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The title compound, C12H15N3O, crystallizes with four independent mol­ecules in the asymmetric unit. The five-membered heterocyclic rings are essentially planar. The crystal packing is stabilized by intra- and inter­molecular hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048392/rz2090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048392/rz2090Isup2.hkl
Contains datablock I

CCDC reference: 630223

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.058
  • wR factor = 0.139
  • Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C46 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 5719 Count of symmetry unique reflns 5814 Completeness (_total/calc) 98.37% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

2-Isopropylamino-1-phenyl-1H-imidazol-5(4H)-one top
Crystal data top
C12H15N3OF(000) = 1856
Mr = 217.27Dx = 1.221 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6872 reflections
a = 19.076 (3) Åθ = 2.2–21.1°
b = 7.6881 (10) ŵ = 0.08 mm1
c = 32.241 (4) ÅT = 298 K
V = 4728.4 (11) Å3Block, colourless
Z = 160.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 28.0°, θmin = 2.1°
φ and ω scansh = 2525
34935 measured reflectionsk = 99
5719 independent reflectionsl = 4140
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0706P)2 + 0.2788P]
where P = (Fo2 + 2Fc2)/3
5719 reflections(Δ/σ)max = 0.001
597 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.19 e Å3
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
C10.58923 (16)0.6139 (4)0.45371 (9)0.0409 (7)
C20.5671 (2)0.7508 (4)0.42957 (10)0.0508 (8)
H20.59640.84550.42500.061*
C30.5011 (2)0.7469 (5)0.41220 (12)0.0595 (9)
H30.48580.83930.39590.071*
C40.4576 (2)0.6055 (5)0.41891 (12)0.0584 (9)
H40.41320.60240.40690.070*
C50.47987 (19)0.4705 (5)0.44317 (12)0.0554 (9)
H50.45030.37670.44810.067*
C60.54605 (17)0.4729 (4)0.46029 (11)0.0469 (7)
H60.56150.37960.47620.056*
C70.71905 (18)0.6437 (5)0.44790 (11)0.0540 (9)
C80.77809 (17)0.6276 (5)0.47814 (11)0.0532 (8)
H8A0.80970.53510.46980.064*
H8B0.80430.73550.47960.064*
C90.67973 (16)0.5853 (4)0.51190 (10)0.0413 (7)
C100.65101 (18)0.5416 (6)0.58469 (11)0.0611 (10)
H100.69830.49220.58610.073*
C110.6530 (3)0.7178 (9)0.60390 (16)0.1052 (18)
H11A0.68640.78880.58950.158*
H11B0.66630.70770.63250.158*
H11C0.60740.77020.60200.158*
C120.6016 (3)0.4194 (9)0.60720 (17)0.103 (2)
H12A0.55520.46770.60720.155*
