Single crystals of the title compound, C
17H
16N
2O
3, were obtained by gas diffusion. The observed diffraction pattern is compatible with a superposition of reflections from two monoclinic unit cells with the space group
C2/
c. The two cells share the
a and
b axes but not the
c axis. Both structures contain layers parallel to (001), with molecules connected by intermolecular N—H
O=C hydrogen bonds. The bonding between adjacent layers is weak. Layer displacements result in a crystal structure containing two closely related polymorphic domains. The structure of one polymorph can be derived from the structure of the other if subsequent layers are displaced by (
a/4,
b/4, 0) for odd-numbered layers and by (
a/4, −
b/4, 0) for even-numbered layers. Three different crystals were analysed and their observed diffraction patterns were similar, showing all three crystals to contain the polymorphic domain structure.
Supporting information
CCDC references: 833420; 833421
For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
(Ia) 1,5-dianilinopentane-1,3,5-trione
top
Crystal data top
C17H16N2O3 | F(000) = 2496 |
Mr = 296.32 | Dx = 1.382 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6859 reflections |
a = 17.6547 (5) Å | θ = 2–30° |
b = 9.8640 (3) Å | µ = 0.10 mm−1 |
c = 33.3982 (8) Å | T = 167 K |
β = 101.560 (1)° | Rod, colourless |
V = 5698.2 (3) Å3 | 0.60 × 0.16 × 0.16 mm |
Z = 16 | |
Data collection top
Siemens SMART 1K CCD area-detector diffractometer | 8099 independent reflections |
Radiation source: normal-focus sealed tube | 1972 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.141 |
ω scans | θmax = 30.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −24→24 |
Tmin = 0.924, Tmax = 0.985 | k = −13→13 |
41943 measured reflections | l = −45→46 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.81 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
8099 reflections | (Δ/σ)max = 0.001 |
399 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | |
O1 | 0.21641 (17) | 0.7450 (3) | 0.32204 (8) | 0.0294 (8) | |
O2 | 0.24719 (16) | 0.9561 (4) | 0.24934 (8) | 0.0362 (10) | |
O3 | 0.28291 (16) | 0.7381 (3) | 0.17972 (8) | 0.0267 (8) | |
O4 | 0.03306 (17) | 0.4879 (3) | 0.17941 (8) | 0.0267 (8) | |
O5 | 0.0000 | 0.7064 (5) | 0.2500 | 0.0401 (14) | |
O6 | 0.03276 (17) | −0.0039 (3) | 0.17832 (9) | 0.0329 (9) | |
O7 | 0.0000 | 0.2074 (5) | 0.2500 | 0.0436 (14) | |
N1 | 0.3286 (2) | 0.6244 (4) | 0.34101 (11) | 0.0225 (9) | |
H1A | 0.3693 | 0.5949 | 0.3322 | 0.027* | |
N2 | 0.1693 (2) | 0.6213 (4) | 0.15975 (10) | 0.0221 (9) | |
H2B | 0.1282 | 0.5930 | 0.1685 | 0.027* | |
N3 | −0.0801 (2) | 0.3718 (4) | 0.15989 (10) | 0.0204 (9) | |
H3B | −0.1206 | 0.3415 | 0.1688 | 0.024* | |
N4 | −0.0777 (2) | −0.1256 (4) | 0.15923 (11) | 0.0226 (9) | |
H4B | −0.1181 | −0.1566 | 0.1681 | 0.027* | |
C1 | 0.3203 (3) | 0.5815 (5) | 0.38029 (13) | 0.0201 (11) | |
C2 | 0.2928 (2) | 0.6685 (4) | 0.40690 (11) | 0.0250 (9) | |
H2A | 0.2747 | 0.7563 | 0.3980 | 0.030* | |
C3 | 0.2920 (2) | 0.6265 (4) | 0.44667 (11) | 0.0280 (10) | |
H3A | 0.2738 | 0.6862 | 0.4650 | 0.034* | |
C4 | 0.3177 (3) | 0.4979 (5) | 0.45959 (13) | 0.0290 (12) | |
H4A | 0.3171 | 0.4696 | 0.4867 | 0.035* | |
C5 | 0.3440 (2) | 0.4110 (4) | 0.43300 (11) | 0.0266 (10) | |
H5A | 0.3610 | 0.3225 | 0.4417 | 0.032* | |
C6 | 0.3455 (2) | 0.4534 (4) | 0.39343 (11) | 0.0242 (10) | |
H6A | 0.3641 | 0.3937 | 0.3753 | 0.029* | |
C7 | 0.2804 (2) | 0.7052 (4) | 0.31631 (12) | 0.0181 (10) | |
C8 | 0.3105 (3) | 0.7590 (4) | 0.27905 (12) | 0.0241 (11) | |
H8A | 0.3540 | 0.8223 | 0.2884 | 0.029* | |
H8B | 0.3302 | 0.6823 | 0.2649 | 0.029* | |
C9 | 0.2480 (2) | 0.8304 (6) | 0.24989 (13) | 0.0277 (13) | |
C10 | 0.1872 (2) | 0.7520 (4) | 0.22182 (12) | 0.0203 (11) | |
H10A | 0.1417 | 0.8106 | 0.2123 | 0.024* | |
H10B | 0.1706 | 0.6742 | 0.2367 | 0.024* | |
C11 | 0.2185 (2) | 0.7001 (4) | 0.18480 (12) | 0.0178 (10) | |
C12 | 0.1771 (3) | 0.5783 (4) | 0.12001 (13) | 0.0209 (11) | |
C13 | 0.2486 (2) | 0.5500 (4) | 0.11017 (11) | 0.0234 (9) | |
H13A | 0.2949 | 0.5567 | 0.1303 | 0.028* | |
C14 | 0.2511 (2) | 0.5117 (4) | 0.07036 (11) | 0.0262 (9) | |
H14A | 0.2995 | 0.4941 | 0.0631 | 0.031* | |
