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The asymmetric unit of the title compound (systematic name:
N,
N′,
N′′-tribenzyloxyiminodicarbonic diamide), C
23H
23N
3O
5, consists of two molecules. In the crystalline state, the molecules are assembled into centrosymmetric dimers by strong N—H
O=C intermolecular hydrogen bonds. The results of IR and NMR spectroscopic analysis are in good agreement with the crystallographic study.
Supporting information
CCDC reference: 601129
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.149
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O13 .. O13 .. 2.68 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact O23 .. O23 .. 2.68 Ang.
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C122
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C112
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C112 -C117 1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C118 -C123 1.37 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11N .. O13 .. 2.75 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21N .. O23 .. 2.66 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
N,
N',
N''-tribenzyloxyiminodicarbonic diamide
top
Crystal data top
C23H23N3O5 | Z = 4 |
Mr = 421.44 | F(000) = 888 |
Triclinic, P1 | Dx = 1.285 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9947 (17) Å | Cell parameters from 1132 reflections |
b = 13.820 (3) Å | θ = 4.6–27.5° |
c = 18.714 (3) Å | µ = 0.09 mm−1 |
α = 100.763 (14)° | T = 295 K |
β = 90.447 (14)° | Prism, colorless |
γ = 107.227 (16)° | 0.60 × 0.36 × 0.21 mm |
V = 2177.9 (8) Å3 | |
Data collection top
Oxford Diffraction Xcalibur CCD diffractometer | 5022 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 4.0° |
ω scans | h = −9→10 |
16124 measured reflections | k = −16→14 |
7635 independent reflections | l = −22→22 |
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)] = 0.048 | All H-atom parameters refined |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
7635 reflections | Δρmax = 0.23 e Å−3 |
744 parameters | Δρmin = −0.22 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: 0.0052 (13) |
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 | |
C11 | 0.4860 (2) | 0.57202 (17) | −0.13221 (13) | 0.0583 (5) | |
C12 | 0.2960 (2) | 0.55625 (15) | 0.00449 (11) | 0.0475 (5) | |
C13 | 0.0713 (3) | 0.32353 (16) | 0.01483 (15) | 0.0596 (6) | |
C14 | 0.1639 (2) | 0.54097 (15) | 0.12038 (10) | 0.0511 (5) | |
C15 | 0.3502 (3) | 0.6692 (2) | 0.28214 (12) | 0.0700 (7) | |
C16 | 0.6071 (2) | 0.67069 (15) | −0.13750 (11) | 0.0509 (5) | |
C17 | 0.6322 (3) | 0.75761 (17) | −0.08268 (13) | 0.0595 (5) | |
C18 | 0.7485 (3) | 0.8466 (2) | −0.08613 (17) | 0.0759 (7) | |
C19 | 0.8413 (4) | 0.8500 (3) | −0.14379 (19) | 0.0911 (9) | |
C25 | 0.8465 (3) | 0.6692 (2) | 0.26311 (13) | 0.0671 (6) | |