H12B0.61720.40420.63530.155*
H12C0.60110.30880.59340.155*
C130.30869 (18)0.8552 (4)0.50193 (11)0.0487 (8)
C140.2917 (2)0.8410 (6)0.46101 (14)0.0700 (11)
H140.32650.82080.44140.084*
C150.2226 (3)0.8566 (6)0.44872 (18)0.0889 (16)
H150.21070.84550.42090.107*
C160.1715 (3)0.8887 (6)0.4776 (2)0.0895 (17)
H160.12490.89920.46940.107*
C170.1888 (3)0.9049 (7)0.5179 (2)0.0906 (16)
H170.15380.92650.53730.109*
C180.2574 (2)0.8899 (6)0.53092 (15)0.0725 (12)
H180.26880.90300.55880.087*
C190.43326 (19)0.9525 (5)0.50224 (12)0.0540 (9)
C200.49631 (19)0.8932 (5)0.52606 (14)0.0608 (10)
H20A0.53400.86290.50720.073*
H20B0.51260.98510.54430.073*
C210.40959 (16)0.7209 (4)0.54306 (10)0.0441 (7)
C220.39785 (18)0.4669 (5)0.58736 (11)0.0508 (8)
H220.43990.51520.60040.061*
C230.4193 (3)0.3147 (7)0.56280 (14)0.0899 (16)
H23A0.37850.25700.55220.135*
H23B0.44530.23590.58010.135*
H23C0.44830.35190.54010.135*
C240.3471 (3)0.4221 (7)0.62112 (15)0.0822 (14)
H24A0.33280.52650.63510.123*
H24B0.36910.34500.64060.123*
H24C0.30670.36620.60930.123*
C250.47023 (16)0.0679 (4)0.32516 (9)0.0383 (7)
C260.44767 (17)0.2013 (4)0.35032 (10)0.0491 (8)
H260.47760.29320.35640.059*
C270.38097 (19)0.1989 (5)0.36647 (11)0.0558 (9)
H270.36600.28930.38350.067*
C280.33633 (18)0.0638 (5)0.35761 (12)0.0565 (9)
H280.29120.06260.36850.068*
C290.35877 (18)0.0704 (5)0.33235 (12)0.0533 (9)
H290.32860.16160.32610.064*
C300.42575 (17)0.0690 (4)0.31650 (10)0.0451 (7)
H300.44110.16040.29990.054*
C310.59995 (18)0.0979 (4)0.33336 (12)0.0504 (8)
C320.65938 (17)0.0927 (5)0.30326 (12)0.0548 (9)
H32A0.68370.20350.30290.066*
H32B0.69250.00260.31100.066*
C330.56273 (15)0.0471 (4)0.26787 (10)0.0418 (7)
C340.53654 (19)0.0074 (6)0.19465 (12)0.0594 (10)
H340.58380.04240.19340.071*
C350.5388 (3)0.1858 (7)0.17505 (15)0.0876 (15)
H35A0.49330.23870.17690.131*
H35B0.55200.17540.14640.131*
H35C0.57240.25670.18930.131*
C360.4874 (2)0.1130 (8)0.17164 (16)0.0937 (18)
H36A0.48630.22390.18530.141*
H36B0.50370.12770.14370.141*
H36C0.44120.06380.17130.141*
C370.20516 (18)0.3675 (4)0.27283 (10)0.0462 (8)
C380.1885 (2)0.3767 (5)0.31442 (12)0.0617 (10)
H380.22270.35840.33450.074*
C390.1206 (3)0.4134 (6)0.32575 (14)0.0781 (13)
H390.10910.42140.35370.094*
C400.0698 (2)0.4382 (5)0.29657 (17)0.0763 (13)
H400.02390.46010.30460.092*
C410.0870 (2)0.4306 (6)0.25525 (15)0.0716 (11)
H410.05270.44930.23530.086*
C420.1548 (2)0.3955 (5)0.24322 (12)0.0574 (9)
H420.16630.39070.21520.069*
