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organic compounds
4-Hydroxycoumarin reacts with 2,3-dichloro-5,6-dicyanobenzoquinone to form the title compound, C25H11Cl2NO8·2C3H7NO, which crystallizes as an N,N-dimethylformamide disolvate. Two coumarin units are fused at their 3-position (through the spiro C atom) and at their 4-position (through an ether linkage) to give a planar moiety.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402416X/lh6281sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680402416X/lh6281Isup2.hkl |
CCDC reference: 247047
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.047
- wR factor = 0.137
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for N3 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for N3' PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C29' PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for N2 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C31 .. 2.96 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 6 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
5'-Aminohydroxymethylene-1',2'-dichloro-spiro[7H- pyrano[3,2 - c;5,6 -
c']dichromene-7,4'-cyclohex-2'-ene]-3',6,6',8-tetraone dimethylformamide
disolvate top
Crystal data top
C25H11Cl2NO8·2C3H7NO | Z = 2 |
Mr = 670.44 | F(000) = 692 |
Triclinic, P1 | Dx = 1.437 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.549 (1) Å | Cell parameters from 905 reflections |
b = 11.720 (1) Å | θ = 2.4–25.7° |
c = 12.458 (1) Å | µ = 0.27 mm−1 |
α = 112.263 (2)° | T = 295 K |
β = 95.223 (2)° | Block, orange |
γ = 91.974 (2)° | 0.31 × 0.22 × 0.16 mm |
V = 1549.6 (3) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 3733 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 27.1°, θmin = 1.8° |
φ and ω scan | h = −14→14 |
13301 measured reflections | k = −14→14 |
6683 independent reflections | l = −15→15 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0658P)2 + 0.1399P] where P = (Fo2 + 2Fc2)/3 |
6683 reflections | (Δ/σ)max = 0.001 |
479 parameters | Δρmax = 0.32 e Å−3 |
99 restraints | Δρmin = −0.25 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.11031 (7) | 0.54702 (7) | 0.84710 (6) | 0.0756 (3) | |
Cl2 | 0.29896 (8) | 0.40792 (8) | 0.93813 (6) | 0.0833 (3) | |
O1 | 0.0726 (1) | 0.4680 (1) | 0.6023 (1) | 0.0474 (4) | |
O2 | 0.3972 (2) | 0.2238 (2) | 0.7489 (1) | 0.0548 (5) | |
