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The title compound, C
24H
29NO
5, the benzyl ester of the Phe–Gly dipeptidomimetic containing a ketomethylene motif, was synthesized from the readily available α,β-unsaturated γ-ketoester. The methylene group in the benzyl part of the molecule is disordered. There is an intermolecular N—H
O hydrogen bond linking the molecules in the crystal structure.
Supporting information
CCDC reference: 271867
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.035
- wR factor = 0.099
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.21 Ratio
| Author Response: see _publ_section_exptl_refinement
|
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19
PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C19 - C20 ... 1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C19 - C24 ... 1.37 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.50 Deg.
C182 -O5 -C181 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.90 Deg.
C181 -C19 -C182 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C24 H29 N O5
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 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
8 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (Version 9; McArdle, 1993).
Crystal data top
C24H29NO5 | F(000) = 880 |
Mr = 411.48 | Dx = 1.222 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yab | Cell parameters from 25 reflections |
a = 9.6080 (19) Å | θ = 12–20° |
b = 22.856 (4) Å | µ = 0.09 mm−1 |
c = 10.2908 (17) Å | T = 298 K |
β = 98.353 (16)° | Block, colourless |
V = 2235.9 (7) Å3 | 0.40 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Enraf-Nonius CAD4 diffractometer | 1759 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.010 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ω–2θ scans | h = 0→11 |
Absorption correction: ψ scan (ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al, 1968) | k = 0→27 |
Tmin = 0.967, Tmax = 0.992 | l = −12→12 |
4262 measured reflections | 3 standard reflections every 120 min |
3941 independent reflections | intensity decay: 2% |
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)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0484P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.001 |
3941 reflections | Δρmax = 0.15 e Å−3 |
389 parameters | Δρmin = −0.14 e Å−3 |
66 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0041 (8) |
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 | Occ. (<1) |
