2-Isopropyl­amino-1-phenyl-1H-imidazol-5(4H)-one

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.

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

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

Crystal data

C12H15N3O	F(000) = 1856
Mr = 217.27	Dx = 1.221 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6872 reflections
a = 19.076 (3) Å	θ = 2.2–21.1°
b = 7.6881 (10) Å	µ = 0.08 mm^−1
c = 32.241 (4) Å	T = 298 K
V = 4728.4 (11) Å^3	Block, colourless
Z = 16	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 28.0°, θmin = 2.1°
φ and ω scans	h = −25→25
34935 measured reflections	k = −9→9
5719 independent reflections	l = −41→40

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0706P)^2 + 0.2788P] where P = (Fo^2 + 2Fc^2)/3
5719 reflections	(Δ/σ)max = 0.001
597 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.58923 (16)	0.6139 (4)	0.45371 (9)	0.0409 (7)
C2	0.5671 (2)	0.7508 (4)	0.42957 (10)	0.0508 (8)
H2	0.5964	0.8455	0.4250	0.061*
C3	0.5011 (2)	0.7469 (5)	0.41220 (12)	0.0595 (9)
H3	0.4858	0.8393	0.3959	0.071*
C4	0.4576 (2)	0.6055 (5)	0.41891 (12)	0.0584 (9)
H4	0.4132	0.6024	0.4069	0.070*
C5	0.47987 (19)	0.4705 (5)	0.44317 (12)	0.0554 (9)
H5	0.4503	0.3767	0.4481	0.067*
C6	0.54605 (17)	0.4729 (4)	0.46029 (11)	0.0469 (7)
H6	0.5615	0.3796	0.4762	0.056*
C7	0.71905 (18)	0.6437 (5)	0.44790 (11)	0.0540 (9)
C8	0.77809 (17)	0.6276 (5)	0.47814 (11)	0.0532 (8)
H8A	0.8097	0.5351	0.4698	0.064*
H8B	0.8043	0.7355	0.4796	0.064*
C9	0.67973 (16)	0.5853 (4)	0.51190 (10)	0.0413 (7)
C10	0.65101 (18)	0.5416 (6)	0.58469 (11)	0.0611 (10)
H10	0.6983	0.4922	0.5861	0.073*
C11	0.6530 (3)	0.7178 (9)	0.60390 (16)	0.1052 (18)
H11A	0.6864	0.7888	0.5895	0.158*
H11B	0.6663	0.7077	0.6325	0.158*
H11C	0.6074	0.7702	0.6020	0.158*
C12	0.6016 (3)	0.4194 (9)	0.60720 (17)	0.103 (2)
H12A	0.5552	0.4677	0.6072	0.155*
H12B	0.6172	0.4042	0.6353	0.155*
H12C	0.6011	0.3088	0.5934	0.155*
C13	0.30869 (18)	0.8552 (4)	0.50193 (11)	0.0487 (8)
C14	0.2917 (2)	0.8410 (6)	0.46101 (14)	0.0700 (11)
H14	0.3265	0.8208	0.4414	0.084*
C15	0.2226 (3)	0.8566 (6)	0.44872 (18)	0.0889 (16)
H15	0.2107	0.8455	0.4209	0.107*
C16	0.1715 (3)	0.8887 (6)	0.4776 (2)	0.0895 (17)
H16	0.1249	0.8992	0.4694	0.107*
C17	0.1888 (3)	0.9049 (7)	0.5179 (2)	0.0906 (16)
H17	0.1538	0.9265	0.5373	0.109*
C18	0.2574 (2)	0.8899 (6)	0.53092 (15)	0.0725 (12)
H18	0.2688	0.9030	0.5588	0.087*
C19	0.43326 (19)	0.9525 (5)	0.50224 (12)	0.0540 (9)
C20	0.49631 (19)	0.8932 (5)	0.52606 (14)	0.0608 (10)
H20A	0.5340	0.8629	0.5072	0.073*
H20B	0.5126	0.9851	0.5443	0.073*