C24 | 0.6657 (2) | 0.54022 (15) | 0.39007 (10) | 0.0484 (5) | |
C23 | 0.5708 (3) | 0.32404 (16) | 0.43819 (14) | 0.0573 (5) | |
C22 | 0.8005 (2) | 0.55752 (14) | 0.51134 (11) | 0.0474 (5) | |
C21 | 0.9866 (2) | 0.57550 (17) | 0.65548 (14) | 0.0592 (5) | |
C228 | 0.8234 (2) | 0.75369 (16) | 0.22898 (11) | 0.0568 (5) | |
C223 | 0.9016 (3) | 0.8559 (2) | 0.25854 (14) | 0.0841 (8) | |
C222 | 0.8760 (4) | 0.9340 (2) | 0.22820 (17) | 0.0976 (10) | |
C221 | 0.7740 (4) | 0.9109 (2) | 0.16821 (16) | 0.0851 (8) | |
C110 | 0.8189 (3) | 0.7653 (3) | −0.19797 (17) | 0.0858 (8) | |
C111 | 0.7008 (3) | 0.6755 (2) | −0.19610 (13) | 0.0660 (6) | |
C112 | −0.0805 (2) | 0.24652 (14) | −0.01588 (12) | 0.0532 (5) | |
C113 | −0.1172 (3) | 0.2190 (2) | −0.08933 (15) | 0.0804 (7) | |
C114 | −0.2575 (4) | 0.1470 (3) | −0.1173 (2) | 0.1006 (10) | |
C115 | −0.3603 (4) | 0.1024 (2) | −0.0721 (3) | 0.0973 (10) | |
C116 | −0.3278 (4) | 0.1304 (2) | 0.0010 (3) | 0.0994 (10) | |
C117 | −0.1889 (3) | 0.2022 (2) | 0.02929 (17) | 0.0794 (7) | |
C118 | 0.3336 (2) | 0.75402 (16) | 0.34099 (11) | 0.0557 (5) | |
C119 | 0.2335 (3) | 0.73244 (18) | 0.39478 (12) | 0.0578 (5) | |
C120 | 0.2161 (3) | 0.8098 (2) | 0.44873 (15) | 0.0716 (7) | |
C121 | 0.2976 (4) | 0.9092 (2) | 0.44898 (17) | 0.0872 (8) | |
C122 | 0.3974 (4) | 0.9323 (2) | 0.3955 (2) | 0.1037 (11) | |
C123 | 0.4166 (4) | 0.8551 (2) | 0.34166 (16) | 0.0843 (8) | |
C220 | 0.6968 (3) | 0.81077 (18) | 0.13857 (14) | 0.0690 (6) | |
C219 | 0.7204 (3) | 0.73266 (17) | 0.16947 (12) | 0.0573 (5) | |
C212 | 0.4146 (2) | 0.25025 (14) | 0.44407 (11) | 0.0508 (5) | |
C217 | 0.3153 (3) | 0.20360 (19) | 0.38248 (15) | 0.0725 (6) | |
C216 | 0.1716 (4) | 0.1358 (2) | 0.3875 (2) | 0.0923 (9) | |
C215 | 0.1223 (4) | 0.1158 (2) | 0.4530 (2) | 0.0884 (9) | |
C214 | 0.2174 (4) | 0.1615 (2) | 0.5148 (2) | 0.0803 (8) | |
C213 | 0.3642 (3) | 0.22897 (18) | 0.51034 (14) | 0.0649 (6) | |
C26 | 1.1113 (2) | 0.67332 (15) | 0.68792 (11) | 0.0513 (5) | |
C211 | 1.2052 (3) | 0.6782 (2) | 0.74839 (13) | 0.0675 (6) | |
C210 | 1.3267 (3) | 0.7666 (2) | 0.77465 (16) | 0.0857 (8) | |
C29 | 1.3539 (3) | 0.8505 (2) | 0.74203 (17) | 0.0847 (8) | |
C28 | 1.2599 (3) | 0.8466 (2) | 0.68295 (16) | 0.0743 (7) | |
C27 | 1.1403 (3) | 0.75911 (17) | 0.65572 (13) | 0.0585 (5) | |
N11 | 0.2589 (2) | 0.52505 (13) | −0.06847 (9) | 0.0503 (4) | |
N12 | 0.19127 (17) | 0.50087 (12) | 0.04792 (8) | 0.0483 (4) | |
N13 | 0.2936 (2) | 0.60930 (15) | 0.15788 (10) | 0.0618 (5) | |
N23 | 0.7960 (2) | 0.60574 (14) | 0.37012 (10) | 0.0569 (4) | |
N22 | 0.69409 (17) | 0.50026 (11) | 0.45207 (8) | 0.0470 (4) | |
N21 | 0.7617 (2) | 0.53005 (13) | 0.57628 (9) | 0.0508 (4) | |
O11 | 0.34687 (15) | 0.59685 (10) | −0.10859 (7) | 0.0554 (4) | |
O12 | 0.41561 (16) | 0.62236 (11) | 0.03163 (8) | 0.0613 (4) | |
O13 | 0.05955 (14) | 0.42515 (9) | 0.01034 (7) | 0.0484 (3) | |