C181 | 1.5779 (10) | 0.3446 (5) | 0.3571 (12) | 0.080 (4) | 0.50 |
H18A | 1.5884 | 0.3461 | 0.2648 | 0.104* | 0.50 |
H18B | 1.5172 | 0.3119 | 0.3707 | 0.104* | 0.50 |
C182 | 1.6109 (11) | 0.3631 (6) | 0.3325 (12) | 0.089 (5) | 0.50 |
H18C | 1.6565 | 0.3859 | 0.2713 | 0.116* | 0.50 |
H18D | 1.5577 | 0.3318 | 0.2846 | 0.116* | 0.50 |
O1 | 0.70516 (14) | 0.54106 (6) | 0.08083 (12) | 0.0509 (4) | |
N1 | 0.86413 (17) | 0.47118 (7) | 0.10717 (18) | 0.0466 (5) | |
O3 | 1.14442 (15) | 0.50649 (7) | 0.19428 (14) | 0.0596 (4) | |
O2 | 0.79986 (15) | 0.51283 (6) | 0.28717 (14) | 0.0595 (4) | |
O5 | 1.51713 (17) | 0.40063 (9) | 0.39874 (19) | 0.0963 (6) | |
O4 | 1.31815 (19) | 0.36080 (9) | 0.3081 (2) | 0.0983 (6) | |
H22 | 2.057 (3) | 0.2990 (12) | 0.659 (3) | 0.105 (10)* | |
H12 | 0.733 (3) | 0.2353 (13) | 0.148 (3) | 0.118 (11)* | |
H11 | 0.623 (3) | 0.2373 (12) | −0.076 (3) | 0.097 (10)* | |
H1 | 0.8611 (17) | 0.4734 (7) | 0.0249 (17) | 0.028 (5)* | |
H6 | 0.9239 (16) | 0.4157 (7) | 0.2501 (16) | 0.024 (4)* | |
H162 | 1.345 (2) | 0.4881 (9) | 0.377 (2) | 0.070 (7)* | |
H4B | 0.726 (3) | 0.6136 (11) | 0.301 (3) | 0.091 (8)* | |
H2C | 0.540 (2) | 0.5330 (10) | 0.273 (2) | 0.078 (8)* | |
H72 | 1.049 (2) | 0.4062 (8) | 0.024 (2) | 0.053 (6)* | |
H71 | 1.094 (2) | 0.3660 (9) | 0.1499 (19) | 0.060 (6)* | |
H152 | 1.1168 (19) | 0.4121 (9) | 0.4020 (18) | 0.044 (6)* | |
H3A | 0.470 (2) | 0.6372 (11) | 0.002 (2) | 0.081 (8)* | |
H161 | 1.336 (2) | 0.4533 (8) | 0.516 (2) | 0.063 (6)* | |
H151 | 1.111 (2) | 0.4769 (9) | 0.445 (2) | 0.066 (7)* | |
H4A | 0.630 (3) | 0.6597 (12) | 0.215 (2) | 0.082 (9)* | |
H13 | 0.906 (2) | 0.3002 (10) | 0.215 (2) | 0.070 (8)* | |
H9 | 0.871 (2) | 0.3683 (9) | −0.1407 (19) | 0.050 (6)* | |
H4C | 0.760 (3) | 0.6463 (12) | 0.171 (3) | 0.098 (10)* | |
H23 | 1.986 (3) | 0.4001 (12) | 0.632 (3) | 0.108 (10)* | |
H3B | 0.607 (3) | 0.6268 (10) | −0.052 (2) | 0.078 (9)* | |
H21 | 1.907 (3) | 0.2254 (14) | 0.555 (3) | 0.121 (11)* | |
H10 | 0.693 (3) | 0.3053 (10) | −0.222 (2) | 0.085 (8)* | |
H2A | 0.452 (3) | 0.5240 (11) | 0.131 (2) | 0.083 (9)* | |
H20 | 1.705 (3) | 0.2501 (11) | 0.428 (2) | 0.084 (9)* | |
H2B | 0.433 (3) | 0.5790 (11) | 0.211 (2) | 0.089 (9)* | |
H24 | 1.790 (2) | 0.4184 (11) | 0.492 (2) | 0.078 (8)* | |
H3C | 0.494 (3) | 0.5756 (13) | −0.065 (3) | 0.125 (12)* | |
C1 | 0.6052 (2) | 0.58389 (9) | 0.1218 (2) | 0.0483 (5) | |
C2 | 0.4974 (3) | 0.55232 (14) | 0.1892 (3) | 0.0657 (7) | |
C3 | 0.5390 (4) | 0.60845 (15) | −0.0087 (3) | 0.0733 (8) | |
