The crystal structure of the title compound, C
29H
22N
2O
4·C
3H
7NO, is stabilized by two N—H
O and six C—H
O intermolecular hydrogen bonds and C—H
π and π–π interactions. The intermolecular hydrogen bonds generate
R12(6) and
R22(32) ring motifs.
Supporting information
CCDC reference: 620528
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.072
- wR factor = 0.203
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.71 mm
PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.20 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C35
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34 .. O5 .. 2.81 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O1 .. 2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H36B .. O3 .. 2.85 Ang.
PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.845(18) ...... 2.22 su-Ra
N2 -H2 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.845(18) ...... 2.22 su-Ra
N2 -H2 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 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
0 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
6 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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).
3-{4-[4-(3-Oxo-1,3-dihydroisobenzofuran-1-
ylamino)benzyl]phenylamino}isobenzofuran-1(3
H)-one dimethylformamide
solvate
top
Crystal data top
C29H22N2O4·C3H7NO | Z = 2 |
Mr = 535.58 | F(000) = 564 |
Triclinic, P1 | Dx = 1.287 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0267 (7) Å | Cell parameters from 13625 reflections |
b = 12.6709 (11) Å | θ = 2.0–27.9° |
c = 14.6529 (13) Å | µ = 0.09 mm−1 |
α = 98.911 (7)° | T = 296 K |
β = 100.893 (7)° | Long prismatic stick, light brown |
γ = 104.746 (6)° | 0.71 × 0.34 × 0.11 mm |
V = 1382.5 (2) Å3 | |
Data collection top
Stoe IPDS-2 diffractometer | 5014 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2712 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.101 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.3°, θmin = 2.0° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.951, Tmax = 0.988 | l = −17→17 |
16524 measured reflections | |
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)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.203 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.1127P)2] where P = (Fo2 + 2Fc2)/3 |
5014 reflections | (Δ/σ)max < 0.001 |
371 parameters | Δρmax = 0.41 e Å−3 |
2 restraints | Δρmin = −0.34 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 | 0.0074 (5) | 0.9750 (4) | 0.8705 (3) | 0.0632 (10) | |
