The title compound, C
24H
18N
4O
3, has a planar bicyclic imidazolo[5,4-
d]pyrimidine core. The planes of the phenyl and methoxyphenoxy substituents form substantial (>30°) dihedral angles with the imidazolopyrimidine plane. Intermolecular C—H
O interactions link the molecules into infinite chains running along the
a axis of the crystal structure.
Supporting information
CCDC reference: 601279
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.096
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.094
Value of mu given = 0.090
STRVA01_ALERT_4_C Flack test results are meaningless.
From the CIF: _refine_ls_abs_structure_Flack 0.000
From the CIF: _refine_ls_abs_structure_Flack_su 1.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 1.00
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 1.00
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 2677
Count of symmetry unique reflns 2730
Completeness (_total/calc) 98.06%
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
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
4 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
2-(4-Methoxyphenoxy)-1,9-diphenyl-1,9-dihydropurin-6-one
top
Crystal data top
C24H18N4O3 | Dx = 1.380 Mg m−3 |
Mr = 410.42 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2809 reflections |
a = 8.0020 (7) Å | θ = 2.2–21.4° |
b = 9.7745 (8) Å | µ = 0.09 mm−1 |
c = 25.255 (2) Å | T = 292 K |
V = 1975.3 (3) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.22 × 0.20 mm |
F(000) = 856 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1958 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 28.0°, θmin = 1.6° |
φ and ω scans | h = −10→10 |
12700 measured reflections | k = −12→12 |
2677 independent reflections | l = −23→32 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
2677 reflections | Δρmax = 0.14 e Å−3 |
281 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.0 (10) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 1.1875 (5) | 1.0966 (4) | 0.69021 (12) | 0.0877 (11) | |
H1A | 1.2717 | 1.0335 | 0.7019 | 0.132* | |
H1B | 1.2277 | 1.1462 | 0.6599 | 0.132* | |
H1C | 1.0882 | 1.0472 | 0.6808 | 0.132* | |
C2 | 1.0940 (3) | 1.1398 (3) | 0.77882 (10) | 0.0551 (7) | |
C3 | 1.0625 (3) | 1.0048 (3) | 0.78992 (10) | 0.0535 (6) | |
H3 | 1.0831 | 0.9380 | 0.7645 | 0.064* | |
C4 | 1.0001 (3) | 0.9681 (3) | 0.83907 (9) | 0.0524 (6) | |
H4 | 0.9782 | 0.8768 | 0.8469 | 0.063* | |
C5 | 0.9712 (3) | 1.0675 (3) | 0.87596 (9) | 0.0480 (6) | |
C6 | 1.0053 (4) | 1.2028 (3) | 0.86524 (10) | 0.0575 (7) | |