C15 | 0.1835 (3) | 0.4990 (5) | 0.04112 (14) | 0.0316 (13) | |
H15A | 0.1857 | 0.4717 | 0.0141 | 0.038* | |
C16 | 0.1130 (2) | 0.5262 (4) | 0.05121 (12) | 0.0278 (10) | |
H16A | 0.0668 | 0.5184 | 0.0311 | 0.033* | |
C17 | 0.1096 (2) | 0.5648 (4) | 0.09077 (11) | 0.0254 (9) | |
H17A | 0.0609 | 0.5821 | 0.0978 | 0.031* | |
C18 | −0.0726 (3) | 0.3286 (5) | 0.12000 (14) | 0.0217 (11) | |
C19 | −0.0021 (2) | 0.2994 (4) | 0.10977 (11) | 0.0238 (9) | |
H19A | 0.0444 | 0.3062 | 0.1297 | 0.029* | |
C20 | −0.0002 (2) | 0.2599 (4) | 0.07002 (12) | 0.0281 (10) | |
H20A | 0.0480 | 0.2393 | 0.0630 | 0.034* | |
C21 | −0.0672 (3) | 0.2501 (5) | 0.04049 (14) | 0.0282 (12) | |
H21A | −0.0652 | 0.2251 | 0.0133 | 0.034* | |
C22 | −0.1369 (2) | 0.2771 (4) | 0.05136 (12) | 0.0303 (10) | |
H22A | −0.1834 | 0.2685 | 0.0315 | 0.036* | |
C23 | −0.1404 (2) | 0.3167 (4) | 0.09076 (12) | 0.0271 (10) | |
H23A | −0.1889 | 0.3356 | 0.0978 | 0.032* | |
C24 | −0.0310 (3) | 0.4553 (4) | 0.18581 (14) | 0.0231 (11) | |
C25 | −0.0616 (2) | 0.5029 (4) | 0.22170 (12) | 0.0216 (11) | |
H25A | −0.0769 | 0.4240 | 0.2366 | 0.026* | |
H25B | −0.1080 | 0.5597 | 0.2124 | 0.026* | |
C26 | 0.0000 | 0.5849 (7) | 0.2500 | 0.0180 (15) | |
C27 | −0.0699 (2) | −0.1705 (5) | 0.11971 (13) | 0.0193 (11) | |
C28 | −0.0426 (2) | −0.0820 (4) | 0.09313 (11) | 0.0255 (10) | |
H28A | −0.0250 | 0.0061 | 0.1020 | 0.031* | |
C29 | −0.0416 (2) | −0.1244 (4) | 0.05369 (12) | 0.0290 (10) | |
H29A | −0.0230 | −0.0645 | 0.0356 | 0.035* | |
C30 | −0.0671 (3) | −0.2513 (5) | 0.04024 (13) | 0.0275 (12) | |
H30A | −0.0661 | −0.2790 | 0.0131 | 0.033* | |
C31 | −0.0941 (2) | −0.3382 (4) | 0.06674 (12) | 0.0301 (10) | |
H31A | −0.1118 | −0.4260 | 0.0576 | 0.036* | |
C32 | −0.0957 (2) | −0.2987 (4) | 0.10653 (12) | 0.0252 (10) | |
H32A | −0.1144 | −0.3590 | 0.1245 | 0.030* | |
C33 | −0.0300 (3) | −0.0403 (4) | 0.18496 (14) | 0.0248 (11) | |
C34 | −0.0612 (2) | 0.0050 (4) | 0.22110 (12) | 0.0230 (11) | |
H34A | −0.0761 | −0.0750 | 0.2357 | 0.028* | |
H34B | −0.1078 | 0.0613 | 0.2119 | 0.028* | |
C35 | 0.0000 | 0.0871 (7) | 0.2500 | 0.0169 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0227 (19) | 0.042 (2) | 0.0263 (18) | 0.0105 (16) | 0.0105 (14) | 0.0027 (16) |
O2 | 0.048 (3) | 0.021 (2) | 0.036 (2) | 0.0008 (16) | −0.0004 (18) | −0.0033 (14) |
O3 | 0.0193 (18) | 0.034 (2) | 0.0283 (18) | −0.0077 (15) | 0.0085 (14) | −0.0027 (15) |
O4 | 0.0204 (18) | 0.034 (2) | 0.0269 (18) | −0.0107 (16) | 0.0068 (14) | −0.0025 (15) |
O5 | 0.055 (4) | 0.020 (3) | 0.045 (3) | 0.000 | 0.009 (3) | 0.000 |
O6 | 0.0212 (19) | 0.048 (2) | 0.0321 (19) | −0.0155 (17) | 0.0099 (15) | −0.0087 (17) |
O7 | 0.061 (4) | 0.018 (3) | 0.051 (3) | 0.000 | 0.008 (3) | 0.000 |
N1 | 0.014 (2) | 0.028 (2) | 0.026 (2) | 0.0061 (18) | 0.0042 (18) | 0.0030 (19) |
N2 | 0.018 (2) | 0.027 (2) | 0.023 (2) | −0.0050 (18) | 0.0070 (18) | −0.0030 (19) |
N3 | 0.022 (2) | 0.023 (2) | 0.018 (2) | −0.0070 (18) | 0.0087 (17) | 0.0003 (18) |
N4 | 0.017 (2) | 0.029 (2) | 0.024 (2) | −0.0063 (18) | 0.0100 (18) | 0.0037 (19) |
C1 | 0.021 (3) | 0.021 (3) | 0.018 (2) | 0.000 (2) | 0.002 (2) | 0.000 (2) |
C2 | 0.026 (2) | 0.025 (2) | 0.024 (2) | 0.0081 (19) | 0.0061 (18) | 0.0021 (19) |
C3 | 0.029 (2) | 0.035 (3) | 0.023 (2) | 0.007 (2) | 0.0099 (19) | −0.002 (2) |
C4 | 0.034 (3) | 0.034 (3) | 0.019 (3) | 0.001 (3) | 0.005 (2) | 0.004 (2) |
C5 | 0.029 (2) | 0.025 (3) | 0.023 (2) | 0.000 (2) | 0.0005 (19) | 0.002 (2) |
C6 | 0.021 (2) | 0.031 (3) | 0.019 (2) | 0.0000 (19) | 0.0017 (18) | −0.004 (2) |
C7 | 0.021 (2) | 0.024 (3) | 0.014 (2) | −0.007 (2) | 0.0127 (18) | −0.0001 (19) |
C8 | 0.027 (3) | 0.022 (3) | 0.026 (3) | −0.006 (2) | 0.012 (2) | −0.003 (2) |
C9 | 0.040 (3) | 0.021 (3) | 0.030 (3) | 0.005 (2) | 0.024 (2) | 0.003 (2) |
C10 | 0.021 (3) | 0.024 (3) | 0.017 (2) | 0.001 (2) | 0.0055 (19) | −0.001 (2) |
C11 | 0.020 (2) | 0.021 (2) | 0.016 (2) | 0.0089 (19) | 0.0109 (19) | 0.0062 (19) |
C12 | 0.019 (3) | 0.021 (3) | 0.024 (3) | −0.004 (2) | 0.007 (2) | 0.004 (2) |
C13 | 0.023 (2) | 0.024 (2) | 0.023 (2) | −0.0051 (18) | 0.0027 (18) | 0.0013 (19) |
C14 | 0.028 (2) | 0.030 (2) | 0.023 (2) | −0.002 (2) | 0.0089 (19) | −0.0013 (19) |
C15 | 0.039 (3) | 0.030 (3) | 0.026 (3) | −0.003 (3) | 0.007 (2) | −0.007 (2) |
