The title compound, C
24H
26N
4O
4, was synthesized by the reaction of methyl {2-[(3-phenyl-1,2,4-oxadiazol-5-yl)methoxy]phenyl}acetate and
N,N-dimethylformamide dimethyl acetal and crystallizes in the triclinic space group
P with two independent molecules in the asymmetric unit. The crystal packing is stabilized mainly by van der Waals interactions.
Supporting information
CCDC reference: 252976
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.073
- wR factor = 0.259
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.259
PLAT084_ALERT_2_C High R2 Value .................................. 0.26
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C21 .. 5.50 su
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C21
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXS97.
Methyl 3-dimethylamino-2-{2-[2-(dimethylamino)-1-(3-phenyl-1,2,4-oxadiazol-5-
yl)vinyloxy]phenyl}acrylate
top
Crystal data top
C24H26N4O4 | Z = 4 |
Mr = 434.49 | F(000) = 920 |
Triclinic, P1 | Dx = 1.254 Mg m−3 |
a = 11.220 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.260 (3) Å | Cell parameters from 25 reflections |
c = 17.762 (4) Å | θ = 10–13° |
α = 71.06 (3)° | µ = 0.09 mm−1 |
β = 86.35 (3)° | T = 293 K |
γ = 85.19 (3)° | Block, colourless |
V = 2301.1 (8) Å3 | 0.50 × 0.30 × 0.20 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 4761 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 26.0°, θmin = 1.2° |
ω/2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.961, Tmax = 0.974 | l = −21→21 |
9501 measured reflections | 3 standard reflections every 200 reflections |
9014 independent reflections | intensity decay: none |
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)] = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.259 | w = 1/[σ2(Fo2) + (0.1P)2 + 1.9P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.019 |
9014 reflections | Δρmax = 0.32 e Å−3 |
578 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0092 (15) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.4433 (3) | 0.7041 (3) | 0.1043 (2) | 0.0757 (10) | |
O2 | 0.2919 (2) | 0.6539 (2) | 0.01330 (16) | 0.0579 (8) | |
O3 | 0.1441 (3) | 0.8162 (3) | −0.22610 (19) | 0.0858 (11) | |
O4 | 0.0136 (3) | 0.7239 (3) | −0.13038 (19) | 0.0754 (9) | |
O5 | 0.9365 (3) | 0.2143 (3) | 0.55314 (18) | 0.0703 (9) | |
O6 | 0.7730 (2) | 0.0645 (2) | 0.56559 (16) | 0.0556 (7) | |
O7 | 0.6299 (4) | −0.1881 (3) | 0.7743 (2) | 0.0861 (11) | |
O8 | 0.5084 (3) | −0.0843 (3) | 0.6783 (2) | 0.0744 (9) | |
N1 | 0.5349 (4) | 0.7096 (4) | 0.1547 (3) | 0.0761 (12) | |
N2 | 0.5286 (3) | 0.5271 (3) | 0.1533 (2) | 0.0553 (9) | |