H6 | 0.9861 | 1.2697 | 0.8907 | 0.069* | |
C7 | 1.0678 (4) | 1.2372 (3) | 0.81667 (11) | 0.0650 (8) | |
H7 | 1.0929 | 1.3281 | 0.8093 | 0.078* | |
C8 | 0.7736 (3) | 0.9875 (3) | 0.94026 (9) | 0.0484 (6) | |
C9 | 0.8539 (3) | 1.0759 (3) | 1.02728 (9) | 0.0470 (6) | |
C10 | 1.0007 (3) | 1.0118 (3) | 1.04056 (10) | 0.0552 (7) | |
H10 | 1.0249 | 0.9253 | 1.0273 | 0.066* | |
C11 | 1.1114 (4) | 1.0769 (4) | 1.07361 (11) | 0.0716 (9) | |
H11 | 1.2128 | 1.0358 | 1.0819 | 0.086* | |
C12 | 1.0722 (5) | 1.2028 (4) | 1.09441 (11) | 0.0844 (11) | |
H12 | 1.1458 | 1.2456 | 1.1176 | 0.101* | |
C13 | 0.9244 (5) | 1.2657 (3) | 1.08107 (13) | 0.0807 (10) | |
H13 | 0.8981 | 1.3506 | 1.0955 | 0.097* | |
C14 | 0.8150 (4) | 1.2036 (3) | 1.04645 (10) | 0.0623 (7) | |
H14 | 0.7169 | 1.2472 | 1.0363 | 0.075* | |
C15 | 0.5816 (3) | 0.9637 (2) | 1.01569 (9) | 0.0464 (6) | |
C16 | 0.4780 (3) | 0.8984 (2) | 0.97720 (9) | 0.0457 (6) | |
C17 | 0.5323 (3) | 0.8849 (2) | 0.92620 (9) | 0.0436 (6) | |
C18 | 0.2820 (3) | 0.7993 (3) | 0.93647 (10) | 0.0539 (6) | |
H18 | 0.1806 | 0.7577 | 0.9285 | 0.065* | |
C19 | 0.3986 (3) | 0.7724 (2) | 0.84561 (9) | 0.0460 (6) | |
C20 | 0.3157 (3) | 0.6529 (3) | 0.83439 (10) | 0.0562 (7) | |
H20 | 0.2696 | 0.6006 | 0.8615 | 0.067* | |
C21 | 0.3017 (4) | 0.6113 (3) | 0.78224 (11) | 0.0649 (8) | |
H21 | 0.2448 | 0.5308 | 0.7745 | 0.078* | |
C22 | 0.3693 (4) | 0.6854 (3) | 0.74211 (11) | 0.0634 (7) | |
H22 | 0.3570 | 0.6571 | 0.7072 | 0.076* | |
C23 | 0.4564 (4) | 0.8034 (3) | 0.75390 (10) | 0.0646 (8) | |
H23 | 0.5065 | 0.8531 | 0.7268 | 0.078* | |
C24 | 0.4699 (4) | 0.8481 (3) | 0.80554 (10) | 0.0575 (7) | |
H24 | 0.5267 | 0.9287 | 0.8132 | 0.069* | |
N1 | 0.6802 (3) | 0.9273 (2) | 0.90514 (7) | 0.0487 (5) | |
N2 | 0.7354 (3) | 1.0076 (2) | 0.99272 (7) | 0.0461 (5) | |
N3 | 0.3194 (3) | 0.8440 (2) | 0.98375 (8) | 0.0552 (6) | |
N4 | 0.4061 (3) | 0.8193 (2) | 0.89938 (7) | 0.0471 (5) | |
O1 | 1.1508 (3) | 1.1891 (2) | 0.73130 (7) | 0.0790 (6) | |
O2 | 0.9243 (2) | 1.0390 (2) | 0.92850 (6) | 0.0642 (6) | |
O3 | 0.5531 (2) | 0.98329 (19) | 1.06255 (6) | 0.0568 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.093 (3) | 0.115 (3) | 0.0552 (18) | −0.004 (2) | 0.0265 (18) | 0.0066 (19) |
C2 | 0.0481 (15) | 0.0701 (17) | 0.0473 (14) | −0.0059 (14) | 0.0027 (12) | 0.0100 (13) |
C3 | 0.0546 (16) | 0.0621 (16) | 0.0438 (14) | 0.0045 (14) | 0.0024 (11) | −0.0068 (12) |
C4 | 0.0573 (16) | 0.0525 (14) | 0.0473 (14) | −0.0070 (12) | −0.0003 (12) | 0.0012 (11) |
