271 (3)0.0826 (15)
H51A0.72420.22270.69710.124*
H51B0.86140.24110.69220.124*
H51C0.78370.24440.76810.124*
C520.8406 (4)0.0451 (4)0.4382 (3)0.0565 (11)
H52A0.89860.06770.39740.068*
C530.6704 (5)0.0789 (4)0.4859 (3)0.0797 (15)
H53A0.66780.04900.52980.120*
H53B0.68430.16150.50540.120*
H53C0.59550.05900.45990.120*
C540.7804 (5)0.0680 (4)0.3598 (3)0.0774 (14)
H54A0.84460.03000.32570.116*
H54B0.70750.04920.33140.116*
H54C0.79840.15010.37640.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.067 (2)0.060 (2)0.095 (2)0.0049 (16)0.0298 (18)0.0141 (17)
O20.0496 (16)0.0637 (18)0.0490 (16)0.0023 (14)0.0027 (13)0.0039 (14)
O30.105 (3)0.101 (3)0.050 (2)0.028 (2)0.0010 (19)0.0182 (18)
O40.076 (2)0.096 (3)0.062 (2)0.0223 (19)0.0046 (17)0.0313 (18)
O50.065 (2)0.093 (2)0.0583 (18)0.0226 (18)0.0084 (15)0.0306 (17)
O60.0519 (16)0.0519 (16)0.0538 (17)0.0034 (13)0.0003 (13)0.0062 (13)
O70.118 (3)0.054 (2)0.076 (2)0.0125 (19)0.024 (2)0.0017 (18)
O80.078 (2)0.0550 (19)0.087 (2)0.0083 (16)0.0188 (19)0.0132 (17)
N10.068 (3)0.065 (3)0.095 (3)0.001 (2)0.030 (2)0.022 (2)
N20.048 (2)0.057 (2)0.054 (2)0.0039 (17)0.0083 (17)0.0093 (17)
N30.076 (3)0.065 (2)0.078 (3)0.019 (2)0.000 (2)0.023 (2)
N40.080 (3)0.065 (3)0.059 (2)0.000 (2)0.016 (2)0.0194 (19)
N50.063 (2)0.093 (3)0.064 (2)0.022 (2)0.007 (2)0.033 (2)
N60.051 (2)0.055 (2)0.053 (2)0.0035 (17)0.0030 (17)0.0135 (17)
N70.086 (3)0.063 (3)0.078 (3)0.001 (2)0.026 (2)0.022 (2)
N80.066 (2)0.059 (2)0.065 (2)0.0086 (19)0.0013 (19)0.0146 (19)
C10.071 (3)0.080 (4)0.062 (3)0.011 (3)0.010 (3)0.000 (3)
C20.067 (3)0.066 (3)0.057 (3)0.002 (2)0.007 (2)0.009 (2)
C30.046 (2)0.066 (3)0.048 (2)0.005 (2)0.0018 (19)0.012 (2)
C40.055 (3)0.080 (3)0.072 (3)0.007 (2)0.003 (2)0.037 (3)
C50.056 (3)0.123 (5)0.081 (4)0.005 (3)0.006 (3)0.058 (4)
C60.062 (3)0.113 (5)0.058 (3)0.018 (3)0.011 (2)0.028 (3)
C70.049 (2)0.057 (3)0.057 (3)0.002 (2)0.004 (2)0.015 (2)
C80.056 (3)0.057 (3)0.049 (2)0.001 (2)0.002 (2)0.009 (2)
C90.050 (2)0.058 (3)0.053 (2)0.002 (2)0.004 (2)0.008 (2)
C100.045 (2)0.058 (2)0.046 (2)0.0076 (19)0.0020 (18)0.021 (2)
C110.060 (3)0.066 (3)0.049 (3)0.009 (2)0.004 (2)0.012 (2)
C120.073 (3)0.087 (4)0.057 (3)0.024 (3)0.016 (3)0.031 (3)
C130.053 (3)0.104 (4)0.077 (3)0.002 (3)0.001 (3)0.039 (3)
C140.056 (3)0.074 (3)0.063 (3)0.001 (2)0.002 (2)0.024 (2)
C150.046 (2)0.057 (2)0.054 (2)0.0034 (19)0.0083 (19)0.022 (2)
C160.049 (2)0.055 (2)0.050 (2)0.002 (2)0.0079 (19)0.011 (2)
C170.066 (3)0.058 (3)0.054 (3)0.000 (2)0.004 (2)0.011 (2)
C180.104 (4)0.130 (5)0.086 (4)0.031 (4)0.008 (3)0.059 (4)