N3 | 0.3170 (4) | 0.9392 (3) | −0.0801 (3) | 0.0720 (11) | |
N4 | 0.2889 (4) | 0.4044 (3) | 0.0247 (2) | 0.0676 (10) | |
N5 | 1.0272 (3) | 0.2944 (4) | 0.5324 (2) | 0.0706 (11) | |
N6 | 1.0133 (3) | 0.2156 (3) | 0.4350 (2) | 0.0537 (9) | |
N7 | 0.8204 (4) | 0.0864 (4) | 0.7628 (2) | 0.0752 (12) | |
N8 | 0.7662 (3) | −0.0295 (3) | 0.4299 (2) | 0.0643 (10) | |
C1 | 0.8137 (5) | 0.4234 (5) | 0.3167 (3) | 0.0768 (15) | |
H1B | 0.8440 | 0.3468 | 0.3346 | 0.092* | |
C2 | 0.7243 (4) | 0.4551 (4) | 0.2629 (3) | 0.0660 (12) | |
H2B | 0.6948 | 0.4005 | 0.2441 | 0.079* | |
C3 | 0.6783 (4) | 0.5695 (4) | 0.2365 (2) | 0.0547 (11) | |
C4 | 0.7251 (4) | 0.6498 (4) | 0.2637 (3) | 0.0662 (12) | |
H4A | 0.6954 | 0.7265 | 0.2459 | 0.079* | |
C5 | 0.8179 (4) | 0.6160 (6) | 0.3183 (3) | 0.0810 (16) | |
H5B | 0.8506 | 0.6699 | 0.3362 | 0.097* | |
C6 | 0.8584 (5) | 0.5028 (6) | 0.3441 (3) | 0.0787 (15) | |
H6B | 0.9179 | 0.4790 | 0.3813 | 0.094* | |
C7 | 0.5799 (4) | 0.6040 (4) | 0.1802 (3) | 0.0551 (10) | |
C8 | 0.4460 (4) | 0.5908 (4) | 0.1072 (2) | 0.0563 (11) | |
C9 | 0.3611 (4) | 0.5633 (4) | 0.0619 (2) | 0.0560 (11) | |
C10 | 0.1806 (3) | 0.6846 (4) | 0.0433 (2) | 0.0487 (10) | |
C11 | 0.1386 (4) | 0.6305 (4) | 0.1197 (2) | 0.0596 (11) | |
H11A | 0.1854 | 0.5715 | 0.1542 | 0.072* | |
C12 | 0.0273 (5) | 0.6640 (5) | 0.1449 (3) | 0.0704 (13) | |
H12A | −0.0006 | 0.6284 | 0.1968 | 0.084* | |
C13 | −0.0433 (4) | 0.7505 (5) | 0.0932 (3) | 0.0760 (14) | |
H13A | −0.1195 | 0.7724 | 0.1093 | 0.091* | |
C14 | 0.0020 (4) | 0.8034 (4) | 0.0173 (3) | 0.0645 (12) | |
H14A | −0.0442 | 0.8635 | −0.0169 | 0.077* | |
C15 | 0.1130 (4) | 0.7713 (4) | −0.0104 (2) | 0.0510 (10) | |
C16 | 0.1585 (4) | 0.8233 (4) | −0.0936 (2) | 0.0529 (10) | |
C17 | 0.1079 (4) | 0.7897 (4) | −0.1567 (3) | 0.0609 (11) | |
C18 | −0.0410 (6) | 0.6898 (6) | −0.1893 (3) | 0.0992 (19) | |
H18A | −0.1064 | 0.6431 | −0.1649 | 0.149* | |
H18B | 0.0171 | 0.6461 | −0.2119 | 0.149* | |
H18C | −0.0703 | 0.7574 | −0.2305 | 0.149* | |
C19 | 0.2545 (4) | 0.8874 (4) | −0.1181 (3) | 0.0633 (12) | |
H19A | 0.2812 | 0.8969 | −0.1703 | 0.076* | |
C20 | 0.4299 (6) | 0.9880 (6) | −0.1153 (4) | 0.114 (2) | |
H20A | 0.4450 | 0.9773 | −0.1663 | 0.171* | |
H20B | 0.4939 | 0.9498 | −0.0809 | 0.171* | |
H20C | 0.4249 | 1.0691 | −0.1217 | 0.171* | |
C21 | 0.2822 (5) | 0.9499 (5) | −0.0030 (4) | 0.0877 (16) | |
H21A | 0.2073 | 0.9157 | 0.0151 | 0.132* | |
H21B | 0.2737 | 1.0302 | −0.0070 | 0.132* | |
H21C | 0.3425 | 0.9110 | 0.0343 | 0.132* | |
C22 | 0.3581 (4) | 0.4514 (4) | 0.0627 (2) | 0.0593 (11) | |
H22A | 0.4136 | 0.3994 | 0.0951 | 0.071* | |