C5 | 0.0381 (13) | 0.0700 (16) | 0.0357 (12) | −0.0060 (13) | 0.0007 (10) | −0.0014 (12) |
C6 | 0.0531 (16) | 0.0634 (16) | 0.0561 (16) | 0.0001 (14) | −0.0007 (13) | −0.0136 (13) |
C7 | 0.073 (2) | 0.0589 (16) | 0.0628 (18) | −0.0099 (15) | −0.0010 (15) | 0.0036 (14) |
C8 | 0.0438 (14) | 0.0624 (15) | 0.0390 (12) | −0.0047 (13) | 0.0022 (11) | −0.0019 (11) |
C9 | 0.0490 (15) | 0.0569 (15) | 0.0352 (12) | −0.0066 (12) | 0.0036 (10) | −0.0018 (11) |
C10 | 0.0549 (16) | 0.0688 (17) | 0.0420 (13) | −0.0035 (14) | −0.0007 (12) | 0.0003 (12) |
C11 | 0.0579 (18) | 0.111 (3) | 0.0455 (16) | −0.0156 (19) | −0.0070 (13) | 0.0029 (17) |
C12 | 0.074 (2) | 0.129 (3) | 0.0498 (17) | −0.047 (2) | 0.0051 (17) | −0.018 (2) |
C13 | 0.094 (3) | 0.080 (2) | 0.068 (2) | −0.031 (2) | 0.0219 (19) | −0.0266 (16) |
C14 | 0.0637 (18) | 0.0652 (17) | 0.0580 (16) | −0.0104 (15) | 0.0113 (14) | −0.0094 (14) |
C15 | 0.0464 (14) | 0.0512 (14) | 0.0416 (14) | 0.0052 (12) | 0.0043 (11) | 0.0019 (11) |
C16 | 0.0431 (14) | 0.0515 (13) | 0.0425 (13) | 0.0008 (12) | 0.0043 (11) | 0.0015 (11) |
C17 | 0.0414 (14) | 0.0488 (13) | 0.0408 (13) | 0.0007 (11) | −0.0003 (11) | −0.0008 (10) |
C18 | 0.0426 (15) | 0.0627 (16) | 0.0564 (15) | −0.0077 (13) | 0.0024 (12) | 0.0026 (13) |
C19 | 0.0412 (14) | 0.0547 (14) | 0.0422 (13) | 0.0019 (12) | −0.0061 (11) | 0.0026 (11) |
C20 | 0.0551 (16) | 0.0616 (16) | 0.0520 (15) | −0.0108 (13) | −0.0073 (13) | 0.0049 (12) |
C21 | 0.0682 (19) | 0.0655 (17) | 0.0610 (17) | −0.0083 (15) | −0.0146 (15) | −0.0057 (15) |
C22 | 0.074 (2) | 0.0706 (18) | 0.0454 (14) | 0.0039 (16) | −0.0118 (14) | −0.0042 (14) |
C23 | 0.075 (2) | 0.0722 (17) | 0.0463 (15) | −0.0020 (16) | 0.0021 (14) | 0.0111 (14) |
C24 | 0.0636 (18) | 0.0568 (15) | 0.0520 (15) | −0.0076 (14) | −0.0033 (14) | 0.0005 (13) |
N1 | 0.0422 (12) | 0.0649 (13) | 0.0390 (11) | −0.0059 (10) | 0.0031 (9) | −0.0022 (10) |
N2 | 0.0451 (11) | 0.0561 (11) | 0.0370 (10) | −0.0023 (10) | 0.0022 (9) | −0.0032 (9) |
N3 | 0.0483 (13) | 0.0654 (14) | 0.0518 (13) | −0.0036 (11) | 0.0061 (10) | 0.0007 (11) |
N4 | 0.0437 (12) | 0.0531 (11) | 0.0444 (11) | −0.0033 (10) | 0.0008 (9) | 0.0007 (9) |
O1 | 0.0916 (16) | 0.0888 (14) | 0.0566 (12) | −0.0147 (13) | 0.0163 (11) | 0.0142 (11) |
O2 | 0.0505 (11) | 0.1038 (15) | 0.0381 (9) | −0.0231 (11) | 0.0026 (8) | −0.0050 (9) |
O3 | 0.0544 (11) | 0.0768 (12) | 0.0391 (9) | 0.0014 (10) | 0.0074 (8) | −0.0031 (9) |
Geometric parameters (Å, º) top
C1—O1 | 1.407 (4) | C12—H12 | 0.9300 |