C21	0.40959 (16)	0.7209 (4)	0.54306 (10)	0.0441 (7)
C22	0.39785 (18)	0.4669 (5)	0.58736 (11)	0.0508 (8)
H22	0.4399	0.5152	0.6004	0.061*
C23	0.4193 (3)	0.3147 (7)	0.56280 (14)	0.0899 (16)
H23A	0.3785	0.2570	0.5522	0.135*
H23B	0.4453	0.2359	0.5801	0.135*
H23C	0.4483	0.3519	0.5401	0.135*
C24	0.3471 (3)	0.4221 (7)	0.62112 (15)	0.0822 (14)
H24A	0.3328	0.5265	0.6351	0.123*
H24B	0.3691	0.3450	0.6406	0.123*
H24C	0.3067	0.3662	0.6093	0.123*
C25	0.47023 (16)	0.0679 (4)	0.32516 (9)	0.0383 (7)
C26	0.44767 (17)	0.2013 (4)	0.35032 (10)	0.0491 (8)
H26	0.4776	0.2932	0.3564	0.059*
C27	0.38097 (19)	0.1989 (5)	0.36647 (11)	0.0558 (9)
H27	0.3660	0.2893	0.3835	0.067*
C28	0.33633 (18)	0.0638 (5)	0.35761 (12)	0.0565 (9)
H28	0.2912	0.0626	0.3685	0.068*
C29	0.35877 (18)	−0.0704 (5)	0.33235 (12)	0.0533 (9)
H29	0.3286	−0.1616	0.3261	0.064*
C30	0.42575 (17)	−0.0690 (4)	0.31650 (10)	0.0451 (7)
H30	0.4411	−0.1604	0.2999	0.054*
C31	0.59995 (18)	0.0979 (4)	0.33336 (12)	0.0504 (8)
C32	0.65938 (17)	0.0927 (5)	0.30326 (12)	0.0548 (9)
H32A	0.6837	0.2035	0.3029	0.066*
H32B	0.6925	0.0026	0.3110	0.066*
C33	0.56273 (15)	0.0471 (4)	0.26787 (10)	0.0418 (7)
C34	0.53654 (19)	0.0074 (6)	0.19465 (12)	0.0594 (10)
H34	0.5838	−0.0424	0.1934	0.071*
C35	0.5388 (3)	0.1858 (7)	0.17505 (15)	0.0876 (15)
H35A	0.4933	0.2387	0.1769	0.131*
H35B	0.5520	0.1754	0.1464	0.131*
H35C	0.5724	0.2567	0.1893	0.131*
C36	0.4874 (2)	−0.1130 (8)	0.17164 (16)	0.0937 (18)
H36A	0.4863	−0.2239	0.1853	0.141*
H36B	0.5037	−0.1277	0.1437	0.141*
H36C	0.4412	−0.0638	0.1713	0.141*
C37	0.20516 (18)	0.3675 (4)	0.27283 (10)	0.0462 (8)
C38	0.1885 (2)	0.3767 (5)	0.31442 (12)	0.0617 (10)
H38	0.2227	0.3584	0.3345	0.074*
C39	0.1206 (3)	0.4134 (6)	0.32575 (14)	0.0781 (13)
H39	0.1091	0.4214	0.3537	0.094*
C40	0.0698 (2)	0.4382 (5)	0.29657 (17)	0.0763 (13)
H40	0.0239	0.4601	0.3046	0.092*
C41	0.0870 (2)	0.4306 (6)	0.25525 (15)	0.0716 (11)
H41	0.0527	0.4493	0.2353	0.086*
C42	0.1548 (2)	0.3955 (5)	0.24322 (12)	0.0574 (9)
H42	0.1663	0.3907	0.2152	0.069*
C43	0.3332 (2)	0.4310 (5)	0.27296 (13)	0.0567 (9)
C44	0.3934 (2)	0.3591 (5)	0.24861 (14)	0.0609 (10)
H44A	0.4113	0.4463	0.2296	0.073*
H44B	0.4310	0.3241	0.2671	0.073*
C45	0.30099 (17)	0.2036 (4)	0.23324 (10)	0.0438 (7)
C46	0.28102 (18)	−0.0515 (4)	0.19055 (12)	0.0496 (8)
H46	0.3245	−0.0126	0.1773	0.060*
C47	0.2286 (2)	−0.0876 (7)	0.15683 (16)	0.0826 (14)
H47A	0.2477	−0.1711	0.1378	0.124*
H47B	0.2182	0.0183	0.1423	0.124*
H47C	0.1863	−0.1330	0.1689	0.124*
C48	0.2975 (3)	−0.2070 (7)	0.21565 (16)	0.0941 (16)
H48A	0.3294	−0.1758	0.2374	0.141*
H48B	0.3187	−0.2938	0.1983	0.141*
