The molecule of the title compound, C
23H
23FN
4O
5, assumes an overall U-shaped conformation and exhibits orientational disorder. The crystal packing is stabilized by intra- and intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 608476
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.059
- wR factor = 0.172
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C22'
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for O4'
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4'
PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 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
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.
Methyl
(
E,
E)-(2-[({[1,3-dimethyl-5-(2-fluorophenoxy)-1
H-pyrazol-4- ylmethylene]amino}oxy)methyl]phenyl)-2-(methoxyimino)acetate
top
Crystal data top
C23H23FN4O5 | F(000) = 1904 |
Mr = 454.45 | Dx = 1.294 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2237 reflections |
a = 14.2781 (10) Å | θ = 2.5–19.0° |
b = 16.1865 (12) Å | µ = 0.10 mm−1 |
c = 20.1828 (15) Å | T = 292 K |
V = 4664.5 (6) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2596 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
φ and ω scans | h = −14→17 |
24306 measured reflections | k = −19→19 |
4578 independent reflections | l = −24→24 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0786P)2 + 0.6674P] where P = (Fo2 + 2Fc2)/3 |
4578 reflections | (Δ/σ)max < 0.001 |
332 parameters | Δρmax = 0.29 e Å−3 |
18 restraints | Δρmin = −0.21 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 | Occ. (<1) |
C1 | 0.5941 (2) | 0.82991 (18) | 0.12779 (14) | 0.0621 (8) | |
C2 | 0.6722 (2) | 0.8323 (2) | 0.08831 (15) | 0.0756 (9) | |
H2 | 0.6732 | 0.8643 | 0.0501 | 0.091* | |
C3 | 0.7486 (2) | 0.7866 (2) | 0.10630 (16) | 0.0801 (10) | |
H3 | 0.8023 | 0.7879 | 0.0802 | 0.096* | |
C4 | 0.7470 (2) | 0.7399 (2) | 0.16131 (16) | 0.0789 (9) | |
H4 | 0.7993 | 0.7087 | 0.1726 | 0.095* | |
C5 | 0.6679 (2) | 0.73766 (19) | 0.20152 (14) | 0.0706 (8) | |
H5 | 0.6674 | 0.7057 | 0.2398 | 0.085* | |
C6 | 0.59098 (18) | 0.78283 (18) | 0.18416 (12) | 0.0545 (7) | |
C7 | 0.50883 (17) | 0.75684 (19) | 0.28322 (13) | 0.0549 (7) | |
N2 | 0.49054 (16) | 0.66827 (14) | 0.36623 (12) | 0.0624 (6) | |
C9 | 0.50914 (17) | 0.74234 (17) | 0.39133 (12) | 0.0514 (6) | |
C8 | 0.52137 (17) | 0.80150 (16) | 0.34056 (12) | 0.0484 (6) | |
C11 | 0.4711 (2) | 0.6092 (2) | 0.25559 (17) | 0.0955 (12) | |
H11A | 0.4988 | 0.6192 | 0.2130 | 0.143* | |
H11B | 0.4045 | 0.6032 | 0.2507 | 0.143* | |