C16 | 0.033 (3) | 0.029 (2) | 0.020 (2) | −0.008 (2) | 0.0002 (19) | −0.0011 (19) |
C17 | 0.020 (2) | 0.028 (2) | 0.027 (2) | −0.0046 (18) | 0.0028 (18) | 0.001 (2) |
C18 | 0.017 (2) | 0.022 (3) | 0.026 (3) | −0.006 (2) | 0.005 (2) | 0.000 (2) |
C19 | 0.019 (2) | 0.025 (2) | 0.026 (2) | 0.0006 (18) | 0.0035 (18) | 0.0048 (19) |
C20 | 0.028 (2) | 0.028 (2) | 0.031 (3) | −0.002 (2) | 0.013 (2) | −0.001 (2) |
C21 | 0.031 (3) | 0.030 (3) | 0.023 (3) | −0.004 (2) | 0.003 (2) | 0.001 (2) |
C22 | 0.025 (2) | 0.036 (3) | 0.026 (2) | −0.006 (2) | −0.0044 (19) | −0.002 (2) |
C23 | 0.022 (2) | 0.032 (3) | 0.028 (2) | −0.0039 (19) | 0.0079 (19) | −0.001 (2) |
C24 | 0.017 (2) | 0.016 (2) | 0.032 (3) | −0.0096 (19) | −0.007 (2) | 0.008 (2) |
C25 | 0.015 (2) | 0.026 (3) | 0.024 (3) | −0.001 (2) | 0.005 (2) | −0.001 (2) |
C26 | 0.015 (3) | 0.026 (4) | 0.013 (3) | 0.000 | 0.001 (3) | 0.000 |
C27 | 0.017 (2) | 0.024 (3) | 0.015 (2) | −0.001 (2) | −0.0013 (19) | 0.001 (2) |
C28 | 0.027 (2) | 0.027 (2) | 0.023 (2) | −0.004 (2) | 0.0067 (18) | 0.002 (2) |
C29 | 0.026 (2) | 0.039 (3) | 0.024 (2) | −0.001 (2) | 0.0076 (19) | 0.008 (2) |
C30 | 0.026 (3) | 0.035 (3) | 0.022 (3) | −0.001 (2) | 0.007 (2) | 0.000 (2) |
C31 | 0.032 (3) | 0.027 (3) | 0.030 (3) | −0.002 (2) | 0.002 (2) | −0.006 (2) |
C32 | 0.023 (2) | 0.022 (2) | 0.031 (3) | −0.0051 (19) | 0.0048 (19) | 0.002 (2) |
C33 | 0.023 (3) | 0.019 (3) | 0.028 (3) | −0.008 (2) | −0.006 (2) | 0.001 (2) |
C34 | 0.015 (2) | 0.027 (3) | 0.027 (3) | −0.003 (2) | 0.004 (2) | 0.001 (2) |
C35 | 0.012 (3) | 0.021 (4) | 0.016 (3) | 0.000 | 0.000 (2) | 0.000 |
Geometric parameters (Å, º) top
O1—C7 | 1.246 (5) | C13—H13A | 0.9500 |
O2—C9 | 1.239 (5) | C14—C15 | 1.389 (6) |
O3—C11 | 1.240 (4) | C14—H14A | 0.9500 |
O4—C24 | 1.235 (5) | C15—C16 | 1.378 (6) |
O5—C26 | 1.198 (7) | C15—H15A | 0.9500 |
O6—C33 | 1.227 (5) | C16—C17 | 1.388 (5) |
O7—C35 | 1.186 (7) | C16—H16A | 0.9500 |
N1—C7 | 1.327 (5) | C17—H17A | 0.9500 |
N1—C1 | 1.414 (5) | C18—C19 | 1.385 (5) |
N1—H1A | 0.8800 | C18—C23 | 1.390 (5) |
N2—C11 | 1.330 (5) | C19—C20 | 1.390 (5) |
N2—C12 | 1.426 (5) | C19—H19A | 0.9500 |
N2—H2B | 0.8800 | C20—C21 | 1.383 (6) |
N3—C24 | 1.370 (5) | C20—H20A | 0.9500 |
N3—C18 | 1.430 (5) | C21—C22 | 1.378 (5) |
N3—H3B | 0.8800 | C21—H21A | 0.9500 |
N4—C33 | 1.366 (5) | C22—C23 | 1.386 (5) |
N4—C27 | 1.425 (5) | C22—H22A | 0.9500 |
N4—H4B | 0.8800 | C23—H23A | 0.9500 |
C1—C6 | 1.382 (5) | C24—C25 | 1.487 (6) |
C1—C2 | 1.390 (5) | C25—C26 | 1.523 (5) |
C2—C3 | 1.394 (5) | C25—H25A | 0.9900 |
C2—H2A | 0.9500 | C25—H25B | 0.9900 |
C3—C4 | 1.387 (5) | C26—C25i | 1.523 (5) |
C3—H3A | 0.9500 | C27—C32 | 1.386 (5) |
C4—C5 | 1.380 (6) | C27—C28 | 1.397 (5) |
C4—H4A | 0.9500 | C28—C29 | 1.385 (5) |
C5—C6 | 1.392 (5) | C28—H28A | 0.9500 |
C5—H5A | 0.9500 | C29—C30 | 1.375 (5) |
C6—H6A | 0.9500 | C29—H29A | 0.9500 |
C7—C8 | 1.542 (5) | C30—C31 | 1.384 (6) |
C8—C9 | 1.495 (6) | C30—H30A | 0.9500 |
C8—H8A | 0.9900 | C31—C32 | 1.391 (5) |
C8—H8B | 0.9900 | C31—H31A | 0.9500 |
C9—C10 | 1.492 (6) | C32—H32A | 0.9500 |
C10—C11 | 1.539 (5) | C33—C34 | 1.491 (6) |
C10—H10A | 0.9900 | C34—C35 | 1.529 (5) |
C10—H10B | 0.9900 | C34—H34A | 0.9900 |
C12—C17 | 1.388 (5) | C34—H34B | 0.9900 |
C12—C13 | 1.396 (5) | C35—C34i | 1.529 (5) |
C13—C14 | 1.391 (5) | | |
| | | |
C7—N1—C1 | 125.7 (4) | C17—C16—H16A | 120.0 |
C7—N1—H1A | 117.1 | C12—C17—C16 | 120.0 (4) |
C1—N1—H1A | 117.1 | C12—C17—H17A | 120.0 |
C11—N2—C12 | 125.9 (4) | C16—C17—H17A | 120.0 |
C11—N2—H2B | 117.0 | C19—C18—C23 | 119.9 (4) |
C12—N2—H2B | 117.0 | C19—C18—N3 | 123.2 (4) |
C24—N3—C18 | 127.1 (4) | C23—C18—N3 | 116.9 (4) |
C24—N3—H3B | 116.5 | C18—C19—C20 | 119.2 (4) |
C18—N3—H3B | 116.5 | C18—C19—H19A | 120.4 |
C33—N4—C27 | 127.7 (4) | C20—C19—H19A | 120.4 |
C33—N4—H4B | 116.1 | C21—C20—C19 | 121.3 (4) |
C27—N4—H4B | 116.1 | C21—C20—H20A | 119.3 |
C6—C1—C2 | 119.5 (4) | C19—C20—H20A | 119.3 |
C6—C1—N1 | 118.7 (4) | C22—C21—C20 | 118.7 (4) |
C2—C1—N1 | 121.5 (4) | C22—C21—H21A | 120.7 |
C1—C2—C3 | 119.8 (4) | C20—C21—H21A | 120.7 |
C1—C2—H2A | 120.1 | C21—C22—C23 | 121.1 (4) |
C3—C2—H2A | 120.1 | C21—C22—H22A | 119.5 |
C4—C3—C2 | 120.2 (4) | C23—C22—H22A | 119.5 |