C23 | 0.3036 (6) | 0.2810 (5) | 0.0373 (3) | 0.0869 (16) | |
H23A | 0.3618 | 0.2460 | 0.0769 | 0.130* | |
H23B | 0.3302 | 0.2681 | −0.0118 | 0.130* | |
H23C | 0.2284 | 0.2472 | 0.0550 | 0.130* | |
C24 | 0.2024 (5) | 0.4682 (5) | −0.0320 (3) | 0.0829 (16) | |
H24A | 0.1992 | 0.5483 | −0.0359 | 0.124* | |
H24B | 0.1251 | 0.4387 | −0.0149 | 0.124* | |
H24C | 0.2248 | 0.4602 | −0.0831 | 0.124* | |
C31 | 1.2869 (5) | 0.5200 (5) | 0.3992 (3) | 0.0785 (15) | |
H31A | 1.3102 | 0.5795 | 0.4155 | 0.094* | |
C32 | 1.1978 (4) | 0.4508 (4) | 0.4425 (3) | 0.0660 (12) | |
H32A | 1.1618 | 0.4641 | 0.4877 | 0.079* | |
C33 | 1.1627 (3) | 0.3622 (4) | 0.4183 (2) | 0.0516 (10) | |
C34 | 1.2171 (4) | 0.3454 (4) | 0.3503 (3) | 0.0623 (12) | |
H34A | 1.1936 | 0.2872 | 0.3327 | 0.075* | |
C35 | 1.3059 (4) | 0.4147 (4) | 0.3087 (3) | 0.0696 (13) | |
H35A | 1.3428 | 0.4020 | 0.2636 | 0.084* | |
C36 | 1.3402 (5) | 0.5015 (5) | 0.3331 (3) | 0.0771 (14) | |
H36A | 1.4000 | 0.5480 | 0.3046 | 0.093* | |
C37 | 1.0681 (4) | 0.2888 (4) | 0.4633 (2) | 0.0544 (10) | |
C38 | 0.9341 (4) | 0.1725 (4) | 0.4915 (2) | 0.0543 (10) | |
C39 | 0.8449 (4) | 0.0927 (4) | 0.4963 (2) | 0.0523 (10) | |
C40 | 0.6763 (3) | 0.1406 (3) | 0.5701 (2) | 0.0463 (9) | |
C41 | 0.6150 (4) | 0.1170 (3) | 0.6439 (2) | 0.0484 (10) | |
C42 | 0.5186 (4) | 0.1904 (4) | 0.6499 (3) | 0.0630 (12) | |
H42A | 0.4774 | 0.1767 | 0.6988 | 0.076* | |
C43 | 0.4799 (4) | 0.2835 (4) | 0.5867 (3) | 0.0651 (12) | |
H43A | 0.4132 | 0.3308 | 0.5927 | 0.078* | |
C44 | 0.5417 (4) | 0.3047 (4) | 0.5154 (3) | 0.0610 (12) | |
H44A | 0.5173 | 0.3681 | 0.4725 | 0.073* | |
C45 | 0.6399 (4) | 0.2339 (3) | 0.5055 (2) | 0.0543 (10) | |
H45A | 0.6807 | 0.2486 | 0.4564 | 0.065* | |
C46 | 0.6565 (4) | 0.0131 (4) | 0.7111 (2) | 0.0546 (10) | |
C47 | 0.6013 (4) | −0.0954 (4) | 0.7257 (3) | 0.0596 (11) | |
C48 | 0.4479 (5) | −0.1877 (4) | 0.6885 (4) | 0.0930 (18) | |
H48A | 0.3842 | −0.1704 | 0.6519 | 0.140* | |
H48B | 0.4155 | −0.2161 | 0.7421 | 0.140* | |
H48C | 0.5037 | −0.2455 | 0.6783 | 0.140* | |
C49 | 0.7513 (4) | 0.0064 (4) | 0.7561 (3) | 0.0613 (12) | |
H49A | 0.7726 | −0.0681 | 0.7888 | 0.074* | |
C50 | 0.9255 (6) | 0.0518 (6) | 0.8096 (4) | 0.106 (2) | |
H50A | 0.9341 | −0.0310 | 0.8308 | 0.159* | |
H50B | 0.9177 | 0.0836 | 0.8526 | 0.159* | |
H50C | 0.9948 | 0.0799 | 0.7766 | 0.159* | |
C51 | 0.7953 (5) | 0.2088 (4) | 0.7271 (3) | 0.0826 (15) | |
H51A | 0.7242 | 0.2227 | 0.6971 | 0.124* | |
H51B | 0.8614 | 0.2411 | 0.6922 | 0.124* | |
H51C | 0.7837 | 0.2444 | 0.7681 | 0.124* | |
C52 | 0.8406 (4) | 0.0451 (4) | 0.4382 (3) | 0.0565 (11) | |
H52A | 0.8986 | 0.0677 | 0.3974 | 0.068* | |