C1—H1A | 0.9600 | C13—C14 | 1.378 (4) |
C1—H1B | 0.9600 | C13—H13 | 0.9300 |
C1—H1C | 0.9600 | C14—H14 | 0.9300 |
C2—C7 | 1.365 (4) | C15—N2 | 1.427 (3) |
C2—O1 | 1.371 (3) | C15—O3 | 1.220 (3) |
C2—C3 | 1.373 (4) | C15—C16 | 1.428 (3) |
C3—C4 | 1.385 (3) | C16—C17 | 1.366 (3) |
C3—H3 | 0.9300 | C16—N3 | 1.386 (3) |
C4—C5 | 1.366 (3) | C17—N1 | 1.362 (3) |
C4—H4 | 0.9300 | C17—N4 | 1.375 (3) |
C5—C6 | 1.377 (4) | C18—N3 | 1.306 (3) |
C5—O2 | 1.407 (3) | C18—N4 | 1.379 (3) |
C6—C7 | 1.367 (4) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.373 (3) |
C7—H7 | 0.9300 | C19—C24 | 1.377 (3) |
C8—N1 | 1.300 (3) | C19—N4 | 1.434 (3) |
C8—N2 | 1.374 (3) | C20—C21 | 1.383 (3) |
C8—O2 | 1.340 (3) | C20—H20 | 0.9300 |
C9—C10 | 1.372 (4) | C21—C22 | 1.358 (4) |
C9—C14 | 1.374 (4) | C21—H21 | 0.9300 |
C9—N2 | 1.451 (3) | C22—C23 | 1.380 (4) |
C10—C11 | 1.373 (4) | C22—H22 | 0.9300 |
C10—H10 | 0.9300 | C23—C24 | 1.380 (3) |
C11—C12 | 1.374 (5) | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—C13 | 1.374 (5) | | |
| | | |
O1—C1—H1A | 109.5 | C9—C14—H14 | 120.7 |
O1—C1—H1B | 109.5 | C13—C14—H14 | 120.7 |
H1A—C1—H1B | 109.5 | O3—C15—N2 | 120.5 (2) |
O1—C1—H1C | 109.5 | O3—C15—C16 | 128.5 (2) |
H1A—C1—H1C | 109.5 | N2—C15—C16 | 110.99 (19) |
H1B—C1—H1C | 109.5 | C17—C16—N3 | 111.5 (2) |
C7—C2—O1 | 114.8 (2) | C17—C16—C15 | 120.0 (2) |
C7—C2—C3 | 119.9 (2) | N3—C16—C15 | 128.4 (2) |
O1—C2—C3 | 125.2 (3) | N1—C17—C16 | 128.0 (2) |
C2—C3—C4 | 119.9 (2) | N1—C17—N4 | 126.0 (2) |
C2—C3—H3 | 120.1 | C16—C17—N4 | 106.0 (2) |
C4—C3—H3 | 120.1 | N3—C18—N4 | 114.1 (2) |
C5—C4—C3 | 119.2 (2) | N3—C18—H18 | 122.9 |
C5—C4—H4 | 120.4 | N4—C18—H18 | 122.9 |
C3—C4—H4 | 120.4 | C20—C19—C24 | 120.4 (2) |
C4—C5—C6 | 121.0 (2) | C20—C19—N4 | 119.2 (2) |
C4—C5—O2 | 123.2 (2) | C24—C19—N4 | 120.4 (2) |
C6—C5—O2 | 115.4 (2) | C19—C20—C21 | 119.0 (2) |
C7—C6—C5 | 119.0 (2) | C19—C20—H20 | 120.5 |
C7—C6—H6 | 120.5 | C21—C20—H20 | 120.5 |
C5—C6—H6 | 120.5 | C22—C21—C20 | 121.5 (3) |
C2—C7—C6 | 120.9 (3) | C22—C21—H21 | 119.3 |
C2—C7—H7 | 119.6 | C20—C21—H21 | 119.3 |
C6—C7—H7 | 119.6 | C21—C22—C23 | 119.1 (3) |
N1—C8—O2 | 122.4 (2) | C21—C22—H22 | 120.5 |
N1—C8—N2 | 126.5 (2) | C23—C22—H22 | 120.5 |
O2—C8—N2 | 111.1 (2) | C24—C23—C22 | 120.5 (3) |
C10—C9—C14 | 121.5 (3) | C24—C23—H23 | 119.7 |
C10—C9—N2 | 119.8 (2) | C22—C23—H23 | 119.7 |
C14—C9—N2 | 118.8 (2) | C19—C24—C23 | 119.5 (2) |
C9—C10—C11 | 119.3 (3) | C19—C24—H24 | 120.3 |
C9—C10—H10 | 120.4 | C23—C24—H24 | 120.3 |
