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The title compound, C
15H
16N
2O
4·0.5H
2O, is the first structurally characterized example of an ester amide of a squaric acid amino acid derivative. There are two conformationally inequivalent organic molecules and a water molecule in the asymmetric unit. Molecules are linked
via N—H
O and O—H
O hydrogen bonds to build the non-centrosymmetric crystal structure.
Supporting information
CCDC reference: 238808
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- H-atom completeness 63%
- R factor = 0.042
- wR factor = 0.134
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.17 Ratio
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 7.11 Ratio
PLAT360_ALERT_2_A Short C(sp3)-C(sp3) Bond C29 - C30 ... 1.22 Ang.
Alert level B
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C29
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 = 0.095
Value of mu given = 0.093
CHEMW01_ALERT_1_C The ratio of given/expected molecular weight as calculated
from the _chemical_formula_sum lies outside
the range 0.99 <> 1.01
Calculated formula weight = 307.3890
Formula weight given = 297.3000
CHEMW01_ALERT_1_C The difference between the given and expected weight for
compound is greater 1 mass unit. Check that all hydrogen
atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C14
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O8
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C21
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C15 H16 N2 O4
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C15 H27 N2 O4.5
Atom count from _chemical_formula_moiety:C15 H17 N2 O4.5
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C15 H27 N2 O4.5
Atom count from the _atom_site data: C15 H17 N2 O4.5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C15 H27 N2 O4.5
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 60.00 60.00 0.00
H 108.00 68.00 40.00
N 8.00 8.00 0.00
O 18.00 18.00 0.00
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 25.98
From the CIF: _reflns_number_total 3261
Count of symmetry unique reflns 3261
Completeness (_total/calc) 100.00%
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
3 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-[(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]-3-phenylpropaneamide
top