C4—C3—H3A | 119.9 | C22—C23—C18 | 119.7 (4) |
C2—C3—H3A | 119.9 | C22—C23—H23A | 120.1 |
C5—C4—C3 | 119.9 (4) | C18—C23—H23A | 120.1 |
C5—C4—H4A | 120.0 | O4—C24—N3 | 122.2 (4) |
C3—C4—H4A | 120.0 | O4—C24—C25 | 123.4 (4) |
C4—C5—C6 | 119.9 (4) | N3—C24—C25 | 114.4 (4) |
C4—C5—H5A | 120.1 | C24—C25—C26 | 109.8 (3) |
C6—C5—H5A | 120.1 | C24—C25—H25A | 109.7 |
C1—C6—C5 | 120.6 (4) | C26—C25—H25A | 109.7 |
C1—C6—H6A | 119.7 | C24—C25—H25B | 109.7 |
C5—C6—H6A | 119.7 | C26—C25—H25B | 109.7 |
O1—C7—N1 | 125.6 (4) | H25A—C25—H25B | 108.2 |
O1—C7—C8 | 119.1 (4) | O5—C26—C25 | 122.1 (3) |
N1—C7—C8 | 115.2 (4) | O5—C26—C25i | 122.1 (3) |
C9—C8—C7 | 111.0 (4) | C25—C26—C25i | 115.8 (6) |
C9—C8—H8A | 109.4 | C32—C27—C28 | 120.1 (4) |
C7—C8—H8A | 109.4 | C32—C27—N4 | 119.4 (4) |
C9—C8—H8B | 109.4 | C28—C27—N4 | 120.3 (4) |
C7—C8—H8B | 109.4 | C29—C28—C27 | 119.2 (4) |
H8A—C8—H8B | 108.0 | C29—C28—H28A | 120.4 |
O2—C9—C10 | 120.3 (5) | C27—C28—H28A | 120.4 |
O2—C9—C8 | 119.1 (4) | C30—C29—C28 | 121.3 (4) |
C10—C9—C8 | 120.6 (5) | C30—C29—H29A | 119.3 |
C9—C10—C11 | 110.4 (3) | C28—C29—H29A | 119.3 |
C9—C10—H10A | 109.6 | C29—C30—C31 | 119.1 (4) |
C11—C10—H10A | 109.6 | C29—C30—H30A | 120.4 |
C9—C10—H10B | 109.6 | C31—C30—H30A | 120.4 |
C11—C10—H10B | 109.6 | C30—C31—C32 | 120.9 (4) |
H10A—C10—H10B | 108.1 | C30—C31—H31A | 119.6 |
O3—C11—N2 | 126.3 (4) | C32—C31—H31A | 119.6 |
O3—C11—C10 | 119.7 (4) | C27—C32—C31 | 119.4 (4) |
N2—C11—C10 | 113.9 (4) | C27—C32—H32A | 120.3 |
C17—C12—C13 | 120.4 (4) | C31—C32—H32A | 120.3 |
C17—C12—N2 | 117.0 (4) | O6—C33—N4 | 122.1 (4) |
C13—C12—N2 | 122.6 (4) | O6—C33—C34 | 123.5 (4) |
C14—C13—C12 | 118.8 (4) | N4—C33—C34 | 114.4 (4) |
C14—C13—H13A | 120.6 | C33—C34—C35 | 109.9 (3) |
C12—C13—H13A | 120.6 | C33—C34—H34A | 109.7 |
C15—C14—C13 | 120.6 (4) | C35—C34—H34A | 109.7 |
C15—C14—H14A | 119.7 | C33—C34—H34B | 109.7 |
C13—C14—H14A | 119.7 | C35—C34—H34B | 109.7 |
C16—C15—C14 | 120.1 (4) | H34A—C34—H34B | 108.2 |
C16—C15—H15A | 119.9 | O7—C35—C34i | 122.0 (3) |
C14—C15—H15A | 119.9 | O7—C35—C34 | 122.0 (3) |
C15—C16—C17 | 120.0 (4) | C34i—C35—C34 | 116.0 (5) |
C15—C16—H16A | 120.0 | | |
| | | |
C7—N1—C1—C6 | 146.3 (4) | C24—N3—C18—C19 | 36.8 (6) |
C7—N1—C1—C2 | −38.6 (7) | C24—N3—C18—C23 | −143.0 (4) |
C6—C1—C2—C3 | 0.8 (6) | C23—C18—C19—C20 | 0.8 (6) |
N1—C1—C2—C3 | −174.2 (4) | N3—C18—C19—C20 | −179.1 (4) |
C1—C2—C3—C4 | −0.7 (6) | C18—C19—C20—C21 | 0.4 (6) |
C2—C3—C4—C5 | −0.1 (6) | C19—C20—C21—C22 | −1.5 (6) |
C3—C4—C5—C6 | 0.8 (6) | C20—C21—C22—C23 | 1.6 (6) |
C2—C1—C6—C5 | −0.2 (6) | C21—C22—C23—C18 | −0.4 (6) |
N1—C1—C6—C5 | 175.0 (4) | C19—C18—C23—C22 | −0.8 (6) |
C4—C5—C6—C1 | −0.6 (6) | N3—C18—C23—C22 | 179.1 (3) |
C1—N1—C7—O1 | −7.6 (7) | C18—N3—C24—O4 | −10.8 (7) |
C1—N1—C7—C8 | 168.5 (4) | C18—N3—C24—C25 | 168.9 (4) |
O1—C7—C8—C9 | −12.6 (5) | O4—C24—C25—C26 | −4.9 (6) |
N1—C7—C8—C9 | 171.1 (4) | N3—C24—C25—C26 | 175.4 (4) |
C7—C8—C9—O2 | 102.5 (4) | C24—C25—C26—O5 | 99.8 (3) |
C7—C8—C9—C10 | −77.5 (4) | C24—C25—C26—C25i | −80.2 (3) |
O2—C9—C10—C11 | 100.6 (4) | C33—N4—C27—C32 | 147.9 (4) |
C8—C9—C10—C11 | −79.4 (4) | C33—N4—C27—C28 | −37.6 (6) |
C12—N2—C11—O3 | −7.9 (7) | C32—C27—C28—C29 | −0.2 (6) |
C12—N2—C11—C10 | 168.6 (4) | N4—C27—C28—C29 | −174.6 (4) |
C9—C10—C11—O3 | −7.6 (5) | C27—C28—C29—C30 | 0.2 (6) |
C9—C10—C11—N2 | 175.6 (4) | C28—C29—C30—C31 | −0.1 (6) |
C11—N2—C12—C17 | −145.3 (4) | C29—C30—C31—C32 | 0.0 (6) |
C11—N2—C12—C13 | 34.9 (6) | C28—C27—C32—C31 | 0.1 (6) |
C17—C12—C13—C14 | 1.7 (6) | N4—C27—C32—C31 | 174.6 (4) |
N2—C12—C13—C14 | −178.5 (4) | C30—C31—C32—C27 | 0.0 (6) |
C12—C13—C14—C15 | −1.4 (6) | C27—N4—C33—O6 | −9.1 (7) |
C13—C14—C15—C16 | 0.9 (7) | C27—N4—C33—C34 | 170.3 (4) |
C14—C15—C16—C17 | −0.7 (6) | O6—C33—C34—C35 | −6.6 (6) |
C13—C12—C17—C16 | −1.5 (6) | N4—C33—C34—C35 | 174.0 (4) |
N2—C12—C17—C16 | 178.6 (3) | C33—C34—C35—O7 | 98.6 (3) |
C15—C16—C17—C12 | 1.0 (6) | C33—C34—C35—C34i | −81.4 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O6ii | 0.88 | 2.08 | 2.940 (5) | 168 |
N2—H2B···O4 | 0.88 | 2.07 | 2.929 (5) | 166 |
N3—H3B···O3iii | 0.88 | 2.08 | 2.944 (5) | 167 |
N4—H4B···O1iv | 0.88 | 2.07 | 2.938 (5) | 168 |
C8—H8B···O2v | 0.99 | 2.61 | 3.237 (6) | 121 |
