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organic compounds
The two N-pthaloylglycine moieties of the title compound, C20H12N2O9·2C3H7NO, are connected through an ether linkage, which apparently has sp2 character [O-C = 1.376 (3) and 1.392 (3) Å; C-O-C = 120.3 (2)°]. The planar N-phthaloyl units are inclined to each other by 65.2 (1)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028253/ya6188sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028253/ya6188Isup2.hkl |
CCDC reference: 232165
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.196
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT241_ALERT_2_A Check High U(eq) as Compared to Neighbors .... C26 PLAT241_ALERT_2_A Check High U(eq) as Compared to Neighbors .... C26'
Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C25 PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C25' PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N4 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N4' PLAT731_ALERT_1_B Bond Calc 0.86(5), Rep 0.850(10) ...... 5.00 su-Rat O9 -H9O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(5), Rep 0.850(10) ...... 5.00 su-Rat O9 -H9O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(5), Rep 0.850(10) ...... 5.00 su-Rat O9 -H9O 1.555 1.555
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 = 0.108 Value of mu given = 0.110 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C24 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C24' PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C20 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O11
2 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.
5,5'-Oxybis[2-(phthalimido)acetic acid] bis-N,N-dimethylformamide
solvate top
Crystal data top
C20H12N2O9·2C3H7NO | Z = 2 |
Mr = 570.51 | F(000) = 596 |
Triclinic, P1 | Dx = 1.365 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.357 (1) Å | Cell parameters from 805 reflections |
b = 11.122 (2) Å | θ = 2.4–23.6° |
c = 15.044 (2) Å | µ = 0.11 mm−1 |
α = 93.053 (2)° | T = 298 K |
β = 96.081 (2)° | Block, colorless |
γ = 90.891 (2)° | 0.50 × 0.39 × 0.14 mm |
V = 1388.2 (3) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 3216 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.1°, θmin = 1.8° |
φ and ω scans | h = −10→10 |
11580 measured reflections | k = −14→14 |
5937 independent reflections | l = −19→18 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1001P)2 + 0.3122P] where P = (Fo2 + 2Fc2)/3 |