C4 | 0.6830 (4) | 0.62989 (13) | 0.2078 (3) | 0.0730 (8) | |
C5 | 0.7894 (2) | 0.50919 (9) | 0.1688 (2) | 0.0428 (5) | |
C6 | 0.9665 (2) | 0.43367 (9) | 0.1832 (2) | 0.0422 (5) | |
C7 | 1.0166 (2) | 0.38596 (10) | 0.0964 (3) | 0.0516 (6) | |
C8 | 0.9040 (2) | 0.34231 (9) | 0.0461 (2) | 0.0473 (5) | |
C9 | 0.8418 (3) | 0.34267 (11) | −0.0827 (3) | 0.0585 (6) | |
C10 | 0.7380 (3) | 0.30259 (12) | −0.1292 (3) | 0.0710 (8) | |
C11 | 0.6948 (3) | 0.26261 (13) | −0.0451 (4) | 0.0809 (9) | |
C12 | 0.7550 (3) | 0.26139 (12) | 0.0829 (4) | 0.0822 (9) | |
C13 | 0.8598 (3) | 0.30065 (11) | 0.1281 (3) | 0.0667 (7) | |
C14 | 1.0931 (2) | 0.46717 (9) | 0.24977 (19) | 0.0428 (5) | |
C15 | 1.1519 (2) | 0.44932 (12) | 0.3875 (2) | 0.0493 (6) | |
C16 | 1.3109 (2) | 0.45203 (11) | 0.4194 (3) | 0.0546 (6) | |
C17 | 1.3795 (2) | 0.39975 (11) | 0.3696 (2) | 0.0582 (6) | |
C19 | 1.7203 (2) | 0.33790 (13) | 0.4415 (2) | 0.0636 (7) | |
C20 | 1.7576 (3) | 0.27986 (15) | 0.4633 (3) | 0.0806 (9) | |
C21 | 1.8819 (4) | 0.26540 (15) | 0.5432 (3) | 0.0884 (9) | |
C22 | 1.9653 (4) | 0.30806 (16) | 0.6028 (3) | 0.0840 (9) | |
C23 | 1.9293 (3) | 0.36500 (14) | 0.5851 (3) | 0.0711 (7) | |
C24 | 1.8070 (3) | 0.37957 (14) | 0.5049 (2) | 0.0665 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C181 | 0.056 (6) | 0.112 (7) | 0.072 (5) | 0.031 (6) | 0.009 (4) | −0.019 (5) |
C182 | 0.038 (4) | 0.136 (10) | 0.091 (7) | 0.016 (5) | 0.002 (4) | −0.030 (6) |
O1 | 0.0488 (8) | 0.0598 (9) | 0.0434 (8) | 0.0192 (7) | 0.0041 (7) | 0.0046 (7) |
N1 | 0.0463 (11) | 0.0585 (11) | 0.0348 (10) | 0.0127 (9) | 0.0053 (8) | 0.0000 (9) |
O3 | 0.0568 (9) | 0.0617 (10) | 0.0590 (9) | −0.0087 (8) | 0.0039 (7) | 0.0130 (8) |
O2 | 0.0664 (10) | 0.0713 (10) | 0.0398 (9) | 0.0204 (8) | 0.0047 (7) | 0.0004 (7) |
O5 | 0.0468 (11) | 0.1281 (17) | 0.1068 (14) | 0.0252 (11) | −0.0131 (10) | −0.0358 (12) |
O4 | 0.0694 (13) | 0.0965 (14) | 0.1239 (16) | 0.0118 (12) | −0.0030 (11) | −0.0348 (13) |
C1 | 0.0436 (13) | 0.0485 (13) | 0.0529 (13) | 0.0130 (11) | 0.0073 (10) | 0.0007 (11) |
C2 | 0.0483 (16) | 0.076 (2) | 0.0733 (19) | 0.0060 (15) | 0.0111 (14) | 0.0040 (17) |
C3 | 0.074 (2) | 0.080 (2) | 0.0661 (18) | 0.0353 (18) | 0.0106 (16) | 0.0137 (16) |
C4 | 0.080 (2) | 0.0518 (18) | 0.086 (2) | 0.0025 (17) | 0.0084 (18) | −0.0065 (16) |
C5 | 0.0387 (11) | 0.0458 (12) | 0.0434 (13) | 0.0023 (10) | 0.0042 (10) | 0.0001 (11) |
C6 | 0.0368 (11) | 0.0454 (12) | 0.0449 (12) | 0.0051 (10) | 0.0069 (10) | 0.0058 (11) |