C430.3332 (2)0.4310 (5)0.27296 (13)0.0567 (9)
C440.3934 (2)0.3591 (5)0.24861 (14)0.0609 (10)
H44A0.41130.44630.22960.073*
H44B0.43100.32410.26710.073*
C450.30099 (17)0.2036 (4)0.23324 (10)0.0438 (7)
C460.28102 (18)0.0515 (4)0.19055 (12)0.0496 (8)
H460.32450.01260.17730.060*
C470.2286 (2)0.0876 (7)0.15683 (16)0.0826 (14)
H47A0.24770.17110.13780.124*
H47B0.21820.01830.14230.124*
H47C0.18630.13300.16890.124*
C480.2975 (3)0.2070 (7)0.21565 (16)0.0941 (16)
H48A0.32940.17580.23740.141*
H48B0.31870.29380.19830.141*
H48C0.25510.25240.22750.141*
N10.65878 (14)0.6175 (4)0.47075 (8)0.0445 (6)
N20.74645 (14)0.5882 (4)0.51814 (9)0.0491 (6)
N30.63071 (15)0.5533 (4)0.54090 (9)0.0536 (7)
H3A0.588 (2)0.579 (5)0.5376 (13)0.064*
N40.38022 (14)0.8414 (4)0.51473 (9)0.0496 (7)
N50.47542 (14)0.7420 (4)0.55016 (10)0.0545 (7)
N60.36779 (16)0.6019 (4)0.56079 (10)0.0542 (8)
H6A0.326 (2)0.580 (5)0.5509 (14)0.065*
N70.54049 (13)0.0719 (3)0.30917 (8)0.0430 (6)
N80.62940 (13)0.0558 (4)0.26250 (9)0.0510 (7)
N90.51518 (15)0.0151 (4)0.23800 (8)0.0512 (7)
H90.471 (2)0.042 (5)0.2438 (13)0.061*
N100.27590 (14)0.3329 (3)0.26081 (9)0.0467 (6)
N110.36714 (14)0.2102 (4)0.22579 (10)0.0519 (7)
N120.25546 (15)0.0907 (4)0.21666 (10)0.0493 (7)
H120.218 (2)0.064 (5)0.2296 (13)0.059*
O10.72099 (15)0.6732 (5)0.41117 (8)0.0831 (10)
O20.42668 (16)1.0714 (4)0.47794 (10)0.0753 (8)
O30.60055 (15)0.1196 (4)0.37045 (9)0.0706 (8)
O40.33241 (17)0.5497 (4)0.29702 (11)0.0821 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (18)0.0435 (17)0.0302 (15)0.0032 (13)0.0006 (13)0.0037 (12)
C20.071 (2)0.0439 (18)0.0371 (16)0.0074 (15)0.0044 (16)0.0020 (14)
C30.079 (3)0.056 (2)0.0434 (18)0.0098 (18)0.0160 (18)0.0049 (16)
C40.055 (2)0.071 (2)0.049 (2)0.0076 (18)0.0096 (16)0.0043 (18)
C50.056 (2)0.055 (2)0.055 (2)0.0107 (16)0.0025 (17)0.0016 (17)
C60.0482 (18)0.0458 (18)0.0466 (18)0.0014 (14)0.0043 (15)0.0049 (14)
C70.055 (2)0.064 (2)0.042 (2)0.0181 (17)0.0054 (16)0.0015 (16)
C80.0470 (19)0.063 (2)0.049 (2)0.0129 (15)0.0074 (16)0.0026 (17)
C90.0447 (17)0.0428 (16)0.0363 (16)0.0042 (13)0.0005 (13)0.0019 (13)
C100.0381 (18)0.107 (3)0.0387 (19)0.0007 (18)0.0024 (15)0.014 (2)
C110.125 (5)0.127 (5)0.064 (3)0.005 (4)0.009 (3)0.024 (3)
C120.068 (3)0.168 (6)0.073 (3)0.014 (3)0.004 (2)0.055 (4)
C130.0518 (19)0.0415 (17)0.053 (2)0.0087 (14)0.0062 (16)0.0072 (15)
C140.079 (3)0.073 (3)0.058 (2)0.012 (2)0.013 (2)0.008 (2)
C150.103 (4)0.078 (3)0.087 (4)0.002 (3)0.045 (3)0.021 (3)