H11C | 0.4967 | 0.5595 | 0.2741 | 0.143* | |
C10 | 0.5133 (2) | 0.7546 (2) | 0.46424 (13) | 0.0719 (8) | |
H10A | 0.5039 | 0.7027 | 0.4862 | 0.108* | |
H10B | 0.4652 | 0.7927 | 0.4775 | 0.108* | |
H10C | 0.5734 | 0.7765 | 0.4762 | 0.108* | |
C12 | 0.54234 (17) | 0.88883 (17) | 0.34325 (13) | 0.0532 (7) | |
H12 | 0.5492 | 0.9176 | 0.3037 | 0.064* | |
C13 | 0.59808 (19) | 1.05228 (17) | 0.44386 (14) | 0.0610 (7) | |
H13A | 0.5508 | 1.0424 | 0.4775 | 0.073* | |
H13B | 0.6014 | 1.1114 | 0.4364 | 0.073* | |
C14 | 0.6912 (2) | 1.02229 (16) | 0.46890 (13) | 0.0565 (7) | |
C15 | 0.6982 (3) | 0.9812 (2) | 0.52888 (16) | 0.0878 (11) | |
H15 | 0.6448 | 0.9731 | 0.5545 | 0.105* | |
C16 | 0.7836 (4) | 0.9520 (2) | 0.5510 (2) | 0.1128 (16) | |
H16 | 0.7873 | 0.9245 | 0.5914 | 0.135* | |
C17 | 0.8628 (3) | 0.9631 (2) | 0.5139 (2) | 0.1026 (13) | |
H17 | 0.9200 | 0.9432 | 0.5291 | 0.123* | |
C18 | 0.8576 (2) | 1.00398 (18) | 0.45404 (16) | 0.0725 (9) | |
H18 | 0.9113 | 1.0112 | 0.4287 | 0.087* | |
C19 | 0.77225 (18) | 1.03426 (15) | 0.43157 (12) | 0.0511 (7) | |
C20 | 0.76735 (16) | 1.07879 (16) | 0.36769 (12) | 0.0486 (6) | |
F1 | 0.51770 (14) | 0.87375 (13) | 0.11107 (10) | 0.1015 (7) | |
N1 | 0.49096 (15) | 0.67817 (15) | 0.29934 (11) | 0.0627 (6) | |
N3 | 0.55184 (15) | 0.92788 (13) | 0.39742 (11) | 0.0563 (6) | |
O1 | 0.50689 (12) | 0.78356 (14) | 0.21933 (9) | 0.0710 (6) | |
O2 | 0.57053 (13) | 1.01248 (11) | 0.38382 (9) | 0.0615 (5) | |
C21 | 0.7280 (4) | 1.2837 (2) | 0.4066 (3) | 0.0852 (15) | 0.83 |
H21A | 0.7725 | 1.3043 | 0.3750 | 0.128* | 0.83 |
H21B | 0.7335 | 1.3142 | 0.4472 | 0.128* | 0.83 |
H21C | 0.6658 | 1.2899 | 0.3892 | 0.128* | 0.83 |
C22 | 0.7794 (7) | 1.0313 (4) | 0.3051 (2) | 0.079 (2) | 0.83 |
C23 | 0.8085 (4) | 0.9115 (3) | 0.2504 (2) | 0.1110 (16) | 0.83 |
H23A | 0.7496 | 0.9101 | 0.2275 | 0.167* | 0.83 |
H23B | 0.8295 | 0.8561 | 0.2585 | 0.167* | 0.83 |
H23C | 0.8538 | 0.9400 | 0.2237 | 0.167* | 0.83 |
O3 | 0.7464 (6) | 1.1966 (3) | 0.4193 (2) | 0.0679 (18) | 0.83 |
O4 | 0.7969 (3) | 0.9556 (2) | 0.31465 (18) | 0.0899 (13) | 0.83 |
O5 | 0.7658 (3) | 1.0621 (2) | 0.25051 (14) | 0.1161 (12) | 0.83 |
N4 | 0.7535 (2) | 1.1569 (2) | 0.35993 (15) | 0.0537 (12) | 0.83 |
C21' | 0.798 (2) | 0.9767 (19) | 0.2193 (9) | 0.115 (8)* | 0.17 |
H21D | 0.7370 | 0.9598 | 0.2046 | 0.172* | 0.17 |
H21E | 0.8445 | 0.9410 | 0.2004 | 0.172* | 0.17 |
H21F | 0.8095 | 1.0326 | 0.2056 | 0.172* | 0.17 |
C22' | 0.754 (3) | 1.1715 (8) | 0.3682 (11) | 0.10 (3)* | 0.17 |