C7 | 0.0474 (14) | 0.0510 (14) | 0.0584 (14) | 0.0077 (12) | 0.0141 (12) | −0.0001 (12) |
C8 | 0.0471 (13) | 0.0400 (12) | 0.0571 (14) | 0.0090 (10) | 0.0158 (11) | −0.0039 (11) |
C9 | 0.0639 (16) | 0.0533 (15) | 0.0610 (17) | 0.0012 (13) | 0.0182 (14) | 0.0002 (13) |
C10 | 0.0688 (18) | 0.0699 (18) | 0.074 (2) | −0.0040 (15) | 0.0097 (16) | −0.0249 (16) |
C11 | 0.070 (2) | 0.0571 (19) | 0.119 (3) | −0.0116 (15) | 0.0274 (19) | −0.0331 (19) |
C12 | 0.103 (2) | 0.0527 (18) | 0.097 (3) | −0.0124 (17) | 0.035 (2) | −0.0002 (17) |
C13 | 0.084 (2) | 0.0529 (16) | 0.0650 (18) | 0.0045 (15) | 0.0154 (15) | 0.0041 (14) |
C14 | 0.0413 (12) | 0.0449 (13) | 0.0441 (12) | 0.0079 (10) | 0.0122 (10) | 0.0030 (10) |
C15 | 0.0428 (13) | 0.0603 (15) | 0.0456 (13) | 0.0005 (12) | 0.0088 (10) | 0.0023 (12) |
C16 | 0.0477 (14) | 0.0659 (17) | 0.0480 (15) | 0.0054 (12) | −0.0002 (11) | 0.0032 (13) |
C17 | 0.0474 (15) | 0.0786 (18) | 0.0458 (13) | 0.0052 (13) | −0.0022 (11) | −0.0011 (13) |
C19 | 0.0481 (14) | 0.085 (2) | 0.0583 (15) | 0.0110 (14) | 0.0098 (12) | −0.0119 (14) |
C20 | 0.080 (2) | 0.082 (2) | 0.085 (2) | −0.0168 (19) | 0.0254 (17) | −0.0169 (18) |
C21 | 0.106 (3) | 0.073 (2) | 0.084 (2) | 0.022 (2) | 0.0057 (19) | 0.0135 (17) |
C22 | 0.078 (2) | 0.103 (3) | 0.0664 (19) | 0.018 (2) | −0.0026 (16) | 0.0016 (18) |
C23 | 0.0619 (17) | 0.085 (2) | 0.0664 (17) | −0.0035 (17) | 0.0103 (14) | 0.0022 (16) |
C24 | 0.0689 (18) | 0.0659 (19) | 0.0648 (16) | 0.0084 (16) | 0.0099 (14) | 0.0036 (15) |
Geometric parameters (Å, º) top
C181—O5 | 1.496 (10) | C7—C8 | 1.507 (3) |
C181—C19 | 1.519 (10) | C7—H72 | 0.97 (2) |
C181—H18A | 0.9700 | C7—H71 | 0.98 (2) |
C181—H18B | 0.9700 | C8—C9 | 1.372 (3) |
C182—O5 | 1.481 (10) | C8—C13 | 1.380 (3) |
C182—C19 | 1.534 (11) | C9—C10 | 1.388 (3) |
C182—H18C | 0.9700 | C9—H9 | 0.91 (2) |
C182—H18D | 0.9700 | C10—C11 | 1.364 (4) |
O1—C5 | 1.338 (2) | C10—H10 | 0.99 (2) |
O1—C1 | 1.475 (2) | C11—C12 | 1.359 (4) |
N1—C5 | 1.343 (2) | C11—H11 | 0.92 (3) |
N1—C6 | 1.446 (3) | C12—C13 | 1.378 (4) |
N1—H1 | 0.844 (17) | C12—H12 | 0.94 (3) |
O3—C14 | 1.208 (2) | C13—H13 | 0.94 (2) |
O2—C5 | 1.211 (2) | C14—C15 | 1.504 (3) |
O5—C17 | 1.313 (3) | C15—C16 | 1.516 (3) |
O4—C17 | 1.197 (3) | C15—H152 | 0.935 (19) |
C1—C4 | 1.502 (3) | C15—H151 | 0.98 (2) |
C1—C3 | 1.508 (3) | C16—C17 | 1.491 (3) |
C1—C2 | 1.511 (3) | C16—H162 | 1.01 (2) |
C2—H2C | 1.00 (2) | C16—H161 | 0.99 (2) |
C2—H2A | 0.95 (2) | C19—C24 | 1.367 (3) |
C2—H2B | 0.92 (3) | C19—C20 | 1.384 (4) |
C3—H3A | 0.95 (2) | C20—C21 | 1.388 (4) |