H48C	0.2551	−0.2524	0.2275	0.141*
N1	0.65878 (14)	0.6175 (4)	0.47075 (8)	0.0445 (6)
N2	0.74645 (14)	0.5882 (4)	0.51814 (9)	0.0491 (6)
N3	0.63071 (15)	0.5533 (4)	0.54090 (9)	0.0536 (7)
H3A	0.588 (2)	0.579 (5)	0.5376 (13)	0.064*
N4	0.38022 (14)	0.8414 (4)	0.51473 (9)	0.0496 (7)
N5	0.47542 (14)	0.7420 (4)	0.55016 (10)	0.0545 (7)
N6	0.36779 (16)	0.6019 (4)	0.56079 (10)	0.0542 (8)
H6A	0.326 (2)	0.580 (5)	0.5509 (14)	0.065*
N7	0.54049 (13)	0.0719 (3)	0.30917 (8)	0.0430 (6)
N8	0.62940 (13)	0.0558 (4)	0.26250 (9)	0.0510 (7)
N9	0.51518 (15)	0.0151 (4)	0.23800 (8)	0.0512 (7)
H9	0.471 (2)	0.042 (5)	0.2438 (13)	0.061*
N10	0.27590 (14)	0.3329 (3)	0.26081 (9)	0.0467 (6)
N11	0.36714 (14)	0.2102 (4)	0.22579 (10)	0.0519 (7)
N12	0.25546 (15)	0.0907 (4)	0.21666 (10)	0.0493 (7)
H12	0.218 (2)	0.064 (5)	0.2296 (13)	0.059*
O1	0.72099 (15)	0.6732 (5)	0.41117 (8)	0.0831 (10)
O2	0.42668 (16)	1.0714 (4)	0.47794 (10)	0.0753 (8)
O3	0.60055 (15)	0.1196 (4)	0.37045 (9)	0.0706 (8)
O4	0.33241 (17)	0.5497 (4)	0.29702 (11)	0.0821 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0488 (18)	0.0435 (17)	0.0302 (15)	−0.0032 (13)	0.0006 (13)	−0.0037 (12)
C2	0.071 (2)	0.0439 (18)	0.0371 (16)	−0.0074 (15)	−0.0044 (16)	0.0020 (14)
C3	0.079 (3)	0.056 (2)	0.0434 (18)	0.0098 (18)	−0.0160 (18)	0.0049 (16)
C4	0.055 (2)	0.071 (2)	0.049 (2)	0.0076 (18)	−0.0096 (16)	−0.0043 (18)
C5	0.056 (2)	0.055 (2)	0.055 (2)	−0.0107 (16)	−0.0025 (17)	−0.0016 (17)
C6	0.0482 (18)	0.0458 (18)	0.0466 (18)	−0.0014 (14)	−0.0043 (15)	0.0049 (14)
C7	0.055 (2)	0.064 (2)	0.042 (2)	−0.0181 (17)	0.0054 (16)	0.0015 (16)
C8	0.0470 (19)	0.063 (2)	0.049 (2)	−0.0129 (15)	0.0074 (16)	−0.0026 (17)
C9	0.0447 (17)	0.0428 (16)	0.0363 (16)	−0.0042 (13)	−0.0005 (13)	0.0019 (13)
C10	0.0381 (18)	0.107 (3)	0.0387 (19)	0.0007 (18)	−0.0024 (15)	0.014 (2)
C11	0.125 (5)	0.127 (5)	0.064 (3)	−0.005 (4)	−0.009 (3)	−0.024 (3)
C12	0.068 (3)	0.168 (6)	0.073 (3)	−0.014 (3)	−0.004 (2)	0.055 (4)
C13	0.0518 (19)	0.0415 (17)	0.053 (2)	0.0087 (14)	−0.0062 (16)	0.0072 (15)
C14	0.079 (3)	0.073 (3)	0.058 (2)	0.012 (2)	−0.013 (2)	0.008 (2)
C15	0.103 (4)	0.078 (3)	0.087 (4)	−0.002 (3)	−0.045 (3)	0.021 (3)
C16	0.060 (3)	0.069 (3)	0.139 (5)	−0.003 (2)	−0.030 (3)	0.040 (3)
C17	0.060 (3)	0.089 (3)	0.123 (5)	0.020 (2)	0.001 (3)	0.025 (3)
C18	0.061 (2)	0.081 (3)	0.075 (3)	0.019 (2)	0.001 (2)	0.005 (2)
C19	0.060 (2)	0.0478 (19)	0.055 (2)	0.0006 (15)	0.0139 (17)	−0.0063 (17)
C20	0.049 (2)	0.060 (2)	0.073 (3)	−0.0064 (16)	0.0131 (18)	−0.0106 (19)
C21	0.0437 (17)	0.0493 (18)	0.0393 (17)	0.0037 (14)	−0.0034 (13)	−0.0036 (14)