C160.060 (3)0.069 (3)0.139 (5)0.003 (2)0.030 (3)0.040 (3)
C170.060 (3)0.089 (3)0.123 (5)0.020 (2)0.001 (3)0.025 (3)
C180.061 (2)0.081 (3)0.075 (3)0.019 (2)0.001 (2)0.005 (2)
C190.060 (2)0.0478 (19)0.055 (2)0.0006 (15)0.0139 (17)0.0063 (17)
C200.049 (2)0.060 (2)0.073 (3)0.0064 (16)0.0131 (18)0.0106 (19)
C210.0437 (17)0.0493 (18)0.0393 (17)0.0037 (14)0.0034 (13)0.0036 (14)
C220.0443 (18)0.061 (2)0.0465 (19)0.0045 (15)0.0123 (15)0.0075 (16)
C230.121 (4)0.087 (3)0.062 (3)0.046 (3)0.019 (3)0.001 (2)
C240.083 (3)0.096 (3)0.068 (3)0.018 (3)0.008 (2)0.027 (3)
C250.0461 (17)0.0400 (15)0.0287 (14)0.0017 (12)0.0002 (12)0.0019 (12)
C260.057 (2)0.0469 (18)0.0436 (18)0.0101 (14)0.0032 (15)0.0062 (14)
C270.065 (2)0.058 (2)0.0452 (19)0.0008 (16)0.0085 (16)0.0135 (16)
C280.0478 (19)0.072 (2)0.050 (2)0.0020 (16)0.0084 (16)0.0084 (18)
C290.0459 (18)0.056 (2)0.058 (2)0.0117 (15)0.0039 (17)0.0075 (17)
C300.0473 (18)0.0447 (17)0.0432 (17)0.0024 (13)0.0043 (14)0.0106 (13)
C310.053 (2)0.0484 (18)0.050 (2)0.0001 (15)0.0103 (17)0.0014 (15)
C320.0398 (17)0.060 (2)0.065 (2)0.0002 (15)0.0083 (17)0.0078 (18)
C330.0353 (15)0.0468 (17)0.0432 (17)0.0050 (12)0.0005 (14)0.0054 (13)
C340.0389 (18)0.095 (3)0.045 (2)0.0087 (18)0.0047 (15)0.011 (2)
C350.082 (3)0.120 (4)0.061 (3)0.019 (3)0.017 (2)0.017 (3)
C360.060 (3)0.153 (5)0.068 (3)0.005 (3)0.001 (2)0.057 (3)
C370.061 (2)0.0337 (15)0.0442 (18)0.0079 (14)0.0025 (15)0.0009 (13)
C380.083 (3)0.061 (2)0.0408 (19)0.0203 (19)0.0013 (18)0.0012 (17)
C390.102 (4)0.080 (3)0.052 (2)0.022 (2)0.030 (2)0.005 (2)
C400.068 (3)0.062 (2)0.099 (4)0.014 (2)0.024 (3)0.000 (2)
C410.067 (3)0.076 (3)0.072 (3)0.020 (2)0.007 (2)0.002 (2)
C420.065 (2)0.062 (2)0.045 (2)0.0151 (18)0.0002 (17)0.0041 (16)
C430.071 (2)0.0415 (18)0.058 (2)0.0054 (16)0.0183 (19)0.0029 (17)
C440.054 (2)0.051 (2)0.078 (3)0.0096 (17)0.0129 (19)0.0138 (19)
C450.0465 (18)0.0441 (16)0.0407 (17)0.0000 (13)0.0025 (14)0.0038 (14)
C460.0463 (18)0.0520 (19)0.051 (2)0.0003 (14)0.0067 (15)0.0103 (15)
C470.082 (3)0.089 (3)0.077 (3)0.010 (2)0.008 (2)0.032 (3)
C480.136 (4)0.074 (3)0.072 (3)0.033 (3)0.011 (3)0.000 (2)
N10.0446 (14)0.0557 (16)0.0331 (14)0.0098 (12)0.0004 (11)0.0028 (11)
N20.0411 (14)0.0598 (17)0.0466 (16)0.0061 (12)0.0026 (12)0.0023 (13)
N30.0379 (14)0.083 (2)0.0400 (16)0.0046 (14)0.0006 (13)0.0107 (14)
N40.0499 (16)0.0495 (16)0.0494 (16)0.0041 (12)0.0001 (13)0.0072 (13)