C23' | 0.724 (3) | 1.2937 (15) | 0.4374 (13) | 0.085 (10)* | 0.17 |
H23D | 0.7618 | 1.3303 | 0.4109 | 0.127* | 0.17 |
H23E | 0.7324 | 1.3070 | 0.4834 | 0.127* | 0.17 |
H23F | 0.6597 | 1.2997 | 0.4255 | 0.127* | 0.17 |
O3' | 0.8026 (15) | 0.9714 (11) | 0.2954 (8) | 0.064 (6)* | 0.17 |
O4' | 0.755 (2) | 1.2062 (15) | 0.4255 (8) | 0.051 (6)* | 0.17 |
O5' | 0.7098 (7) | 1.2058 (5) | 0.3209 (5) | 0.064 (3)* | 0.17 |
N4' | 0.770 (2) | 1.0509 (12) | 0.3070 (5) | 0.027 (4)* | 0.17 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0638 (19) | 0.0645 (19) | 0.0579 (17) | 0.0084 (14) | −0.0126 (15) | 0.0043 (14) |
C2 | 0.081 (2) | 0.086 (2) | 0.0597 (18) | −0.0092 (18) | 0.0026 (17) | 0.0125 (16) |
C3 | 0.067 (2) | 0.106 (3) | 0.067 (2) | −0.0008 (19) | 0.0122 (16) | −0.0009 (19) |
C4 | 0.064 (2) | 0.095 (3) | 0.077 (2) | 0.0215 (17) | 0.0070 (17) | 0.0023 (19) |
C5 | 0.068 (2) | 0.085 (2) | 0.0591 (17) | 0.0168 (16) | 0.0033 (15) | 0.0175 (15) |
C6 | 0.0520 (16) | 0.0708 (18) | 0.0408 (14) | 0.0081 (13) | −0.0037 (12) | −0.0052 (13) |
C7 | 0.0436 (15) | 0.070 (2) | 0.0506 (16) | 0.0028 (13) | 0.0007 (11) | −0.0001 (14) |
N2 | 0.0623 (15) | 0.0592 (15) | 0.0656 (15) | −0.0062 (11) | 0.0034 (12) | −0.0030 (12) |
C9 | 0.0484 (16) | 0.0548 (17) | 0.0511 (15) | −0.0057 (12) | 0.0018 (11) | −0.0009 (13) |
C8 | 0.0436 (14) | 0.0511 (16) | 0.0507 (15) | −0.0021 (12) | −0.0017 (11) | 0.0016 (12) |
C11 | 0.087 (2) | 0.093 (3) | 0.106 (3) | −0.0080 (19) | −0.007 (2) | −0.048 (2) |
C10 | 0.089 (2) | 0.075 (2) | 0.0520 (16) | −0.0087 (16) | 0.0005 (14) | 0.0075 (15) |
C12 | 0.0416 (15) | 0.0617 (18) | 0.0563 (16) | 0.0000 (12) | −0.0014 (12) | 0.0145 (14) |
C13 | 0.0580 (17) | 0.0529 (17) | 0.0720 (18) | −0.0096 (13) | 0.0134 (14) | −0.0041 (14) |
C14 | 0.071 (2) | 0.0410 (15) | 0.0572 (16) | −0.0141 (13) | −0.0036 (14) | 0.0004 (13) |
C15 | 0.124 (3) | 0.073 (2) | 0.067 (2) | −0.038 (2) | −0.013 (2) | 0.0174 (17) |
C16 | 0.173 (5) | 0.075 (3) | 0.091 (3) | −0.032 (3) | −0.058 (3) | 0.031 (2) |
C17 | 0.128 (4) | 0.054 (2) | 0.126 (3) | 0.006 (2) | −0.065 (3) | 0.003 (2) |
C18 | 0.071 (2) | 0.0556 (19) | 0.091 (2) | 0.0109 (15) | −0.0227 (17) | −0.0152 (17) |
C19 | 0.0565 (17) | 0.0386 (15) | 0.0582 (16) | −0.0007 (12) | −0.0078 (13) | −0.0073 (12) |
C20 | 0.0392 (14) | 0.0496 (17) | 0.0569 (16) | −0.0042 (11) | 0.0039 (11) | −0.0043 (13) |
F1 | 0.0923 (14) | 0.1155 (17) | 0.0966 (14) | 0.0308 (11) | −0.0131 (11) | 0.0354 (12) |
N1 | 0.0609 (15) | 0.0690 (17) | 0.0584 (14) | −0.0045 (12) | −0.0028 (11) | −0.0146 (12) |