C22	0.0443 (18)	0.061 (2)	0.0465 (19)	0.0045 (15)	−0.0123 (15)	0.0075 (16)
C23	0.121 (4)	0.087 (3)	0.062 (3)	0.046 (3)	−0.019 (3)	0.001 (2)
C24	0.083 (3)	0.096 (3)	0.068 (3)	0.018 (3)	0.008 (2)	0.027 (3)
C25	0.0461 (17)	0.0400 (15)	0.0287 (14)	0.0017 (12)	−0.0002 (12)	0.0019 (12)
C26	0.057 (2)	0.0469 (18)	0.0436 (18)	−0.0101 (14)	0.0032 (15)	−0.0062 (14)
C27	0.065 (2)	0.058 (2)	0.0452 (19)	0.0008 (16)	0.0085 (16)	−0.0135 (16)
C28	0.0478 (19)	0.072 (2)	0.050 (2)	−0.0020 (16)	0.0084 (16)	−0.0084 (18)
C29	0.0459 (18)	0.056 (2)	0.058 (2)	−0.0117 (15)	−0.0039 (17)	−0.0075 (17)
C30	0.0473 (18)	0.0447 (17)	0.0432 (17)	0.0024 (13)	−0.0043 (14)	−0.0106 (13)
C31	0.053 (2)	0.0484 (18)	0.050 (2)	0.0001 (15)	−0.0103 (17)	−0.0014 (15)
C32	0.0398 (17)	0.060 (2)	0.065 (2)	0.0002 (15)	−0.0083 (17)	−0.0078 (18)
C33	0.0353 (15)	0.0468 (17)	0.0432 (17)	0.0050 (12)	0.0005 (14)	−0.0054 (13)
C34	0.0389 (18)	0.095 (3)	0.045 (2)	0.0087 (18)	0.0047 (15)	−0.011 (2)
C35	0.082 (3)	0.120 (4)	0.061 (3)	0.019 (3)	0.017 (2)	0.017 (3)
C36	0.060 (3)	0.153 (5)	0.068 (3)	−0.005 (3)	−0.001 (2)	−0.057 (3)
C37	0.061 (2)	0.0337 (15)	0.0442 (18)	0.0079 (14)	0.0025 (15)	−0.0009 (13)
C38	0.083 (3)	0.061 (2)	0.0408 (19)	0.0203 (19)	0.0013 (18)	0.0012 (17)
C39	0.102 (4)	0.080 (3)	0.052 (2)	0.022 (2)	0.030 (2)	0.005 (2)
C40	0.068 (3)	0.062 (2)	0.099 (4)	0.014 (2)	0.024 (3)	0.000 (2)
C41	0.067 (3)	0.076 (3)	0.072 (3)	0.020 (2)	−0.007 (2)	0.002 (2)
C42	0.065 (2)	0.062 (2)	0.045 (2)	0.0151 (18)	0.0002 (17)	0.0041 (16)
C43	0.071 (2)	0.0415 (18)	0.058 (2)	−0.0054 (16)	−0.0183 (19)	0.0029 (17)
C44	0.054 (2)	0.051 (2)	0.078 (3)	−0.0096 (17)	−0.0129 (19)	0.0138 (19)
C45	0.0465 (18)	0.0441 (16)	0.0407 (17)	0.0000 (13)	0.0025 (14)	0.0038 (14)
C46	0.0463 (18)	0.0520 (19)	0.051 (2)	−0.0003 (14)	0.0067 (15)	−0.0103 (15)
C47	0.082 (3)	0.089 (3)	0.077 (3)	0.010 (2)	−0.008 (2)	−0.032 (3)
C48	0.136 (4)	0.074 (3)	0.072 (3)	0.033 (3)	0.011 (3)	0.000 (2)
N1	0.0446 (14)	0.0557 (16)	0.0331 (14)	−0.0098 (12)	−0.0004 (11)	0.0028 (11)
N2	0.0411 (14)	0.0598 (17)	0.0466 (16)	−0.0061 (12)	−0.0026 (12)	0.0023 (13)
N3	0.0379 (14)	0.083 (2)	0.0400 (16)	0.0046 (14)	−0.0006 (13)	0.0107 (14)
N4	0.0499 (16)	0.0495 (16)	0.0494 (16)	0.0041 (12)	−0.0001 (13)	0.0072 (13)
N5	0.0452 (15)	0.0620 (18)	0.0564 (17)	0.0011 (13)	−0.0025 (14)	−0.0023 (15)
N6	0.0432 (16)	0.0611 (18)	0.0583 (18)	−0.0014 (14)	−0.0140 (14)	0.0148 (14)
N7	0.0395 (14)	0.0507 (15)	0.0389 (14)	0.0001 (11)	−0.0033 (11)	−0.0031 (12)
N8	0.0401 (15)	0.0607 (17)	0.0522 (17)	0.0042 (12)	−0.0012 (13)	−0.0089 (14)