Crystal data top
C15H16N2O4·0.5H2O | F(000) = 628 |
Mr = 297.3 | Dx = 1.247 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 22 reflections |
a = 9.244 (3) Å | θ = 18.0–19.1° |
b = 12.115 (3) Å | µ = 0.09 mm−1 |
c = 14.2116 (19) Å | T = 293 K |
β = 95.78 (2)° | Prism, colorless |
V = 1583.4 (7) Å3 | 0.26 × 0.26 × 0.18 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.047 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 1.4° |
Graphite monochromator | h = 0→11 |
non–profiled ω/2θ scans | k = −14→14 |
6597 measured reflections | l = −17→17 |
3261 independent reflections | 3 standard reflections every 120 min |
1854 reflections with I > 2σ(I) | intensity decay: 8% |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0843P)2 + 0.0866P] where P = (Fo2 + 2Fc2)/3 |
3261 reflections | (Δ/σ)max < 0.001 |
396 parameters | Δρmax = 0.21 e Å−3 |
2 restraints | Δρmin = −0.14 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 | |
C1 | 0.1569 (7) | 0.6879 (4) | 0.7569 (4) | 0.0857 (16) | |
H1 | 0.2356 | 0.7213 | 0.7324 | 0.103* | |
C2 | 0.0276 (10) | 0.6764 (6) | 0.7004 (6) | 0.122 (3) | |
H2 | 0.0195 | 0.7012 | 0.6382 | 0.146* | |
C3 | −0.0876 (9) | 0.6288 (8) | 0.7362 (9) | 0.138 (4) | |
H3 | −0.1750 | 0.6214 | 0.6982 | 0.166* | |
C4 | −0.0775 (8) | 0.5924 (8) | 0.8252 (9) | 0.135 (3) | |
H4 | −0.1574 | 0.5598 | 0.8488 | 0.162* | |
C5 | 0.0523 (7) | 0.6033 (6) | 0.8823 (5) | 0.0990 (18) | |
H5 | 0.0591 | 0.5782 | 0.9444 | 0.119* | |
C6 | 0.1712 (5) | 0.6510 (4) | 0.8478 (4) | 0.0711 (13) | |
C7 | 0.3138 (5) | 0.6560 (4) | 0.9080 (3) | 0.0695 (13) | |
H7A | 0.2963 | 0.6637 | 0.9738 | 0.083* | |
H7B | 0.3678 | 0.7203 | 0.8906 | 0.083* | |
C8 | 0.4043 (5) | 0.5517 (4) | 0.8959 (3) | 0.0562 (10) | |
H8 | 0.3462 | 0.4868 | 0.9087 | 0.067* | |
C9 | 0.5427 (5) | 0.5514 (4) | 0.9633 (3) | 0.0655 (12) | |
C10 | 0.3816 (4) | 0.4774 (4) | 0.7356 (3) | 0.0549 (10) | |
C11 | 0.3928 (5) | 0.4630 (4) | 0.6335 (3) | 0.0682 (12) | |
C12 | 0.2894 (5) | 0.3684 (4) | 0.6345 (3) | 0.0670 (12) | |
C13 | 0.2844 (5) | 0.3897 (4) | 0.7339 (3) | 0.0582 (11) | |
C14 | 0.1106 (7) | 0.2623 (5) | 0.7783 (4) | 0.098 (2) | |
H14A | 0.1567 | 0.1990 | 0.7521 | 0.117* | |
H14B | 0.0365 | 0.2902 | 0.7311 | 0.117* | |
C15 | 0.0440 (6) | 0.2297 (5) | 0.8646 (4) | 0.0883 (16) | |
H15A | −0.0272 | 0.1732 | 0.8491 | 0.106* | |