O3 | 0.2321 (2) | 0.1979 (2) | 0.3500 (2) | 0.0514 (4) | |
O4 | 0.1188 (2) | 0.1268 (2) | 0.6520 (2) | 0.0583 (5) | |
O5 | 0.1246 (1) | −0.0591 (2) | 0.5161 (2) | 0.0495 (4) | |
O6 | 0.4150 (1) | 0.0509 (1) | 0.4014 (1) | 0.0390 (4) | |
O7 | 0.5724 (1) | 0.4043 (1) | 0.5411 (1) | 0.0470 (4) | |
O8 | 0.4459 (2) | 0.4663 (2) | 0.6690 (2) | 0.0570 (5) | |
O9 | 0.3001 (2) | 0.2024 (3) | 0.1623 (2) | 0.1012 (8) | |
O10 | 0.0011 (8) | 0.1918 (6) | 0.1526 (5) | 0.083 (2) | 0.721 (7) |
O10' | 0.025 (2) | 0.188 (2) | 0.134 (2) | 0.175 (15) | 0.279 (7) |
N1 | 0.1028 (2) | 0.3439 (2) | 0.3817 (2) | 0.0541 (6) | |
N2 | 0.4559 (2) | 0.2249 (2) | 0.0769 (2) | 0.0641 (6) | |
N3 | −0.0456 (5) | 0.1369 (7) | −0.0444 (5) | 0.068 (2) | 0.721 (7) |
N3' | −0.022 (1) | 0.156 (1) | −0.039 (1) | 0.068 (6) | 0.279 (7) |
C1 | 0.1782 (2) | 0.2866 (2) | 0.4243 (2) | 0.0386 (5) | |
C2 | 0.2069 (2) | 0.3144 (2) | 0.5448 (2) | 0.0335 (5) | |
C3 | 0.1491 (2) | 0.4061 (2) | 0.6264 (2) | 0.0376 (5) | |
C4 | 0.1825 (2) | 0.4334 (2) | 0.7534 (2) | 0.0441 (6) | |
C5 | 0.2623 (2) | 0.3755 (2) | 0.7925 (2) | 0.0469 (6) | |
C6 | 0.3258 (2) | 0.2775 (2) | 0.7131 (2) | 0.0403 (5) | |
C7 | 0.3001 (2) | 0.2420 (2) | 0.5800 (2) | 0.0334 (5) | |
C8 | 0.2646 (2) | 0.1037 (2) | 0.5271 (2) | 0.0350 (5) | |
C9 | 0.1661 (2) | 0.0626 (2) | 0.5710 (2) | 0.0429 (6) | |
C10 | 0.1778 (2) | −0.1416 (2) | 0.4276 (2) | 0.0452 (6) | |
C11 | 0.1295 (2) | −0.2628 (2) | 0.3803 (3) | 0.0616 (8) | |
C12 | 0.1814 (3) | −0.3476 (2) | 0.2933 (3) | 0.0690 (9) | |
C13 | 0.2799 (3) | −0.3157 (2) | 0.2532 (3) | 0.0655 (8) | |
C14 | 0.3275 (2) | −0.1954 (2) | 0.2997 (2) | 0.0495 (6) | |
C15 | 0.2762 (2) | −0.1068 (2) | 0.3885 (2) | 0.0398 (5) | |
C16 | 0.3179 (2) | 0.0213 (2) | 0.4439 (2) | 0.0353 (5) | |
C17 | 0.4625 (2) | 0.1703 (2) | 0.4524 (2) | 0.0342 (5) | |
C18 | 0.5674 (2) | 0.1922 (2) | 0.4074 (2) | 0.0358 (5) | |
C19 | 0.6205 (2) | 0.1010 (2) | 0.3219 (2) | 0.0440 (6) | |
C20 | 0.7211 (2) | 0.1328 (2) | 0.2846 (2) | 0.0527 (7) | |
C21 | 0.7685 (2) | 0.2534 (3) | 0.3307 (2) | 0.0580 (7) | |
C22 | 0.7176 (2) | 0.3435 (2) | 0.4149 (2) | 0.0525 (7) | |
C23 | 0.6179 (2) | 0.3119 (2) | 0.4534 (2) | 0.0404 (5) | |
C24 | 0.4749 (2) | 0.3821 (2) | 0.5875 (2) | 0.0408 (5) | |
C25 | 0.4157 (2) | 0.2600 (2) | 0.5366 (2) | 0.0334 (5) | |
C26 | 0.3957 (3) | 0.2558 (3) | 0.1656 (3) | 0.0760 (9) | |
C27 | 0.4145 (3) | 0.1235 (3) | −0.0297 (3) | 0.094 (1) | |