C2 | −0.1747 (5) | 0.9633 (3) | 0.8757 (2) | 0.0551 (9) | |
C3 | −0.2809 (6) | 1.0314 (4) | 0.8541 (3) | 0.0727 (12) | |
H3 | −0.2378 | 1.0970 | 0.8340 | 0.087* | |
C4 | −0.4514 (7) | 0.9978 (4) | 0.8637 (3) | 0.0832 (14) | |
H4 | −0.5258 | 1.0418 | 0.8502 | 0.100* | |
C5 | −0.5164 (6) | 0.8995 (4) | 0.8934 (3) | 0.0770 (12) | |
H5 | −0.6331 | 0.8786 | 0.8990 | 0.092* | |
C6 | −0.4101 (5) | 0.8330 (4) | 0.9142 (3) | 0.0660 (10) | |
H6 | −0.4533 | 0.7670 | 0.9338 | 0.079* | |
C7 | −0.2383 (5) | 0.8664 (3) | 0.9056 (2) | 0.0526 (9) | |
C8 | −0.0949 (5) | 0.8093 (3) | 0.9207 (3) | 0.0527 (9) | |
H8 | −0.0595 | 0.8093 | 0.9885 | 0.063* | |
C9 | −0.0459 (4) | 0.6256 (3) | 0.8789 (2) | 0.0484 (8) | |
C10 | 0.1162 (5) | 0.6518 (3) | 0.9438 (3) | 0.0541 (9) | |
H10 | 0.1656 | 0.7231 | 0.9821 | 0.065* | |
C11 | 0.2052 (5) | 0.5713 (3) | 0.9518 (2) | 0.0551 (9) | |
H11 | 0.3133 | 0.5897 | 0.9960 | 0.066* | |
C12 | 0.1371 (5) | 0.4656 (3) | 0.8962 (2) | 0.0509 (8) | |
C13 | −0.0241 (5) | 0.4402 (3) | 0.8314 (3) | 0.0608 (10) | |
H13 | −0.0724 | 0.3691 | 0.7926 | 0.073* | |
C14 | −0.1143 (5) | 0.5190 (3) | 0.8235 (3) | 0.0553 (9) | |
H14 | −0.2234 | 0.4998 | 0.7800 | 0.066* | |
C15 | 0.2365 (6) | 0.3789 (3) | 0.9027 (3) | 0.0638 (10) | |
H15A | 0.3246 | 0.4020 | 0.9628 | 0.077* | |
H15B | 0.1534 | 0.3086 | 0.9033 | 0.077* | |
C21 | 0.5116 (5) | 0.3352 (3) | 0.3846 (3) | 0.0585 (9) | |
C22 | 0.6984 (5) | 0.3360 (3) | 0.3985 (2) | 0.0522 (9) | |
C23 | 0.7979 (6) | 0.3207 (3) | 0.3330 (3) | 0.0684 (11) | |
H23 | 0.7490 | 0.3078 | 0.2680 | 0.082* | |
C24 | 0.9702 (6) | 0.3250 (4) | 0.3669 (3) | 0.0742 (12) | |
H24 | 1.0402 | 0.3150 | 0.3243 | 0.089* | |
C25 | 1.0433 (5) | 0.3441 (3) | 0.4640 (3) | 0.0675 (11) | |
H25 | 1.1607 | 0.3453 | 0.4852 | 0.081* | |
C26 | 0.9449 (5) | 0.3612 (3) | 0.5290 (3) | 0.0587 (9) | |
H26 | 0.9943 | 0.3751 | 0.5940 | 0.070* | |
C27 | 0.7701 (4) | 0.3572 (3) | 0.4949 (2) | 0.0474 (8) | |
C28 | 0.6346 (4) | 0.3745 (3) | 0.5479 (2) | 0.0490 (8) | |
H28 | 0.6720 | 0.4518 | 0.5842 | 0.059* | |
C29 | 0.5032 (4) | 0.3193 (3) | 0.6772 (2) | 0.0450 (8) | |
C30 | 0.4168 (5) | 0.4006 (3) | 0.6811 (3) | 0.0540 (9) | |
H30 | 0.4150 | 0.4424 | 0.6342 | 0.065* | |
C31 | 0.3334 (5) | 0.4209 (3) | 0.7528 (3) | 0.0545 (9) | |
H31 | 0.2786 | 0.4774 | 0.7540 | 0.065* | |
C32 | 0.3283 (4) | 0.3596 (3) | 0.8235 (2) | 0.0472 (8) | |
C33 | 0.4110 (5) | 0.2756 (3) | 0.8170 (3) | 0.0554 (9) | |