H15B | −0.0019 | 0.2926 | 0.8898 | 0.106* | |
H15C | 0.1181 | 0.2020 | 0.9108 | 0.106* | |
C16 | −0.4378 (8) | 0.1520 (6) | 0.7746 (4) | 0.1006 (19) | |
H16 | −0.4926 | 0.1149 | 0.8160 | 0.121* | |
C17 | −0.3854 (11) | 0.2557 (8) | 0.7977 (7) | 0.141 (3) | |
H17 | −0.4021 | 0.2865 | 0.8556 | 0.170* | |
C18 | −0.3102 (11) | 0.3134 (8) | 0.7381 (11) | 0.156 (4) | |
H18 | −0.2774 | 0.3843 | 0.7536 | 0.188* | |
C19 | −0.2826 (10) | 0.2658 (8) | 0.6535 (9) | 0.139 (3) | |
H19 | −0.2301 | 0.3050 | 0.6121 | 0.167* | |
C20 | −0.3316 (7) | 0.1604 (5) | 0.6292 (5) | 0.0973 (19) | |
H20 | −0.3120 | 0.1291 | 0.5722 | 0.117* | |
C21 | −0.4104 (5) | 0.1022 (4) | 0.6911 (4) | 0.0715 (13) | |
C22 | −0.4626 (5) | −0.0115 (4) | 0.6669 (3) | 0.0655 (12) | |
H22A | −0.5142 | −0.0106 | 0.6040 | 0.079* | |
H22B | −0.5312 | −0.0333 | 0.7109 | 0.079* | |
C23 | −0.3409 (4) | −0.0981 (4) | 0.6697 (3) | 0.0563 (11) | |
H23 | −0.2796 | −0.0844 | 0.6186 | 0.068* | |
C24 | −0.4098 (5) | −0.2129 (4) | 0.6585 (3) | 0.0605 (12) | |
C25 | −0.1134 (4) | −0.0731 (3) | 0.7721 (3) | 0.0507 (9) | |
C26 | −0.0053 (4) | −0.0740 (4) | 0.8551 (3) | 0.0573 (11) | |
C27 | 0.1076 (5) | −0.0412 (4) | 0.7924 (3) | 0.0655 (12) | |
C28 | −0.0071 (4) | −0.0408 (4) | 0.7158 (3) | 0.0631 (12) | |
C29 | 0.1163 (8) | 0.0086 (10) | 0.5855 (5) | 0.153 (4) | |
H29A | 0.1290 | 0.0879 | 0.5902 | 0.184* | |
H29B | 0.1967 | −0.0254 | 0.6241 | 0.184* | |
C30 | 0.1233 (13) | −0.0185 (17) | 0.5036 (9) | 0.313 (13) | |
H30A | 0.2154 | 0.0037 | 0.4841 | 0.469* | |
H30B | 0.0464 | 0.0165 | 0.4640 | 0.469* | |
H30C | 0.1136 | −0.0972 | 0.4980 | 0.469* | |
N1 | 0.5547 (4) | 0.4757 (4) | 1.0279 (3) | 0.0750 (11) | |
H1A | 0.6310 | 0.4730 | 1.0678 | 0.090* | |
H1B | 0.4862 | 0.4282 | 1.0310 | 0.090* | |
N2 | 0.4432 (4) | 0.5452 (3) | 0.7989 (2) | 0.0553 (9) | |
H2A | 0.5103 | 0.5884 | 0.7826 | 0.066* | |
N3 | −0.4076 (5) | −0.2624 (4) | 0.5774 (3) | 0.0772 (11) | |
H3A | −0.4452 | −0.3271 | 0.5690 | 0.093* | |
H3B | −0.3687 | −0.2305 | 0.5321 | 0.093* | |
N4 | −0.2530 (3) | −0.0967 (3) | 0.7604 (2) | 0.0550 (9) | |
H4A | −0.2952 | −0.1123 | 0.8100 | 0.066* | |
O1 | 0.6376 (4) | 0.6212 (4) | 0.9560 (3) | 0.1103 (14) | |
O2 | 0.4588 (5) | 0.5094 (3) | 0.5749 (2) | 0.0913 (11) | |
O3 | 0.2346 (4) | 0.3035 (4) | 0.5751 (2) | 0.0953 (12) | |