C28 | 0.5631 (3) | 0.2923 (4) | 0.0801 (4) | 0.112 (1) | |
C29 | 0.0318 (5) | 0.1819 (5) | 0.0536 (5) | 0.086 (2) | 0.721 (7) |
C30 | −0.1604 (5) | 0.1046 (5) | −0.0381 (5) | 0.107 (2) | 0.721 (7) |
C31 | −0.0068 (6) | 0.1217 (8) | −0.1530 (5) | 0.133 (3) | 0.721 (7) |
C29' | −0.057 (1) | 0.1304 (11) | 0.051 (1) | 0.084 (5) | 0.279 (7) |
C30' | 0.072 (1) | 0.2256 (15) | −0.043 (2) | 0.136 (7) | 0.279 (7) |
C31' | −0.100 (2) | 0.094 (2) | −0.156 (1) | 0.16 (1) | 0.279 (7) |
H3o | 0.232 (3) | 0.200 (3) | 0.283 (1) | 0.08 (1)* | |
H1n1 | 0.075 (2) | 0.317 (2) | 0.311 (1) | 0.07 (1)* | |
H1n2 | 0.062 (2) | 0.394 (2) | 0.428 (1) | 0.05 (1)* | |
H11 | 0.0635 | −0.2856 | 0.4072 | 0.074* | |
H12 | 0.1495 | −0.4290 | 0.2602 | 0.083* | |
H13 | 0.3143 | −0.3755 | 0.1946 | 0.079* | |
H14 | 0.3935 | −0.1734 | 0.2722 | 0.059* | |
H19 | 0.5884 | 0.0197 | 0.2905 | 0.053* | |
H20 | 0.7571 | 0.0726 | 0.2280 | 0.063* | |
H21 | 0.8359 | 0.2739 | 0.3043 | 0.070* | |
H22 | 0.7497 | 0.4248 | 0.4456 | 0.063* | |
H26 | 0.4255 | 0.3207 | 0.2343 | 0.091* | |
H27a | 0.3547 | 0.0737 | −0.0154 | 0.141* | |
H27b | 0.4779 | 0.0740 | −0.0589 | 0.141* | |
H27c | 0.3831 | 0.1547 | −0.0864 | 0.141* | |
H28a | 0.5817 | 0.3566 | 0.1561 | 0.168* | |
H28b | 0.5548 | 0.3283 | 0.0225 | 0.168* | |
H28c | 0.6246 | 0.2371 | 0.0639 | 0.168* | |
H29 | 0.1081 | 0.2058 | 0.0486 | 0.103* | 0.721 (7) |
H30a | −0.1720 | 0.1221 | 0.0417 | 0.160* | 0.721 (7) |
H30b | −0.1780 | 0.0180 | −0.0835 | 0.160* | 0.721 (7) |
H30c | −0.2109 | 0.1515 | −0.0684 | 0.160* | 0.721 (7) |
H31a | −0.0379 | 0.1829 | −0.1790 | 0.200* | 0.721 (7) |
H31b | −0.0331 | 0.0407 | −0.2092 | 0.200* | 0.721 (7) |
H31c | 0.0768 | 0.1311 | −0.1445 | 0.200* | 0.721 (7) |
H29' | −0.1231 | 0.0839 | 0.0529 | 0.101* | 0.279 (7) |
H30d | 0.1111 | 0.2684 | 0.0341 | 0.204* | 0.279 (7) |
H30e | 0.0472 | 0.2846 | −0.0752 | 0.204* | 0.279 (7) |
H30f | 0.1246 | 0.1731 | −0.0917 | 0.204* | 0.279 (7) |
H31d | −0.0651 | 0.0224 | −0.2053 | 0.241* | 0.279 (7) |
H31e | −0.1086 | 0.1513 | −0.1937 | 0.241* | 0.279 (7) |
H31f | −0.1757 | 0.0689 | −0.1421 | 0.241* | 0.279 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0842 (5) | 0.0705 (5) | 0.0629 (5) | 0.0342 (4) | 0.0277 (4) | 0.0085 (4) |
Cl2 | 0.1135 (7) | 0.0960 (6) | 0.0367 (4) | 0.0358 (5) | 0.0131 (4) | 0.0180 (4) |
O1 | 0.040 (1) | 0.045 (1) | 0.063 (1) | 0.011 (1) | 0.009 (1) | 0.025 (1) |