N3 | 0.0561 (14) | 0.0515 (14) | 0.0614 (14) | −0.0125 (11) | −0.0015 (11) | 0.0060 (11) |
O1 | 0.0541 (12) | 0.1112 (18) | 0.0476 (11) | 0.0151 (10) | −0.0047 (9) | 0.0047 (11) |
O2 | 0.0624 (12) | 0.0499 (11) | 0.0721 (12) | −0.0088 (9) | −0.0049 (9) | 0.0098 (9) |
C21 | 0.096 (4) | 0.037 (2) | 0.123 (5) | 0.003 (2) | 0.020 (4) | 0.001 (3) |
C22 | 0.065 (4) | 0.092 (6) | 0.080 (3) | 0.006 (4) | 0.014 (2) | −0.016 (3) |
C23 | 0.131 (4) | 0.109 (4) | 0.093 (3) | 0.024 (3) | 0.005 (3) | −0.043 (3) |
O3 | 0.088 (3) | 0.041 (2) | 0.074 (3) | −0.005 (2) | 0.0076 (16) | −0.0058 (15) |
O4 | 0.140 (3) | 0.070 (2) | 0.060 (2) | 0.028 (2) | 0.002 (2) | −0.0159 (19) |
O5 | 0.190 (4) | 0.091 (2) | 0.0677 (19) | −0.008 (2) | 0.016 (2) | −0.0121 (17) |
N4 | 0.057 (2) | 0.0494 (19) | 0.0544 (19) | −0.0144 (14) | 0.0020 (13) | 0.0020 (14) |
Geometric parameters (Å, º) top
C1—F1 | 1.344 (3) | C15—H15 | 0.9300 |
C1—C6 | 1.370 (4) | C16—C17 | 1.368 (6) |
C1—C2 | 1.371 (4) | C16—H16 | 0.9300 |
C2—C3 | 1.367 (4) | C17—C18 | 1.380 (5) |
C2—H2 | 0.9300 | C17—H17 | 0.9300 |
C3—C4 | 1.343 (4) | C18—C19 | 1.389 (4) |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.391 (4) | C19—C20 | 1.479 (3) |
C4—H4 | 0.9300 | C20—N4 | 1.290 (4) |
C5—C6 | 1.365 (4) | C20—N4' | 1.307 (9) |
C5—H5 | 0.9300 | C20—C22 | 1.488 (5) |
C6—O1 | 1.395 (3) | C20—C22' | 1.512 (9) |
C7—N1 | 1.339 (4) | N3—O2 | 1.422 (3) |
C7—O1 | 1.360 (3) | C21—O3 | 1.457 (5) |
C7—C8 | 1.376 (3) | C21—H21A | 0.9600 |
N2—C9 | 1.328 (3) | C21—H21B | 0.9600 |
N2—N1 | 1.360 (3) | C21—H21C | 0.9600 |
C9—C8 | 1.413 (3) | C22—O5 | 1.225 (5) |
C9—C10 | 1.486 (4) | C22—O4 | 1.265 (6) |
C8—C12 | 1.446 (4) | C23—O4 | 1.489 (4) |
C11—N1 | 1.452 (4) | C23—H23A | 0.9600 |
C11—H11A | 0.9600 | C23—H23B | 0.9600 |
C11—H11B | 0.9600 | C23—H23C | 0.9600 |
C11—H11C | 0.9600 | O3—N4 | 1.362 (5) |
C10—H10A | 0.9600 | C21'—O3' | 1.539 (9) |
C10—H10B | 0.9600 | C21'—H21D | 0.9600 |
C10—H10C | 0.9600 | C21'—H21E | 0.9600 |
C12—N3 | 1.270 (3) | C21'—H21F | 0.9600 |
C12—H12 | 0.9300 | C22'—O5' | 1.274 (9) |
C13—O2 | 1.428 (3) | C22'—O4' | 1.286 (9) |
C13—C14 | 1.503 (4) | C23'—O4' | 1.500 (9) |
C13—H13A | 0.9700 | C23'—H23D | 0.9600 |
C13—H13B | 0.9700 | C23'—H23E | 0.9600 |
C14—C15 | 1.385 (4) | C23'—H23F | 0.9600 |
C14—C19 | 1.394 (4) | O3'—N4' | 1.387 (9) |
C15—C16 | 1.382 (6) | | |
| | | |
F1—C1—C6 | 118.4 (3) | C16—C15—H15 | 119.7 |
F1—C1—C2 | 120.0 (3) | C14—C15—H15 | 119.7 |
C6—C1—C2 | 121.6 (3) | C17—C16—C15 | 120.5 (4) |