C10—H10B···O2v | 0.99 | 2.58 | 3.216 (5) | 122 |
C25—H25A···O7 | 0.99 | 2.52 | 3.188 (6) | 124 |
C34—H34A···O5vi | 0.99 | 2.53 | 3.218 (6) | 126 |
C2—H2A···Cg(C12–C17)ii | 0.95 | 2.94 | 3.691 (4) | 137 |
C5—H5A···Cg(C12–C17)v | 0.95 | 2.95 | 3.719 (4) | 138 |
C28—H28A···Cg(C18–C23) | 0.95 | 2.95 | 3.701 (4) | 137 |
C31—H31A···Cg(C18–C23)vi | 0.95 | 2.97 | 3.723 (4) | 137 |
Symmetry codes: (ii) −x+1/2, y+1/2, −z+1/2; (iii) x−1/2, y−1/2, z; (iv) −x, y−1, −z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) x, y−1, z. |
(Ib) 1,5-dianilinopentane-1,3,5-trione
top
Crystal data top
C17H16N2O3 | F(000) = 2496 |
Mr = 296.32 | Dx = 1.382 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6859 reflections |
a = 17.6547 (5) Å | θ = 2–30° |
b = 9.8640 (3) Å | µ = 0.10 mm−1 |
c = 32.7904 (8) Å | T = 167 K |
β = 93.733 (1)° | Rod, colourless |
V = 5698.2 (3) Å3 | 0.60 × 0.16 × 0.16 mm |
Z = 16 | |
Data collection top
Siemens SMART 1K CCD area-detector diffractometer | 8093 independent reflections |
Radiation source: normal-focus sealed tube | 1858 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.176 |
ω scans | θmax = 30.2°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −24→24 |
Tmin = 0.924, Tmax = 0.985 | k = −13→13 |
41837 measured reflections | l = −42→46 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.83 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
8093 reflections | (Δ/σ)max = 0.001 |
399 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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 | |
O1 | 0.18104 (19) | 0.1294 (4) | 0.17803 (10) | 0.0313 (10) | |
O2 | 0.2478 (2) | −0.0809 (4) | 0.25092 (11) | 0.0386 (11) | |
O3 | 0.31778 (18) | 0.1368 (4) | 0.32028 (10) | 0.0282 (9) | |
O4 | 0.06879 (18) | 0.3876 (4) | 0.32047 (10) | 0.0266 (9) | |
O5 | 0.0000 | 0.1690 (5) | 0.2500 | 0.0374 (15) | |
O6 | 0.06905 (18) | 0.8792 (4) | 0.32184 (10) | 0.0297 (10) | |
O7 | 0.0000 | 0.6668 (6) | 0.2500 | 0.0414 (16) | |
N1 | 0.2828 (2) | 0.2507 (4) | 0.15923 (11) | 0.0218 (11) | |
H1A | 0.3276 | 0.2820 | 0.1681 | 0.026* | |
N2 | 0.2143 (2) | 0.2539 (4) | 0.34016 (11) | 0.0210 (11) | |
H2B | 0.1692 | 0.2842 | 0.3315 | 0.025* | |
N3 | −0.0352 (2) | 0.5021 (4) | 0.34030 (12) | 0.0222 (11) | |
H3B | −0.0811 | 0.5284 | 0.3317 | 0.027* | |
N4 | −0.0324 (2) | 1.0015 (4) | 0.34093 (12) | 0.0230 (11) | |
H4B | −0.0771 | 1.0323 | 0.3318 | 0.028* | |
C1 | 0.2547 (3) | 0.2951 (5) | 0.11969 (14) | 0.0169 (12) | |
C2 | 0.2148 (2) | 0.2062 (5) | 0.09324 (13) | 0.0246 (11) | |
H2A | 0.2021 | 0.1179 | 0.1021 | 0.030* | |
C3 | 0.1936 (3) | 0.2484 (5) | 0.05352 (14) | 0.0291 (12) | |
H3A | 0.1656 | 0.1889 | 0.0354 | 0.035* | |
C4 | 0.2131 (3) | 0.3765 (6) | 0.04026 (16) | 0.0315 (15) | |
H4A | 0.1996 | 0.4041 | 0.0130 | 0.038* | |
C5 | 0.2524 (3) | 0.4637 (5) | 0.06689 (13) | 0.0275 (12) | |
H5A | 0.2646 | 0.5524 | 0.0581 | 0.033* | |
C6 | 0.2739 (2) | 0.4225 (5) | 0.10632 (13) | 0.0233 (12) | |
H6A | 0.3020 | 0.4823 | 0.1243 | 0.028* | |
C7 | 0.2478 (3) | 0.1651 (5) | 0.18476 (15) | 0.0218 (12) | |
C8 | 0.2961 (3) | 0.1178 (5) | 0.22095 (14) | 0.0222 (13) | |
H8A | 0.3210 | 0.1965 | 0.2349 | 0.027* | |
H8B | 0.3361 | 0.0565 | 0.2120 | 0.027* | |
C9 | 0.2476 (3) | 0.0438 (5) | 0.25018 (17) | 0.0260 (13) | |
C10 | 0.2011 (3) | 0.1238 (5) | 0.27832 (14) | 0.0218 (13) | |
H10A | 0.1781 | 0.2029 | 0.2636 | 0.026* | |
H10B | 0.1597 | 0.0667 | 0.2878 | 0.026* | |
C11 | 0.2507 (3) | 0.1707 (5) | 0.31391 (15) | 0.0212 (12) | |
C12 | 0.2422 (3) | 0.2952 (5) | 0.37942 (16) | 0.0225 (13) | |
C13 | 0.3181 (3) | 0.3247 (4) | 0.38994 (13) | 0.0251 (12) | |
H13A | 0.3545 | 0.3185 | 0.3699 | 0.030* | |
C14 | 0.3406 (3) | 0.3634 (5) | 0.42967 (13) | 0.0265 (12) | |
H14A | 0.3926 | 0.3821 | 0.4367 | 0.032* | |
C15 | 0.2885 (3) | 0.3749 (6) | 0.45892 (16) | 0.0282 (14) | |
H15A | 0.3046 | 0.4013 | 0.4860 | 0.034* | |
C16 | 0.2129 (3) | 0.3483 (5) | 0.44904 (13) | 0.0292 (12) | |
H16A | 0.1770 | 0.3564 | 0.4692 | 0.035* | |
C17 | 0.1891 (3) | 0.3092 (5) | 0.40921 (13) | 0.0263 (12) | |
H17A | 0.1369 | 0.2921 | 0.4023 | 0.032* | |
C18 | −0.0080 (3) | 0.5469 (5) | 0.37983 (16) | 0.0215 (13) | |
C19 | 0.0686 (2) | 0.5758 (4) | 0.39018 (13) | 0.0223 (11) | |