O2 | 0.056 (1) | 0.070 (1) | 0.047 (1) | 0.024 (1) | 0.007 (1) | 0.029 (1) |
O3 | 0.064 (1) | 0.053 (1) | 0.038 (1) | 0.012 (1) | 0.010 (1) | 0.017 (1) |
O4 | 0.053 (1) | 0.062 (1) | 0.065 (1) | 0.006 (1) | 0.030 (1) | 0.025 (1) |
O5 | 0.041 (1) | 0.047 (1) | 0.065 (1) | −0.002 (1) | 0.012 (1) | 0.025 (1) |
O6 | 0.036 (1) | 0.031 (1) | 0.047 (1) | −0.001 (1) | 0.013 (1) | 0.010 (1) |
O7 | 0.043 (1) | 0.036 (1) | 0.059 (1) | −0.002 (1) | 0.015 (1) | 0.013 (1) |
O8 | 0.058 (1) | 0.039 (1) | 0.058 (1) | 0.000 (1) | 0.019 (1) | −0.001 (1) |
O9 | 0.102 (2) | 0.135 (2) | 0.062 (1) | −0.020 (2) | 0.011 (1) | 0.035 (2) |
O10 | 0.112 (3) | 0.093 (4) | 0.036 (2) | 0.020 (2) | 0.010 (3) | 0.014 (2) |
O10' | 0.24 (3) | 0.18 (2) | 0.10 (2) | 0.02 (1) | 0.08 (1) | 0.02 (1) |
N1 | 0.053 (1) | 0.060 (2) | 0.051 (2) | 0.011 (1) | −0.003 (1) | 0.025 (1) |
N2 | 0.073 (2) | 0.069 (2) | 0.047 (1) | −0.001 (1) | 0.011 (1) | 0.018 (1) |
N3 | 0.068 (4) | 0.085 (4) | 0.054 (4) | 0.005 (3) | 0.014 (3) | 0.030 (3) |
N3' | 0.063 (9) | 0.09 (1) | 0.04 (1) | 0.003 (7) | −0.011 (7) | 0.014 (7) |
C1 | 0.039 (1) | 0.036 (1) | 0.043 (1) | 0.000 (1) | 0.004 (1) | 0.018 (1) |
C2 | 0.031 (1) | 0.033 (1) | 0.039 (1) | 0.002 (1) | 0.005 (1) | 0.016 (1) |
C3 | 0.033 (1) | 0.033 (1) | 0.049 (1) | −0.001 (1) | 0.007 (1) | 0.017 (1) |
C4 | 0.045 (1) | 0.039 (1) | 0.046 (1) | 0.004 (1) | 0.015 (1) | 0.010 (1) |
C5 | 0.053 (2) | 0.052 (2) | 0.035 (1) | 0.006 (1) | 0.011 (1) | 0.014 (1) |
C6 | 0.039 (1) | 0.046 (1) | 0.039 (1) | 0.004 (1) | 0.007 (1) | 0.019 (1) |
C7 | 0.031 (1) | 0.035 (1) | 0.037 (1) | 0.005 (1) | 0.009 (1) | 0.015 (1) |
C8 | 0.032 (1) | 0.035 (1) | 0.041 (1) | 0.002 (1) | 0.005 (1) | 0.018 (1) |
C9 | 0.038 (1) | 0.046 (1) | 0.053 (2) | 0.003 (1) | 0.008 (1) | 0.027 (1) |
C10 | 0.036 (1) | 0.043 (1) | 0.060 (2) | −0.002 (1) | −0.002 (1) | 0.025 (1) |
C11 | 0.049 (2) | 0.047 (2) | 0.090 (2) | −0.011 (1) | −0.002 (2) | 0.031 (2) |
C12 | 0.062 (2) | 0.037 (2) | 0.094 (2) | −0.013 (1) | −0.010 (2) | 0.016 (2) |
C13 | 0.066 (2) | 0.039 (2) | 0.073 (2) | 0.000 (1) | −0.002 (2) | 0.004 (1) |
C14 | 0.045 (1) | 0.041 (1) | 0.056 (2) | 0.001 (1) | 0.002 (1) | 0.011 (1) |
C15 | 0.035 (1) | 0.035 (1) | 0.048 (1) | 0.001 (1) | −0.001 (1) | 0.017 (1) |
C16 | 0.031 (1) | 0.038 (3) | 0.041 (1) | 0.001 (1) | 0.004 (1) | 0.019 (1) |