H33 | 0.4072 | 0.2309 | 0.8618 | 0.066* | |
C34 | 0.4978 (5) | 0.2564 (3) | 0.7469 (3) | 0.0534 (9) | |
H34 | 0.5539 | 0.2006 | 0.7460 | 0.064* | |
C35 | 0.9305 (9) | 0.1156 (5) | 0.6487 (4) | 0.1014 (17) | |
H35 | 1.0429 | 0.1667 | 0.6704 | 0.122* | |
C36 | 0.7810 (17) | −0.0745 (10) | 0.5933 (8) | 0.261 (8) | |
H36A | 0.6758 | −0.0510 | 0.5809 | 0.391* | |
H36B | 0.7773 | −0.1160 | 0.6428 | 0.391* | |
H36C | 0.7874 | −0.1209 | 0.5365 | 0.391* | |
C37 | 1.0992 (14) | −0.0147 (8) | 0.6295 (6) | 0.186 (4) | |
H37A | 1.1946 | 0.0521 | 0.6376 | 0.279* | |
H37B | 1.0937 | −0.0664 | 0.5729 | 0.279* | |
H37C | 1.1191 | −0.0480 | 0.6835 | 0.279* | |
N1 | −0.1462 (4) | 0.7006 (3) | 0.8689 (2) | 0.0571 (8) | |
N2 | 0.5983 (4) | 0.3019 (3) | 0.6088 (2) | 0.0541 (8) | |
N3 | 0.9228 (9) | 0.0146 (5) | 0.6205 (4) | 0.1229 (18) | |
O1 | 0.1114 (4) | 1.0504 (3) | 0.8516 (3) | 0.0931 (10) | |
O2 | 0.0531 (3) | 0.8848 (2) | 0.89352 (19) | 0.0637 (7) | |
O3 | 0.4012 (4) | 0.3188 (3) | 0.3116 (2) | 0.0853 (9) | |
O4 | 0.4745 (3) | 0.3572 (2) | 0.46952 (18) | 0.0593 (7) | |
O5 | 0.8055 (8) | 0.1518 (5) | 0.6499 (4) | 0.165 (2) | |
H1 | −0.221 (5) | 0.685 (3) | 0.8137 (19) | 0.077 (13)* | |
H2 | 0.653 (5) | 0.253 (3) | 0.610 (3) | 0.062 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.064 (2) | 0.063 (3) | 0.059 (2) | 0.013 (2) | 0.0103 (18) | 0.0188 (19) |
C2 | 0.061 (2) | 0.058 (2) | 0.0501 (19) | 0.0245 (18) | 0.0124 (16) | 0.0124 (17) |
C3 | 0.081 (3) | 0.069 (3) | 0.076 (3) | 0.035 (2) | 0.014 (2) | 0.023 (2) |
C4 | 0.093 (4) | 0.090 (4) | 0.082 (3) | 0.058 (3) | 0.014 (3) | 0.018 (3) |
C5 | 0.063 (3) | 0.096 (4) | 0.083 (3) | 0.041 (3) | 0.023 (2) | 0.014 (3) |
C6 | 0.060 (2) | 0.077 (3) | 0.071 (3) | 0.030 (2) | 0.0238 (19) | 0.019 (2) |
C7 | 0.055 (2) | 0.061 (2) | 0.0454 (19) | 0.0257 (18) | 0.0121 (15) | 0.0087 (17) |
C8 | 0.053 (2) | 0.058 (2) | 0.0502 (19) | 0.0204 (18) | 0.0115 (16) | 0.0147 (17) |
C9 | 0.0462 (18) | 0.056 (2) | 0.0477 (18) | 0.0211 (17) | 0.0121 (15) | 0.0143 (17) |
C10 | 0.0486 (19) | 0.052 (2) | 0.056 (2) | 0.0157 (17) | 0.0033 (16) | 0.0035 (16) |
C11 | 0.0476 (19) | 0.070 (3) | 0.050 (2) | 0.0240 (18) | 0.0069 (15) | 0.0127 (18) |
C12 | 0.056 (2) | 0.059 (2) | 0.0478 (19) | 0.0250 (18) | 0.0189 (16) | 0.0183 (17) |
C13 | 0.063 (2) | 0.056 (2) | 0.059 (2) | 0.0177 (19) | 0.0107 (18) | 0.0048 (18) |
C14 | 0.0465 (19) | 0.059 (2) | 0.054 (2) | 0.0169 (17) | 0.0010 (15) | 0.0051 (18) |
C15 | 0.079 (3) | 0.071 (3) | 0.062 (2) | 0.041 (2) | 0.027 (2) | 0.029 (2) |