C53 | 0.6704 (5) | −0.0789 (4) | 0.4859 (3) | 0.0797 (15) | |
H53A | 0.6678 | −0.0490 | 0.5298 | 0.120* | |
H53B | 0.6843 | −0.1615 | 0.5054 | 0.120* | |
H53C | 0.5955 | −0.0590 | 0.4599 | 0.120* | |
C54 | 0.7804 (5) | −0.0680 (4) | 0.3598 (3) | 0.0774 (14) | |
H54A | 0.8446 | −0.0300 | 0.3257 | 0.116* | |
H54B | 0.7075 | −0.0492 | 0.3314 | 0.116* | |
H54C | 0.7984 | −0.1501 | 0.3764 | 0.116* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.067 (2) | 0.060 (2) | 0.095 (2) | 0.0049 (16) | −0.0298 (18) | −0.0141 (17) |
O2 | 0.0496 (16) | 0.0637 (18) | 0.0490 (16) | 0.0023 (14) | −0.0027 (13) | −0.0039 (14) |
O3 | 0.105 (3) | 0.101 (3) | 0.050 (2) | −0.028 (2) | −0.0010 (19) | −0.0182 (18) |
O4 | 0.076 (2) | 0.096 (3) | 0.062 (2) | −0.0223 (19) | −0.0046 (17) | −0.0313 (18) |
O5 | 0.065 (2) | 0.093 (2) | 0.0583 (18) | −0.0226 (18) | 0.0084 (15) | −0.0306 (17) |
O6 | 0.0519 (16) | 0.0519 (16) | 0.0538 (17) | 0.0034 (13) | 0.0003 (13) | −0.0062 (13) |
O7 | 0.118 (3) | 0.054 (2) | 0.076 (2) | −0.0125 (19) | −0.024 (2) | −0.0017 (18) |
O8 | 0.078 (2) | 0.0550 (19) | 0.087 (2) | −0.0083 (16) | −0.0188 (19) | −0.0132 (17) |
N1 | 0.068 (3) | 0.065 (3) | 0.095 (3) | 0.001 (2) | −0.030 (2) | −0.022 (2) |
N2 | 0.048 (2) | 0.057 (2) | 0.054 (2) | 0.0039 (17) | −0.0083 (17) | −0.0093 (17) |
N3 | 0.076 (3) | 0.065 (2) | 0.078 (3) | −0.019 (2) | 0.000 (2) | −0.023 (2) |
N4 | 0.080 (3) | 0.065 (3) | 0.059 (2) | 0.000 (2) | −0.016 (2) | −0.0194 (19) |
N5 | 0.063 (2) | 0.093 (3) | 0.064 (2) | −0.022 (2) | 0.007 (2) | −0.033 (2) |
N6 | 0.051 (2) | 0.055 (2) | 0.053 (2) | −0.0035 (17) | −0.0030 (17) | −0.0135 (17) |
N7 | 0.086 (3) | 0.063 (3) | 0.078 (3) | 0.001 (2) | −0.026 (2) | −0.022 (2) |
N8 | 0.066 (2) | 0.059 (2) | 0.065 (2) | −0.0086 (19) | 0.0013 (19) | −0.0146 (19) |
C1 | 0.071 (3) | 0.080 (4) | 0.062 (3) | 0.011 (3) | −0.010 (3) | 0.000 (3) |
C2 | 0.067 (3) | 0.066 (3) | 0.057 (3) | −0.002 (2) | −0.007 (2) | −0.009 (2) |
C3 | 0.046 (2) | 0.066 (3) | 0.048 (2) | −0.005 (2) | 0.0018 (19) | −0.012 (2) |
C4 | 0.055 (3) | 0.080 (3) | 0.072 (3) | 0.007 (2) | −0.003 (2) | −0.037 (3) |
C5 | 0.056 (3) | 0.123 (5) | 0.081 (4) | 0.005 (3) | −0.006 (3) | −0.058 (4) |
C6 | 0.062 (3) | 0.113 (5) | 0.058 (3) | 0.018 (3) | −0.011 (2) | −0.028 (3) |
C7 | 0.049 (2) | 0.057 (3) | 0.057 (3) | 0.002 (2) | −0.004 (2) | −0.015 (2) |
C8 | 0.056 (3) | 0.057 (3) | 0.049 (2) | −0.001 (2) | 0.002 (2) | −0.009 (2) |
C9 | 0.050 (2) | 0.058 (3) | 0.053 (2) | −0.002 (2) | −0.004 (2) | −0.008 (2) |
C10 | 0.045 (2) | 0.058 (2) | 0.046 (2) | −0.0076 (19) | 0.0020 (18) | −0.021 (2) |
C11 | 0.060 (3) | 0.066 (3) | 0.049 (3) | −0.009 (2) | −0.004 (2) | −0.012 (2) |