C17 | 0.032 (1) | 0.032 (1) | 0.039 (1) | 0.000 (1) | 0.004 (1) | 0.015 (1) |
C18 | 0.031 (1) | 0.039 (1) | 0.041 (1) | 0.001 (1) | 0.006 (1) | 0.018 (1) |
C19 | 0.044 (1) | 0.047 (1) | 0.041 (1) | 0.003 (1) | 0.013 (1) | 0.015 (1) |
C20 | 0.048 (2) | 0.059 (2) | 0.050 (2) | 0.009 (1) | 0.021 (1) | 0.017 (1) |
C21 | 0.043 (2) | 0.072 (2) | 0.065 (2) | −0.002 (1) | 0.019 (1) | 0.031 (2) |
C22 | 0.043 (1) | 0.052 (2) | 0.066 (2) | −0.005 (1) | 0.013 (1) | 0.027 (1) |
C23 | 0.036 (1) | 0.039 (1) | 0.047 (1) | 0.003 (1) | 0.008 (1) | 0.018 (1) |
C24 | 0.037 (1) | 0.039 (1) | 0.045 (1) | 0.004 (1) | 0.006 (1) | 0.015 (1) |
C25 | 0.032 (1) | 0.032 (1) | 0.037 (1) | 0.003 (1) | 0.005 (1) | 0.013 (1) |
C26 | 0.071 (2) | 0.095 (2) | 0.050 (2) | −0.014 (1) | 0.006 (2) | 0.017 (2) |
C27 | 0.137 (3) | 0.084 (2) | 0.051 (2) | 0.006 (2) | 0.008 (2) | 0.014 (2) |
C28 | 0.088 (3) | 0.120 (3) | 0.106 (3) | −0.019 (2) | 0.035 (2) | 0.016 (3) |
C29 | 0.093 (4) | 0.098 (4) | 0.075 (4) | 0.013 (3) | 0.015 (3) | 0.041 (4) |
C30 | 0.087 (4) | 0.126 (5) | 0.097 (4) | −0.010 (3) | 0.014 (3) | 0.033 (4) |
C31 | 0.123 (6) | 0.223 (9) | 0.068 (4) | 0.028 (6) | 0.024 (4) | 0.069 (5) |
C29' | 0.09 (1) | 0.069 (8) | 0.09 (1) | 0.020 (7) | 0.018 (9) | 0.030 (8) |
C30' | 0.11 (1) | 0.13 (1) | 0.16 (2) | −0.03 (1) | 0.02 (1) | 0.05 (1) |
C31' | 0.18 (2) | 0.18 (2) | 0.11 (1) | −0.02 (2) | −0.07 (2) | 0.06 (1) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.705 (2) | C15—C16 | 1.438 (3) |
Cl2—C5 | 1.716 (2) | C17—C18 | 1.435 (3) |
O1—C3 | 1.248 (2) | C17—C25 | 1.343 (3) |
O2—C6 | 1.206 (3) | C18—C19 | 1.398 (3) |
O3—C1 | 1.321 (3) | C18—C23 | 1.382 (3) |
O4—C9 | 1.199 (3) | C19—C20 | 1.380 (3) |
O5—C9 | 1.372 (3) | C20—C21 | 1.379 (4) |
O5—C10 | 1.373 (3) | C21—C22 | 1.370 (3) |
O6—C16 | 1.370 (2) | C22—C23 | 1.377 (3) |
O6—C17 | 1.368 (2) | C24—C25 | 1.443 (3) |
O7—C23 | 1.375 (3) | O3—H3o | 0.84 (1) |
O7—C24 | 1.372 (3) | N1—H1n1 | 0.84 (1) |
O8—C24 | 1.201 (3) | N1—H1n2 | 0.85 (1) |
O9—C26 | 1.239 (3) | C11—H11 | 0.93 |
O10—C29 | 1.28 (1) | C12—H12 | 0.93 |
O10'—C29' | 1.29 (1) | C13—H13 | 0.93 |
N1—C1 | 1.310 (3) | C14—H14 | 0.93 |
N2—C26 | 1.299 (4) | C19—H19 | 0.93 |
N2—C27 | 1.434 (4) | C20—H20 | 0.93 |
N2—C28 | 1.435 (4) | C21—H21 | 0.93 |
N3—C29 | 1.359 (6) | C22—H22 | 0.93 |
N3—C30 | 1.384 (6) | C26—H26 | 0.93 |
N3—C31 | 1.413 (6) | C27—H27a | 0.96 |
N3'—C29' | 1.350 (8) | C27—H27b | 0.96 |