C21 | 0.057 (2) | 0.061 (2) | 0.057 (2) | 0.0187 (18) | 0.0040 (18) | 0.0213 (18) |
C22 | 0.058 (2) | 0.052 (2) | 0.051 (2) | 0.0212 (17) | 0.0136 (16) | 0.0164 (16) |
C23 | 0.087 (3) | 0.068 (3) | 0.060 (2) | 0.030 (2) | 0.027 (2) | 0.019 (2) |
C24 | 0.077 (3) | 0.078 (3) | 0.089 (3) | 0.035 (2) | 0.046 (2) | 0.028 (2) |
C25 | 0.049 (2) | 0.069 (3) | 0.096 (3) | 0.025 (2) | 0.027 (2) | 0.027 (2) |
C26 | 0.048 (2) | 0.065 (3) | 0.067 (2) | 0.0197 (18) | 0.0117 (17) | 0.0192 (19) |
C27 | 0.0471 (18) | 0.046 (2) | 0.054 (2) | 0.0177 (15) | 0.0142 (15) | 0.0162 (16) |
C28 | 0.0418 (17) | 0.054 (2) | 0.0509 (19) | 0.0161 (15) | 0.0059 (14) | 0.0130 (16) |
C29 | 0.0393 (17) | 0.046 (2) | 0.0485 (18) | 0.0132 (15) | 0.0066 (14) | 0.0097 (15) |
C30 | 0.058 (2) | 0.063 (2) | 0.057 (2) | 0.0296 (19) | 0.0210 (17) | 0.0280 (18) |
C31 | 0.058 (2) | 0.053 (2) | 0.065 (2) | 0.0294 (18) | 0.0193 (17) | 0.0244 (18) |
C32 | 0.0454 (18) | 0.052 (2) | 0.0487 (18) | 0.0195 (15) | 0.0109 (14) | 0.0146 (15) |
C33 | 0.062 (2) | 0.053 (2) | 0.061 (2) | 0.0231 (18) | 0.0169 (18) | 0.0267 (18) |
C34 | 0.058 (2) | 0.044 (2) | 0.066 (2) | 0.0244 (17) | 0.0164 (18) | 0.0182 (17) |
C35 | 0.140 (5) | 0.065 (3) | 0.111 (4) | 0.050 (3) | 0.029 (4) | 0.021 (3) |
C36 | 0.315 (16) | 0.179 (10) | 0.170 (9) | −0.111 (10) | 0.039 (9) | 0.022 (8) |
C37 | 0.256 (11) | 0.194 (9) | 0.152 (7) | 0.156 (9) | 0.041 (7) | 0.023 (6) |
N1 | 0.0571 (18) | 0.056 (2) | 0.0538 (18) | 0.0264 (15) | −0.0036 (14) | 0.0035 (15) |
N2 | 0.0562 (18) | 0.060 (2) | 0.0594 (18) | 0.0303 (16) | 0.0196 (14) | 0.0228 (15) |
N3 | 0.190 (6) | 0.079 (3) | 0.096 (3) | 0.042 (4) | 0.026 (3) | 0.013 (3) |
O1 | 0.077 (2) | 0.091 (2) | 0.110 (3) | 0.0079 (18) | 0.0216 (18) | 0.048 (2) |
O2 | 0.0525 (15) | 0.0690 (18) | 0.0728 (17) | 0.0204 (13) | 0.0142 (12) | 0.0211 (14) |
O3 | 0.0763 (19) | 0.105 (2) | 0.0672 (18) | 0.0267 (17) | −0.0084 (15) | 0.0268 (17) |
O4 | 0.0455 (13) | 0.0786 (18) | 0.0592 (16) | 0.0270 (12) | 0.0077 (11) | 0.0220 (13) |
O5 | 0.212 (5) | 0.176 (5) | 0.210 (5) | 0.144 (5) | 0.112 (4) | 0.116 (4) |
Geometric parameters (Å, º) top
C1—O1 | 1.204 (5) | C23—C24 | 1.362 (6) |
C1—O2 | 1.357 (5) | C23—H23 | 0.9300 |
C1—C2 | 1.449 (6) | C24—C25 | 1.390 (6) |
C2—C7 | 1.375 (5) | C24—H24 | 0.9300 |
C2—C3 | 1.389 (5) | C25—C26 | 1.373 (6) |
C3—C4 | 1.368 (7) | C25—H25 | 0.9300 |
C3—H3 | 0.9300 | C26—C27 | 1.382 (5) |
C4—C5 | 1.391 (7) | C26—H26 | 0.9300 |
C4—H4 | 0.9300 | C27—C28 | 1.491 (5) |