5937 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.45 e Å−3 |
42 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.7968 (3) | 0.7373 (3) | 0.8005 (2) | 0.088 (1) | |
O2 | 0.5903 (4) | 0.6219 (3) | 0.8209 (2) | 0.126 (1) | |
O3 | 0.2254 (3) | 0.7823 (2) | 0.7142 (2) | 0.073 (1) | |
O4 | 0.5804 (2) | 0.5198 (2) | 0.6072 (1) | 0.061 (1) | |
O5 | 0.0118 (2) | 0.2564 (2) | 0.5259 (1) | 0.058 (1) | |
O6 | 0.4477 (2) | −0.2186 (2) | 0.4822 (1) | 0.065 (1) | |
O7 | 0.1130 (3) | −0.0714 (2) | 0.2572 (2) | 0.081 (1) | |
O8 | 0.5043 (3) | −0.0895 (3) | 0.2487 (2) | 0.083 (1) | |
O9 | 0.5015 (6) | −0.2662 (3) | 0.1734 (3) | 0.150 (2) | |
O10 | 0.9111 (4) | 0.6653 (4) | 0.9562 (2) | 0.125 (1) | |
O11 | 0.707 (1) | −0.154 (1) | 0.0860 (9) | 0.135 (3) | 0.50 |
O11' | 0.627 (1) | −0.157 (1) | 0.0535 (9) | 0.135 (3) | 0.50 |
N1 | 0.4315 (3) | 0.6720 (2) | 0.6638 (2) | 0.049 (1) | |
N2 | 0.2897 (3) | −0.1682 (2) | 0.3556 (2) | 0.056 (1) | |
N3 | 0.8443 (5) | 0.5733 (4) | 1.0805 (3) | 0.106 (1) | |
N4 | 0.735 (3) | 0.032 (1) | 0.030 (1) | 0.099 (4) | 0.50 |
N4' | 0.776 (3) | 0.010 (1) | 0.038 (1) | 0.099 (4) | 0.50 |
C1 | 0.6533 (4) | 0.6959 (3) | 0.7801 (2) | 0.065 (1) | |
C2 | 0.5671 (4) | 0.7483 (3) | 0.6991 (2) | 0.058 (1) | |
C3 | 0.2724 (3) | 0.6913 (3) | 0.6788 (2) | 0.050 (1) | |
C4 | 0.1818 (3) | 0.5818 (2) | 0.6429 (2) | 0.043 (1) | |
C5 | 0.0211 (3) | 0.5505 (3) | 0.6399 (2) | 0.050 (1) | |
C6 | −0.0298 (3) | 0.4397 (2) | 0.6018 (2) | 0.048 (1) | |
C7 | 0.0785 (3) | 0.3615 (2) | 0.5673 (2) | 0.045 (1) | |
C8 | 0.2415 (3) | 0.3914 (2) | 0.5697 (2) | 0.044 (1) | |
C9 | 0.2889 (3) | 0.5023 (2) | 0.6083 (2) | 0.042 (1) | |
C10 | 0.4520 (3) | 0.5594 (2) | 0.6235 (2) | 0.046 (1) | |
C11 | 0.1083 (3) | 0.1582 (2) | 0.5106 (2) | 0.046 (1) | |
C12 | 0.2043 (3) | 0.1111 (2) | 0.5804 (2) | 0.051 (1) | |
C13 | 0.2903 (3) | 0.0088 (2) | 0.5659 (2) | 0.049 (1) | |
C14 | 0.2767 (3) | −0.0437 (2) | 0.4809 (2) | 0.044 (1) | |
C15 | 0.1789 (3) | 0.0035 (2) | 0.4119 (2) | 0.046 (1) | |
C16 | 0.0929 (3) | 0.1061 (2) | 0.4251 (2) | 0.049 (1) | |
C17 | 0.3514 (3) | −0.1534 (2) | 0.4451 (2) | 0.049 (1) | |
C18 | 0.1837 (3) | −0.0770 (3) | 0.3304 (2) | 0.056 (1) | |
C19 | 0.3470 (4) | −0.2539 (3) | 0.2916 (2) | 0.067 (1) | |
C20 | 0.4625 (5) | −0.1924 (4) | 0.2366 (2) | 0.072 (1) | |
C21 | 0.8186 (6) | 0.5989 (5) | 0.9961 (3) | 0.108 (1) | |
C22 | 0.9759 (9) | 0.6284 (6) | 1.1376 (4) | 0.170 (3) | |