N3'—C30' | 1.361 (8) | C27—H27c | 0.96 |
N3'—C31' | 1.54 (2) | C28—H28a | 0.96 |
C1—C2 | 1.414 (3) | C28—H28b | 0.96 |
C2—C3 | 1.407 (3) | C28—H28c | 0.96 |
C2—C7 | 1.526 (3) | C29—H29 | 0.93 |
C3—C4 | 1.500 (3) | C30—H30a | 0.96 |
C4—C5 | 1.326 (3) | C30—H30b | 0.96 |
C5—C6 | 1.471 (3) | C30—H30c | 0.96 |
C6—C7 | 1.545 (3) | C31—H31a | 0.96 |
C7—C25 | 1.523 (3) | C31—H31b | 0.96 |
C7—C8 | 1.524 (3) | C31—H31c | 0.96 |
C8—C9 | 1.450 (3) | C29'—H29' | 0.93 |
C8—C16 | 1.336 (3) | C30'—H30d | 0.96 |
C10—C11 | 1.388 (3) | C30'—H30e | 0.96 |
C10—C15 | 1.384 (3) | C30'—H30f | 0.96 |
C11—C12 | 1.366 (4) | C31'—H31d | 0.96 |
C12—C13 | 1.378 (4) | C31'—H31e | 0.96 |
C13—C14 | 1.377 (3) | C31'—H31f | 0.96 |
C14—C15 | 1.394 (3) | ||
C9—O5—C10 | 121.9 (2) | C21—C22—C23 | 118.9 (2) |
C16—O6—C17 | 117.4 (2) | O7—C23—C18 | 121.6 (2) |
C23—O7—C24 | 121.6 (2) | O7—C23—C22 | 116.9 (2) |
C26—N2—C27 | 120.4 (3) | C18—C23—C22 | 121.5 (2) |
C26—N2—C28 | 121.9 (3) | O7—C24—O8 | 117.0 (2) |
C27—N2—C28 | 117.6 (3) | O7—C24—C25 | 118.2 (2) |
C29—N3—C30 | 120.5 (5) | O8—C24—C25 | 124.8 (2) |
C29—N3—C31 | 119.2 (6) | C7—C25—C17 | 123.6 (2) |
C30—N3—C31 | 120.4 (6) | C7—C25—C24 | 117.1 (2) |
C29'—N3'—C30' | 130 (2) | C24—C25—C17 | 119.3 (2) |
C29'—N3'—C31' | 116 (1) | O9—C26—N2 | 122.7 (3) |
C30'—N3'—C31' | 114 (1) | O10'—C29'—N3' | 102 (2) |
O3—C1—N1 | 117.9 (2) | C1—O3—H3o | 115 (2) |
O3—C1—C2 | 117.7 (2) | C1—N1—H1n1 | 124 (2) |
N1—C1—C2 | 124.4 (2) | C1—N1—H1n2 | 118 (2) |
C1—C2—C3 | 119.3 (2) | H1n1—N1—H1n2 | 114 (2) |
C1—C2—C7 | 117.8 (2) | C12—C11—H11 | 120.9 |
C3—C2—C7 | 123.0 (2) | C10—C11—H11 | 120.9 |
O1—C3—C2 | 125.5 (2) | C11—C12—H12 | 119.2 |
O1—C3—C4 | 116.8 (2) | C13—C12—H12 | 119.2 |
C2—C3—C4 | 117.7 (2) | C14—C13—H13 | 120.0 |
C3—C4—C5 | 123.8 (2) | C12—C13—H13 | 120.0 |
Cl1—C4—C3 | 115.0 (2) | C13—C14—H14 | 120.2 |
Cl1—C4—C5 | 121.2 (2) | C15—C14—H14 | 120.2 |
C4—C5—C6 | 122.0 (2) | C20—C19—H19 | 120.4 |
Cl2—C5—C4 | 123.0 (2) | C18—C19—H19 | 120.4 |
Cl2—C5—C6 | 115.0 (2) | C21—C20—H20 | 119.8 |
O2—C6—C5 | 121.9 (2) | C19—C20—H20 | 119.8 |
O2—C6—C7 | 119.1 (2) | C22—C21—H21 | 119.6 |
C5—C6—C7 | 119.1 (2) | C20—C21—H21 | 119.6 |
C2—C7—C8 | 111.0 (2) | C21—C22—H22 | 120.5 |
C2—C7—C25 | 111.2 (2) | C23—C22—H22 | 120.5 |
C8—C7—C25 | 106.9 (2) | O9—C26—H26 | 118.7 |
C6—C7—C25 | 106.5 (2) | N2—C26—H26 | 118.7 |
C2—C7—C6 | 114.5 (2) | N2—C27—H27a | 109.5 |