C12 | 0.073 (3) | 0.087 (4) | 0.057 (3) | −0.024 (3) | 0.016 (3) | −0.031 (3) |
C13 | 0.053 (3) | 0.104 (4) | 0.077 (3) | 0.002 (3) | 0.001 (3) | −0.039 (3) |
C14 | 0.056 (3) | 0.074 (3) | 0.063 (3) | 0.001 (2) | −0.002 (2) | −0.024 (2) |
C15 | 0.046 (2) | 0.057 (2) | 0.054 (2) | −0.0034 (19) | −0.0083 (19) | −0.022 (2) |
C16 | 0.049 (2) | 0.055 (2) | 0.050 (2) | 0.002 (2) | −0.0079 (19) | −0.011 (2) |
C17 | 0.066 (3) | 0.058 (3) | 0.054 (3) | 0.000 (2) | −0.004 (2) | −0.011 (2) |
C18 | 0.104 (4) | 0.130 (5) | 0.086 (4) | −0.031 (4) | −0.008 (3) | −0.059 (4) |
C19 | 0.071 (3) | 0.058 (3) | 0.055 (3) | −0.005 (2) | −0.006 (2) | −0.009 (2) |
C20 | 0.093 (5) | 0.107 (5) | 0.148 (6) | −0.049 (4) | 0.012 (4) | −0.041 (4) |
C21 | 0.094 (4) | 0.071 (3) | 0.108 (5) | −0.017 (3) | −0.013 (3) | −0.037 (3) |
C22 | 0.062 (3) | 0.065 (3) | 0.046 (2) | −0.003 (2) | −0.002 (2) | −0.011 (2) |
C23 | 0.112 (5) | 0.080 (4) | 0.070 (3) | −0.009 (3) | −0.022 (3) | −0.021 (3) |
C24 | 0.081 (4) | 0.104 (4) | 0.070 (3) | 0.011 (3) | −0.027 (3) | −0.036 (3) |
C31 | 0.077 (3) | 0.074 (3) | 0.088 (4) | −0.021 (3) | −0.008 (3) | −0.026 (3) |
C32 | 0.069 (3) | 0.068 (3) | 0.064 (3) | −0.001 (3) | −0.007 (2) | −0.027 (2) |
C33 | 0.041 (2) | 0.058 (3) | 0.052 (2) | 0.0020 (19) | −0.0075 (19) | −0.014 (2) |
C34 | 0.060 (3) | 0.065 (3) | 0.057 (3) | −0.001 (2) | −0.007 (2) | −0.014 (2) |
C35 | 0.069 (3) | 0.067 (3) | 0.065 (3) | −0.005 (3) | 0.005 (2) | −0.012 (2) |
C36 | 0.069 (3) | 0.073 (3) | 0.079 (4) | −0.010 (3) | 0.000 (3) | −0.010 (3) |
C37 | 0.051 (2) | 0.061 (3) | 0.051 (2) | 0.002 (2) | −0.009 (2) | −0.017 (2) |
C38 | 0.046 (2) | 0.062 (3) | 0.053 (3) | 0.005 (2) | −0.005 (2) | −0.016 (2) |
C39 | 0.048 (2) | 0.057 (3) | 0.047 (2) | 0.003 (2) | 0.0035 (19) | −0.012 (2) |
C40 | 0.042 (2) | 0.043 (2) | 0.054 (2) | −0.0067 (18) | −0.0020 (18) | −0.0158 (18) |
C41 | 0.053 (2) | 0.045 (2) | 0.047 (2) | −0.0080 (19) | −0.0013 (19) | −0.0129 (18) |
C42 | 0.062 (3) | 0.060 (3) | 0.062 (3) | 0.003 (2) | 0.005 (2) | −0.017 (2) |
C43 | 0.060 (3) | 0.051 (3) | 0.080 (3) | 0.008 (2) | −0.001 (3) | −0.020 (2) |
C44 | 0.057 (3) | 0.046 (2) | 0.069 (3) | 0.003 (2) | −0.014 (2) | −0.004 (2) |
C45 | 0.054 (2) | 0.053 (2) | 0.048 (2) | 0.001 (2) | −0.0062 (19) | −0.005 (2) |
C46 | 0.063 (3) | 0.054 (3) | 0.043 (2) | 0.002 (2) | −0.006 (2) | −0.0104 (19) |
C47 | 0.073 (3) | 0.049 (3) | 0.051 (2) | −0.004 (2) | −0.001 (2) | −0.008 (2) |
C48 | 0.091 (4) | 0.063 (3) | 0.125 (5) | −0.021 (3) | −0.021 (4) | −0.023 (3) |
C49 | 0.076 (3) | 0.053 (3) | 0.048 (2) | 0.002 (2) | −0.005 (2) | −0.008 (2) |