O14 | 0.03898 (17) | 0.50977 (12) | 0.14511 (8) | 0.0651 (4) | |
O15 | 0.26213 (17) | 0.67409 (12) | 0.21962 (7) | 0.0681 (4) | |
O25 | 0.76378 (17) | 0.67237 (11) | 0.32762 (8) | 0.0648 (4) | |
O24 | 0.53865 (16) | 0.51079 (12) | 0.35762 (8) | 0.0632 (4) | |
O23 | 0.56165 (14) | 0.42660 (9) | 0.46911 (7) | 0.0474 (3) | |
O22 | 0.92132 (16) | 0.62112 (11) | 0.50195 (8) | 0.0597 (4) | |
O21 | 0.85086 (15) | 0.60281 (10) | 0.63599 (7) | 0.0553 (4) | |
H11A | 0.517 (3) | 0.5341 (16) | −0.0950 (13) | 0.070 (6)* | |
H11B | 0.461 (2) | 0.5185 (17) | −0.1790 (14) | 0.074 (7)* | |
H11N | 0.159 (3) | 0.5010 (17) | −0.0853 (13) | 0.069 (7)* | |
H13A | 0.088 (3) | 0.3217 (16) | 0.0636 (14) | 0.070 (7)* | |
H13B | 0.159 (3) | 0.314 (2) | −0.0191 (16) | 0.099 (8)* | |
H13N | 0.364 (3) | 0.6430 (18) | 0.1318 (14) | 0.075 (8)* | |
H15A | 0.463 (3) | 0.6852 (18) | 0.2689 (13) | 0.081 (7)* | |
H15B | 0.302 (4) | 0.597 (3) | 0.292 (2) | 0.138 (13)* | |
H17 | 0.573 (3) | 0.7568 (16) | −0.0432 (13) | 0.067 (6)* | |
H18 | 0.762 (3) | 0.902 (2) | −0.0496 (15) | 0.088 (9)* | |
H19 | 0.912 (4) | 0.907 (3) | −0.1469 (19) | 0.125 (12)* | |
H25A | 0.955 (4) | 0.689 (2) | 0.2827 (16) | 0.102 (9)* | |
H25B | 0.797 (4) | 0.593 (3) | 0.2309 (18) | 0.120 (11)* | |
H23N | 0.868 (3) | 0.6376 (18) | 0.4076 (14) | 0.076 (7)* | |
H23A | 0.659 (3) | 0.3140 (17) | 0.4673 (13) | 0.079 (7)* | |
H23B | 0.595 (3) | 0.3225 (16) | 0.3861 (14) | 0.068 (6)* | |
H21N | 0.660 (3) | 0.5108 (16) | 0.5854 (12) | 0.066 (7)* | |
H21B | 0.958 (3) | 0.5300 (18) | 0.6917 (14) | 0.077 (7)* | |
H21A | 1.022 (3) | 0.5338 (17) | 0.6078 (14) | 0.078 (7)* | |
H223 | 0.972 (3) | 0.871 (2) | 0.3017 (18) | 0.107 (9)* | |
H222 | 0.932 (3) | 1.007 (2) | 0.2506 (15) | 0.107 (9)* | |
H221 | 0.760 (3) | 0.970 (2) | 0.1496 (18) | 0.118 (10)* | |
H110 | 0.885 (4) | 0.767 (2) | −0.2421 (18) | 0.111 (9)* | |
H111 | 0.684 (3) | 0.614 (2) | −0.2345 (16) | 0.094 (8)* | |
H113 | −0.046 (3) | 0.264 (2) | −0.1203 (16) | 0.094 (8)* | |
H114 | −0.285 (4) | 0.132 (2) | −0.169 (2) | 0.115 (10)* | |
H115 | −0.456 (5) | 0.053 (3) | −0.095 (2) | 0.139 (12)* | |
H116 | −0.401 (4) | 0.104 (3) | 0.036 (2) | 0.127 (11)* | |
H117 | −0.155 (3) | 0.226 (2) | 0.0819 (18) | 0.103 (9)* | |
H119 | 0.172 (3) | 0.660 (2) | 0.3955 (13) | 0.085 (8)* | |
H120 | 0.153 (3) | 0.794 (2) | 0.4846 (17) | 0.099 (9)* | |
H121 | 0.281 (3) | 0.959 (2) | 0.4869 (18) | 0.109 (10)* | |
H122 | 0.449 (4) | 0.999 (3) | 0.3928 (18) | 0.121 (11)* | |
H123 | 0.484 (3) | 0.869 (2) | 0.3038 (17) | 0.099 (9)* | |
H220 | 0.624 (3) | 0.796 (2) | 0.0966 (16) | 0.095 (8)* | |
H219 | 0.666 (2) | 0.6627 (17) | 0.1484 (12) | 0.062 (6)* | |
H217 | 0.352 (3) | 0.221 (2) | 0.3340 (16) | 0.095 (8)* | |
H216 | 0.102 (4) | 0.108 (3) | 0.343 (2) | 0.133 (12)* | |
H215 | 0.017 (4) | 0.067 (2) | 0.4551 (15) | 0.100 (9)* | |