C5—C6 | 1.370 (5) | C28—N2 | 1.394 (4) |
C5—H5 | 0.9300 | C28—O4 | 1.497 (4) |
C6—C7 | 1.372 (5) | C28—H28 | 0.9800 |
C6—H6 | 0.9300 | C29—C30 | 1.381 (4) |
C7—C8 | 1.508 (4) | C29—C34 | 1.389 (5) |
C8—N1 | 1.383 (5) | C29—N2 | 1.394 (4) |
C8—O2 | 1.485 (4) | C30—C31 | 1.375 (5) |
C8—H8 | 0.9800 | C30—H30 | 0.9300 |
C9—C14 | 1.378 (5) | C31—C32 | 1.388 (5) |
C9—C10 | 1.386 (5) | C31—H31 | 0.9300 |
C9—N1 | 1.400 (4) | C32—C33 | 1.391 (5) |
C10—C11 | 1.393 (5) | C33—C34 | 1.372 (5) |
C10—H10 | 0.9300 | C33—H33 | 0.9300 |
C11—C12 | 1.371 (5) | C34—H34 | 0.9300 |
C11—H11 | 0.9300 | C35—O5 | 1.207 (7) |
C12—C13 | 1.381 (5) | C35—N3 | 1.264 (7) |
C12—C15 | 1.516 (5) | C35—H35 | 0.9300 |
C13—C14 | 1.382 (5) | C36—N3 | 1.328 (10) |
C13—H13 | 0.9300 | C36—H36A | 0.9600 |
C14—H14 | 0.9300 | C36—H36B | 0.9600 |
C15—C32 | 1.509 (5) | C36—H36C | 0.9600 |
C15—H15A | 0.9700 | C37—N3 | 1.540 (10) |
C15—H15B | 0.9700 | C37—H37A | 0.9600 |
C21—O3 | 1.204 (4) | C37—H37B | 0.9600 |
C21—O4 | 1.338 (5) | C37—H37C | 0.9600 |
C21—C22 | 1.471 (5) | N1—H1 | 0.871 (19) |
C22—C27 | 1.376 (5) | N2—H2 | 0.845 (18) |
C22—C23 | 1.382 (5) | | |
| | | |
O1—C1—O2 | 121.6 (4) | C23—C24—H24 | 119.4 |
O1—C1—C2 | 129.3 (4) | C25—C24—H24 | 119.4 |
O2—C1—C2 | 109.1 (3) | C26—C25—C24 | 121.0 (4) |
C7—C2—C3 | 121.4 (4) | C26—C25—H25 | 119.5 |
C7—C2—C1 | 108.7 (3) | C24—C25—H25 | 119.5 |
C3—C2—C1 | 129.8 (4) | C25—C26—C27 | 118.0 (4) |
C4—C3—C2 | 117.1 (4) | C25—C26—H26 | 121.0 |
C4—C3—H3 | 121.5 | C27—C26—H26 | 121.0 |
C2—C3—H3 | 121.5 | C22—C27—C26 | 120.4 (3) |
C3—C4—C5 | 121.6 (4) | C22—C27—C28 | 109.9 (3) |
C3—C4—H4 | 119.2 | C26—C27—C28 | 129.7 (3) |
C5—C4—H4 | 119.2 | N2—C28—C27 | 115.0 (3) |
C6—C5—C4 | 120.7 (4) | N2—C28—O4 | 111.0 (3) |
C6—C5—H5 | 119.7 | C27—C28—O4 | 102.6 (3) |
C4—C5—H5 | 119.7 | N2—C28—H28 | 109.4 |
C5—C6—C7 | 118.2 (4) | C27—C28—H28 | 109.4 |
C5—C6—H6 | 120.9 | O4—C28—H28 | 109.4 |
C7—C6—H6 | 120.9 | C30—C29—C34 | 117.5 (3) |
C6—C7—C2 | 121.0 (3) | C30—C29—N2 | 122.3 (3) |
C6—C7—C8 | 129.8 (4) | C34—C29—N2 | 120.2 (3) |
C2—C7—C8 | 109.2 (3) | C31—C30—C29 | 121.2 (3) |
N1—C8—O2 | 113.6 (3) | C31—C30—H30 | 119.4 |
N1—C8—C7 | 113.4 (3) | C29—C30—H30 | 119.4 |
O2—C8—C7 | 102.5 (3) | C30—C31—C32 | 122.0 (3) |
N1—C8—H8 | 109.1 | C30—C31—H31 | 119.0 |
O2—C8—H8 | 109.1 | C32—C31—H31 | 119.0 |
C7—C8—H8 | 109.1 | C31—C32—C33 | 116.2 (3) |
C14—C9—C10 | 118.2 (3) | C31—C32—C15 | 123.3 (3) |
C14—C9—N1 | 118.3 (3) | C33—C32—C15 | 120.5 (3) |