C50 | 0.096 (4) | 0.112 (5) | 0.113 (5) | 0.000 (4) | −0.044 (4) | −0.033 (4) |
C51 | 0.098 (4) | 0.070 (3) | 0.084 (4) | −0.013 (3) | −0.024 (3) | −0.024 (3) |
C52 | 0.052 (3) | 0.052 (2) | 0.058 (3) | −0.001 (2) | −0.001 (2) | −0.008 (2) |
C53 | 0.079 (4) | 0.072 (3) | 0.086 (4) | −0.022 (3) | 0.007 (3) | −0.020 (3) |
C54 | 0.098 (4) | 0.069 (3) | 0.071 (3) | −0.011 (3) | −0.001 (3) | −0.028 (3) |
Geometric parameters (Å, º) top
O1—C8 | 1.371 (5) | C18—H18B | 0.9600 |
O1—N1 | 1.424 (5) | C18—H18C | 0.9600 |
O2—C9 | 1.378 (5) | C19—H19A | 0.9300 |
O2—C10 | 1.397 (5) | C20—H20A | 0.9600 |
O3—C17 | 1.220 (5) | C20—H20B | 0.9600 |
O4—C17 | 1.351 (5) | C20—H20C | 0.9600 |
O4—C18 | 1.433 (6) | C21—H21A | 0.9600 |
O5—C38 | 1.354 (5) | C21—H21B | 0.9600 |
O5—N5 | 1.422 (5) | C21—H21C | 0.9600 |
O6—C40 | 1.386 (5) | C22—H22A | 0.9300 |
O6—C39 | 1.389 (5) | C23—H23A | 0.9600 |
O7—C47 | 1.215 (5) | C23—H23B | 0.9600 |
O8—C47 | 1.351 (5) | C23—H23C | 0.9600 |
O8—C48 | 1.443 (6) | C24—H24A | 0.9600 |
N1—C7 | 1.295 (6) | C24—H24B | 0.9600 |
N2—C8 | 1.303 (5) | C24—H24C | 0.9600 |
N2—C7 | 1.367 (5) | C31—C36 | 1.359 (7) |
N3—C19 | 1.328 (6) | C31—C32 | 1.389 (7) |
N3—C21 | 1.445 (7) | C31—H31A | 0.9300 |
N3—C20 | 1.462 (7) | C32—C33 | 1.384 (6) |
N4—C22 | 1.336 (6) | C32—H32A | 0.9300 |
N4—C24 | 1.432 (6) | C33—C34 | 1.385 (6) |
N4—C23 | 1.453 (6) | C33—C37 | 1.470 (6) |
N5—C37 | 1.304 (5) | C34—C35 | 1.379 (6) |
N6—C38 | 1.303 (5) | C34—H34A | 0.9300 |
N6—C37 | 1.365 (5) | C35—C36 | 1.364 (7) |
N7—C49 | 1.338 (6) | C35—H35A | 0.9300 |
N7—C51 | 1.437 (6) | C36—H36A | 0.9300 |
N7—C50 | 1.441 (6) | C38—C39 | 1.437 (6) |
N8—C52 | 1.337 (5) | C39—C52 | 1.345 (6) |
N8—C53 | 1.448 (6) | C40—C45 | 1.385 (5) |
N8—C54 | 1.462 (6) | C40—C41 | 1.396 (5) |
C1—C6 | 1.364 (7) | C41—C42 | 1.369 (6) |
C1—C2 | 1.373 (6) | C41—C46 | 1.499 (6) |
C1—H1B | 0.9300 | C42—C43 | 1.377 (6) |
C2—C3 | 1.391 (6) | C42—H42A | 0.9300 |
C2—H2B | 0.9300 | C43—C44 | 1.363 (6) |
C3—C4 | 1.380 (6) | C43—H43A | 0.9300 |
C3—C7 | 1.479 (6) | C44—C45 | 1.383 (6) |
C4—C5 | 1.411 (7) | C44—H44A | 0.9300 |
C4—H4A | 0.9300 | C45—H45A | 0.9300 |
C5—C6 | 1.361 (8) | C46—C49 | 1.353 (6) |
C5—H5B | 0.9300 | C46—C47 | 1.454 (6) |
C6—H6B | 0.9300 | C48—H48A | 0.9600 |
C8—C9 | 1.414 (6) | C48—H48B | 0.9600 |
C9—C22 | 1.371 (6) | C48—H48C | 0.9600 |
C10—C11 | 1.374 (6) | C49—H49A | 0.9300 |
C10—C15 | 1.383 (6) | C50—H50A | 0.9600 |
C11—C12 | 1.375 (6) | C50—H50B | 0.9600 |
C11—H11A | 0.9300 | C50—H50C | 0.9600 |
C12—C13 | 1.384 (7) | C51—H51A | 0.9600 |
C12—H12A | 0.9300 | C51—H51B | 0.9600 |
C13—C14 | 1.377 (7) | C51—H51C | 0.9600 |