C23 | 0.7368 (8) | 0.4907 (6) | 1.1171 (4) | 0.146 (2) | |
C24 | 0.746 (3) | −0.037 (2) | 0.099 (2) | 0.137 (4) | 0.50 |
C25 | 0.721 (3) | −0.024 (2) | −0.058 (2) | 0.154 (6) | 0.50 |
C26 | 0.743 (2) | 0.163 (2) | 0.046 (1) | 0.179 (5) | 0.50 |
C24' | 0.700 (3) | −0.056 (2) | 0.091 (2) | 0.137 (4) | 0.50 |
C25' | 0.769 (3) | 0.009 (2) | −0.056 (2) | 0.154 (6) | 0.50 |
C26' | 0.844 (2) | 0.129 (2) | 0.070 (1) | 0.179 (5) | 0.50 |
H1o | 0.834 (5) | 0.715 (4) | 0.852 (1) | 0.105* | |
H9o | 0.581 (5) | −0.230 (5) | 0.154 (4) | 0.180* | |
H2a | 0.5301 | 0.8280 | 0.7150 | 0.070* | |
H2b | 0.6404 | 0.7559 | 0.6537 | 0.070* | |
H5 | −0.0512 | 0.6033 | 0.6630 | 0.060* | |
H6 | −0.1378 | 0.4169 | 0.5991 | 0.058* | |
H8 | 0.3140 | 0.3390 | 0.5463 | 0.053* | |
H12 | 0.2107 | 0.1488 | 0.6374 | 0.061* | |
H13 | 0.3555 | −0.0237 | 0.6122 | 0.059* | |
H16 | 0.0279 | 0.1386 | 0.3788 | 0.059* | |
H19a | 0.2566 | −0.2887 | 0.2523 | 0.081* | |
H19b | 0.4012 | −0.3184 | 0.3227 | 0.081* | |
H21 | 0.7263 | 0.5663 | 0.9629 | 0.129* | |
H22a | 1.0251 | 0.6901 | 1.1066 | 0.255* | |
H22b | 1.0539 | 0.5687 | 1.1537 | 0.255* | |
H22C | 0.9371 | 0.6636 | 1.1907 | 0.255* | |
H23a | 0.6480 | 0.4693 | 1.0730 | 0.219* | |
H23b | 0.6974 | 0.5285 | 1.1691 | 0.219* | |
H23C | 0.7937 | 0.4195 | 1.1334 | 0.219* | |
H24 | 0.7805 | −0.0046 | 0.1556 | 0.165* | 0.50 |
H25a | 0.8228 | −0.0560 | −0.0695 | 0.231* | 0.50 |
H25b | 0.6896 | 0.0352 | −0.1003 | 0.231* | 0.50 |
H25c | 0.6412 | −0.0872 | −0.0623 | 0.231* | 0.50 |
H26a | 0.7503 | 0.1832 | 0.1089 | 0.268* | 0.50 |
H26b | 0.6478 | 0.1976 | 0.0168 | 0.268* | 0.50 |
H26c | 0.8360 | 0.1949 | 0.0219 | 0.268* | 0.50 |
H25d | 0.7800 | −0.0719 | −0.0796 | 0.231* | 0.50 |
H25e | 0.8550 | 0.0587 | −0.0723 | 0.231* | 0.50 |
H25f | 0.6677 | 0.0397 | −0.0799 | 0.231* | 0.50 |
H24' | 0.6969 | −0.0339 | 0.1508 | 0.165* | 0.50 |
H26d | 0.7697 | 0.1702 | 0.1051 | 0.268* | 0.50 |
H26e | 0.8615 | 0.1751 | 0.0197 | 0.268* | 0.50 |
H26f | 0.9439 | 0.1196 | 0.1062 | 0.268* | 0.50 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.065 (2) | 0.104 (2) | 0.090 (2) | −0.016 (1) | −0.014 (1) | 0.015 (2) |
O2 | 0.116 (2) | 0.161 (3) | 0.096 (2) | −0.060 (2) | −0.034 (2) | 0.070 (2) |
O3 | 0.069 (1) | 0.053 (1) | 0.094 (2) | 0.013 (1) | 0.008 (1) | −0.011 (1) |
O4 | 0.040 (1) | 0.061 (1) | 0.084 (1) | 0.005 (1) | 0.012 (1) | 0.002 (1) |
O5 | 0.036 (1) | 0.046 (1) | 0.091 (2) | 0.005 (1) | 0.003 (1) | −0.004 (1) |
O6 | 0.061 (1) | 0.058 (1) | 0.078 (1) | 0.021 (1) | 0.009 (1) | 0.017 (1) |