N9	0.0321 (14)	0.084 (2)	0.0380 (15)	0.0077 (13)	0.0025 (11)	−0.0136 (14)
N10	0.0535 (16)	0.0432 (14)	0.0436 (15)	0.0023 (12)	−0.0021 (13)	−0.0025 (12)
N11	0.0409 (15)	0.0540 (16)	0.0609 (18)	−0.0053 (12)	0.0036 (13)	0.0011 (14)
N12	0.0398 (14)	0.0559 (16)	0.0522 (17)	−0.0022 (13)	0.0115 (13)	−0.0137 (13)
O1	0.0746 (19)	0.138 (3)	0.0371 (14)	−0.0319 (18)	0.0097 (13)	0.0062 (16)
O2	0.091 (2)	0.0585 (17)	0.076 (2)	0.0009 (14)	0.0133 (16)	0.0144 (15)
O3	0.0686 (17)	0.094 (2)	0.0487 (16)	−0.0105 (14)	−0.0163 (13)	−0.0040 (14)
O4	0.107 (2)	0.0518 (16)	0.088 (2)	−0.0036 (14)	−0.0240 (18)	−0.0202 (16)

Geometric parameters (Å, º)

C1—C2	1.376 (5)	C25—N7	1.436 (4)
C1—C6	1.378 (5)	C26—C27	1.375 (5)
C1—N1	1.436 (4)	C26—H26	0.9300
C2—C3	1.378 (5)	C27—C28	1.373 (5)
C2—H2	0.9300	C27—H27	0.9300
C3—C4	1.385 (6)	C28—C29	1.382 (5)
C3—H3	0.9300	C28—H28	0.9300
C4—C5	1.367 (5)	C29—C30	1.376 (5)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.378 (5)	C30—H30	0.9300
C5—H5	0.9300	C31—O3	1.208 (4)
C6—H6	0.9300	C31—N7	1.391 (4)
C7—O1	1.206 (4)	C31—C32	1.493 (5)
C7—N1	1.380 (4)	C32—N8	1.461 (5)
C7—C8	1.495 (5)	C32—H32A	0.9700
C8—N2	1.456 (5)	C32—H32B	0.9700
C8—H8A	0.9700	C33—N8	1.285 (4)
C8—H8B	0.9700	C33—N9	1.345 (4)
C9—N2	1.289 (4)	C33—N7	1.411 (4)
C9—N3	1.345 (4)	C34—N9	1.457 (5)
C9—N1	1.407 (4)	C34—C35	1.511 (7)
C10—N3	1.467 (5)	C34—C36	1.511 (6)
C10—C11	1.490 (7)	C34—H34	0.9800
C10—C12	1.516 (6)	C35—H35A	0.9600
C10—H10	0.9800	C35—H35B	0.9600
C11—H11A	0.9600	C35—H35C	0.9600
C11—H11B	0.9600	C36—H36A	0.9600
C11—H11C	0.9600	C36—H36B	0.9600
C12—H12A	0.9600	C36—H36C	0.9600
C12—H12B	0.9600	C37—C42	1.372 (5)
C12—H12C	0.9600	C37—C38	1.380 (5)
C13—C14	1.363 (6)	C37—N10	1.429 (4)
C13—C18	1.379 (6)	C38—C39	1.375 (6)
C13—N4	1.429 (4)	C38—H38	0.9300
C14—C15	1.382 (6)	C39—C40	1.363 (7)
C14—H14	0.9300	C39—H39	0.9300
C15—C16	1.370 (8)	C40—C41	1.373 (7)
C15—H15	0.9300	C40—H40	0.9300
C16—C17	1.346 (8)	C41—C42	1.375 (6)
C16—H16	0.9300	C41—H41	0.9300
C17—C18	1.379 (7)	C42—H42	0.9300
C17—H17	0.9300	C43—O4	1.198 (5)
C18—H18	0.9300	C43—N10	1.385 (4)
C19—O2	1.210 (4)	C43—C44	1.496 (6)
C19—N4	1.384 (5)	C44—N11	1.450 (5)
C19—C20	1.498 (6)	C44—H44A	0.9700
C20—N5	1.454 (5)	C44—H44B	0.9700
C20—H20A	0.9700	C45—N11	1.286 (4)
C20—H20B	0.9700	C45—N12	1.339 (4)
C21—N5	1.287 (4)	C45—N10	1.417 (4)
C21—N6	1.341 (4)	C46—N12	1.463 (4)
C21—N4	1.417 (4)	C46—C48	1.478 (6)
C22—N6	1.462 (4)	C46—C47	1.503 (6)
C22—C23	1.471 (6)	C46—H46	0.9800
C22—C24	1.497 (6)	C47—H47A	0.9600
C22—H22	0.9800	C47—H47B	0.9600
C23—H23A	0.9600	C47—H47C	0.9600
C23—H23B	0.9600	C48—H48A	0.9600
C23—H23C	0.9600	C48—H48B	0.9600