C13—H13A | 0.9300 | C52—H52A | 0.9300 |
C14—C15 | 1.384 (6) | C53—H53A | 0.9600 |
C14—H14A | 0.9300 | C53—H53B | 0.9600 |
C15—C16 | 1.482 (6) | C53—H53C | 0.9600 |
C16—C19 | 1.351 (6) | C54—H54A | 0.9600 |
C16—C17 | 1.472 (6) | C54—H54B | 0.9600 |
C18—H18A | 0.9600 | C54—H54C | 0.9600 |
| | | |
C8—O1—N1 | 105.9 (3) | N4—C23—H23B | 109.5 |
C9—O2—C10 | 118.4 (3) | H23A—C23—H23B | 109.5 |
C17—O4—C18 | 115.7 (4) | N4—C23—H23C | 109.5 |
C38—O5—N5 | 106.1 (3) | H23A—C23—H23C | 109.5 |
C40—O6—C39 | 117.6 (3) | H23B—C23—H23C | 109.5 |
C47—O8—C48 | 116.3 (4) | N4—C24—H24A | 109.5 |
C7—N1—O1 | 103.2 (4) | N4—C24—H24B | 109.5 |
C8—N2—C7 | 103.3 (4) | H24A—C24—H24B | 109.5 |
C19—N3—C21 | 124.1 (4) | N4—C24—H24C | 109.5 |
C19—N3—C20 | 120.3 (5) | H24A—C24—H24C | 109.5 |
C21—N3—C20 | 115.6 (5) | H24B—C24—H24C | 109.5 |
C22—N4—C24 | 124.6 (4) | C36—C31—C32 | 120.7 (5) |
C22—N4—C23 | 119.5 (4) | C36—C31—H31A | 119.7 |
C24—N4—C23 | 115.9 (4) | C32—C31—H31A | 119.7 |
C37—N5—O5 | 102.8 (3) | C31—C32—C33 | 119.8 (5) |
C38—N6—C37 | 102.8 (4) | C31—C32—H32A | 120.1 |
C49—N7—C51 | 124.0 (4) | C33—C32—H32A | 120.1 |
C49—N7—C50 | 120.0 (4) | C34—C33—C32 | 118.8 (4) |
C51—N7—C50 | 116.0 (5) | C34—C33—C37 | 120.8 (4) |
C52—N8—C53 | 125.3 (4) | C32—C33—C37 | 120.4 (4) |
C52—N8—C54 | 119.5 (4) | C35—C34—C33 | 120.3 (5) |
C53—N8—C54 | 115.2 (4) | C35—C34—H34A | 119.9 |
C6—C1—C2 | 120.8 (5) | C33—C34—H34A | 119.9 |
C6—C1—H1B | 119.6 | C36—C35—C34 | 120.6 (5) |
C2—C1—H1B | 119.6 | C36—C35—H35A | 119.7 |
C1—C2—C3 | 119.6 (5) | C34—C35—H35A | 119.7 |
C1—C2—H2B | 120.2 | C31—C36—C35 | 119.9 (5) |
C3—C2—H2B | 120.2 | C31—C36—H36A | 120.1 |
C4—C3—C2 | 119.4 (4) | C35—C36—H36A | 120.1 |
C4—C3—C7 | 120.6 (4) | N5—C37—N6 | 115.6 (4) |
C2—C3—C7 | 120.0 (4) | N5—C37—C33 | 121.0 (4) |
C3—C4—C5 | 120.4 (5) | N6—C37—C33 | 123.3 (4) |
C3—C4—H4A | 119.8 | N6—C38—O5 | 112.8 (4) |
C5—C4—H4A | 119.8 | N6—C38—C39 | 130.1 (4) |
C6—C5—C4 | 118.5 (5) | O5—C38—C39 | 117.0 (4) |
C6—C5—H5B | 120.7 | C52—C39—O6 | 124.4 (4) |
C4—C5—H5B | 120.7 | C52—C39—C38 | 119.8 (4) |
C1—C6—C5 | 121.4 (5) | O6—C39—C38 | 115.6 (4) |
C1—C6—H6B | 119.3 | C45—C40—O6 | 122.9 (4) |
C5—C6—H6B | 119.3 | C45—C40—C41 | 121.1 (4) |
N1—C7—N2 | 115.7 (4) | O6—C40—C41 | 116.0 (3) |
N1—C7—C3 | 121.6 (4) | C42—C41—C40 | 117.2 (4) |
N2—C7—C3 | 122.7 (4) | C42—C41—C46 | 124.0 (4) |
N2—C8—O1 | 112.0 (4) | C40—C41—C46 | 118.8 (4) |
N2—C8—C9 | 131.6 (4) | C41—C42—C43 | 123.1 (4) |
O1—C8—C9 | 116.4 (4) | C41—C42—H42A | 118.5 |
C22—C9—O2 | 123.2 (4) | C43—C42—H42A | 118.5 |
C22—C9—C8 | 119.4 (4) | C44—C43—C42 | 118.5 (4) |
O2—C9—C8 | 117.1 (4) | C44—C43—H43A | 120.8 |