O4 | 0.2178 (4) | 0.3475 (3) | 0.8041 (2) | 0.0718 (9) | |
O5 | −0.4633 (4) | −0.2531 (3) | 0.7263 (2) | 0.0822 (10) | |
O6 | −0.0083 (3) | −0.0944 (3) | 0.9388 (2) | 0.0782 (9) | |
O7 | 0.2383 (3) | −0.0227 (4) | 0.8026 (2) | 0.0889 (11) | |
O8 | −0.0177 (3) | −0.0206 (4) | 0.6244 (2) | 0.0918 (13) | |
O9 | 0.3044 (5) | 0.3391 (4) | 1.0522 (2) | 0.0743 (9) | |
HW1 | 0.321 (6) | 0.265 (6) | 1.049 (4) | 0.10 (2)* | |
HW2 | 0.208 (8) | 0.343 (6) | 1.036 (5) | 0.12 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.094 (4) | 0.063 (3) | 0.095 (4) | 0.004 (3) | −0.014 (3) | 0.004 (3) |
C2 | 0.128 (6) | 0.085 (5) | 0.141 (6) | 0.017 (5) | −0.042 (6) | −0.002 (4) |
C3 | 0.088 (6) | 0.103 (6) | 0.209 (10) | 0.028 (5) | −0.053 (7) | −0.033 (7) |
C4 | 0.069 (5) | 0.118 (7) | 0.220 (10) | 0.006 (4) | 0.027 (6) | −0.045 (7) |
C5 | 0.083 (4) | 0.092 (4) | 0.126 (5) | 0.003 (3) | 0.029 (4) | −0.019 (4) |
C6 | 0.067 (3) | 0.058 (3) | 0.089 (4) | 0.010 (2) | 0.010 (3) | −0.013 (3) |
C7 | 0.075 (3) | 0.073 (3) | 0.061 (3) | −0.005 (3) | 0.011 (2) | −0.015 (2) |
C8 | 0.056 (2) | 0.067 (3) | 0.046 (2) | −0.004 (2) | 0.0069 (18) | 0.003 (2) |
C9 | 0.067 (3) | 0.076 (3) | 0.054 (2) | −0.013 (3) | 0.004 (2) | 0.005 (2) |
C10 | 0.062 (2) | 0.056 (3) | 0.047 (2) | 0.008 (2) | 0.0092 (18) | −0.003 (2) |
C11 | 0.086 (3) | 0.068 (3) | 0.053 (2) | 0.007 (3) | 0.017 (2) | 0.000 (2) |
C12 | 0.087 (3) | 0.066 (3) | 0.049 (2) | 0.000 (3) | 0.011 (2) | −0.008 (2) |
C13 | 0.067 (3) | 0.057 (3) | 0.052 (2) | −0.001 (2) | 0.011 (2) | −0.002 (2) |
C14 | 0.129 (5) | 0.091 (4) | 0.075 (3) | −0.049 (4) | 0.019 (3) | −0.017 (3) |
C15 | 0.086 (4) | 0.093 (4) | 0.089 (4) | −0.028 (3) | 0.024 (3) | −0.011 (3) |
C16 | 0.116 (5) | 0.090 (5) | 0.094 (4) | 0.025 (4) | −0.001 (4) | −0.003 (3) |
C17 | 0.160 (8) | 0.081 (6) | 0.173 (8) | 0.026 (6) | −0.036 (7) | −0.027 (6) |
C18 | 0.134 (7) | 0.063 (5) | 0.256 (14) | −0.003 (5) | −0.059 (8) | 0.004 (7) |
C19 | 0.118 (6) | 0.088 (6) | 0.205 (10) | −0.022 (5) | −0.013 (6) | 0.042 (6) |
C20 | 0.102 (4) | 0.083 (4) | 0.103 (4) | −0.013 (4) | −0.010 (3) | 0.026 (3) |
C21 | 0.065 (3) | 0.073 (3) | 0.073 (3) | 0.004 (3) | −0.011 (2) | 0.022 (3) |
C22 | 0.054 (2) | 0.073 (3) | 0.067 (3) | −0.004 (2) | −0.003 (2) | 0.014 (2) |
C23 | 0.050 (2) | 0.076 (3) | 0.043 (2) | −0.009 (2) | 0.0028 (17) | 0.011 (2) |