C3—H3B | 0.94 (2) | C20—H20 | 0.89 (3) |
C3—H3C | 1.01 (3) | C21—C22 | 1.351 (4) |
C4—H4B | 1.05 (3) | C21—H21 | 0.95 (3) |
C4—H4A | 0.86 (3) | C22—C23 | 1.352 (4) |
C4—H4C | 0.96 (3) | C22—H22 | 1.01 (3) |
C6—C14 | 1.514 (3) | C23—C24 | 1.375 (3) |
C6—C7 | 1.531 (3) | C23—H23 | 1.05 (3) |
C6—H6 | 0.945 (16) | C24—H24 | 0.91 (2) |
| | | |
O5—C181—C19 | 106.2 (7) | C9—C8—C13 | 117.7 (2) |
O5—C181—H18A | 110.5 | C9—C8—C7 | 121.2 (2) |
C19—C181—H18A | 110.5 | C13—C8—C7 | 121.1 (2) |
O5—C181—H18B | 110.5 | C8—C9—C10 | 121.3 (3) |
C19—C181—H18B | 110.5 | C8—C9—H9 | 120.5 (12) |
H18A—C181—H18B | 108.7 | C10—C9—H9 | 118.1 (12) |
O5—C182—C19 | 106.2 (8) | C11—C10—C9 | 119.5 (3) |
O5—C182—H18C | 110.5 | C11—C10—H10 | 121.8 (14) |
C19—C182—H18C | 110.5 | C9—C10—H10 | 118.6 (14) |
O5—C182—H18D | 110.5 | C12—C11—C10 | 120.2 (3) |
C19—C182—H18D | 110.5 | C12—C11—H11 | 120.7 (17) |
H18C—C182—H18D | 108.7 | C10—C11—H11 | 119.1 (17) |
C5—O1—C1 | 121.51 (15) | C11—C12—C13 | 120.1 (3) |
C5—N1—C6 | 119.75 (18) | C11—C12—H12 | 126.5 (18) |
C5—N1—H1 | 119.5 (12) | C13—C12—H12 | 113.4 (18) |
C6—N1—H1 | 120.0 (11) | C12—C13—C8 | 121.1 (3) |
C17—O5—C182 | 123.1 (5) | C12—C13—H13 | 122.5 (14) |
C17—O5—C181 | 110.1 (5) | C8—C13—H13 | 116.3 (14) |
C182—O5—C181 | 23.5 (9) | O3—C14—C15 | 121.60 (19) |
O1—C1—C4 | 110.1 (2) | O3—C14—C6 | 121.25 (18) |
O1—C1—C3 | 101.55 (18) | C15—C14—C6 | 117.15 (19) |
C4—C1—C3 | 111.9 (2) | C14—C15—C16 | 114.96 (19) |
O1—C1—C2 | 109.41 (19) | C14—C15—H152 | 107.6 (12) |
C4—C1—C2 | 112.3 (2) | C16—C15—H152 | 112.2 (12) |
C3—C1—C2 | 111.0 (2) | C14—C15—H151 | 105.4 (12) |
C1—C2—H2C | 112.6 (13) | C16—C15—H151 | 108.6 (12) |
C1—C2—H2A | 108.7 (15) | H152—C15—H151 | 107.7 (17) |
H2C—C2—H2A | 110 (2) | C17—C16—C15 | 112.0 (2) |
C1—C2—H2B | 109.2 (16) | C17—C16—H162 | 108.5 (12) |
H2C—C2—H2B | 107 (2) | C15—C16—H162 | 108.8 (13) |
H2A—C2—H2B | 110 (2) | C17—C16—H161 | 108.3 (12) |
C1—C3—H3A | 111.4 (14) | C15—C16—H161 | 107.9 (12) |
C1—C3—H3B | 110.9 (15) | H162—C16—H161 | 111.4 (18) |
H3A—C3—H3B | 107 (2) | O4—C17—O5 | 122.3 (2) |
C1—C3—H3C | 109.1 (17) | O4—C17—C16 | 124.7 (2) |
H3A—C3—H3C | 110 (2) | O5—C17—C16 | 113.0 (2) |
H3B—C3—H3C | 109 (2) | C24—C19—C20 | 117.8 (3) |
C1—C4—H4B | 112.5 (14) | C24—C19—C181 | 129.7 (5) |
C1—C4—H4A | 110.7 (17) | C20—C19—C181 | 112.3 (5) |
H4B—C4—H4A | 111 (2) | C24—C19—C182 | 113.2 (6) |
C1—C4—H4C | 113.1 (17) | C20—C19—C182 | 127.7 (6) |
H4B—C4—H4C | 106 (2) | C181—C19—C182 | 22.9 (9) |
H4A—C4—H4C | 103 (2) | C19—C20—C21 | 120.3 (3) |