C190.071 (3)0.058 (3)0.055 (3)0.005 (2)0.006 (2)0.009 (2)
C200.093 (5)0.107 (5)0.148 (6)0.049 (4)0.012 (4)0.041 (4)
C210.094 (4)0.071 (3)0.108 (5)0.017 (3)0.013 (3)0.037 (3)
C220.062 (3)0.065 (3)0.046 (2)0.003 (2)0.002 (2)0.011 (2)
C230.112 (5)0.080 (4)0.070 (3)0.009 (3)0.022 (3)0.021 (3)
C240.081 (4)0.104 (4)0.070 (3)0.011 (3)0.027 (3)0.036 (3)
C310.077 (3)0.074 (3)0.088 (4)0.021 (3)0.008 (3)0.026 (3)
C320.069 (3)0.068 (3)0.064 (3)0.001 (3)0.007 (2)0.027 (2)
C330.041 (2)0.058 (3)0.052 (2)0.0020 (19)0.0075 (19)0.014 (2)
C340.060 (3)0.065 (3)0.057 (3)0.001 (2)0.007 (2)0.014 (2)
C350.069 (3)0.067 (3)0.065 (3)0.005 (3)0.005 (2)0.012 (2)
C360.069 (3)0.073 (3)0.079 (4)0.010 (3)0.000 (3)0.010 (3)
C370.051 (2)0.061 (3)0.051 (2)0.002 (2)0.009 (2)0.017 (2)
C380.046 (2)0.062 (3)0.053 (3)0.005 (2)0.005 (2)0.016 (2)
C390.048 (2)0.057 (3)0.047 (2)0.003 (2)0.0035 (19)0.012 (2)
C400.042 (2)0.043 (2)0.054 (2)0.0067 (18)0.0020 (18)0.0158 (18)
C410.053 (2)0.045 (2)0.047 (2)0.0080 (19)0.0013 (19)0.0129 (18)
C420.062 (3)0.060 (3)0.062 (3)0.003 (2)0.005 (2)0.017 (2)
C430.060 (3)0.051 (3)0.080 (3)0.008 (2)0.001 (3)0.020 (2)
C440.057 (3)0.046 (2)0.069 (3)0.003 (2)0.014 (2)0.004 (2)
C450.054 (2)0.053 (2)0.048 (2)0.001 (2)0.0062 (19)0.005 (2)
C460.063 (3)0.054 (3)0.043 (2)0.002 (2)0.006 (2)0.0104 (19)
C470.073 (3)0.049 (3)0.051 (2)0.004 (2)0.001 (2)0.008 (2)
C480.091 (4)0.063 (3)0.125 (5)0.021 (3)0.021 (4)0.023 (3)
C490.076 (3)0.053 (3)0.048 (2)0.002 (2)0.005 (2)0.008 (2)
C500.096 (4)0.112 (5)0.113 (5)0.000 (4)0.044 (4)0.033 (4)
C510.098 (4)0.070 (3)0.084 (4)0.013 (3)0.024 (3)0.024 (3)
C520.052 (3)0.052 (2)0.058 (3)0.001 (2)0.001 (2)0.008 (2)
C530.079 (4)0.072 (3)0.086 (4)0.022 (3)0.007 (3)0.020 (3)
C540.098 (4)0.069 (3)0.071 (3)0.011 (3)0.001 (3)0.028 (3)
Geometric parameters (Å, º) top
O1—C81.371 (5)C18—H18B0.9600
O1—N11.424 (5)C18—H18C0.9600
O2—C91.378 (5)C19—H19A0.9300
O2—C101.397 (5)C20—H20A0.9600
O3—C171.220 (5)C20—H20B0.9600
O4—C171.351 (5)C20—H20C0.9600
O4—C181.433 (6)C21—H21A0.9600
O5—C381.354 (5)C21—H21B0.9600
O5—N51.422 (5)C21—H21C0.9600
O6—C401.386 (5)C22—H22A0.9300
O6—C391.389 (5)C23—H23A0.9600
O7—C471.215 (5)C23—H23B0.9600
O8—C471.351 (5)C23—H23C0.9600
O8—C481.443 (6)C24—H24A0.9600
N1—C71.295 (6)C24—H24B0.9600
N2—C81.303 (5)C24—H24C0.9600
N2—C71.367 (5)C31—C361.359 (7)
N3—C191.328 (6)C31—C321.389 (7)
N3—C211.445 (7)C31—H31A0.9300
N3—C201.462 (7)C32—C331.384 (6)
N4—C221.336 (6)C32—H32A0.9300
N4—C241.432 (6)C33—C341.385 (6)