N50.0452 (15)0.0620 (18)0.0564 (17)0.0011 (13)0.0025 (14)0.0023 (15)
N60.0432 (16)0.0611 (18)0.0583 (18)0.0014 (14)0.0140 (14)0.0148 (14)
N70.0395 (14)0.0507 (15)0.0389 (14)0.0001 (11)0.0033 (11)0.0031 (12)
N80.0401 (15)0.0607 (17)0.0522 (17)0.0042 (12)0.0012 (13)0.0089 (14)
N90.0321 (14)0.084 (2)0.0380 (15)0.0077 (13)0.0025 (11)0.0136 (14)
N100.0535 (16)0.0432 (14)0.0436 (15)0.0023 (12)0.0021 (13)0.0025 (12)
N110.0409 (15)0.0540 (16)0.0609 (18)0.0053 (12)0.0036 (13)0.0011 (14)
N120.0398 (14)0.0559 (16)0.0522 (17)0.0022 (13)0.0115 (13)0.0137 (13)
O10.0746 (19)0.138 (3)0.0371 (14)0.0319 (18)0.0097 (13)0.0062 (16)
O20.091 (2)0.0585 (17)0.076 (2)0.0009 (14)0.0133 (16)0.0144 (15)
O30.0686 (17)0.094 (2)0.0487 (16)0.0105 (14)0.0163 (13)0.0040 (14)
O40.107 (2)0.0518 (16)0.088 (2)0.0036 (14)0.0240 (18)0.0202 (16)
Geometric parameters (Å, º) top
C1—C21.376 (5)C25—N71.436 (4)
C1—C61.378 (5)C26—C271.375 (5)
C1—N11.436 (4)C26—H260.9300
C2—C31.378 (5)C27—C281.373 (5)
C2—H20.9300C27—H270.9300
C3—C41.385 (6)C28—C291.382 (5)
C3—H30.9300C28—H280.9300
C4—C51.367 (5)C29—C301.376 (5)
C4—H40.9300C29—H290.9300
C5—C61.378 (5)C30—H300.9300
C5—H50.9300C31—O31.208 (4)
C6—H60.9300C31—N71.391 (4)
C7—O11.206 (4)C31—C321.493 (5)
C7—N11.380 (4)C32—N81.461 (5)
C7—C81.495 (5)C32—H32A0.9700
C8—N21.456 (5)C32—H32B0.9700
C8—H8A0.9700C33—N81.285 (4)
C8—H8B0.9700C33—N91.345 (4)
C9—N21.289 (4)C33—N71.411 (4)
C9—N31.345 (4)C34—N91.457 (5)
C9—N11.407 (4)C34—C351.511 (7)
C10—N31.467 (5)C34—C361.511 (6)
C10—C111.490 (7)C34—H340.9800
C10—C121.516 (6)C35—H35A0.9600
C10—H100.9800C35—H35B0.9600
C11—H11A0.9600C35—H35C0.9600
C11—H11B0.9600C36—H36A0.9600
C11—H11C0.9600C36—H36B0.9600
C12—H12A0.9600C36—H36C0.9600
C12—H12B0.9600C37—C421.372 (5)
C12—H12C0.9600C37—C381.380 (5)
C13—C141.363 (6)C37—N101.429 (4)
C13—C181.379 (6)C38—C391.375 (6)
C13—N41.429 (4)C38—H380.9300
C14—C151.382 (6)C39—C401.363 (7)
C14—H140.9300C39—H390.9300
C15—C161.370 (8)C40—C411.373 (7)
C15—H150.9300C40—H400.9300
C16—C171.346 (8)C41—C421.375 (6)
C16—H160.9300C41—H410.9300
C17—C181.379 (7)C42—H420.9300
C17—H170.9300C43—O41.198 (5)
C18—H180.9300C43—N101.385 (4)
C19—O21.210 (4)C43—C441.496 (6)
C19—N41.384 (5)C44—N111.450 (5)
C19—C201.498 (6)C44—H44A0.9700
C20—N51.454 (5)C44—H44B0.9700
C20—H20A0.9700C45—N111.286 (4)
C20—H20B0.9700C45—N121.339 (4)
C21—N51.287 (4)C45—N101.417 (4)
C21—N61.341 (4)C46—N121.463 (4)
C21—N41.417 (4)C46—C481.478 (6)
C22—N61.462 (4)C46—C471.503 (6)