H214 | 0.191 (3) | 0.151 (2) | 0.5615 (17) | 0.098 (9)* | |
H213 | 0.431 (3) | 0.2619 (16) | 0.5524 (13) | 0.066 (6)* | |
H211 | 1.188 (3) | 0.622 (2) | 0.7716 (16) | 0.093 (9)* | |
H210 | 1.388 (3) | 0.7679 (19) | 0.8147 (16) | 0.094 (8)* | |
H29 | 1.429 (4) | 0.913 (2) | 0.7600 (17) | 0.108 (10)* | |
H28 | 1.273 (3) | 0.9088 (19) | 0.6651 (14) | 0.079 (7)* | |
H27 | 1.079 (3) | 0.7568 (17) | 0.6146 (14) | 0.073 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.0496 (12) | 0.0632 (13) | 0.0591 (14) | 0.0158 (11) | 0.0120 (10) | 0.0069 (12) |
C12 | 0.0403 (11) | 0.0517 (11) | 0.0495 (12) | 0.0117 (9) | 0.0028 (9) | 0.0115 (9) |
C13 | 0.0563 (13) | 0.0556 (13) | 0.0680 (16) | 0.0161 (10) | −0.0032 (11) | 0.0166 (11) |
C14 | 0.0466 (12) | 0.0637 (12) | 0.0436 (11) | 0.0171 (10) | 0.0001 (9) | 0.0115 (9) |
C15 | 0.0747 (17) | 0.0933 (19) | 0.0430 (12) | 0.0341 (15) | −0.0031 (11) | 0.0020 (12) |
C16 | 0.0440 (11) | 0.0624 (12) | 0.0492 (11) | 0.0178 (9) | 0.0042 (9) | 0.0155 (10) |
C17 | 0.0574 (13) | 0.0703 (14) | 0.0535 (13) | 0.0209 (11) | 0.0092 (11) | 0.0161 (11) |
C18 | 0.0728 (17) | 0.0618 (15) | 0.0860 (19) | 0.0095 (13) | 0.0055 (14) | 0.0153 (14) |
C19 | 0.0757 (19) | 0.084 (2) | 0.111 (3) | 0.0055 (16) | 0.0230 (17) | 0.0430 (19) |
C25 | 0.0720 (17) | 0.0851 (17) | 0.0511 (13) | 0.0257 (14) | 0.0155 (11) | 0.0268 (12) |
C24 | 0.0479 (12) | 0.0577 (11) | 0.0422 (11) | 0.0187 (10) | 0.0084 (9) | 0.0112 (9) |
C23 | 0.0543 (13) | 0.0513 (12) | 0.0666 (15) | 0.0186 (10) | 0.0105 (11) | 0.0080 (10) |
C22 | 0.0441 (11) | 0.0478 (10) | 0.0508 (12) | 0.0134 (9) | 0.0046 (9) | 0.0122 (9) |
C21 | 0.0518 (12) | 0.0645 (13) | 0.0648 (15) | 0.0178 (11) | −0.0038 (10) | 0.0214 (12) |
C228 | 0.0573 (12) | 0.0613 (12) | 0.0476 (12) | 0.0085 (10) | 0.0115 (9) | 0.0159 (10) |
C223 | 0.0945 (19) | 0.0817 (18) | 0.0546 (15) | −0.0075 (15) | −0.0160 (13) | 0.0170 (13) |
C222 | 0.127 (3) | 0.0604 (16) | 0.0784 (19) | −0.0116 (16) | −0.0161 (17) | 0.0146 (14) |
C221 | 0.108 (2) | 0.0624 (16) | 0.0794 (18) | 0.0121 (15) | −0.0023 (16) | 0.0241 (13) |
C110 | 0.0776 (18) | 0.105 (2) | 0.0807 (19) | 0.0234 (17) | 0.0321 (15) | 0.0384 (17) |
C111 | 0.0594 (14) | 0.0805 (16) | 0.0612 (14) | 0.0221 (13) | 0.0169 (11) | 0.0196 (13) |
C112 | 0.0508 (12) | 0.0488 (11) | 0.0619 (13) | 0.0157 (9) | 0.0050 (10) | 0.0140 (10) |
C113 | 0.0721 (17) | 0.0903 (18) | 0.0639 (16) | 0.0029 (14) | 0.0027 (13) | 0.0146 (14) |
C114 | 0.101 (2) | 0.094 (2) | 0.086 (2) | 0.0067 (19) | −0.0245 (19) | 0.0037 (18) |
C115 | 0.0706 (19) | 0.0642 (17) | 0.143 (3) | −0.0003 (15) | −0.017 (2) | 0.0206 (19) |
C116 | 0.075 (2) | 0.0770 (18) | 0.138 (3) | −0.0008 (16) | 0.030 (2) | 0.040 (2) |
C117 | 0.0824 (18) | 0.0685 (15) | 0.0810 (19) | 0.0097 (14) | 0.0226 (15) | 0.0198 (14) |