N4—C231.453 (6)C33—C371.470 (6)
N5—C371.304 (5)C34—C351.379 (6)
N6—C381.303 (5)C34—H34A0.9300
N6—C371.365 (5)C35—C361.364 (7)
N7—C491.338 (6)C35—H35A0.9300
N7—C511.437 (6)C36—H36A0.9300
N7—C501.441 (6)C38—C391.437 (6)
N8—C521.337 (5)C39—C521.345 (6)
N8—C531.448 (6)C40—C451.385 (5)
N8—C541.462 (6)C40—C411.396 (5)
C1—C61.364 (7)C41—C421.369 (6)
C1—C21.373 (6)C41—C461.499 (6)
C1—H1B0.9300C42—C431.377 (6)
C2—C31.391 (6)C42—H42A0.9300
C2—H2B0.9300C43—C441.363 (6)
C3—C41.380 (6)C43—H43A0.9300
C3—C71.479 (6)C44—C451.383 (6)
C4—C51.411 (7)C44—H44A0.9300
C4—H4A0.9300C45—H45A0.9300
C5—C61.361 (8)C46—C491.353 (6)
C5—H5B0.9300C46—C471.454 (6)
C6—H6B0.9300C48—H48A0.9600
C8—C91.414 (6)C48—H48B0.9600
C9—C221.371 (6)C48—H48C0.9600
C10—C111.374 (6)C49—H49A0.9300
C10—C151.383 (6)C50—H50A0.9600
C11—C121.375 (6)C50—H50B0.9600
C11—H11A0.9300C50—H50C0.9600
C12—C131.384 (7)C51—H51A0.9600
C12—H12A0.9300C51—H51B0.9600
C13—C141.377 (7)C51—H51C0.9600
C13—H13A0.9300C52—H52A0.9300
C14—C151.384 (6)C53—H53A0.9600
C14—H14A0.9300C53—H53B0.9600
C15—C161.482 (6)C53—H53C0.9600
C16—C191.351 (6)C54—H54A0.9600
C16—C171.472 (6)C54—H54B0.9600
C18—H18A0.9600C54—H54C0.9600
C8—O1—N1105.9 (3)N4—C23—H23B109.5
C9—O2—C10118.4 (3)H23A—C23—H23B109.5
C17—O4—C18115.7 (4)N4—C23—H23C109.5
C38—O5—N5106.1 (3)H23A—C23—H23C109.5
C40—O6—C39117.6 (3)H23B—C23—H23C109.5
C47—O8—C48116.3 (4)N4—C24—H24A109.5
C7—N1—O1103.2 (4)N4—C24—H24B109.5
C8—N2—C7103.3 (4)H24A—C24—H24B109.5
C19—N3—C21124.1 (4)N4—C24—H24C109.5
C19—N3—C20120.3 (5)H24A—C24—H24C109.5
C21—N3—C20115.6 (5)H24B—C24—H24C109.5
C22—N4—C24124.6 (4)C36—C31—C32120.7 (5)
C22—N4—C23119.5 (4)C36—C31—H31A119.7
C24—N4—C23115.9 (4)C32—C31—H31A119.7
C37—N5—O5102.8 (3)C31—C32—C33119.8 (5)
C38—N6—C37102.8 (4)C31—C32—H32A120.1
C49—N7—C51124.0 (4)C33—C32—H32A120.1
C49—N7—C50120.0 (4)C34—C33—C32118.8 (4)
C51—N7—C50116.0 (5)C34—C33—C37120.8 (4)
C52—N8—C53125.3 (4)C32—C33—C37120.4 (4)
C52—N8—C54119.5 (4)C35—C34—C33120.3 (5)
C53—N8—C54115.2 (4)C35—C34—H34A119.9
C6—C1—C2120.8 (5)C33—C34—H34A119.9
C6—C1—H1B119.6C36—C35—C34120.6 (5)
C2—C1—H1B119.6C36—C35—H35A119.7
C1—C2—C3119.6 (5)C34—C35—H35A119.7
C1—C2—H2B120.2C31—C36—C35119.9 (5)
C3—C2—H2B120.2C31—C36—H36A120.1
C4—C3—C2119.4 (4)C35—C36—H36A120.1
C4—C3—C7120.6 (4)N5—C37—N6115.6 (4)
C2—C3—C7120.0 (4)N5—C37—C33121.0 (4)
C3—C4—C5120.4 (5)N6—C37—C33123.3 (4)
C3—C4—H4A119.8N6—C38—O5112.8 (4)
C5—C4—H4A119.8N6—C38—C39130.1 (4)
C6—C5—C4118.5 (5)O5—C38—C39117.0 (4)
C6—C5—H5B120.7C52—C39—O6124.4 (4)
C4—C5—H5B120.7C52—C39—C38119.8 (4)
C1—C6—C5121.4 (5)O6—C39—C38115.6 (4)