C3—C2—C1 | 118.7 (3) | C17—C16—H16 | 119.7 |
C3—C2—H2 | 120.7 | C15—C16—H16 | 119.7 |
C1—C2—H2 | 120.7 | C16—C17—C18 | 119.9 (4) |
C4—C3—C2 | 120.7 (3) | C16—C17—H17 | 120.1 |
C4—C3—H3 | 119.7 | C18—C17—H17 | 120.1 |
C2—C3—H3 | 119.7 | C17—C18—C19 | 120.1 (3) |
C3—C4—C5 | 120.7 (3) | C17—C18—H18 | 119.9 |
C3—C4—H4 | 119.6 | C19—C18—H18 | 119.9 |
C5—C4—H4 | 119.6 | C18—C19—C14 | 120.2 (3) |
C6—C5—C4 | 119.3 (3) | C18—C19—C20 | 119.9 (3) |
C6—C5—H5 | 120.3 | C14—C19—C20 | 120.0 (2) |
C4—C5—H5 | 120.3 | N4—C20—N4' | 103.3 (9) |
C5—C6—C1 | 119.0 (3) | N4—C20—C19 | 126.2 (2) |
C5—C6—O1 | 124.5 (2) | N4'—C20—C19 | 130.4 (9) |
C1—C6—O1 | 116.5 (2) | N4—C20—C22 | 114.9 (3) |
N1—C7—O1 | 121.9 (2) | C19—C20—C22 | 118.9 (3) |
N1—C7—C8 | 108.7 (2) | N4'—C20—C22' | 110.7 (12) |
O1—C7—C8 | 129.2 (3) | C19—C20—C22' | 118.9 (9) |
C9—N2—N1 | 105.7 (2) | C22—C20—C22' | 122.2 (9) |
N2—C9—C8 | 111.1 (2) | C7—N1—N2 | 110.7 (2) |
N2—C9—C10 | 120.4 (2) | C7—N1—C11 | 128.4 (3) |
C8—C9—C10 | 128.5 (2) | N2—N1—C11 | 120.8 (3) |
C7—C8—C9 | 103.7 (2) | C12—N3—O2 | 109.5 (2) |
C7—C8—C12 | 124.9 (2) | C7—O1—C6 | 117.5 (2) |
C9—C8—C12 | 131.4 (2) | N3—O2—C13 | 108.81 (19) |
N1—C11—H11A | 109.5 | O5—C22—O4 | 124.2 (5) |
N1—C11—H11B | 109.5 | O5—C22—C20 | 122.3 (5) |
H11A—C11—H11B | 109.5 | O4—C22—C20 | 113.2 (4) |
N1—C11—H11C | 109.5 | N4—O3—C21 | 108.3 (4) |
H11A—C11—H11C | 109.5 | C22—O4—C23 | 110.7 (4) |
H11B—C11—H11C | 109.5 | C20—N4—O3 | 111.5 (3) |
C9—C10—H10A | 109.5 | O3'—C21'—H21D | 109.5 |
C9—C10—H10B | 109.5 | O3'—C21'—H21E | 109.5 |
H10A—C10—H10B | 109.5 | H21D—C21'—H21E | 109.5 |
C9—C10—H10C | 109.5 | O3'—C21'—H21F | 109.5 |
H10A—C10—H10C | 109.5 | H21D—C21'—H21F | 109.5 |
H10B—C10—H10C | 109.5 | H21E—C21'—H21F | 109.5 |
N3—C12—C8 | 122.7 (2) | O5'—C22'—O4' | 119.0 (12) |
N3—C12—H12 | 118.6 | O5'—C22'—C20 | 119.3 (11) |
C8—C12—H12 | 118.6 | O4'—C22'—C20 | 116.1 (18) |
O2—C13—C14 | 112.5 (2) | O4'—C23'—H23D | 109.5 |
O2—C13—H13A | 109.1 | O4'—C23'—H23E | 109.5 |
C14—C13—H13A | 109.1 | H23D—C23'—H23E | 109.5 |
O2—C13—H13B | 109.1 | O4'—C23'—H23F | 109.5 |
C14—C13—H13B | 109.1 | H23D—C23'—H23F | 109.5 |
H13A—C13—H13B | 107.8 | H23E—C23'—H23F | 109.5 |
C15—C14—C19 | 118.7 (3) | N4'—O3'—C21' | 95.8 (15) |
C15—C14—C13 | 120.8 (3) | C22'—O4'—C23' | 123.8 (15) |
C19—C14—C13 | 120.5 (2) | C20—N4'—O3' | 119.3 (15) |
C16—C15—C14 | 120.6 (4) | | |
| | | |
F1—C1—C2—C3 | −179.5 (3) | O1—C7—N1—N2 | −175.6 (2) |
C6—C1—C2—C3 | −0.4 (5) | C8—C7—N1—N2 | 0.3 (3) |
C1—C2—C3—C4 | 0.5 (5) | O1—C7—N1—C11 | 2.6 (4) |