C118 | 0.0576 (12) | 0.0638 (13) | 0.0419 (11) | 0.0147 (10) | −0.0031 (9) | 0.0075 (9) |
C119 | 0.0598 (13) | 0.0577 (13) | 0.0545 (13) | 0.0155 (11) | 0.0014 (10) | 0.0114 (10) |
C120 | 0.0817 (17) | 0.0783 (18) | 0.0599 (15) | 0.0315 (14) | 0.0120 (13) | 0.0142 (13) |
C121 | 0.113 (2) | 0.0714 (18) | 0.0758 (19) | 0.0357 (17) | 0.0053 (16) | −0.0028 (15) |
C122 | 0.128 (3) | 0.0581 (17) | 0.104 (3) | −0.0032 (17) | 0.000 (2) | 0.0159 (17) |
C123 | 0.0918 (19) | 0.0773 (18) | 0.0689 (17) | 0.0005 (15) | 0.0136 (15) | 0.0187 (14) |
C220 | 0.0687 (15) | 0.0689 (15) | 0.0636 (15) | 0.0108 (12) | −0.0067 (12) | 0.0157 (12) |
C219 | 0.0560 (13) | 0.0524 (12) | 0.0566 (13) | 0.0070 (10) | 0.0057 (10) | 0.0090 (10) |
C212 | 0.0520 (11) | 0.0420 (10) | 0.0589 (13) | 0.0162 (9) | 0.0030 (9) | 0.0079 (9) |
C217 | 0.0767 (17) | 0.0651 (14) | 0.0678 (16) | 0.0131 (13) | −0.0093 (13) | 0.0077 (12) |
C216 | 0.0731 (19) | 0.0792 (18) | 0.106 (3) | 0.0069 (15) | −0.0208 (18) | 0.0007 (17) |
C215 | 0.0622 (17) | 0.0544 (15) | 0.140 (3) | 0.0081 (13) | 0.0094 (19) | 0.0140 (17) |
C214 | 0.087 (2) | 0.0654 (15) | 0.094 (2) | 0.0229 (15) | 0.0335 (17) | 0.0268 (15) |
C213 | 0.0712 (16) | 0.0620 (13) | 0.0593 (15) | 0.0168 (12) | 0.0043 (12) | 0.0116 (11) |
C26 | 0.0445 (11) | 0.0636 (12) | 0.0479 (11) | 0.0190 (10) | 0.0051 (8) | 0.0121 (9) |
C211 | 0.0652 (15) | 0.0788 (16) | 0.0606 (14) | 0.0242 (13) | −0.0075 (11) | 0.0157 (13) |
C210 | 0.0765 (18) | 0.104 (2) | 0.0705 (17) | 0.0290 (17) | −0.0248 (14) | 0.0006 (16) |
C29 | 0.0670 (17) | 0.0730 (17) | 0.099 (2) | 0.0120 (14) | −0.0116 (15) | −0.0048 (16) |
C28 | 0.0685 (16) | 0.0612 (15) | 0.0877 (18) | 0.0109 (13) | 0.0054 (13) | 0.0153 (13) |
C27 | 0.0587 (13) | 0.0658 (14) | 0.0527 (13) | 0.0199 (11) | 0.0045 (10) | 0.0140 (11) |
N11 | 0.0412 (10) | 0.0632 (10) | 0.0422 (9) | 0.0071 (8) | 0.0041 (7) | 0.0140 (8) |
N12 | 0.0398 (9) | 0.0559 (9) | 0.0422 (9) | 0.0059 (7) | 0.0003 (7) | 0.0069 (7) |
N13 | 0.0509 (11) | 0.0800 (12) | 0.0436 (10) | 0.0132 (10) | 0.0021 (8) | −0.0039 (9) |
N23 | 0.0507 (10) | 0.0679 (11) | 0.0570 (11) | 0.0146 (9) | 0.0067 (9) | 0.0293 (9) |
N22 | 0.0409 (9) | 0.0525 (9) | 0.0457 (9) | 0.0075 (7) | 0.0054 (7) | 0.0155 (7) |
N21 | 0.0427 (10) | 0.0616 (10) | 0.0444 (10) | 0.0096 (8) | 0.0012 (7) | 0.0117 (8) |
O11 | 0.0465 (8) | 0.0696 (9) | 0.0559 (8) | 0.0183 (7) | 0.0100 (6) | 0.0252 (7) |
O12 | 0.0482 (8) | 0.0695 (9) | 0.0522 (8) | −0.0013 (7) | 0.0004 (6) | 0.0087 (7) |
O13 | 0.0401 (7) | 0.0503 (7) | 0.0499 (8) | 0.0061 (6) | −0.0037 (6) | 0.0105 (6) |
O14 | 0.0495 (9) | 0.0933 (11) | 0.0481 (8) | 0.0137 (8) | 0.0064 (7) | 0.0159 (7) |
O15 | 0.0720 (10) | 0.0868 (10) | 0.0443 (8) | 0.0328 (9) | −0.0057 (7) | −0.0038 (7) |
O25 | 0.0735 (10) | 0.0793 (10) | 0.0570 (9) | 0.0334 (8) | 0.0220 (7) | 0.0340 (7) |