C22—C231.471 (6)C46—H460.9800
C22—C241.497 (6)C47—H47A0.9600
C22—H220.9800C47—H47B0.9600
C23—H23A0.9600C47—H47C0.9600
C23—H23B0.9600C48—H48A0.9600
C23—H23C0.9600C48—H48B0.9600
C24—H24A0.9600C48—H48C0.9600
C24—H24B0.9600N3—H3A0.84 (4)
C24—H24C0.9600N6—H6A0.87 (4)
C25—C261.377 (4)N9—H90.90 (4)
C25—C301.380 (4)N12—H120.85 (4)
C2—C1—C6120.4 (3)C28—C29—H29120.0
C2—C1—N1119.1 (3)C29—C30—C25120.1 (3)
C6—C1—N1120.5 (3)C29—C30—H30119.9
C1—C2—C3119.6 (3)C25—C30—H30119.9
C1—C2—H2120.2O3—C31—N7125.7 (3)
C3—C2—H2120.2O3—C31—C32129.8 (3)
C2—C3—C4120.1 (3)N7—C31—C32104.5 (3)
C2—C3—H3119.9N8—C32—C31107.0 (3)
C4—C3—H3119.9N8—C32—H32A110.3
C5—C4—C3119.9 (3)C31—C32—H32A110.3
C5—C4—H4120.1N8—C32—H32B110.3
C3—C4—H4120.1C31—C32—H32B110.3
C4—C5—C6120.3 (3)H32A—C32—H32B108.6
C4—C5—H5119.9N8—C33—N9125.5 (3)
C6—C5—H5119.9N8—C33—N7114.7 (3)
C5—C6—C1119.7 (3)N9—C33—N7119.8 (3)
C5—C6—H6120.1N9—C34—C35111.8 (3)
C1—C6—H6120.1N9—C34—C36108.8 (3)
O1—C7—N1125.2 (3)C35—C34—C36111.6 (4)
O1—C7—C8129.3 (3)N9—C34—H34108.2
N1—C7—C8105.5 (3)C35—C34—H34108.2
N2—C8—C7106.4 (3)C36—C34—H34108.2
N2—C8—H8A110.4C34—C35—H35A109.5
C7—C8—H8A110.4C34—C35—H35B109.5
N2—C8—H8B110.4H35A—C35—H35B109.5
C7—C8—H8B110.4C34—C35—H35C109.5
H8A—C8—H8B108.6H35A—C35—H35C109.5
N2—C9—N3125.5 (3)H35B—C35—H35C109.5
N2—C9—N1115.1 (3)C34—C36—H36A109.5
N3—C9—N1119.3 (3)C34—C36—H36B109.5
N3—C10—C11110.6 (4)H36A—C36—H36B109.5
N3—C10—C12109.5 (3)C34—C36—H36C109.5
C11—C10—C12112.3 (5)H36A—C36—H36C109.5
N3—C10—H10108.1H36B—C36—H36C109.5
C11—C10—H10108.1C42—C37—C38120.4 (3)
C12—C10—H10108.1C42—C37—N10120.2 (3)
C10—C11—H11A109.5C38—C37—N10119.4 (3)
C10—C11—H11B109.5C39—C38—C37119.1 (4)
H11A—C11—H11B109.5C39—C38—H38120.5
C10—C11—H11C109.5C37—C38—H38120.5
H11A—C11—H11C109.5C40—C39—C38120.9 (4)
H11B—C11—H11C109.5C40—C39—H39119.5
C10—C12—H12A109.5C38—C39—H39119.5
C10—C12—H12B109.5C39—C40—C41119.6 (4)
H12A—C12—H12B109.5C39—C40—H40120.2
C10—C12—H12C109.5C41—C40—H40120.2
H12A—C12—H12C109.5C40—C41—C42120.4 (4)
H12B—C12—H12C109.5C40—C41—H41119.8
C14—C13—C18120.2 (4)C42—C41—H41119.8
C14—C13—N4120.0 (3)C37—C42—C41119.5 (4)
C18—C13—N4119.8 (3)C37—C42—H42120.2
C13—C14—C15119.8 (5)C41—C42—H42120.2
C13—C14—H14120.1O4—C43—N10126.0 (4)
C15—C14—H14120.1O4—C43—C44129.1 (4)
C16—C15—C14120.0 (5)N10—C43—C44104.8 (3)
C16—C15—H15120.0N11—C44—C43107.0 (3)
C14—C15—H15120.0N11—C44—H44A110.3
C17—C16—C15119.8 (4)C43—C44—H44A110.3
C17—C16—H16120.1N11—C44—H44B110.3
C15—C16—H16120.1C43—C44—H44B110.3