H19A | 0.1051 | 0.5688 | 0.3703 | 0.027* | |
C20 | 0.0902 (3) | 0.6149 (5) | 0.42996 (13) | 0.0280 (12) | |
H20A | 0.1421 | 0.6348 | 0.4371 | 0.034* | |
C21 | 0.0378 (3) | 0.6254 (5) | 0.45938 (16) | 0.0287 (14) | |
H21A | 0.0533 | 0.6506 | 0.4866 | 0.034* | |
C22 | −0.0380 (3) | 0.5984 (5) | 0.44835 (14) | 0.0290 (12) | |
H22A | −0.0746 | 0.6071 | 0.4682 | 0.035* | |
C23 | −0.0608 (3) | 0.5592 (4) | 0.40924 (13) | 0.0264 (12) | |
H23A | −0.1128 | 0.5405 | 0.4023 | 0.032* | |
C24 | 0.0019 (3) | 0.4242 (5) | 0.31506 (14) | 0.0198 (12) | |
C25 | −0.0480 (3) | 0.3715 (5) | 0.27813 (14) | 0.0203 (13) | |
H25A | −0.0886 | 0.3127 | 0.2877 | 0.024* | |
H25B | −0.0721 | 0.4488 | 0.2631 | 0.024* | |
C26 | 0.0000 | 0.2919 (8) | 0.2500 | 0.0197 (17) | |
C27 | −0.0048 (3) | 1.0446 (6) | 0.38087 (15) | 0.0221 (13) | |
C28 | 0.0363 (2) | 0.9575 (5) | 0.40708 (13) | 0.0260 (12) | |
H28A | 0.0503 | 0.8700 | 0.3981 | 0.031* | |
C29 | 0.0565 (2) | 0.9994 (5) | 0.44643 (13) | 0.0284 (12) | |
H29A | 0.0840 | 0.9396 | 0.4647 | 0.034* | |
C30 | 0.0373 (3) | 1.1274 (6) | 0.45974 (16) | 0.0283 (14) | |
H30A | 0.0516 | 1.1556 | 0.4869 | 0.034* | |
C31 | −0.0026 (3) | 1.2133 (5) | 0.43318 (14) | 0.0294 (12) | |
H31A | −0.0158 | 1.3013 | 0.4421 | 0.035* | |
C32 | −0.0240 (2) | 1.1728 (5) | 0.39322 (13) | 0.0264 (12) | |
H32A | −0.0512 | 1.2327 | 0.3749 | 0.032* | |
C33 | 0.0028 (3) | 0.9201 (5) | 0.31649 (14) | 0.0205 (12) | |
C34 | −0.0460 (3) | 0.8681 (6) | 0.27890 (15) | 0.0251 (13) | |
H34A | −0.0873 | 0.8104 | 0.2883 | 0.030* | |
H34B | −0.0695 | 0.9464 | 0.2641 | 0.030* | |
C35 | 0.0000 | 0.7874 (8) | 0.2500 | 0.0193 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.023 (2) | 0.045 (3) | 0.026 (2) | −0.0125 (19) | −0.0022 (17) | 0.0052 (19) |
O2 | 0.054 (3) | 0.024 (2) | 0.038 (2) | 0.000 (2) | 0.009 (2) | −0.001 (2) |
O3 | 0.018 (2) | 0.035 (2) | 0.031 (2) | 0.0071 (18) | 0.0030 (17) | −0.0018 (18) |
O4 | 0.017 (2) | 0.033 (2) | 0.029 (2) | 0.0099 (17) | −0.0029 (16) | −0.0031 (18) |
O5 | 0.053 (4) | 0.015 (3) | 0.044 (4) | 0.000 | 0.007 (3) | 0.000 |
O6 | 0.018 (2) | 0.044 (3) | 0.027 (2) | 0.0108 (19) | −0.0037 (16) | −0.0057 (19) |
O7 | 0.063 (4) | 0.016 (3) | 0.046 (4) | 0.000 | 0.005 (3) | 0.000 |
N1 | 0.012 (2) | 0.029 (3) | 0.024 (3) | −0.008 (2) | −0.0011 (19) | −0.002 (2) |
N2 | 0.021 (3) | 0.024 (3) | 0.017 (2) | 0.008 (2) | −0.0059 (19) | −0.001 (2) |
N3 | 0.016 (3) | 0.027 (3) | 0.022 (3) | 0.005 (2) | −0.0026 (19) | −0.004 (2) |
N4 | 0.013 (2) | 0.028 (3) | 0.028 (3) | 0.003 (2) | 0.003 (2) | 0.000 (2) |
C1 | 0.017 (3) | 0.023 (3) | 0.010 (3) | 0.000 (2) | 0.000 (2) | 0.002 (2) |
C2 | 0.025 (3) | 0.026 (3) | 0.021 (3) | 0.001 (2) | −0.001 (2) | 0.006 (2) |
C3 | 0.026 (3) | 0.031 (3) | 0.030 (3) | −0.005 (2) | −0.004 (2) | −0.001 (2) |
C4 | 0.033 (4) | 0.041 (4) | 0.020 (3) | −0.006 (3) | 0.001 (3) | −0.006 (3) |
C5 | 0.037 (3) | 0.023 (3) | 0.024 (3) | 0.003 (2) | 0.007 (2) | 0.007 (2) |
C6 | 0.025 (3) | 0.020 (3) | 0.026 (3) | −0.005 (2) | 0.005 (2) | −0.008 (2) |
C7 | 0.024 (3) | 0.013 (3) | 0.030 (3) | −0.008 (2) | 0.011 (2) | −0.002 (2) |
C8 | 0.018 (3) | 0.023 (3) | 0.026 (3) | −0.004 (2) | −0.001 (2) | −0.002 (2) |
C9 | 0.026 (3) | 0.019 (3) | 0.030 (3) | −0.011 (3) | −0.018 (2) | 0.005 (3) |
C10 | 0.015 (3) | 0.026 (3) | 0.025 (3) | 0.005 (2) | 0.006 (2) | −0.004 (2) |
C11 | 0.021 (3) | 0.013 (3) | 0.031 (3) | 0.007 (2) | 0.012 (2) | 0.008 (2) |
C12 | 0.011 (3) | 0.022 (3) | 0.035 (3) | 0.004 (2) | 0.007 (2) | 0.005 (3) |
C13 | 0.032 (3) | 0.023 (3) | 0.021 (3) | 0.004 (2) | 0.005 (2) | 0.002 (2) |
C14 | 0.023 (3) | 0.030 (3) | 0.026 (3) | −0.003 (2) | 0.000 (2) | 0.003 (2) |
C15 | 0.033 (4) | 0.031 (4) | 0.021 (3) | 0.002 (3) | −0.001 (3) | 0.001 (3) |
C16 | 0.040 (3) | 0.032 (3) | 0.017 (3) | 0.005 (3) | 0.010 (2) | −0.001 (2) |
C17 | 0.019 (3) | 0.031 (3) | 0.029 (3) | 0.008 (2) | 0.003 (2) | −0.003 (2) |
C18 | 0.017 (3) | 0.019 (3) | 0.028 (3) | 0.006 (2) | 0.001 (2) | 0.008 (3) |
C19 | 0.014 (2) | 0.026 (3) | 0.027 (3) | 0.002 (2) | 0.003 (2) | 0.004 (2) |
C20 | 0.028 (3) | 0.027 (3) | 0.028 (3) | 0.005 (2) | −0.007 (2) | −0.005 (2) |
C21 | 0.033 (4) | 0.028 (3) | 0.025 (3) | 0.001 (3) | 0.000 (3) | −0.010 (3) |