O24 | 0.0505 (9) | 0.0855 (10) | 0.0521 (8) | 0.0140 (8) | 0.0016 (7) | 0.0209 (7) |
O23 | 0.0428 (7) | 0.0443 (7) | 0.0523 (8) | 0.0086 (6) | 0.0081 (6) | 0.0106 (6) |
O22 | 0.0493 (8) | 0.0667 (9) | 0.0562 (9) | 0.0020 (7) | 0.0026 (6) | 0.0204 (7) |
O21 | 0.0468 (8) | 0.0699 (9) | 0.0480 (8) | 0.0206 (7) | −0.0012 (6) | 0.0040 (6) |
Geometric parameters (Å, º) top
C11—O11 | 1.444 (2) | C112—C117 | 1.376 (3) |
C11—C16 | 1.493 (3) | C113—C114 | 1.382 (4) |
C11—H11A | 1.03 (2) | C113—H113 | 1.02 (3) |
C11—H11B | 1.01 (2) | C114—C115 | 1.348 (5) |
C12—O12 | 1.219 (2) | C114—H114 | 0.96 (3) |
C12—N11 | 1.360 (3) | C115—C116 | 1.355 (5) |
C12—N12 | 1.397 (2) | C115—H115 | 0.97 (4) |
C13—O13 | 1.457 (3) | C116—C117 | 1.373 (4) |
C13—C112 | 1.492 (3) | C116—H116 | 0.97 (4) |
C13—H13A | 0.93 (3) | C117—H117 | 0.99 (3) |
C13—H13B | 1.04 (3) | C118—C119 | 1.371 (3) |
C14—O14 | 1.207 (2) | C118—C123 | 1.372 (3) |
C14—N13 | 1.354 (3) | C119—C120 | 1.373 (3) |
C14—N12 | 1.418 (2) | C119—H119 | 1.00 (3) |
C15—O15 | 1.431 (3) | C120—C121 | 1.351 (4) |
C15—C118 | 1.494 (3) | C120—H120 | 0.90 (3) |
C15—H15A | 1.01 (3) | C121—C122 | 1.368 (5) |
C15—H15B | 1.02 (4) | C121—H121 | 0.94 (3) |
C16—C17 | 1.386 (3) | C122—C123 | 1.376 (4) |
C16—C111 | 1.388 (3) | C122—H122 | 0.91 (3) |
C17—C18 | 1.371 (3) | C123—H123 | 0.95 (3) |
C17—H17 | 0.91 (2) | C220—C219 | 1.382 (3) |
C18—C19 | 1.368 (4) | C220—H220 | 0.97 (3) |
C18—H18 | 0.91 (3) | C219—H219 | 0.95 (2) |
C19—C110 | 1.361 (4) | C212—C213 | 1.377 (3) |
C19—H19 | 0.86 (3) | C212—C217 | 1.381 (3) |
C25—O25 | 1.424 (3) | C217—C216 | 1.369 (4) |
C25—C228 | 1.495 (3) | C217—H217 | 1.01 (3) |
C25—H25A | 0.98 (3) | C216—C215 | 1.357 (5) |
C25—H25B | 1.07 (3) | C216—H216 | 0.97 (4) |
C24—O24 | 1.209 (2) | C215—C214 | 1.364 (4) |
C24—N23 | 1.355 (3) | C215—H215 | 0.99 (3) |
C24—N22 | 1.426 (2) | C214—C213 | 1.386 (4) |
C23—O23 | 1.454 (2) | C214—H214 | 0.93 (3) |
C23—C212 | 1.491 (3) | C213—H213 | 0.94 (2) |
C23—H23A | 1.02 (3) | C26—C211 | 1.386 (3) |
C23—H23B | 1.00 (2) | C26—C27 | 1.387 (3) |
C22—O22 | 1.216 (2) | C211—C210 | 1.380 (4) |
C22—N21 | 1.358 (3) | C211—H211 | 0.93 (3) |
C22—N22 | 1.407 (2) | C210—C29 | 1.370 (4) |
C21—O21 | 1.443 (2) | C210—H210 | 0.92 (3) |
C21—C26 | 1.497 (3) | C29—C28 | 1.370 (4) |
C21—H21B | 0.99 (3) | C29—H29 | 0.92 (3) |
C21—H21A | 1.07 (3) | C28—C27 | 1.367 (3) |
C228—C219 | 1.374 (3) | C28—H28 | 0.96 (3) |
C228—C223 | 1.382 (3) | C27—H27 | 0.93 (2) |
C223—C222 | 1.383 (4) | N11—O11 | 1.413 (2) |
C223—H223 | 0.98 (3) | N11—H11N | 0.89 (2) |
C222—C221 | 1.371 (4) | N12—O13 | 1.4040 (19) |
C222—H222 | 1.00 (3) | N13—O15 | 1.409 (2) |
C221—C220 | 1.357 (3) | N13—H13N | 0.88 (3) |
C221—H221 | 0.99 (3) | N23—O25 | 1.411 (2) |
C110—C111 | 1.379 (4) | N23—H23N | 0.90 (3) |
C110—H110 | 1.02 (3) | N22—O23 | 1.4022 (19) |
C111—H111 | 0.98 (3) | N21—O21 | 1.411 (2) |