C6—C7—C8 | 106.4 (2) | N2—C27—H27b | 109.5 |
C7—C8—C9 | 116.4 (2) | H27a—C27—H27b | 109.5 |
C7—C8—C16 | 124.0 (2) | N2—C27—H27c | 109.5 |
C9—C8—C16 | 119.6 (2) | H27a—C27—H27c | 109.5 |
O4—C9—O5 | 117.7 (2) | H27b—C27—H27c | 109.5 |
O4—C9—C8 | 124.8 (2) | N2—C28—H28a | 109.5 |
O5—C9—C8 | 117.5 (2) | N2—C28—H28b | 109.5 |
O5—C10—C11 | 116.8 (2) | H28a—C28—H28b | 109.5 |
O5—C10—C15 | 121.9 (2) | N2—C28—H28c | 109.5 |
C11—C10—C15 | 121.3 (2) | H28a—C28—H28c | 109.5 |
C10—C11—C12 | 118.3 (3) | H28b—C28—H28c | 109.5 |
C11—C12—C13 | 121.6 (3) | O10—C29—N3 | 120.9 (7) |
C12—C13—C14 | 120.1 (3) | O10—C29—H29 | 119.6 |
C13—C14—C15 | 119.5 (2) | N3—C29—H29 | 119.6 |
C10—C15—C14 | 119.2 (2) | O10'—C29'—H29' | 128.9 |
C10—C15—C16 | 116.2 (2) | N3'—C29'—H29' | 128.9 |
C14—C15—C16 | 124.6 (2) | N3'—C30'—H30d | 109.5 |
O6—C16—C8 | 123.6 (2) | N3'—C30'—H30e | 109.5 |
O6—C16—C15 | 113.8 (2) | H30d—C30'—H30e | 109.5 |
C8—C16—C15 | 122.6 (2) | N3'—C30'—H30f | 109.5 |
O6—C17—C18 | 114.0 (2) | H30d—C30'—H30f | 109.5 |
O6—C17—C25 | 123.6 (2) | H30e—C30'—H30f | 109.5 |
C18—C17—C25 | 122.4 (2) | N3'—C31'—H31d | 109.5 |
C17—C18—C19 | 124.3 (2) | N3'—C31'—H31e | 109.5 |
C17—C18—C23 | 116.7 (2) | H31d—C31'—H31e | 109.5 |
C19—C18—C23 | 119.0 (2) | N3'—C31'—H31f | 109.5 |
C18—C19—C20 | 119.3 (2) | H31d—C31'—H31f | 109.5 |
C19—C20—C21 | 120.4 (2) | H31e—C31'—H31f | 109.5 |
C20—C21—C22 | 120.9 (2) | ||
N1—C1—C2—C3 | 2.5 (3) | C11—C10—C15—C16 | 179.8 (2) |
O3—C1—C2—C3 | −178.3 (2) | C13—C14—C15—C10 | −0.3 (4) |
N1—C1—C2—C7 | −177.8 (2) | C13—C14—C15—C16 | 179.9 (2) |
O3—C1—C2—C7 | 1.5 (3) | C9—C8—C16—O6 | −176.6 (2) |
C1—C2—C3—O1 | −0.4 (3) | C7—C8—C16—O6 | 3.9 (3) |
C7—C2—C3—O1 | 179.8 (2) | C9—C8—C16—C15 | 5.0 (3) |
C1—C2—C3—C4 | −179.6 (2) | C7—C8—C16—C15 | −174.4 (2) |
C7—C2—C3—C4 | 0.6 (3) | C17—O6—C16—C8 | 3.7 (3) |
O1—C3—C4—C5 | −179.9 (2) | C17—O6—C16—C15 | −177.8 (2) |
C2—C3—C4—C5 | −0.6 (3) | C10—C15—C16—C8 | −1.2 (3) |
O1—C3—C4—Cl1 | −0.2 (3) | C14—C15—C16—C8 | 178.6 (2) |
C2—C3—C4—Cl1 | 179.1 (2) | C10—C15—C16—O6 | −179.7 (2) |
C3—C4—C5—C6 | −0.1 (4) | C14—C15—C16—O6 | 0.1 (3) |
Cl1—C4—C5—C6 | −179.8 (2) | C16—O6—C17—C25 | −3.6 (3) |
C3—C4—C5—Cl2 | −179.9 (2) | C16—O6—C17—C18 | 176.8 (2) |
Cl1—C4—C5—Cl2 | 0.4 (3) | C25—C17—C18—C23 | −1.2 (3) |
C4—C5—C6—O2 | −179.0 (2) | O6—C17—C18—C23 | 178.4 (2) |
Cl2—C5—C6—O2 | 0.8 (3) | C25—C17—C18—C19 | 178.4 (2) |