C2—C3—C4—C5 | −0.7 (5) | C8—C7—N1—C11 | 178.5 (3) |
C3—C4—C5—C6 | 0.8 (5) | C9—N2—N1—C7 | −0.4 (3) |
C4—C5—C6—C1 | −0.6 (4) | C9—N2—N1—C11 | −178.7 (2) |
C4—C5—C6—O1 | 178.0 (3) | C8—C12—N3—O2 | −179.0 (2) |
F1—C1—C6—C5 | 179.6 (3) | N1—C7—O1—C6 | −92.7 (3) |
C2—C1—C6—C5 | 0.4 (4) | C8—C7—O1—C6 | 92.3 (3) |
F1—C1—C6—O1 | 0.9 (4) | C5—C6—O1—C7 | 18.8 (4) |
C2—C1—C6—O1 | −178.3 (3) | C1—C6—O1—C7 | −162.6 (3) |
N1—N2—C9—C8 | 0.3 (3) | C12—N3—O2—C13 | −169.4 (2) |
N1—N2—C9—C10 | 179.4 (2) | C14—C13—O2—N3 | 67.6 (2) |
N1—C7—C8—C9 | −0.1 (3) | N4—C20—C22—O5 | −8.6 (10) |
O1—C7—C8—C9 | 175.4 (2) | N4'—C20—C22—O5 | 8 (7) |
N1—C7—C8—C12 | 179.7 (2) | C19—C20—C22—O5 | 171.6 (7) |
O1—C7—C8—C12 | −4.7 (4) | C22'—C20—C22—O5 | −11 (2) |
N2—C9—C8—C7 | −0.1 (3) | N4—C20—C22—O4 | 177.2 (6) |
C10—C9—C8—C7 | −179.1 (3) | N4'—C20—C22—O4 | −167 (8) |
N2—C9—C8—C12 | −180.0 (2) | C19—C20—C22—O4 | −2.7 (9) |
C10—C9—C8—C12 | 1.1 (5) | C22'—C20—C22—O4 | 174.7 (19) |
C7—C8—C12—N3 | 178.8 (2) | O5—C22—O4—C23 | 6.0 (12) |
C9—C8—C12—N3 | −1.4 (4) | C20—C22—O4—C23 | −179.8 (5) |
O2—C13—C14—C15 | −116.1 (3) | N4'—C20—N4—O3 | 178.7 (14) |
O2—C13—C14—C19 | 62.9 (3) | C19—C20—N4—O3 | 2.0 (5) |
C19—C14—C15—C16 | −0.5 (5) | C22—C20—N4—O3 | −177.8 (6) |
C13—C14—C15—C16 | 178.5 (3) | C22'—C20—N4—O3 | −14 (14) |
C14—C15—C16—C17 | −0.1 (6) | C21—O3—N4—C20 | −178.2 (5) |
C15—C16—C17—C18 | 0.1 (6) | N4—C20—C22'—O5' | 17 (10) |
C16—C17—C18—C19 | 0.4 (5) | N4'—C20—C22'—O5' | 30 (4) |
C17—C18—C19—C14 | −1.1 (4) | C19—C20—C22'—O5' | −149 (2) |
C17—C18—C19—C20 | 179.3 (3) | C22—C20—C22'—O5' | 34 (4) |
C15—C14—C19—C18 | 1.1 (4) | N4—C20—C22'—O4' | 170 (16) |
C13—C14—C19—C18 | −177.9 (2) | N4'—C20—C22'—O4' | −177 (3) |
C15—C14—C19—C20 | −179.3 (2) | C19—C20—C22'—O4' | 5 (4) |
C13—C14—C19—C20 | 1.7 (4) | C22—C20—C22'—O4' | −173 (2) |
C18—C19—C20—N4 | −108.8 (3) | O5'—C22'—O4'—C23' | −14 (6) |
C14—C19—C20—N4 | 71.6 (4) | C20—C22'—O4'—C23' | −168 (3) |
C18—C19—C20—N4' | 75.4 (17) | N4—C20—N4'—O3' | 167 (2) |
C14—C19—C20—N4' | −104.2 (17) | C19—C20—N4'—O3' | −16 (3) |
C18—C19—C20—C22 | 71.0 (5) | C22—C20—N4'—O3' | 2 (6) |
C14—C19—C20—C22 | −108.6 (5) | C22'—C20—N4'—O3' | 166 (3) |
C18—C19—C20—C22' | −106.5 (18) | C21'—O3'—N4'—C20 | −176 (2) |
C14—C19—C20—C22' | 73.9 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O3 | 0.97 | 2.51 | 3.192 (9) | 127 |
C11—H11B···O5i | 0.96 | 2.52 | 3.470 (5) | 169 |
C5—H5···O5ii | 0.93 | 2.52 | 3.154 (5) | 126 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, z. |