C24 | 0.053 (3) | 0.077 (3) | 0.050 (2) | −0.006 (2) | 0.001 (2) | 0.011 (2) |
C25 | 0.048 (2) | 0.051 (2) | 0.053 (2) | −0.0017 (19) | 0.0049 (18) | −0.0041 (18) |
C26 | 0.061 (2) | 0.058 (3) | 0.052 (3) | −0.003 (2) | 0.001 (2) | −0.008 (2) |
C27 | 0.053 (3) | 0.078 (3) | 0.065 (3) | −0.006 (2) | 0.004 (2) | −0.016 (2) |
C28 | 0.055 (2) | 0.082 (3) | 0.053 (2) | −0.008 (2) | 0.0076 (19) | −0.008 (2) |
C29 | 0.101 (4) | 0.284 (12) | 0.077 (4) | −0.087 (7) | 0.025 (3) | −0.008 (6) |
C30 | 0.224 (12) | 0.54 (3) | 0.199 (11) | −0.200 (17) | 0.140 (10) | −0.187 (16) |
N1 | 0.065 (2) | 0.092 (3) | 0.065 (2) | −0.008 (2) | −0.0063 (18) | 0.018 (2) |
N2 | 0.059 (2) | 0.059 (2) | 0.0489 (18) | −0.0043 (18) | 0.0101 (16) | 0.0000 (17) |
N3 | 0.097 (3) | 0.077 (3) | 0.058 (2) | −0.016 (3) | 0.012 (2) | −0.001 (2) |
N4 | 0.0440 (18) | 0.072 (2) | 0.0490 (18) | −0.0048 (17) | 0.0031 (14) | 0.0058 (17) |
O1 | 0.089 (3) | 0.112 (3) | 0.124 (3) | −0.041 (3) | −0.019 (2) | 0.037 (3) |
O2 | 0.138 (3) | 0.084 (2) | 0.0568 (18) | −0.016 (2) | 0.035 (2) | −0.0009 (17) |
O3 | 0.122 (3) | 0.101 (3) | 0.065 (2) | −0.026 (2) | 0.020 (2) | −0.027 (2) |
O4 | 0.088 (2) | 0.072 (2) | 0.0563 (17) | −0.0249 (19) | 0.0145 (15) | −0.0086 (15) |
O5 | 0.100 (3) | 0.084 (2) | 0.0668 (19) | −0.033 (2) | 0.0276 (18) | 0.0035 (18) |
O6 | 0.080 (2) | 0.095 (3) | 0.0580 (19) | −0.0121 (19) | −0.0029 (15) | 0.0008 (18) |
O7 | 0.0472 (18) | 0.129 (3) | 0.088 (2) | −0.019 (2) | −0.0014 (15) | −0.015 (2) |
O8 | 0.0646 (19) | 0.153 (4) | 0.0586 (19) | −0.027 (2) | 0.0124 (15) | 0.003 (2) |
O9 | 0.080 (3) | 0.083 (3) | 0.0614 (19) | −0.004 (2) | 0.0161 (17) | −0.0014 (18) |
Geometric parameters (Å, º) top
C1—C6 | 1.361 (7) | C17—H17 | 0.930 |
C1—C2 | 1.377 (9) | C18—C19 | 1.380 (14) |
C1—H1 | 0.930 | C18—H18 | 0.930 |
C2—C3 | 1.354 (12) | C19—C20 | 1.386 (12) |
C2—H2 | 0.930 | C19—H19 | 0.930 |
C3—C4 | 1.333 (12) | C20—C21 | 1.390 (8) |
C3—H3 | 0.930 | C20—H20 | 0.930 |
C4—C5 | 1.386 (11) | C21—C22 | 1.488 (8) |
C4—H4 | 0.930 | C22—C23 | 1.536 (6) |
C5—C6 | 1.375 (8) | C22—H22A | 0.970 |
C5—H5 | 0.930 | C22—H22B | 0.970 |
C6—C7 | 1.498 (7) | C23—N4 | 1.453 (5) |
C7—C8 | 1.535 (7) | C23—C24 | 1.531 (7) |
C7—H7A | 0.970 | C23—H23 | 0.980 |
C7—H7B | 0.970 | C24—O5 | 1.227 (5) |
C8—N2 | 1.461 (5) | C24—N3 | 1.302 (6) |