C22 | 0.027 (3) | 0.031 (3) | 0.030 (3) | 0.008 (2) | 0.008 (2) | −0.003 (3) |
C23 | 0.023 (3) | 0.029 (3) | 0.027 (3) | 0.001 (2) | 0.002 (2) | 0.003 (2) |
C24 | 0.018 (3) | 0.027 (3) | 0.014 (3) | −0.003 (2) | 0.001 (2) | 0.004 (2) |
C25 | 0.018 (3) | 0.023 (3) | 0.019 (3) | −0.008 (2) | −0.004 (2) | 0.002 (2) |
C26 | 0.019 (4) | 0.023 (5) | 0.017 (4) | 0.000 | −0.002 (3) | 0.000 |
C27 | 0.030 (3) | 0.024 (3) | 0.012 (3) | 0.001 (3) | 0.002 (2) | −0.005 (2) |
C28 | 0.026 (3) | 0.026 (3) | 0.026 (3) | 0.014 (2) | 0.004 (2) | 0.005 (2) |
C29 | 0.023 (3) | 0.044 (3) | 0.018 (3) | 0.006 (3) | −0.002 (2) | 0.008 (2) |
C30 | 0.029 (3) | 0.032 (4) | 0.024 (3) | −0.002 (3) | 0.002 (3) | −0.006 (3) |
C31 | 0.029 (3) | 0.030 (3) | 0.030 (3) | 0.003 (2) | 0.006 (2) | −0.001 (3) |
C32 | 0.023 (3) | 0.033 (3) | 0.023 (3) | 0.002 (2) | 0.002 (2) | −0.001 (2) |
C33 | 0.019 (3) | 0.028 (3) | 0.013 (2) | −0.009 (2) | −0.013 (2) | 0.001 (2) |
C34 | 0.022 (3) | 0.028 (3) | 0.025 (3) | −0.003 (2) | −0.003 (2) | 0.002 (3) |
C35 | 0.017 (4) | 0.029 (5) | 0.012 (4) | 0.000 | 0.012 (3) | 0.000 |
Geometric parameters (Å, º) top
O1—C7 | 1.237 (5) | C13—H13A | 0.9500 |
O2—C9 | 1.230 (6) | C14—C15 | 1.376 (6) |
O3—C11 | 1.235 (5) | C14—H14A | 0.9500 |
O4—C24 | 1.237 (5) | C15—C16 | 1.378 (6) |
O5—C26 | 1.212 (8) | C15—H15A | 0.9500 |
O6—C33 | 1.240 (5) | C16—C17 | 1.400 (6) |
O7—C35 | 1.190 (8) | C16—H16A | 0.9500 |
N1—C7 | 1.365 (6) | C17—H17A | 0.9500 |
N1—C1 | 1.426 (6) | C18—C23 | 1.389 (6) |
N1—H1A | 0.8800 | C18—C19 | 1.402 (6) |
N2—C11 | 1.378 (5) | C19—C20 | 1.390 (6) |
N2—C12 | 1.408 (6) | C19—H19A | 0.9500 |
N2—H2B | 0.8800 | C20—C21 | 1.384 (6) |
N3—C24 | 1.332 (6) | C20—H20A | 0.9500 |
N3—C18 | 1.423 (6) | C21—C22 | 1.389 (6) |
N3—H3B | 0.8800 | C21—H21A | 0.9500 |
N4—C33 | 1.317 (6) | C22—C23 | 1.374 (6) |
N4—C27 | 1.432 (6) | C22—H22A | 0.9500 |
N4—H4B | 0.8800 | C23—H23A | 0.9500 |
C1—C6 | 1.380 (6) | C24—C25 | 1.540 (6) |
C1—C2 | 1.393 (6) | C25—C26 | 1.512 (6) |
C2—C3 | 1.395 (6) | C25—H25A | 0.9900 |
C2—H2A | 0.9500 | C25—H25B | 0.9900 |
C3—C4 | 1.388 (7) | C26—C25i | 1.512 (6) |
C3—H3A | 0.9500 | C27—C32 | 1.377 (6) |
C4—C5 | 1.380 (7) | C27—C28 | 1.386 (6) |
C4—H4A | 0.9500 | C28—C29 | 1.380 (6) |
C5—C6 | 1.385 (5) | C28—H28A | 0.9500 |
C5—H5A | 0.9500 | C29—C30 | 1.386 (7) |
C6—H6A | 0.9500 | C29—H29A | 0.9500 |
C7—C8 | 1.490 (6) | C30—C31 | 1.376 (7) |
C8—C9 | 1.514 (7) | C30—H30A | 0.9500 |
C8—H8A | 0.9900 | C31—C32 | 1.398 (6) |
C8—H8B | 0.9900 | C31—H31A | 0.9500 |
C9—C10 | 1.498 (7) | C32—H32A | 0.9500 |
C10—C11 | 1.486 (6) | C33—C34 | 1.544 (6) |
C10—H10A | 0.9900 | C34—C35 | 1.514 (6) |
C10—H10B | 0.9900 | C34—H34A | 0.9900 |
C12—C13 | 1.391 (6) | C34—H34B | 0.9900 |
C12—C17 | 1.404 (6) | C35—C34i | 1.514 (6) |
C13—C14 | 1.391 (6) | | |
| | | |
C7—N1—C1 | 127.1 (4) | C17—C16—H16A | 120.0 |
C7—N1—H1A | 116.4 | C16—C17—C12 | 120.2 (4) |
C1—N1—H1A | 116.4 | C16—C17—H17A | 119.9 |
C11—N2—C12 | 126.4 (4) | C12—C17—H17A | 119.9 |
C11—N2—H2B | 116.8 | C23—C18—C19 | 119.6 (5) |
C12—N2—H2B | 116.8 | C23—C18—N3 | 117.2 (4) |
C24—N3—C18 | 126.5 (4) | C19—C18—N3 | 123.1 (4) |
C24—N3—H3B | 116.8 | C20—C19—C18 | 119.1 (4) |
C18—N3—H3B | 116.8 | C20—C19—H19A | 120.5 |
C33—N4—C27 | 126.3 (4) | C18—C19—H19A | 120.5 |
C33—N4—H4B | 116.8 | C21—C20—C19 | 121.3 (4) |
C27—N4—H4B | 116.8 | C21—C20—H20A | 119.4 |
C6—C1—C2 | 120.0 (4) | C19—C20—H20A | 119.4 |
C6—C1—N1 | 119.4 (4) | C20—C21—C22 | 118.8 (5) |
C2—C1—N1 | 120.3 (4) | C20—C21—H21A | 120.6 |
C1—C2—C3 | 119.2 (4) | C22—C21—H21A | 120.6 |
C1—C2—H2A | 120.4 | C23—C22—C21 | 121.0 (5) |
C3—C2—H2A | 120.4 | C23—C22—H22A | 119.5 |
C4—C3—C2 | 120.5 (4) | C21—C22—H22A | 119.5 |
C4—C3—H3A | 119.8 | C22—C23—C18 | 120.2 (4) |
C2—C3—H3A | 119.8 | C22—C23—H23A | 119.9 |
C5—C4—C3 | 119.6 (5) | C18—C23—H23A | 119.9 |
C5—C4—H4A | 120.2 | O4—C24—N3 | 125.7 (5) |
C3—C4—H4A | 120.2 | O4—C24—C25 | 120.4 (5) |
C4—C5—C6 | 120.3 (5) | N3—C24—C25 | 113.8 (4) |
C4—C5—H5A | 119.9 | C26—C25—C24 | 109.9 (4) |
C6—C5—H5A | 119.9 | C26—C25—H25A | 109.7 |
C1—C6—C5 | 120.4 (4) | C24—C25—H25A | 109.7 |
C1—C6—H6A | 119.8 | C26—C25—H25B | 109.7 |
C5—C6—H6A | 119.8 | C24—C25—H25B | 109.7 |
O1—C7—N1 | 122.1 (5) | H25A—C25—H25B | 108.2 |