O7 | 0.087 (2) | 0.089 (2) | 0.063 (1) | 0.018 (1) | −0.008 (1) | 0.004 (1) |
O8 | 0.087 (2) | 0.089 (2) | 0.073 (2) | −0.017 (2) | 0.015 (1) | 0.003 (1) |
O9 | 0.233 (4) | 0.089 (2) | 0.150 (3) | 0.017 (2) | 0.126 (3) | −0.001 (2) |
O10 | 0.102 (2) | 0.160 (3) | 0.110 (2) | −0.016 (2) | −0.018 (2) | 0.035 (2) |
O11 | 0.149 (8) | 0.134 (3) | 0.136 (7) | 0.013 (6) | 0.075 (6) | 0.017 (5) |
O11' | 0.149 (8) | 0.134 (3) | 0.136 (7) | 0.013 (6) | 0.075 (6) | 0.017 (5) |
N1 | 0.044 (1) | 0.044 (1) | 0.058 (1) | 0.002 (1) | 0.001 (1) | 0.004 (1) |
N2 | 0.058 (1) | 0.052 (1) | 0.059 (2) | 0.010 (1) | 0.012 (1) | 0.006 (1) |
N3 | 0.113 (3) | 0.117 (3) | 0.085 (2) | −0.003 (2) | −0.009 (2) | 0.024 (2) |
N4 | 0.108 (9) | 0.110 (5) | 0.084 (4) | 0.005 (5) | 0.032 (5) | 0.013 (4) |
N4' | 0.108 (9) | 0.110 (5) | 0.084 (4) | 0.005 (5) | 0.032 (5) | 0.013 (4) |
C1 | 0.059 (2) | 0.066 (2) | 0.065 (2) | −0.008 (2) | −0.006 (2) | 0.001 (2) |
C2 | 0.058 (2) | 0.050 (2) | 0.066 (2) | −0.006 (1) | 0.002 (1) | 0.005 (1) |
C3 | 0.051 (2) | 0.048 (2) | 0.051 (2) | 0.011 (1) | 0.006 (1) | 0.006 (1) |
C4 | 0.042 (1) | 0.043 (1) | 0.045 (1) | 0.010 (1) | 0.006 (1) | 0.009 (1) |
C5 | 0.042 (2) | 0.056 (2) | 0.055 (2) | 0.018 (1) | 0.013 (1) | 0.009 (1) |
C6 | 0.034 (1) | 0.051 (2) | 0.063 (2) | 0.008 (1) | 0.010 (1) | 0.012 (1) |
C7 | 0.039 (1) | 0.044 (2) | 0.053 (2) | 0.006 (1) | 0.007 (1) | 0.011 (1) |
C8 | 0.035 (1) | 0.043 (2) | 0.056 (2) | 0.008 (1) | 0.009 (1) | 0.003 (1) |
C9 | 0.035 (1) | 0.045 (2) | 0.046 (1) | 0.008 (1) | 0.006 (1) | 0.010 (1) |
C10 | 0.040 (1) | 0.049 (2) | 0.050 (2) | 0.006 (1) | 0.004 (1) | 0.010 (1) |
C11 | 0.033 (1) | 0.037 (1) | 0.069 (2) | 0.002 (1) | 0.007 (1) | 0.007 (1) |
C12 | 0.043 (2) | 0.048 (2) | 0.061 (2) | −0.004 (1) | 0.003 (1) | 0.002 (1) |
C13 | 0.040 (1) | 0.047 (2) | 0.060 (2) | 0.003 (1) | 0.002 (1) | 0.012 (1) |
C14 | 0.034 (1) | 0.043 (1) | 0.058 (2) | −0.001 (1) | 0.007 (1) | 0.013 (1) |
C15 | 0.039 (1) | 0.043 (1) | 0.058 (2) | 0.000 (1) | 0.007 (1) | 0.011 (1) |
C16 | 0.037 (1) | 0.048 (2) | 0.063 (2) | 0.001 (1) | 0.002 (1) | 0.016 (1) |
C17 | 0.041 (1) | 0.046 (2) | 0.061 (2) | 0.001 (1) | 0.011 (1) | 0.013 (1) |
C18 | 0.051 (2) | 0.059 (2) | 0.059 (2) | 0.004 (1) | 0.005 (1) | 0.011 (1) |
C19 | 0.076 (2) | 0.060 (2) | 0.067 (2) | 0.011 (2) | 0.015 (2) | 0.004 (2) |
C20 | 0.084 (2) | 0.074 (2) | 0.060 (2) | 0.024 (2) | 0.020 (2) | 0.006 (2) |