C8—C9 | 1.519 (6) | C25—N4 | 1.315 (5) |
C8—H8 | 0.980 | C25—C28 | 1.384 (6) |
C9—O1 | 1.229 (6) | C25—C26 | 1.467 (6) |
C9—N1 | 1.295 (6) | C26—O6 | 1.218 (5) |
C10—N2 | 1.306 (5) | C26—C27 | 1.492 (6) |
C10—C13 | 1.390 (6) | C27—O7 | 1.223 (5) |
C10—C11 | 1.475 (6) | C27—C28 | 1.441 (6) |
C11—O2 | 1.218 (5) | C28—O8 | 1.317 (5) |
C11—C12 | 1.493 (7) | C29—C30 | 1.218 (10) |
C12—O3 | 1.226 (5) | C29—O8 | 1.450 (7) |
C12—C13 | 1.440 (6) | C29—H29A | 0.970 |
C13—O4 | 1.327 (5) | C29—H29B | 0.970 |
C14—O4 | 1.452 (6) | C30—H30A | 0.960 |
C14—C15 | 1.480 (7) | C30—H30B | 0.960 |
C14—H14A | 0.970 | C30—H30C | 0.960 |
C14—H14B | 0.970 | N1—H1A | 0.860 |
C15—H15A | 0.960 | N1—H1B | 0.860 |
C15—H15B | 0.960 | N2—H2A | 0.860 |
C15—H15C | 0.960 | N3—H3A | 0.860 |
C16—C17 | 1.375 (11) | N3—H3B | 0.860 |
C16—C21 | 1.377 (8) | N4—H4A | 0.860 |
C16—H16 | 0.930 | O9—HW1 | 0.91 (7) |
C17—C18 | 1.344 (14) | O9—HW2 | 0.90 (7) |
| | | |
C6—C1—C2 | 121.0 (7) | C19—C18—H18 | 120.5 |
C6—C1—H1 | 119.5 | C18—C19—C20 | 121.1 (9) |
C2—C1—H1 | 119.5 | C18—C19—H19 | 119.4 |
C3—C2—C1 | 119.6 (8) | C20—C19—H19 | 119.4 |
C3—C2—H2 | 120.2 | C19—C20—C21 | 119.3 (8) |
C1—C2—H2 | 120.2 | C19—C20—H20 | 120.4 |
C4—C3—C2 | 120.9 (8) | C21—C20—H20 | 120.4 |
C4—C3—H3 | 119.5 | C16—C21—C20 | 118.5 (6) |
C2—C3—H3 | 119.5 | C16—C21—C22 | 121.4 (5) |
C3—C4—C5 | 119.9 (8) | C20—C21—C22 | 120.1 (5) |
C3—C4—H4 | 120.1 | C21—C22—C23 | 114.0 (4) |
C5—C4—H4 | 120.1 | C21—C22—H22A | 108.8 |
C6—C5—C4 | 120.5 (7) | C23—C22—H22A | 108.8 |
C6—C5—H5 | 119.8 | C21—C22—H22B | 108.8 |
C4—C5—H5 | 119.8 | C23—C22—H22B | 108.8 |
C1—C6—C5 | 118.1 (6) | H22A—C22—H22B | 107.7 |
C1—C6—C7 | 121.6 (5) | N4—C23—C24 | 107.0 (3) |
C5—C6—C7 | 120.1 (5) | N4—C23—C22 | 111.0 (4) |
C6—C7—C8 | 111.1 (4) | C24—C23—C22 | 108.8 (3) |
C6—C7—H7A | 109.4 | N4—C23—H23 | 110.0 |
C8—C7—H7A | 109.4 | C24—C23—H23 | 110.0 |
C6—C7—H7B | 109.4 | C22—C23—H23 | 110.0 |
C8—C7—H7B | 109.4 | O5—C24—N3 | 123.8 (5) |
H7A—C7—H7B | 108.0 | O5—C24—C23 | 118.4 (4) |
N2—C8—C9 | 108.9 (3) | N3—C24—C23 | 117.9 (4) |
N2—C8—C7 | 109.8 (3) | N4—C25—C28 | 137.1 (4) |
C9—C8—C7 | 111.4 (4) | N4—C25—C26 | 132.8 (4) |
N2—C8—H8 | 108.9 | C28—C25—C26 | 90.0 (3) |
C9—C8—H8 | 108.9 | O6—C26—C25 | 134.9 (4) |
C7—C8—H8 | 108.9 | O6—C26—C27 | 136.3 (4) |
O1—C9—N1 | 122.4 (4) | C25—C26—C27 | 88.8 (3) |