C24—H24A	0.9600	C48—H48C	0.9600
C24—H24B	0.9600	N3—H3A	0.84 (4)
C24—H24C	0.9600	N6—H6A	0.87 (4)
C25—C26	1.377 (4)	N9—H9	0.90 (4)
C25—C30	1.380 (4)	N12—H12	0.85 (4)
C2—C1—C6	120.4 (3)	C28—C29—H29	120.0
C2—C1—N1	119.1 (3)	C29—C30—C25	120.1 (3)
C6—C1—N1	120.5 (3)	C29—C30—H30	119.9
C1—C2—C3	119.6 (3)	C25—C30—H30	119.9
C1—C2—H2	120.2	O3—C31—N7	125.7 (3)
C3—C2—H2	120.2	O3—C31—C32	129.8 (3)
C2—C3—C4	120.1 (3)	N7—C31—C32	104.5 (3)
C2—C3—H3	119.9	N8—C32—C31	107.0 (3)
C4—C3—H3	119.9	N8—C32—H32A	110.3
C5—C4—C3	119.9 (3)	C31—C32—H32A	110.3
C5—C4—H4	120.1	N8—C32—H32B	110.3
C3—C4—H4	120.1	C31—C32—H32B	110.3
C4—C5—C6	120.3 (3)	H32A—C32—H32B	108.6
C4—C5—H5	119.9	N8—C33—N9	125.5 (3)
C6—C5—H5	119.9	N8—C33—N7	114.7 (3)
C5—C6—C1	119.7 (3)	N9—C33—N7	119.8 (3)
C5—C6—H6	120.1	N9—C34—C35	111.8 (3)
C1—C6—H6	120.1	N9—C34—C36	108.8 (3)
O1—C7—N1	125.2 (3)	C35—C34—C36	111.6 (4)
O1—C7—C8	129.3 (3)	N9—C34—H34	108.2
N1—C7—C8	105.5 (3)	C35—C34—H34	108.2
N2—C8—C7	106.4 (3)	C36—C34—H34	108.2
N2—C8—H8A	110.4	C34—C35—H35A	109.5
C7—C8—H8A	110.4	C34—C35—H35B	109.5
N2—C8—H8B	110.4	H35A—C35—H35B	109.5
C7—C8—H8B	110.4	C34—C35—H35C	109.5
H8A—C8—H8B	108.6	H35A—C35—H35C	109.5
N2—C9—N3	125.5 (3)	H35B—C35—H35C	109.5
N2—C9—N1	115.1 (3)	C34—C36—H36A	109.5
N3—C9—N1	119.3 (3)	C34—C36—H36B	109.5
N3—C10—C11	110.6 (4)	H36A—C36—H36B	109.5
N3—C10—C12	109.5 (3)	C34—C36—H36C	109.5
C11—C10—C12	112.3 (5)	H36A—C36—H36C	109.5
N3—C10—H10	108.1	H36B—C36—H36C	109.5
C11—C10—H10	108.1	C42—C37—C38	120.4 (3)
C12—C10—H10	108.1	C42—C37—N10	120.2 (3)
C10—C11—H11A	109.5	C38—C37—N10	119.4 (3)
C10—C11—H11B	109.5	C39—C38—C37	119.1 (4)
H11A—C11—H11B	109.5	C39—C38—H38	120.5
C10—C11—H11C	109.5	C37—C38—H38	120.5
H11A—C11—H11C	109.5	C40—C39—C38	120.9 (4)
H11B—C11—H11C	109.5	C40—C39—H39	119.5
C10—C12—H12A	109.5	C38—C39—H39	119.5
C10—C12—H12B	109.5	C39—C40—C41	119.6 (4)
H12A—C12—H12B	109.5	C39—C40—H40	120.2
C10—C12—H12C	109.5	C41—C40—H40	120.2
H12A—C12—H12C	109.5	C40—C41—C42	120.4 (4)
H12B—C12—H12C	109.5	C40—C41—H41	119.8
C14—C13—C18	120.2 (4)	C42—C41—H41	119.8
C14—C13—N4	120.0 (3)	C37—C42—C41	119.5 (4)
C18—C13—N4	119.8 (3)	C37—C42—H42	120.2
C13—C14—C15	119.8 (5)	C41—C42—H42	120.2
C13—C14—H14	120.1	O4—C43—N10	126.0 (4)
C15—C14—H14	120.1	O4—C43—C44	129.1 (4)
C16—C15—C14	120.0 (5)	N10—C43—C44	104.8 (3)
C16—C15—H15	120.0	N11—C44—C43	107.0 (3)
C14—C15—H15	120.0	N11—C44—H44A	110.3
C17—C16—C15	119.8 (4)	C43—C44—H44A	110.3
C17—C16—H16	120.1	N11—C44—H44B	110.3
C15—C16—H16	120.1	C43—C44—H44B	110.3
C16—C17—C18	121.3 (5)	H44A—C44—H44B	108.6
C16—C17—H17	119.3	N11—C45—N12	126.0 (3)