C21 | 0.095 (3) | 0.120 (4) | 0.108 (4) | −0.009 (3) | −0.006 (3) | 0.036 (3) |
C22 | 0.202 (7) | 0.177 (6) | 0.114 (4) | −0.032 (5) | −0.059 (5) | 0.020 (4) |
C23 | 0.155 (5) | 0.159 (5) | 0.134 (4) | 0.004 (4) | 0.036 (4) | 0.059 (4) |
C24 | 0.15 (1) | 0.157 (6) | 0.118 (5) | −0.022 (6) | 0.060 (6) | 0.012 (5) |
C25 | 0.17 (1) | 0.18 (1) | 0.109 (4) | −0.007 (8) | 0.033 (6) | 0.019 (6) |
C26 | 0.19 (1) | 0.173 (8) | 0.178 (8) | −0.025 (8) | 0.039 (8) | 0.006 (6) |
C24' | 0.15 (1) | 0.157 (6) | 0.118 (5) | −0.022 (6) | 0.060 (6) | 0.012 (5) |
C25' | 0.17 (1) | 0.18 (1) | 0.109 (4) | −0.007 (8) | 0.033 (6) | 0.019 (6) |
C26' | 0.19 (1) | 0.173 (8) | 0.178 (8) | −0.025 (8) | 0.039 (8) | 0.006 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.278 (4) | N4—C25 | 1.41 (1) |
O2—C1 | 1.200 (4) | N4—C26 | 1.47 (1) |
O3—C3 | 1.209 (3) | O11'—C24' | 1.33 (1) |
O4—C10 | 1.210 (3) | N4'—C24' | 1.31 (1) |
O5—C7 | 1.376 (3) | N4'—C25' | 1.41 (1) |
O5—C11 | 1.392 (3) | N4'—C26' | 1.47 (1) |
O6—C17 | 1.204 (3) | O1—H1o | 0.86 (1) |
O7—C18 | 1.199 (3) | O9—H9o | 0.85 (1) |
O8—C20 | 1.190 (4) | C2—H2a | 0.97 |
O9—C20 | 1.294 (4) | C2—H2b | 0.97 |
O10—C21 | 1.277 (5) | C5—H5 | 0.93 |
N1—C2 | 1.442 (4) | C6—H6 | 0.93 |
N1—C3 | 1.390 (3) | C8—H8 | 0.93 |
N1—C10 | 1.383 (3) | C12—H12 | 0.93 |
N2—C17 | 1.390 (4) | C13—H13 | 0.93 |
N2—C18 | 1.398 (4) | C16—H16 | 0.93 |
N2—C19 | 1.442 (4) | C19—H19a | 0.97 |
N3—C21 | 1.313 (6) | C19—H19b | 0.97 |
N3—C22 | 1.430 (6) | C21—H21 | 0.93 |
N3—C23 | 1.444 (6) | C22—H22a | 0.96 |
C1—C2 | 1.499 (4) | C22—H22b | 0.96 |
C3—C4 | 1.471 (4) | C22—H22c | 0.96 |
C4—C5 | 1.378 (4) | C23—H23a | 0.96 |
C4—C9 | 1.389 (3) | C23—H23b | 0.96 |
C5—C6 | 1.374 (4) | C23—H23c | 0.96 |
C6—C7 | 1.385 (4) | C24—H24 | 0.93 |
C7—C8 | 1.394 (4) | C25—H25a | 0.96 |
C8—C9 | 1.369 (4) | C25—H25b | 0.96 |
C9—C10 | 1.485 (4) | C25—H25c | 0.96 |
C11—C16 | 1.375 (4) | C26—H26a | 0.96 |
C11—C12 | 1.383 (4) | C26—H26b | 0.96 |
C12—C13 | 1.376 (4) | C26—H26c | 0.96 |
C13—C14 | 1.369 (4) | C25'—H25d | 0.96 |
C14—C15 | 1.384 (4) | C25'—H25e | 0.96 |
C14—C17 | 1.480 (4) | C25'—H25f | 0.96 |
C15—C16 | 1.375 (4) | C24'—H24' | 0.93 |
C15—C18 | 1.483 (4) | C26'—H26d | 0.96 |
C19—C20 | 1.514 (5) | C26'—H26e | 0.96 |
O11—C24 | 1.33 (1) | C26'—H26f | 0.96 |
N4—C24 | 1.32 (1) | ||
C7—O5—C11 | 120.3 (2) | C24'—N4'—C25' | 131 (2) |
C10—N1—C2 | 121.6 (2) | C24'—N4'—C26' | 121 (2) |
C10—N1—C3 | 112.2 (2) | C25'—N4'—C26' | 105 (2) |
C2—N1—C3 | 125.4 (2) | N4'—C24'—O11' | 117 (2) |