O1—C9—C8 | 120.6 (4) | O6—C26—C28 | 178.2 (4) |
N1—C9—C8 | 117.0 (4) | O7—C27—C28 | 137.0 (4) |
N2—C10—C13 | 136.8 (4) | O7—C27—C26 | 136.1 (4) |
N2—C10—C11 | 133.0 (4) | C28—C27—C26 | 86.9 (3) |
C13—C10—C11 | 90.1 (4) | O8—C28—C25 | 129.5 (4) |
O2—C11—C10 | 135.1 (5) | O8—C28—C27 | 136.2 (4) |
O2—C11—C12 | 136.5 (4) | C25—C28—C27 | 94.3 (3) |
C10—C11—C12 | 88.4 (4) | O8—C28—C26 | 176.2 (3) |
O2—C11—C13 | 178.2 (4) | C30—C29—O8 | 115.4 (7) |
O3—C12—C13 | 137.6 (5) | C30—C29—H29A | 108.4 |
O3—C12—C11 | 134.9 (4) | O8—C29—H29A | 108.4 |
C13—C12—C11 | 87.5 (4) | C30—C29—H29B | 108.4 |
O4—C13—C10 | 129.0 (4) | O8—C29—H29B | 108.4 |
O4—C13—C12 | 137.0 (4) | H29A—C29—H29B | 107.5 |
C10—C13—C12 | 94.0 (3) | C29—C30—H30A | 109.5 |
O4—C13—C11 | 175.7 (4) | C29—C30—H30B | 109.5 |
O4—C14—C15 | 108.2 (4) | H30A—C30—H30B | 109.5 |
O4—C14—H14A | 110.1 | C29—C30—H30C | 109.5 |
C15—C14—H14A | 110.1 | H30A—C30—H30C | 109.5 |
O4—C14—H14B | 110.1 | H30B—C30—H30C | 109.5 |
C15—C14—H14B | 110.1 | C9—N1—H1A | 120.0 |
H14A—C14—H14B | 108.4 | C9—N1—H1B | 120.0 |
C14—C15—H15A | 109.5 | H1A—N1—H1B | 120.0 |
C14—C15—H15B | 109.5 | C10—N2—C8 | 123.5 (3) |
H15A—C15—H15B | 109.5 | C10—N2—H2A | 118.3 |
C14—C15—H15C | 109.5 | C8—N2—H2A | 118.3 |
H15A—C15—H15C | 109.5 | C24—N3—H3A | 120.0 |
H15B—C15—H15C | 109.5 | C24—N3—H3B | 120.0 |
C17—C16—C21 | 121.0 (8) | H3A—N3—H3B | 120.0 |
C17—C16—H16 | 119.5 | C25—N4—C23 | 124.7 (3) |
C21—C16—H16 | 119.5 | C25—N4—H4A | 117.7 |
C18—C17—C16 | 121.1 (10) | C23—N4—H4A | 117.7 |
C18—C17—H17 | 119.4 | C13—O4—C14 | 116.2 (3) |
C16—C17—H17 | 119.4 | C28—O8—C29 | 116.1 (4) |
C17—C18—C19 | 119.0 (9) | HW1—O9—HW2 | 102 (6) |
C17—C18—H18 | 120.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O7i | 0.86 | 2.10 | 2.922 (5) | 160 |
N1—H1B···O9 | 0.86 | 2.05 | 2.894 (5) | 169 |
N2—H2A···O5ii | 0.86 | 2.10 | 2.821 (4) | 141 |
N3—H3A···O2iii | 0.86 | 2.17 | 3.026 (5) | 170 |
N3—H3B···O3iv | 0.86 | 2.10 | 2.930 (5) | 162 |
N4—H4A···O9v | 0.86 | 2.05 | 2.860 (4) | 155 |
O9—HW1···O1vi | 0.91 (8) | 1.78 (8) | 2.698 (6) | 177 (6) |
O9—HW2···O6vii | 0.89 (6) | 2.06 (6) | 2.869 (6) | 149 (5) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) x+1, y+1, z; (iii) x−1, y−1, z; (iv) −x, y−1/2, −z+1; (v) −x, y−1/2, −z+2; (vi) −x+1, y−1/2, −z+2; (vii) −x, y+1/2, −z+2. |
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