C112—C113 | 1.366 (3) | N21—H21N | 0.90 (2) |
| | | |
O11—C11—C16 | 107.69 (17) | C115—C116—C117 | 120.3 (3) |
O11—C11—H11A | 107.3 (13) | C115—C116—H116 | 123 (2) |
C16—C11—H11A | 113.6 (12) | C117—C116—H116 | 117 (2) |
O11—C11—H11B | 109.9 (13) | C116—C117—C112 | 120.7 (3) |
C16—C11—H11B | 114.4 (13) | C116—C117—H117 | 125.2 (17) |
H11A—C11—H11B | 103.7 (17) | C112—C117—H117 | 114.1 (17) |
O12—C12—N11 | 124.23 (18) | C119—C118—C123 | 118.8 (2) |
O12—C12—N12 | 120.73 (17) | C119—C118—C15 | 120.6 (2) |
N11—C12—N12 | 114.86 (16) | C123—C118—C15 | 120.6 (2) |
O13—C13—C112 | 106.98 (16) | C118—C119—C120 | 121.1 (2) |
O13—C13—H13A | 108.5 (13) | C118—C119—H119 | 120.4 (14) |
C112—C13—H13A | 110.0 (14) | C120—C119—H119 | 118.5 (14) |
O13—C13—H13B | 104.8 (15) | C121—C120—C119 | 119.9 (3) |
C112—C13—H13B | 109.5 (15) | C121—C120—H120 | 120.6 (18) |
H13A—C13—H13B | 117 (2) | C119—C120—H120 | 119.5 (18) |
O14—C14—N13 | 125.68 (19) | C120—C121—C122 | 119.8 (3) |
O14—C14—N12 | 121.39 (18) | C120—C121—H121 | 116.4 (19) |
N13—C14—N12 | 112.74 (18) | C122—C121—H121 | 123.7 (19) |
O15—C15—C118 | 105.37 (18) | C121—C122—C123 | 120.6 (3) |
O15—C15—H15A | 106.3 (14) | C121—C122—H122 | 122 (2) |
C118—C15—H15A | 109.6 (14) | C123—C122—H122 | 118 (2) |
O15—C15—H15B | 105 (2) | C118—C123—C122 | 119.8 (3) |
C118—C15—H15B | 114 (2) | C118—C123—H123 | 118.1 (17) |
H15A—C15—H15B | 115 (3) | C122—C123—H123 | 122.1 (17) |
C17—C16—C111 | 118.9 (2) | C221—C220—C219 | 119.8 (2) |
C17—C16—C11 | 120.70 (19) | C221—C220—H220 | 119.1 (16) |
C111—C16—C11 | 120.4 (2) | C219—C220—H220 | 121.1 (16) |
C18—C17—C16 | 120.5 (2) | C228—C219—C220 | 121.5 (2) |
C18—C17—H17 | 118.4 (14) | C228—C219—H219 | 119.2 (13) |
C16—C17—H17 | 121.1 (14) | C220—C219—H219 | 119.3 (13) |
C19—C18—C17 | 120.0 (3) | C213—C212—C217 | 118.5 (2) |
C19—C18—H18 | 121.6 (18) | C213—C212—C23 | 121.4 (2) |
C17—C18—H18 | 118.4 (18) | C217—C212—C23 | 120.0 (2) |
C110—C19—C18 | 120.3 (3) | C216—C217—C212 | 120.3 (3) |
C110—C19—H19 | 119 (2) | C216—C217—H217 | 121.6 (15) |
C18—C19—H19 | 120 (2) | C212—C217—H217 | 118.1 (15) |
O25—C25—C228 | 105.35 (18) | C215—C216—C217 | 120.8 (3) |
O25—C25—H25A | 102.3 (17) | C215—C216—H216 | 121 (2) |
C228—C25—H25A | 108.9 (17) | C217—C216—H216 | 118 (2) |
O25—C25—H25B | 106.3 (17) | C216—C215—C214 | 120.1 (3) |
C228—C25—H25B | 114.2 (17) | C216—C215—H215 | 119.0 (17) |
H25A—C25—H25B | 118 (2) | C214—C215—H215 | 120.9 (17) |
O24—C24—N23 | 125.72 (19) | C215—C214—C213 | 119.7 (3) |
O24—C24—N22 | 121.11 (18) | C215—C214—H214 | 124.4 (18) |
N23—C24—N22 | 112.99 (17) | C213—C214—H214 | 116.0 (18) |
O23—C23—C212 | 106.44 (15) | C212—C213—C214 | 120.6 (3) |
O23—C23—H23A | 106.4 (13) | C212—C213—H213 | 118.4 (14) |
C212—C23—H23A | 114.1 (14) | C214—C213—H213 | 121.0 (14) |
O23—C23—H23B | 107.8 (12) | C211—C26—C27 | 118.8 (2) |