C17—N2—C18 | 112.0 (2) | C1—O1—H1o | 110 (3) |
C17—N2—C19 | 124.7 (2) | C20—O9—H9o | 103 (5) |
C18—N2—C19 | 122.5 (3) | N1—C2—H2a | 109.6 |
C21—N3—C22 | 120.7 (5) | C1—C2—H2a | 109.6 |
C21—N3—C23 | 119.9 (4) | N1—C2—H2b | 109.6 |
C22—N3—C23 | 119.4 (4) | C1—C2—H2b | 109.6 |
O1—C1—O2 | 124.4 (3) | H2a—C2—H2b | 108.1 |
O1—C1—C2 | 113.9 (3) | C6—C5—H5 | 120.8 |
O2—C1—C2 | 121.7 (3) | C4—C5—H5 | 120.8 |
N1—C2—C1 | 110.1 (2) | C5—C6—H6 | 119.7 |
O3—C3—N1 | 124.3 (3) | C7—C6—H6 | 119.7 |
O3—C3—C4 | 129.6 (3) | C9—C8—H8 | 121.9 |
N1—C3—C4 | 106.0 (2) | C7—C8—H8 | 121.9 |
C3—C4—C5 | 131.5 (2) | C13—C12—H12 | 119.9 |
C3—C4—C9 | 108.2 (2) | C11—C12—H12 | 119.9 |
C5—C4—C9 | 120.3 (2) | C14—C13—H13 | 121.1 |
C4—C5—C6 | 118.4 (2) | C12—C13—H13 | 121.1 |
C5—C6—C7 | 120.6 (2) | C11—C16—H16 | 121.8 |
O5—C7—C6 | 115.2 (2) | C15—C16—H16 | 121.8 |
O5—C7—C8 | 122.7 (2) | N2—C19—H19a | 109.6 |
C6—C7—C8 | 121.9 (2) | C20—C19—H19a | 109.6 |
C7—C8—C9 | 116.3 (2) | N2—C19—H19b | 109.6 |
C4—C9—C8 | 122.5 (2) | C20—C19—H19b | 109.6 |
C4—C9—C10 | 107.8 (2) | H19a—C19—H19b | 108.1 |
C8—C9—C10 | 129.7 (2) | O10—C21—H21 | 117.6 |
O4—C10—N1 | 124.5 (2) | N3—C21—H21 | 117.6 |
O4—C10—C9 | 129.7 (3) | N3—C22—H22a | 109.5 |
N1—C10—C9 | 105.8 (2) | N3—C22—H22b | 109.5 |
C12—C11—O5 | 120.7 (3) | H22a—C22—H22b | 109.5 |
C16—C11—O5 | 116.5 (2) | N3—C22—H22c | 109.5 |
C12—C11—C16 | 122.6 (2) | H22a—C22—H22c | 109.5 |
C11—C12—C13 | 120.2 (3) | H22b—C22—H22c | 109.5 |
C12—C13—C14 | 117.8 (3) | N3—C23—H23a | 109.5 |
C13—C14—C15 | 121.4 (2) | N3—C23—H23b | 109.5 |
C13—C14—C17 | 130.3 (2) | H23a—C23—H23b | 109.5 |
C15—C14—C17 | 108.3 (2) | N3—C23—H23c | 109.5 |
C14—C15—C16 | 121.6 (3) | H23a—C23—H23c | 109.5 |
C14—C15—C18 | 108.2 (2) | H23b—C23—H23c | 109.5 |
C16—C15—C18 | 130.2 (3) | N4—C24—H24 | 120.1 |
C11—C16—C15 | 116.4 (2) | O11—C24—H24 | 120.1 |
O6—C17—N2 | 124.6 (3) | N4'—C25'—H25d | 109.5 |
O6—C17—C14 | 129.5 (3) | N4'—C25'—H25e | 109.5 |
N2—C17—C14 | 105.9 (2) | H25d—C25'—H25e | 109.5 |
O7—C18—N2 | 124.4 (3) | N4'—C25'—H25f | 109.5 |
O7—C18—C15 | 130.0 (3) | H25d—C25'—H25f | 109.5 |
N2—C18—C15 | 105.6 (2) | H25e—C25'—H25f | 109.5 |
N2—C19—C20 | 110.1 (3) | N4'—C24'—H24' | 121.6 |
O8—C20—O9 | 126.1 (4) | O11'—C24'—H24' | 121.6 |
O8—C20—C19 | 123.8 (3) | N4'—C26'—H26d | 109.5 |
O9—C20—C19 | 110.1 (3) | N4'—C26'—H26e | 109.5 |
O10—C21—N3 | 124.7 (5) | H26d—C26'—H26e | 109.5 |
C24—N4—C25 | 119 (2) | N4'—C26'—H26f | 109.5 |