O2—C5—O1 | 126.65 (18) | C19—C20—H20 | 123.2 (17) |
O2—C5—N1 | 123.17 (19) | C21—C20—H20 | 116.5 (17) |
O1—C5—N1 | 110.19 (18) | C22—C21—C20 | 120.0 (3) |
N1—C6—C14 | 112.55 (16) | C22—C21—H21 | 121 (2) |
N1—C6—C7 | 110.67 (18) | C20—C21—H21 | 119 (2) |
C14—C6—C7 | 108.91 (16) | C21—C22—C23 | 120.7 (3) |
N1—C6—H6 | 108.6 (9) | C21—C22—H22 | 121.7 (16) |
C14—C6—H6 | 107.2 (9) | C23—C22—H22 | 117.6 (16) |
C7—C6—H6 | 108.8 (9) | C22—C23—C24 | 119.6 (3) |
C8—C7—C6 | 113.67 (17) | C22—C23—H23 | 124.8 (15) |
C8—C7—H72 | 110.2 (12) | C24—C23—H23 | 115.6 (15) |
C6—C7—H72 | 106.0 (12) | C19—C24—C23 | 121.7 (3) |
C8—C7—H71 | 109.8 (12) | C19—C24—H24 | 121.7 (16) |
C6—C7—H71 | 106.5 (12) | C23—C24—H24 | 116.4 (16) |
H72—C7—H71 | 110.6 (17) | | |
| | | |
C19—C182—O5—C17 | −135.1 (5) | N1—C6—C14—C15 | 139.93 (19) |
C19—C182—O5—C181 | −73.3 (19) | C7—C6—C14—C15 | −97.0 (2) |
C19—C181—O5—C17 | −156.6 (6) | O3—C14—C15—C16 | −37.0 (3) |
C19—C181—O5—C182 | 75.3 (19) | C6—C14—C15—C16 | 143.0 (2) |
C5—O1—C1—C4 | 60.2 (3) | C14—C15—C16—C17 | −80.4 (3) |
C5—O1—C1—C3 | 179.0 (2) | C182—O5—C17—O4 | 15.9 (7) |
C5—O1—C1—C2 | −63.7 (2) | C181—O5—C17—O4 | −6.0 (6) |
C1—O1—C5—O2 | −3.8 (3) | C182—O5—C17—C16 | −163.3 (6) |
C1—O1—C5—N1 | 176.37 (16) | C181—O5—C17—C16 | 174.7 (6) |
C6—N1—C5—O2 | −2.3 (3) | C15—C16—C17—O4 | 2.2 (3) |
C6—N1—C5—O1 | 177.61 (17) | C15—C16—C17—O5 | −178.6 (2) |
C5—N1—C6—C14 | −69.5 (2) | O5—C181—C19—C24 | −23.8 (11) |
C5—N1—C6—C7 | 168.39 (18) | O5—C181—C19—C20 | 150.2 (6) |
N1—C6—C7—C8 | −67.1 (3) | O5—C181—C19—C182 | −73 (2) |
C14—C6—C7—C8 | 168.64 (19) | O5—C182—C19—C24 | −65.6 (8) |
C6—C7—C8—C9 | 106.5 (2) | O5—C182—C19—C20 | 128.3 (6) |
C6—C7—C8—C13 | −73.5 (3) | O5—C182—C19—C181 | 75.1 (18) |
C13—C8—C9—C10 | 0.0 (3) | C24—C19—C20—C21 | −2.4 (4) |
C7—C8—C9—C10 | −179.9 (2) | C181—C19—C20—C21 | −177.2 (6) |
C8—C9—C10—C11 | 1.2 (4) | C182—C19—C20—C21 | 163.1 (6) |
C9—C10—C11—C12 | −1.2 (4) | C19—C20—C21—C22 | 1.7 (4) |
C10—C11—C12—C13 | 0.1 (4) | C20—C21—C22—C23 | −0.2 (5) |
C11—C12—C13—C8 | 1.1 (4) | C21—C22—C23—C24 | −0.5 (4) |
C9—C8—C13—C12 | −1.1 (3) | C20—C19—C24—C23 | 1.7 (4) |
C7—C8—C13—C12 | 178.8 (2) | C181—C19—C24—C23 | 175.5 (6) |
N1—C6—C14—O3 | −40.1 (3) | C182—C19—C24—C23 | −165.8 (5) |
C7—C6—C14—O3 | 83.0 (2) | C22—C23—C24—C19 | −0.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.84 (2) | 2.295 (17) | 3.133 (1) | 172 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
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