C4—C5—C6—C7 | 0.8 (3) | O6—C17—C18—C19 | −1.9 (3) |
Cl2—C5—C6—C7 | −179.4 (2) | C23—C18—C19—C20 | −0.8 (3) |
C3—C2—C7—C25 | −120.7 (2) | C17—C18—C19—C20 | 179.6 (2) |
C1—C2—C7—C25 | 59.5 (2) | C18—C19—C20—C21 | −0.3 (4) |
C3—C2—C7—C8 | 120.5 (2) | C19—C20—C21—C22 | 0.6 (4) |
C1—C2—C7—C8 | −59.3 (2) | C20—C21—C22—C23 | 0.2 (4) |
C3—C2—C7—C6 | 0.0 (3) | C24—O7—C23—C22 | −178.5 (2) |
C1—C2—C7—C6 | −179.7 (2) | C24—O7—C23—C18 | 0.3 (3) |
O2—C6—C7—C25 | −57.6 (3) | C21—C22—C23—O7 | 177.6 (2) |
C5—C6—C7—C25 | 122.6 (2) | C21—C22—C23—C18 | −1.2 (4) |
O2—C6—C7—C8 | 56.1 (3) | C19—C18—C23—O7 | −177.2 (2) |
C5—C6—C7—C8 | −123.7 (2) | C17—C18—C23—O7 | 2.4 (3) |
O2—C6—C7—C2 | 179.1 (2) | C19—C18—C23—C22 | 1.5 (3) |
C5—C6—C7—C2 | −0.8 (3) | C17—C18—C23—C22 | −178.8 (2) |
C25—C7—C8—C16 | −9.9 (3) | C23—O7—C24—O8 | 175.2 (2) |
C2—C7—C8—C16 | 111.4 (2) | C23—O7—C24—C25 | −4.2 (3) |
C6—C7—C8—C16 | −123.4 (2) | O6—C17—C25—C24 | 177.8 (2) |
C25—C7—C8—C9 | 170.6 (2) | C18—C17—C25—C24 | −2.6 (3) |
C2—C7—C8—C9 | −68.0 (2) | O6—C17—C25—C7 | −4.1 (3) |
C6—C7—C8—C9 | 57.1 (2) | C18—C17—C25—C7 | 175.5 (2) |
C10—O5—C9—O4 | −175.6 (2) | O8—C24—C25—C17 | −174.1 (2) |
C10—O5—C9—C8 | 4.0 (3) | O7—C24—C25—C17 | 5.3 (3) |
C16—C8—C9—O4 | 173.2 (2) | O8—C24—C25—C7 | 7.7 (3) |
C7—C8—C9—O4 | −7.3 (3) | O7—C24—C25—C7 | −172.9 (2) |
C16—C8—C9—O5 | −6.3 (3) | C8—C7—C25—C17 | 10.0 (3) |
C7—C8—C9—O5 | 173.1 (2) | C2—C7—C25—C17 | −111.2 (2) |
C9—O5—C10—C15 | −0.2 (3) | C6—C7—C25—C17 | 123.4 (2) |
C9—O5—C10—C11 | 178.7 (2) | C8—C7—C25—C24 | −171.9 (2) |
O5—C10—C11—C12 | −179.1 (2) | C2—C7—C25—C24 | 66.9 (2) |
C15—C10—C11—C12 | −0.2 (4) | C6—C7—C25—C24 | −58.5 (2) |
C10—C11—C12—C13 | 0.6 (4) | C27—N2—C26—O9 | −1.5 (5) |
C11—C12—C13—C14 | −1.0 (5) | C28—N2—C26—O9 | 176.4 (3) |
C12—C13—C14—C15 | 0.8 (4) | C30—N3—C29—O10 | 2.1 (9) |
O5—C10—C15—C14 | 178.8 (2) | C31—N3—C29—O10 | −176.9 (6) |
C11—C10—C15—C14 | 0.0 (4) | C30'—N3'—C29'—O10' | −2 (2) |
O5—C10—C15—C16 | −1.4 (3) | C31'—N3'—C29'—O10' | 177 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···O9 | 0.84 (1) | 1.77 (2) | 2.553 (3) | 154 (3) |
N1—H1n1···O10 | 0.84 (1) | 2.05 (1) | 2.845 (5) | 158 (3) |
N1—H1n1···O10′ | 0.84 (1) | 2.17 (2) | 2.96 (2) | 159 (3) |
N1—H1n2···O1i | 0.85 (1) | 2.39 (2) | 3.008 (3) | 130 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
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