O1—C7—C8 | 122.8 (5) | O5—C26—C25i | 121.3 (3) |
N1—C7—C8 | 115.1 (4) | O5—C26—C25 | 121.3 (3) |
C7—C8—C9 | 109.7 (4) | C25i—C26—C25 | 117.5 (7) |
C7—C8—H8A | 109.7 | C32—C27—C28 | 121.0 (4) |
C9—C8—H8A | 109.7 | C32—C27—N4 | 117.8 (4) |
C7—C8—H8B | 109.7 | C28—C27—N4 | 121.1 (5) |
C9—C8—H8B | 109.7 | C29—C28—C27 | 119.2 (4) |
H8A—C8—H8B | 108.2 | C29—C28—H28A | 120.4 |
O2—C9—C10 | 121.1 (6) | C27—C28—H28A | 120.4 |
O2—C9—C8 | 119.5 (6) | C28—C29—C30 | 120.9 (4) |
C10—C9—C8 | 119.4 (5) | C28—C29—H29A | 119.6 |
C11—C10—C9 | 109.2 (4) | C30—C29—H29A | 119.6 |
C11—C10—H10A | 109.8 | C31—C30—C29 | 119.2 (5) |
C9—C10—H10A | 109.8 | C31—C30—H30A | 120.4 |
C11—C10—H10B | 109.8 | C29—C30—H30A | 120.4 |
C9—C10—H10B | 109.8 | C30—C31—C32 | 120.9 (5) |
H10A—C10—H10B | 108.3 | C30—C31—H31A | 119.6 |
O3—C11—N2 | 122.4 (5) | C32—C31—H31A | 119.6 |
O3—C11—C10 | 123.9 (5) | C27—C32—C31 | 118.8 (4) |
N2—C11—C10 | 113.6 (4) | C27—C32—H32A | 120.6 |
C13—C12—C17 | 118.8 (5) | C31—C32—H32A | 120.6 |
C13—C12—N2 | 124.1 (4) | O6—C33—N4 | 126.1 (4) |
C17—C12—N2 | 117.0 (4) | O6—C33—C34 | 118.4 (5) |
C14—C13—C12 | 120.1 (4) | N4—C33—C34 | 115.4 (4) |
C14—C13—H13A | 119.9 | C35—C34—C33 | 112.4 (4) |
C12—C13—H13A | 119.9 | C35—C34—H34A | 109.1 |
C15—C14—C13 | 120.8 (4) | C33—C34—H34A | 109.1 |
C15—C14—H14A | 119.6 | C35—C34—H34B | 109.1 |
C13—C14—H14A | 119.6 | C33—C34—H34B | 109.1 |
C14—C15—C16 | 120.1 (5) | H34A—C34—H34B | 107.9 |
C14—C15—H15A | 120.0 | O7—C35—C34 | 121.7 (3) |
C16—C15—H15A | 120.0 | O7—C35—C34i | 121.7 (3) |
C15—C16—C17 | 119.9 (4) | C34—C35—C34i | 116.5 (7) |
C15—C16—H16A | 120.0 | | |
| | | |
C7—N1—C1—C6 | 148.4 (5) | C24—N3—C18—C23 | −145.4 (5) |
C7—N1—C1—C2 | −37.9 (7) | C24—N3—C18—C19 | 33.2 (7) |
C6—C1—C2—C3 | −0.9 (7) | C23—C18—C19—C20 | 0.7 (7) |
N1—C1—C2—C3 | −174.5 (4) | N3—C18—C19—C20 | −177.9 (4) |
C1—C2—C3—C4 | 1.0 (7) | C18—C19—C20—C21 | 0.2 (7) |
C2—C3—C4—C5 | −1.4 (7) | C19—C20—C21—C22 | −1.1 (8) |
C3—C4—C5—C6 | 1.7 (8) | C20—C21—C22—C23 | 1.3 (8) |
C2—C1—C6—C5 | 1.2 (7) | C21—C22—C23—C18 | −0.4 (7) |
N1—C1—C6—C5 | 174.9 (4) | C19—C18—C23—C22 | −0.6 (7) |
C4—C5—C6—C1 | −1.6 (7) | N3—C18—C23—C22 | 178.2 (4) |
C1—N1—C7—O1 | −9.9 (8) | C18—N3—C24—O4 | −6.6 (8) |
C1—N1—C7—C8 | 169.8 (5) | C18—N3—C24—C25 | 169.1 (4) |
O1—C7—C8—C9 | −9.8 (7) | O4—C24—C25—C26 | −7.6 (7) |
N1—C7—C8—C9 | 170.5 (4) | N3—C24—C25—C26 | 176.4 (4) |
C7—C8—C9—O2 | 101.5 (5) | C24—C25—C26—O5 | 101.5 (4) |
C7—C8—C9—C10 | −79.7 (5) | C24—C25—C26—C25i | −78.5 (4) |
O2—C9—C10—C11 | 98.8 (5) | C33—N4—C27—C32 | 146.8 (5) |
C8—C9—C10—C11 | −80.0 (5) | C33—N4—C27—C28 | −36.7 (7) |
C12—N2—C11—O3 | −9.9 (8) | C32—C27—C28—C29 | 1.5 (7) |
C12—N2—C11—C10 | 168.7 (5) | N4—C27—C28—C29 | −174.8 (4) |
C9—C10—C11—O3 | −6.0 (7) | C27—C28—C29—C30 | −0.9 (7) |
C9—C10—C11—N2 | 175.5 (4) | C28—C29—C30—C31 | 0.1 (7) |
C11—N2—C12—C13 | 36.8 (8) | C29—C30—C31—C32 | 0.1 (8) |
C11—N2—C12—C17 | −144.4 (5) | C28—C27—C32—C31 | −1.3 (7) |
C17—C12—C13—C14 | 1.9 (7) | N4—C27—C32—C31 | 175.2 (4) |
N2—C12—C13—C14 | −179.3 (4) | C30—C31—C32—C27 | 0.5 (7) |
C12—C13—C14—C15 | −0.9 (7) | C27—N4—C33—O6 | −8.7 (8) |
C13—C14—C15—C16 | −0.1 (8) | C27—N4—C33—C34 | 168.6 (5) |
C14—C15—C16—C17 | 0.1 (8) | O6—C33—C34—C35 | −8.5 (7) |
C15—C16—C17—C12 | 0.9 (7) | N4—C33—C34—C35 | 174.1 (5) |
C13—C12—C17—C16 | −1.9 (7) | C33—C34—C35—O7 | 99.7 (4) |
N2—C12—C17—C16 | 179.2 (4) | C33—C34—C35—C34i | −80.3 (4) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O6ii | 0.88 | 2.07 | 2.936 (5) | 168 |
N2—H2B···O4 | 0.88 | 2.06 | 2.922 (5) | 168 |
N3—H3B···O3iii | 0.88 | 2.09 | 2.952 (5) | 165 |
N4—H4B···O1iv | 0.88 | 2.08 | 2.942 (5) | 167 |
C8—H8A···O2v | 0.99 | 2.57 | 3.221 (6) | 124 |
C10—H10A···O2v | 0.99 | 2.56 | 3.214 (6) | 123 |
C25—H25B···O7 | 0.99 | 2.55 | 3.187 (7) | 122 |
C34—H34B···O5vi | 0.99 | 2.57 | 3.235 (7) | 124 |
C2—H2A···Cg1(C12–C17)ii | 0.95 | 2.93 | 3.694 (5) | 138 |
C5—H5A···Cg1(C12–C17)v | 0.95 | 2.95 | 3.715 (5) | 139 |
C28—H28A···Cg2(C18–C23) | 0.95 | 2.96 | 3.701 (5) | 136 |
C31—H31A···Cg2(C18–C23)vi | 0.95 | 2.97 | 3.727 (5) | 137 |
Symmetry codes: (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, y+1/2, z; (iv) −x, y+1, −z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, y+1, z. |