C11—C10—H10 | 120.4 | C8—N1—C17 | 111.75 (19) |
C10—C11—C12 | 120.0 (3) | C8—N2—C15 | 122.7 (2) |
C10—C11—H11 | 120.0 | C8—N2—C9 | 120.0 (2) |
C12—C11—H11 | 120.0 | C15—N2—C9 | 117.23 (18) |
C13—C12—C11 | 120.2 (3) | C18—N3—C16 | 103.2 (2) |
C13—C12—H12 | 119.9 | C17—N4—C18 | 105.07 (19) |
C11—C12—H12 | 119.9 | C17—N4—C19 | 130.3 (2) |
C12—C13—C14 | 120.3 (3) | C18—N4—C19 | 124.6 (2) |
C12—C13—H13 | 119.8 | C2—O1—C1 | 119.3 (2) |
C14—C13—H13 | 119.8 | C8—O2—C5 | 121.54 (19) |
C9—C14—C13 | 118.7 (3) | | |
| | | |
C7—C2—C3—C4 | 1.7 (4) | N2—C8—N1—C17 | 0.6 (4) |
O1—C2—C3—C4 | −177.9 (2) | C16—C17—N1—C8 | −0.4 (4) |
C2—C3—C4—C5 | −0.2 (4) | N4—C17—N1—C8 | 179.4 (2) |
C3—C4—C5—C6 | −0.9 (4) | N1—C8—N2—C15 | −0.4 (4) |
C3—C4—C5—O2 | −173.3 (2) | O2—C8—N2—C15 | 179.5 (2) |
C4—C5—C6—C7 | 0.5 (4) | N1—C8—N2—C9 | 179.4 (2) |
O2—C5—C6—C7 | 173.5 (2) | O2—C8—N2—C9 | −0.6 (3) |
O1—C2—C7—C6 | 177.5 (3) | O3—C15—N2—C8 | 179.7 (2) |
C3—C2—C7—C6 | −2.1 (4) | C16—C15—N2—C8 | 0.0 (3) |
C5—C6—C7—C2 | 1.0 (4) | O3—C15—N2—C9 | −0.2 (3) |
C14—C9—C10—C11 | −0.2 (4) | C16—C15—N2—C9 | −179.9 (2) |
N2—C9—C10—C11 | −179.5 (2) | C10—C9—N2—C8 | −69.1 (3) |
C9—C10—C11—C12 | 2.2 (4) | C14—C9—N2—C8 | 111.6 (3) |
C10—C11—C12—C13 | −1.8 (5) | C10—C9—N2—C15 | 110.8 (3) |
C11—C12—C13—C14 | −0.5 (5) | C14—C9—N2—C15 | −68.5 (3) |
C10—C9—C14—C13 | −2.1 (4) | N4—C18—N3—C16 | 0.7 (3) |
N2—C9—C14—C13 | 177.2 (2) | C17—C16—N3—C18 | −0.1 (3) |
C12—C13—C14—C9 | 2.4 (4) | C15—C16—N3—C18 | 179.1 (2) |
O3—C15—C16—C17 | −179.5 (2) | N1—C17—N4—C18 | −178.9 (2) |
N2—C15—C16—C17 | 0.2 (3) | C16—C17—N4—C18 | 0.9 (3) |
O3—C15—C16—N3 | 1.4 (4) | N1—C17—N4—C19 | 3.9 (4) |
N2—C15—C16—N3 | −178.9 (2) | C16—C17—N4—C19 | −176.3 (2) |
N3—C16—C17—N1 | 179.3 (2) | N3—C18—N4—C17 | −1.0 (3) |
C15—C16—C17—N1 | 0.0 (4) | N3—C18—N4—C19 | 176.4 (2) |
N3—C16—C17—N4 | −0.5 (3) | C20—C19—N4—C17 | 143.9 (3) |
C15—C16—C17—N4 | −179.8 (2) | C24—C19—N4—C17 | −37.7 (4) |
C24—C19—C20—C21 | −1.4 (4) | C20—C19—N4—C18 | −32.8 (4) |
N4—C19—C20—C21 | 177.0 (2) | C24—C19—N4—C18 | 145.6 (3) |
C19—C20—C21—C22 | 0.6 (5) | C7—C2—O1—C1 | 177.7 (3) |
C20—C21—C22—C23 | 1.3 (5) | C3—C2—O1—C1 | −2.6 (4) |
C21—C22—C23—C24 | −2.3 (5) | N1—C8—O2—C5 | 18.8 (4) |
C20—C19—C24—C23 | 0.5 (4) | N2—C8—O2—C5 | −161.1 (2) |
N4—C19—C24—C23 | −177.9 (2) | C4—C5—O2—C8 | −69.5 (3) |
C22—C23—C24—C19 | 1.4 (4) | C6—C5—O2—C8 | 117.7 (3) |
O2—C8—N1—C17 | −179.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O3i | 0.93 | 2.58 | 3.315 (3) | 137 |
Symmetry code: (i) x−1/2, −y+3/2, −z+2. |