C1—C6—H6B119.3C45—C40—O6122.9 (4)
C5—C6—H6B119.3C45—C40—C41121.1 (4)
N1—C7—N2115.7 (4)O6—C40—C41116.0 (3)
N1—C7—C3121.6 (4)C42—C41—C40117.2 (4)
N2—C7—C3122.7 (4)C42—C41—C46124.0 (4)
N2—C8—O1112.0 (4)C40—C41—C46118.8 (4)
N2—C8—C9131.6 (4)C41—C42—C43123.1 (4)
O1—C8—C9116.4 (4)C41—C42—H42A118.5
C22—C9—O2123.2 (4)C43—C42—H42A118.5
C22—C9—C8119.4 (4)C44—C43—C42118.5 (4)
O2—C9—C8117.1 (4)C44—C43—H43A120.8
C11—C10—C15122.0 (4)C42—C43—H43A120.8
C11—C10—O2122.9 (4)C43—C44—C45121.3 (4)
C15—C10—O2115.1 (3)C43—C44—H44A119.4
C10—C11—C12119.8 (4)C45—C44—H44A119.4
C10—C11—H11A120.1C44—C45—C40118.9 (4)
C12—C11—H11A120.1C44—C45—H45A120.6
C11—C12—C13120.3 (4)C40—C45—H45A120.6
C11—C12—H12A119.9C49—C46—C47114.8 (4)
C13—C12—H12A119.9C49—C46—C41125.5 (4)
C14—C13—C12118.4 (5)C47—C46—C41119.3 (4)
C14—C13—H13A120.8O7—C47—O8120.7 (4)
C12—C13—H13A120.8O7—C47—C46126.9 (4)
C13—C14—C15123.0 (5)O8—C47—C46112.3 (4)
C13—C14—H14A118.5O8—C48—H48A109.5
C15—C14—H14A118.5O8—C48—H48B109.5
C10—C15—C14116.5 (4)H48A—C48—H48B109.5
C10—C15—C16120.5 (4)O8—C48—H48C109.5
C14—C15—C16123.0 (4)H48A—C48—H48C109.5
C19—C16—C17114.1 (4)H48B—C48—H48C109.5
C19—C16—C15126.9 (4)N7—C49—C46132.3 (4)
C17—C16—C15118.4 (4)N7—C49—H49A113.8
O3—C17—O4121.3 (4)C46—C49—H49A113.8
O3—C17—C16125.7 (4)N7—C50—H50A109.5
O4—C17—C16112.9 (4)N7—C50—H50B109.5
O4—C18—H18A109.5H50A—C50—H50B109.5
O4—C18—H18B109.5N7—C50—H50C109.5
H18A—C18—H18B109.5H50A—C50—H50C109.5
O4—C18—H18C109.5H50B—C50—H50C109.5
H18A—C18—H18C109.5N7—C51—H51A109.5
H18B—C18—H18C109.5N7—C51—H51B109.5
N3—C19—C16130.9 (4)H51A—C51—H51B109.5
N3—C19—H19A114.6N7—C51—H51C109.5
C16—C19—H19A114.6H51A—C51—H51C109.5
N3—C20—H20A109.5H51B—C51—H51C109.5
N3—C20—H20B109.5C39—C52—N8130.2 (4)
H20A—C20—H20B109.5C39—C52—H52A114.9
N3—C20—H20C109.5N8—C52—H52A114.9
H20A—C20—H20C109.5N8—C53—H53A109.5
H20B—C20—H20C109.5N8—C53—H53B109.5
N3—C21—H21A109.5H53A—C53—H53B109.5
N3—C21—H21B109.5N8—C53—H53C109.5
H21A—C21—H21B109.5H53A—C53—H53C109.5
N3—C21—H21C109.5H53B—C53—H53C109.5
H21A—C21—H21C109.5N8—C54—H54A109.5
H21B—C21—H21C109.5N8—C54—H54B109.5
N4—C22—C9130.8 (4)H54A—C54—H54B109.5
N4—C22—H22A114.6N8—C54—H54C109.5
C9—C22—H22A114.6H54A—C54—H54C109.5
N4—C23—H23A109.5H54B—C54—H54C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19A···O30.932.332.747 (6)107
C23—H23A···O7i0.962.513.280 (6)137
C24—H24A···O20.962.142.918 (7)137
C49—H49A···O70.932.342.763 (6)107
C53—H53A···O60.962.162.929 (6)136
Symmetry code: (i) x+1, y, z+1.
 

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