C24—N4—C26 | 119 (2) | H26d—C26'—H26f | 109.5 |
C25—N4—C26 | 122 (2) | H26e—C26'—H26f | 109.5 |
N4—C24—O11 | 120 (2) | ||
C10—N1—C2—C1 | −69.2 (3) | O5—C11—C12—C13 | 175.3 (2) |
C3—N1—C2—C1 | 99.4 (3) | C11—C12—C13—C14 | −0.2 (4) |
O2—C1—C2—N1 | −18.5 (5) | C12—C13—C14—C15 | −0.6 (4) |
O1—C1—C2—N1 | 161.4 (3) | C12—C13—C14—C17 | −179.2 (2) |
C10—N1—C3—O3 | 179.0 (3) | C13—C14—C15—C16 | 1.0 (4) |
C2—N1—C3—O3 | 9.5 (4) | C17—C14—C15—C16 | 179.9 (2) |
C10—N1—C3—C4 | −1.3 (3) | C13—C14—C15—C18 | −177.0 (2) |
C2—N1—C3—C4 | −170.8 (2) | C17—C14—C15—C18 | 1.9 (3) |
O3—C3—C4—C5 | −0.7 (5) | C12—C11—C16—C15 | −0.1 (4) |
N1—C3—C4—C5 | 179.6 (3) | O5—C11—C16—C15 | −175.1 (2) |
O3—C3—C4—C9 | 179.6 (3) | C14—C15—C16—C11 | −0.6 (4) |
N1—C3—C4—C9 | 0.0 (3) | C18—C15—C16—C11 | 176.8 (3) |
C9—C4—C5—C6 | −0.1 (4) | C18—N2—C17—O6 | −178.3 (3) |
C3—C4—C5—C6 | −179.8 (3) | C19—N2—C17—O6 | −8.6 (4) |
C4—C5—C6—C7 | 0.0 (4) | C18—N2—C17—C14 | 0.8 (3) |
C11—O5—C7—C6 | −162.5 (2) | C19—N2—C17—C14 | 170.6 (2) |
C11—O5—C7—C8 | 21.6 (4) | C13—C14—C17—O6 | −3.9 (5) |
C5—C6—C7—O5 | −176.0 (2) | C15—C14—C17—O6 | 177.4 (3) |
C5—C6—C7—C8 | 0.0 (4) | C13—C14—C17—N2 | 177.0 (3) |
O5—C7—C8—C9 | 176.0 (2) | C15—C14—C17—N2 | −1.7 (3) |
C6—C7—C8—C9 | 0.3 (4) | C17—N2—C18—O7 | −178.6 (3) |
C7—C8—C9—C4 | −0.4 (4) | C19—N2—C18—O7 | 11.3 (5) |
C7—C8—C9—C10 | 178.1 (2) | C17—N2—C18—C15 | 0.3 (3) |
C5—C4—C9—C8 | 0.4 (4) | C19—N2—C18—C15 | −169.7 (3) |
C3—C4—C9—C8 | −179.9 (2) | C16—C15—C18—O7 | −0.3 (5) |
C5—C4—C9—C10 | −178.5 (2) | C14—C15—C18—O7 | 177.4 (3) |
C3—C4—C9—C10 | 1.2 (3) | C16—C15—C18—N2 | −179.1 (3) |
C3—N1—C10—O4 | −176.7 (2) | C14—C15—C18—N2 | −1.4 (3) |
C2—N1—C10—O4 | −6.8 (4) | C17—N2—C19—C20 | −98.2 (3) |
C3—N1—C10—C9 | 2.1 (3) | C18—N2—C19—C20 | 70.5 (4) |
C2—N1—C10—C9 | 172.0 (2) | N2—C19—C20—O8 | 3.4 (5) |
C8—C9—C10—O4 | −2.0 (5) | N2—C19—C20—O9 | −173.7 (3) |
C4—C9—C10—O4 | 176.7 (3) | C22—N3—C21—O10 | 5.5 (8) |
C8—C9—C10—N1 | 179.3 (3) | C23—N3—C21—O10 | −176.0 (5) |
C4—C9—C10—N1 | −2.0 (3) | C25—N4—C24—O11 | −16 (4) |
C7—O5—C11—C16 | −129.7 (3) | C26—N4—C24—O11 | 167 (2) |
C7—O5—C11—C12 | 55.2 (3) | C25'—N4'—C24'—O11' | 15 (4) |
C16—C11—C12—C13 | 0.5 (4) | C26'—N4'—C24'—O11' | 173 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O10 | 0.86 (1) | 1.75 (1) | 2.607 (4) | 179 (4) |
O9—H9o···O11 | 0.85 (1) | 1.78 (3) | 2.61 (1) | 163 (7) |
O9—H9o···O11′ | 0.85 (1) | 1.84 (5) | 2.54 (1) | 139 (6) |
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