C16—C17—C18121.3 (5)H44A—C44—H44B108.6
C16—C17—H17119.3N11—C45—N12126.0 (3)
C18—C17—H17119.3N11—C45—N10114.9 (3)
C17—C18—C13118.9 (5)N12—C45—N10119.1 (3)
C17—C18—H18120.6N12—C46—C48111.1 (3)
C13—C18—H18120.6N12—C46—C47109.4 (3)
O2—C19—N4125.4 (4)C48—C46—C47112.8 (4)
O2—C19—C20130.2 (4)N12—C46—H46107.8
N4—C19—C20104.5 (3)C48—C46—H46107.8
N5—C20—C19107.3 (3)C47—C46—H46107.8
N5—C20—H20A110.3C46—C47—H47A109.5
C19—C20—H20A110.3C46—C47—H47B109.5
N5—C20—H20B110.3H47A—C47—H47B109.5
C19—C20—H20B110.3C46—C47—H47C109.5
H20A—C20—H20B108.5H47A—C47—H47C109.5
N5—C21—N6126.2 (3)H47B—C47—H47C109.5
N5—C21—N4114.7 (3)C46—C48—H48A109.5
N6—C21—N4119.1 (3)C46—C48—H48B109.5
N6—C22—C23111.0 (3)H48A—C48—H48B109.5
N6—C22—C24109.6 (3)C46—C48—H48C109.5
C23—C22—C24112.9 (4)H48A—C48—H48C109.5
N6—C22—H22107.7H48B—C48—H48C109.5
C23—C22—H22107.7C7—N1—C9107.0 (3)
C24—C22—H22107.7C7—N1—C1124.6 (3)
C22—C23—H23A109.5C9—N1—C1128.3 (3)
C22—C23—H23B109.5C9—N2—C8105.9 (3)
H23A—C23—H23B109.5C9—N3—C10119.8 (3)
C22—C23—H23C109.5C9—N3—H3A123 (3)
H23A—C23—H23C109.5C10—N3—H3A113 (3)
H23B—C23—H23C109.5C19—N4—C21107.6 (3)
C22—C24—H24A109.5C19—N4—C13124.6 (3)
C22—C24—H24B109.5C21—N4—C13127.7 (3)
H24A—C24—H24B109.5C21—N5—C20105.9 (3)
C22—C24—H24C109.5C21—N6—C22120.0 (3)
H24A—C24—H24C109.5C21—N6—H6A121 (3)
H24B—C24—H24C109.5C22—N6—H6A116 (3)
C26—C25—C30119.7 (3)C31—N7—C33107.7 (3)
C26—C25—N7119.2 (3)C31—N7—C25124.3 (3)
C30—C25—N7121.2 (3)C33—N7—C25128.1 (2)
C27—C26—C25120.2 (3)C33—N8—C32106.0 (3)
C27—C26—H26119.9C33—N9—C34120.4 (3)
C25—C26—H26119.9C33—N9—H9117 (3)
C28—C27—C26120.3 (3)C34—N9—H9118 (3)
C28—C27—H27119.8C43—N10—C45107.0 (3)
C26—C27—H27119.8C43—N10—C37124.6 (3)
C27—C28—C29119.7 (3)C45—N10—C37128.3 (3)
C27—C28—H28120.2C45—N11—C44105.9 (3)
C29—C28—H28120.2C45—N12—C46119.9 (3)
C30—C29—C28120.0 (3)C45—N12—H12120 (3)
C30—C29—H29120.0C46—N12—H12112 (3)
C6—C1—C2—C30.5 (5)C12—C10—N3—C9150.6 (4)
N1—C1—C2—C3178.4 (3)O2—C19—N4—C21179.7 (3)
C1—C2—C3—C40.2 (5)C20—C19—N4—C211.6 (4)
C2—C3—C4—C50.7 (6)O2—C19—N4—C132.7 (6)
C3—C4—C5—C61.3 (6)C20—C19—N4—C13176.0 (3)
C4—C5—C6—C11.5 (5)N5—C21—N4—C190.0 (4)
C2—C1—C6—C51.1 (5)N6—C21—N4—C19177.8 (3)
N1—C1—C6—C5179.0 (3)N5—C21—N4—C13177.5 (3)
O1—C7—C8—N2178.9 (4)N6—C21—N4—C130.4 (5)
N1—C7—C8—N21.0 (4)C14—C13—N4—C1961.3 (5)
C18—C13—C14—C151.8 (6)C18—C13—N4—C19116.1 (4)
N4—C13—C14—C15179.2 (4)C14—C13—N4—C21121.7 (4)
C13—C14—C15—C160.9 (7)C18—C13—N4—C2161.0 (5)