C18—C17—H17	119.3	N11—C45—N10	114.9 (3)
C17—C18—C13	118.9 (5)	N12—C45—N10	119.1 (3)
C17—C18—H18	120.6	N12—C46—C48	111.1 (3)
C13—C18—H18	120.6	N12—C46—C47	109.4 (3)
O2—C19—N4	125.4 (4)	C48—C46—C47	112.8 (4)
O2—C19—C20	130.2 (4)	N12—C46—H46	107.8
N4—C19—C20	104.5 (3)	C48—C46—H46	107.8
N5—C20—C19	107.3 (3)	C47—C46—H46	107.8
N5—C20—H20A	110.3	C46—C47—H47A	109.5
C19—C20—H20A	110.3	C46—C47—H47B	109.5
N5—C20—H20B	110.3	H47A—C47—H47B	109.5
C19—C20—H20B	110.3	C46—C47—H47C	109.5
H20A—C20—H20B	108.5	H47A—C47—H47C	109.5
N5—C21—N6	126.2 (3)	H47B—C47—H47C	109.5
N5—C21—N4	114.7 (3)	C46—C48—H48A	109.5
N6—C21—N4	119.1 (3)	C46—C48—H48B	109.5
N6—C22—C23	111.0 (3)	H48A—C48—H48B	109.5
N6—C22—C24	109.6 (3)	C46—C48—H48C	109.5
C23—C22—C24	112.9 (4)	H48A—C48—H48C	109.5
N6—C22—H22	107.7	H48B—C48—H48C	109.5
C23—C22—H22	107.7	C7—N1—C9	107.0 (3)
C24—C22—H22	107.7	C7—N1—C1	124.6 (3)
C22—C23—H23A	109.5	C9—N1—C1	128.3 (3)
C22—C23—H23B	109.5	C9—N2—C8	105.9 (3)
H23A—C23—H23B	109.5	C9—N3—C10	119.8 (3)
C22—C23—H23C	109.5	C9—N3—H3A	123 (3)
H23A—C23—H23C	109.5	C10—N3—H3A	113 (3)
H23B—C23—H23C	109.5	C19—N4—C21	107.6 (3)
C22—C24—H24A	109.5	C19—N4—C13	124.6 (3)
C22—C24—H24B	109.5	C21—N4—C13	127.7 (3)
H24A—C24—H24B	109.5	C21—N5—C20	105.9 (3)
C22—C24—H24C	109.5	C21—N6—C22	120.0 (3)
H24A—C24—H24C	109.5	C21—N6—H6A	121 (3)
H24B—C24—H24C	109.5	C22—N6—H6A	116 (3)
C26—C25—C30	119.7 (3)	C31—N7—C33	107.7 (3)
C26—C25—N7	119.2 (3)	C31—N7—C25	124.3 (3)
C30—C25—N7	121.2 (3)	C33—N7—C25	128.1 (2)
C27—C26—C25	120.2 (3)	C33—N8—C32	106.0 (3)
C27—C26—H26	119.9	C33—N9—C34	120.4 (3)
C25—C26—H26	119.9	C33—N9—H9	117 (3)
C28—C27—C26	120.3 (3)	C34—N9—H9	118 (3)
C28—C27—H27	119.8	C43—N10—C45	107.0 (3)
C26—C27—H27	119.8	C43—N10—C37	124.6 (3)
C27—C28—C29	119.7 (3)	C45—N10—C37	128.3 (3)
C27—C28—H28	120.2	C45—N11—C44	105.9 (3)
C29—C28—H28	120.2	C45—N12—C46	119.9 (3)
C30—C29—C28	120.0 (3)	C45—N12—H12	120 (3)
C30—C29—H29	120.0	C46—N12—H12	112 (3)
C6—C1—C2—C3	0.5 (5)	C12—C10—N3—C9	−150.6 (4)
N1—C1—C2—C3	178.4 (3)	O2—C19—N4—C21	179.7 (3)
C1—C2—C3—C4	−0.2 (5)	C20—C19—N4—C21	−1.6 (4)
C2—C3—C4—C5	0.7 (6)	O2—C19—N4—C13	−2.7 (6)
C3—C4—C5—C6	−1.3 (6)	C20—C19—N4—C13	176.0 (3)
C4—C5—C6—C1	1.5 (5)	N5—C21—N4—C19	0.0 (4)
C2—C1—C6—C5	−1.1 (5)	N6—C21—N4—C19	177.8 (3)
N1—C1—C6—C5	−179.0 (3)	N5—C21—N4—C13	−177.5 (3)
O1—C7—C8—N2	−178.9 (4)	N6—C21—N4—C13	0.4 (5)
N1—C7—C8—N2	1.0 (4)	C14—C13—N4—C19	61.3 (5)
C18—C13—C14—C15	−1.8 (6)	C18—C13—N4—C19	−116.1 (4)
N4—C13—C14—C15	−179.2 (4)	C14—C13—N4—C21	−121.7 (4)
C13—C14—C15—C16	0.9 (7)	C18—C13—N4—C21	61.0 (5)
C14—C15—C16—C17	0.0 (7)	N6—C21—N5—C20	−176.0 (3)