C212—C23—H23B | 110.7 (13) | C211—C26—C21 | 120.7 (2) |
H23A—C23—H23B | 110.9 (19) | C27—C26—C21 | 120.47 (19) |
O22—C22—N21 | 124.53 (18) | C210—C211—C26 | 120.0 (3) |
O22—C22—N22 | 120.67 (18) | C210—C211—H211 | 119.1 (17) |
N21—C22—N22 | 114.62 (17) | C26—C211—H211 | 120.9 (17) |
O21—C21—C26 | 107.78 (16) | C29—C210—C211 | 120.4 (3) |
O21—C21—H21B | 108.4 (13) | C29—C210—H210 | 121.1 (17) |
C26—C21—H21B | 110.5 (13) | C211—C210—H210 | 118.5 (17) |
O21—C21—H21A | 109.2 (12) | C28—C29—C210 | 119.8 (3) |
C26—C21—H21A | 112.0 (12) | C28—C29—H29 | 116.8 (19) |
H21B—C21—H21A | 108.9 (18) | C210—C29—H29 | 123 (2) |
C219—C228—C223 | 118.2 (2) | C27—C28—C29 | 120.5 (3) |
C219—C228—C25 | 121.4 (2) | C27—C28—H28 | 121.0 (15) |
C223—C228—C25 | 120.4 (2) | C29—C28—H28 | 118.1 (15) |
C228—C223—C222 | 120.2 (2) | C28—C27—C26 | 120.5 (2) |
C228—C223—H223 | 118.3 (17) | C28—C27—H27 | 119.6 (14) |
C222—C223—H223 | 121.4 (17) | C26—C27—H27 | 119.9 (15) |
C221—C222—C223 | 120.5 (3) | C12—N11—O11 | 112.36 (15) |
C221—C222—H222 | 120.2 (17) | C12—N11—H11N | 119.9 (15) |
C223—C222—H222 | 119.4 (17) | O11—N11—H11N | 111.2 (15) |
C220—C221—C222 | 119.9 (3) | C12—N12—O13 | 115.54 (14) |
C220—C221—H221 | 123.6 (18) | C12—N12—C14 | 124.77 (16) |
C222—C221—H221 | 116.5 (18) | O13—N12—C14 | 112.89 (14) |
C19—C110—C111 | 120.5 (3) | C14—N13—O15 | 113.66 (17) |
C19—C110—H110 | 121.1 (16) | C14—N13—H13N | 116.3 (16) |
C111—C110—H110 | 118.4 (16) | O15—N13—H13N | 112.9 (16) |
C110—C111—C16 | 119.7 (2) | C24—N23—O25 | 113.23 (16) |
C110—C111—H111 | 121.3 (16) | C24—N23—H23N | 113.0 (16) |
C16—C111—H111 | 118.9 (16) | O25—N23—H23N | 114.5 (16) |
C113—C112—C117 | 118.0 (2) | O23—N22—C22 | 115.61 (15) |
C113—C112—C13 | 121.2 (2) | O23—N22—C24 | 112.75 (14) |
C117—C112—C13 | 120.7 (2) | C22—N22—C24 | 124.03 (15) |
C112—C113—C114 | 120.8 (3) | C22—N21—O21 | 112.63 (16) |
C112—C113—H113 | 115.8 (15) | C22—N21—H21N | 118.2 (15) |
C114—C113—H113 | 122.4 (15) | O21—N21—H21N | 110.5 (14) |
C115—C114—C113 | 120.2 (3) | N11—O11—C11 | 111.21 (14) |
C115—C114—H114 | 119.8 (19) | N12—O13—C13 | 108.79 (13) |
C113—C114—H114 | 120 (2) | N13—O15—C15 | 109.30 (15) |
C114—C115—C116 | 119.9 (3) | N23—O25—C25 | 110.38 (15) |
C114—C115—H115 | 116 (2) | N22—O23—C23 | 108.70 (13) |
C116—C115—H115 | 124 (2) | N21—O21—C21 | 111.00 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N13—H13N···O12 | 0.88 (3) | 1.92 (3) | 2.627 (2) | 136 (2) |
N23—H23N···O22 | 0.90 (3) | 1.90 (3) | 2.650 (2) | 140 (2) |
N11—H11N···O13i | 0.89 (2) | 2.75 (3) | 3.286 (1) | 119 (1) |
N11—H11N···O14i | 0.89 (2) | 2.05 (3) | 2.896 (2) | 158 (2) |
N21—H21N···O24ii | 0.90 (2) | 2.06 (3) | 2.926 (2) | 160 (2) |
N21—H21N···O23ii | 0.90 (2) | 2.66 (3) | 3.275 (2) | 126 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
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