C11—C10—C15 | 122.0 (4) | C42—C43—H43A | 120.8 |
C11—C10—O2 | 122.9 (4) | C43—C44—C45 | 121.3 (4) |
C15—C10—O2 | 115.1 (3) | C43—C44—H44A | 119.4 |
C10—C11—C12 | 119.8 (4) | C45—C44—H44A | 119.4 |
C10—C11—H11A | 120.1 | C44—C45—C40 | 118.9 (4) |
C12—C11—H11A | 120.1 | C44—C45—H45A | 120.6 |
C11—C12—C13 | 120.3 (4) | C40—C45—H45A | 120.6 |
C11—C12—H12A | 119.9 | C49—C46—C47 | 114.8 (4) |
C13—C12—H12A | 119.9 | C49—C46—C41 | 125.5 (4) |
C14—C13—C12 | 118.4 (5) | C47—C46—C41 | 119.3 (4) |
C14—C13—H13A | 120.8 | O7—C47—O8 | 120.7 (4) |
C12—C13—H13A | 120.8 | O7—C47—C46 | 126.9 (4) |
C13—C14—C15 | 123.0 (5) | O8—C47—C46 | 112.3 (4) |
C13—C14—H14A | 118.5 | O8—C48—H48A | 109.5 |
C15—C14—H14A | 118.5 | O8—C48—H48B | 109.5 |
C10—C15—C14 | 116.5 (4) | H48A—C48—H48B | 109.5 |
C10—C15—C16 | 120.5 (4) | O8—C48—H48C | 109.5 |
C14—C15—C16 | 123.0 (4) | H48A—C48—H48C | 109.5 |
C19—C16—C17 | 114.1 (4) | H48B—C48—H48C | 109.5 |
C19—C16—C15 | 126.9 (4) | N7—C49—C46 | 132.3 (4) |
C17—C16—C15 | 118.4 (4) | N7—C49—H49A | 113.8 |
O3—C17—O4 | 121.3 (4) | C46—C49—H49A | 113.8 |
O3—C17—C16 | 125.7 (4) | N7—C50—H50A | 109.5 |
O4—C17—C16 | 112.9 (4) | N7—C50—H50B | 109.5 |
O4—C18—H18A | 109.5 | H50A—C50—H50B | 109.5 |
O4—C18—H18B | 109.5 | N7—C50—H50C | 109.5 |
H18A—C18—H18B | 109.5 | H50A—C50—H50C | 109.5 |
O4—C18—H18C | 109.5 | H50B—C50—H50C | 109.5 |
H18A—C18—H18C | 109.5 | N7—C51—H51A | 109.5 |
H18B—C18—H18C | 109.5 | N7—C51—H51B | 109.5 |
N3—C19—C16 | 130.9 (4) | H51A—C51—H51B | 109.5 |
N3—C19—H19A | 114.6 | N7—C51—H51C | 109.5 |
C16—C19—H19A | 114.6 | H51A—C51—H51C | 109.5 |
N3—C20—H20A | 109.5 | H51B—C51—H51C | 109.5 |
N3—C20—H20B | 109.5 | C39—C52—N8 | 130.2 (4) |
H20A—C20—H20B | 109.5 | C39—C52—H52A | 114.9 |
N3—C20—H20C | 109.5 | N8—C52—H52A | 114.9 |
H20A—C20—H20C | 109.5 | N8—C53—H53A | 109.5 |
H20B—C20—H20C | 109.5 | N8—C53—H53B | 109.5 |
N3—C21—H21A | 109.5 | H53A—C53—H53B | 109.5 |
N3—C21—H21B | 109.5 | N8—C53—H53C | 109.5 |
H21A—C21—H21B | 109.5 | H53A—C53—H53C | 109.5 |
N3—C21—H21C | 109.5 | H53B—C53—H53C | 109.5 |
H21A—C21—H21C | 109.5 | N8—C54—H54A | 109.5 |
H21B—C21—H21C | 109.5 | N8—C54—H54B | 109.5 |
N4—C22—C9 | 130.8 (4) | H54A—C54—H54B | 109.5 |
N4—C22—H22A | 114.6 | N8—C54—H54C | 109.5 |
C9—C22—H22A | 114.6 | H54A—C54—H54C | 109.5 |
N4—C23—H23A | 109.5 | H54B—C54—H54C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19A···O3 | 0.93 | 2.33 | 2.747 (6) | 107 |
C23—H23A···O7i | 0.96 | 2.51 | 3.280 (6) | 137 |
C24—H24A···O2 | 0.96 | 2.14 | 2.918 (7) | 137 |
C49—H49A···O7 | 0.93 | 2.34 | 2.763 (6) | 107 |
C53—H53A···O6 | 0.96 | 2.16 | 2.929 (6) | 136 |
Symmetry code: (i) −x+1, −y, −z+1. |