C15—C16—C17—C18	0.0 (8)	N4—C21—N5—C20	1.6 (4)
C16—C17—C18—C13	−0.9 (7)	C19—C20—N5—C21	−2.5 (4)
C14—C13—C18—C17	1.8 (6)	N5—C21—N6—C22	−7.7 (5)
N4—C13—C18—C17	179.2 (4)	N4—C21—N6—C22	174.8 (3)
O2—C19—C20—N5	−178.9 (4)	C23—C22—N6—C21	−87.7 (5)
N4—C19—C20—N5	2.5 (4)	C24—C22—N6—C21	146.9 (4)
C30—C25—C26—C27	−0.5 (5)	O3—C31—N7—C33	−178.3 (4)
N7—C25—C26—C27	−179.1 (3)	C32—C31—N7—C33	1.8 (3)
C25—C26—C27—C28	−0.1 (5)	O3—C31—N7—C25	0.3 (5)
C26—C27—C28—C29	0.1 (6)	C32—C31—N7—C25	−179.6 (3)
C27—C28—C29—C30	0.6 (6)	N8—C33—N7—C31	−0.7 (4)
C28—C29—C30—C25	−1.2 (5)	N9—C33—N7—C31	178.5 (3)
C26—C25—C30—C29	1.2 (5)	N8—C33—N7—C25	−179.2 (3)
N7—C25—C30—C29	179.7 (3)	N9—C33—N7—C25	0.0 (5)
O3—C31—C32—N8	177.8 (4)	C26—C25—N7—C31	50.7 (4)
N7—C31—C32—N8	−2.3 (4)	C30—C25—N7—C31	−127.8 (3)
C42—C37—C38—C39	0.4 (6)	C26—C25—N7—C33	−131.0 (3)
N10—C37—C38—C39	178.7 (3)	C30—C25—N7—C33	50.6 (4)
C37—C38—C39—C40	0.9 (6)	N9—C33—N8—C32	−180.0 (3)
C38—C39—C40—C41	−1.6 (7)	N7—C33—N8—C32	−0.8 (4)
C39—C40—C41—C42	1.0 (7)	C31—C32—N8—C33	1.9 (4)
C38—C37—C42—C41	−0.9 (5)	N8—C33—N9—C34	−7.4 (5)
N10—C37—C42—C41	−179.2 (3)	N7—C33—N9—C34	173.5 (3)
C40—C41—C42—C37	0.2 (6)	C35—C34—N9—C33	−84.7 (4)
O4—C43—C44—N11	177.1 (4)	C36—C34—N9—C33	151.6 (4)
N10—C43—C44—N11	−4.7 (4)	O4—C43—N10—C45	−178.1 (4)
O1—C7—N1—C9	179.3 (4)	C44—C43—N10—C45	3.7 (4)
C8—C7—N1—C9	−0.7 (4)	O4—C43—N10—C37	5.2 (6)
O1—C7—N1—C1	2.8 (6)	C44—C43—N10—C37	−173.1 (3)
C8—C7—N1—C1	−177.1 (3)	N11—C45—N10—C43	−1.3 (4)
N2—C9—N1—C7	0.1 (4)	N12—C45—N10—C43	−179.7 (3)
N3—C9—N1—C7	−179.3 (3)	N11—C45—N10—C37	175.2 (3)
N2—C9—N1—C1	176.4 (3)	N12—C45—N10—C37	−3.1 (5)
N3—C9—N1—C1	−3.0 (5)	C42—C37—N10—C43	122.2 (4)
C2—C1—N1—C7	−52.9 (4)	C38—C37—N10—C43	−56.1 (5)
C6—C1—N1—C7	125.0 (4)	C42—C37—N10—C45	−53.8 (5)
C2—C1—N1—C9	131.4 (3)	C38—C37—N10—C45	127.9 (4)
C6—C1—N1—C9	−50.7 (5)	N12—C45—N11—C44	176.5 (3)
N3—C9—N2—C8	179.9 (3)	N10—C45—N11—C44	−1.8 (4)
N1—C9—N2—C8	0.6 (4)	C43—C44—N11—C45	4.0 (4)
C7—C8—N2—C9	−1.0 (4)	N11—C45—N12—C46	6.3 (5)
N2—C9—N3—C10	8.4 (5)	N10—C45—N12—C46	−175.5 (3)
N1—C9—N3—C10	−172.2 (3)	C48—C46—N12—C45	89.2 (4)
C11—C10—N3—C9	85.1 (5)	C47—C46—N12—C45	−145.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···N11	0.90 (4)	2.43 (4)	3.222 (4)	148 (3)
N3—H3A···N5	0.84 (4)	2.52 (4)	3.312 (4)	157 (4)
C29—H29···O4^i	0.93	2.41	3.175 (4)	140
C5—H5···O2^i	0.93	2.58	3.421 (5)	151
N12—H12···N8^ii	0.85 (4)	2.20 (4)	3.039 (4)	169 (4)
C38—H38···O1^iii	0.93	2.48	3.203 (5)	134
N6—H6A···N2^iii	0.87 (4)	2.26 (4)	3.063 (4)	153 (4)

Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y, z; (iii) x−1/2, −y+1, z.