C14—C15—C16—C170.0 (7)N6—C21—N5—C20176.0 (3)
C15—C16—C17—C180.0 (8)N4—C21—N5—C201.6 (4)
C16—C17—C18—C130.9 (7)C19—C20—N5—C212.5 (4)
C14—C13—C18—C171.8 (6)N5—C21—N6—C227.7 (5)
N4—C13—C18—C17179.2 (4)N4—C21—N6—C22174.8 (3)
O2—C19—C20—N5178.9 (4)C23—C22—N6—C2187.7 (5)
N4—C19—C20—N52.5 (4)C24—C22—N6—C21146.9 (4)
C30—C25—C26—C270.5 (5)O3—C31—N7—C33178.3 (4)
N7—C25—C26—C27179.1 (3)C32—C31—N7—C331.8 (3)
C25—C26—C27—C280.1 (5)O3—C31—N7—C250.3 (5)
C26—C27—C28—C290.1 (6)C32—C31—N7—C25179.6 (3)
C27—C28—C29—C300.6 (6)N8—C33—N7—C310.7 (4)
C28—C29—C30—C251.2 (5)N9—C33—N7—C31178.5 (3)
C26—C25—C30—C291.2 (5)N8—C33—N7—C25179.2 (3)
N7—C25—C30—C29179.7 (3)N9—C33—N7—C250.0 (5)
O3—C31—C32—N8177.8 (4)C26—C25—N7—C3150.7 (4)
N7—C31—C32—N82.3 (4)C30—C25—N7—C31127.8 (3)
C42—C37—C38—C390.4 (6)C26—C25—N7—C33131.0 (3)
N10—C37—C38—C39178.7 (3)C30—C25—N7—C3350.6 (4)
C37—C38—C39—C400.9 (6)N9—C33—N8—C32180.0 (3)
C38—C39—C40—C411.6 (7)N7—C33—N8—C320.8 (4)
C39—C40—C41—C421.0 (7)C31—C32—N8—C331.9 (4)
C38—C37—C42—C410.9 (5)N8—C33—N9—C347.4 (5)
N10—C37—C42—C41179.2 (3)N7—C33—N9—C34173.5 (3)
C40—C41—C42—C370.2 (6)C35—C34—N9—C3384.7 (4)
O4—C43—C44—N11177.1 (4)C36—C34—N9—C33151.6 (4)
N10—C43—C44—N114.7 (4)O4—C43—N10—C45178.1 (4)
O1—C7—N1—C9179.3 (4)C44—C43—N10—C453.7 (4)
C8—C7—N1—C90.7 (4)O4—C43—N10—C375.2 (6)
O1—C7—N1—C12.8 (6)C44—C43—N10—C37173.1 (3)
C8—C7—N1—C1177.1 (3)N11—C45—N10—C431.3 (4)
N2—C9—N1—C70.1 (4)N12—C45—N10—C43179.7 (3)
N3—C9—N1—C7179.3 (3)N11—C45—N10—C37175.2 (3)
N2—C9—N1—C1176.4 (3)N12—C45—N10—C373.1 (5)
N3—C9—N1—C13.0 (5)C42—C37—N10—C43122.2 (4)
C2—C1—N1—C752.9 (4)C38—C37—N10—C4356.1 (5)
C6—C1—N1—C7125.0 (4)C42—C37—N10—C4553.8 (5)
C2—C1—N1—C9131.4 (3)C38—C37—N10—C45127.9 (4)
C6—C1—N1—C950.7 (5)N12—C45—N11—C44176.5 (3)
N3—C9—N2—C8179.9 (3)N10—C45—N11—C441.8 (4)
N1—C9—N2—C80.6 (4)C43—C44—N11—C454.0 (4)
C7—C8—N2—C91.0 (4)N11—C45—N12—C466.3 (5)
N2—C9—N3—C108.4 (5)N10—C45—N12—C46175.5 (3)
N1—C9—N3—C10172.2 (3)C48—C46—N12—C4589.2 (4)
C11—C10—N3—C985.1 (5)C47—C46—N12—C45145.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9···N110.90 (4)2.43 (4)3.222 (4)148 (3)
N3—H3A···N50.84 (4)2.52 (4)3.312 (4)157 (4)
C29—H29···O4i0.932.413.175 (4)140
C5—H5···O2i0.932.583.421 (5)151
N12—H12···N8ii0.85 (4)2.20 (4)3.039 (4)169 (4)
C38—H38···O1iii0.932.483.203 (5)134
N6—H6A···N2iii0.87 (4)2.26 (4)3.063 (4)153 (4)
Symmetry codes: (i) x, y1, z; (ii) x1/2, y, z; (iii) x1/2, y+1, z.
 

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