C10—C9—N1 | 123.5 (3) | C34—C33—C32 | 122.2 (3) |
C9—C10—C11 | 120.0 (3) | C34—C33—H33 | 118.9 |
C9—C10—H10 | 120.0 | C32—C33—H33 | 118.9 |
C11—C10—H10 | 120.0 | C33—C34—C29 | 120.9 (3) |
C12—C11—C10 | 121.6 (3) | C33—C34—H34 | 119.5 |
C12—C11—H11 | 119.2 | C29—C34—H34 | 119.5 |
C10—C11—H11 | 119.2 | O5—C35—N3 | 126.0 (7) |
C11—C12—C13 | 118.1 (3) | O5—C35—H35 | 117.0 |
C11—C12—C15 | 121.6 (3) | N3—C35—H35 | 117.0 |
C13—C12—C15 | 120.3 (4) | N3—C36—H36A | 109.5 |
C12—C13—C14 | 120.8 (4) | N3—C36—H36B | 109.5 |
C12—C13—H13 | 119.6 | H36A—C36—H36B | 109.5 |
C14—C13—H13 | 119.6 | N3—C36—H36C | 109.5 |
C9—C14—C13 | 121.3 (3) | H36A—C36—H36C | 109.5 |
C9—C14—H14 | 119.4 | H36B—C36—H36C | 109.5 |
C13—C14—H14 | 119.4 | N3—C37—H37A | 109.5 |
C32—C15—C12 | 115.1 (3) | N3—C37—H37B | 109.5 |
C32—C15—H15A | 108.5 | H37A—C37—H37B | 109.5 |
C12—C15—H15A | 108.5 | N3—C37—H37C | 109.5 |
C32—C15—H15B | 108.5 | H37A—C37—H37C | 109.5 |
C12—C15—H15B | 108.5 | H37B—C37—H37C | 109.5 |
H15A—C15—H15B | 107.5 | C8—N1—C9 | 124.4 (3) |
O3—C21—O4 | 121.5 (3) | C8—N1—H1 | 118 (3) |
O3—C21—C22 | 129.3 (4) | C9—N1—H1 | 114 (3) |
O4—C21—C22 | 109.2 (3) | C29—N2—C28 | 122.6 (3) |
C27—C22—C23 | 121.8 (3) | C29—N2—H2 | 120 (3) |
C27—C22—C21 | 107.7 (3) | C28—N2—H2 | 117 (3) |
C23—C22—C21 | 130.5 (3) | C35—N3—C36 | 128.6 (10) |
C24—C23—C22 | 117.6 (4) | C35—N3—C37 | 117.6 (7) |
C24—C23—H23 | 121.2 | C36—N3—C37 | 113.3 (9) |
C22—C23—H23 | 121.2 | C1—O2—C8 | 110.5 (3) |
C23—C24—C25 | 121.2 (4) | C21—O4—C28 | 110.6 (2) |
| | | |
O1—C1—C2—C7 | −176.3 (4) | C23—C22—C27—C26 | −1.5 (5) |
O2—C1—C2—C7 | 2.2 (4) | C21—C22—C27—C26 | 179.1 (3) |
O1—C1—C2—C3 | 4.9 (7) | C23—C22—C27—C28 | 177.7 (3) |
O2—C1—C2—C3 | −176.6 (4) | C21—C22—C27—C28 | −1.7 (4) |
C7—C2—C3—C4 | −0.1 (6) | C25—C26—C27—C22 | 0.4 (5) |
C1—C2—C3—C4 | 178.5 (4) | C25—C26—C27—C28 | −178.7 (4) |
C2—C3—C4—C5 | −0.3 (7) | C22—C27—C28—N2 | 122.1 (3) |
C3—C4—C5—C6 | 0.3 (7) | C26—C27—C28—N2 | −58.8 (5) |
C4—C5—C6—C7 | 0.3 (7) | C22—C27—C28—O4 | 1.6 (4) |
C5—C6—C7—C2 | −0.8 (6) | C26—C27—C28—O4 | −179.3 (3) |
C5—C6—C7—C8 | −178.0 (4) | C34—C29—C30—C31 | 2.0 (5) |
C3—C2—C7—C6 | 0.7 (6) | N2—C29—C30—C31 | −175.8 (3) |
C1—C2—C7—C6 | −178.2 (3) | C29—C30—C31—C32 | −1.4 (6) |
C3—C2—C7—C8 | 178.4 (3) | C30—C31—C32—C33 | −0.7 (6) |
C1—C2—C7—C8 | −0.5 (4) | C30—C31—C32—C15 | −179.4 (4) |
C6—C7—C8—N1 | 53.4 (5) | C12—C15—C32—C31 | 4.2 (6) |
C2—C7—C8—N1 | −124.0 (3) | C12—C15—C32—C33 | −174.5 (4) |
C6—C7—C8—O2 | 176.3 (4) | C31—C32—C33—C34 | 2.1 (6) |
C2—C7—C8—O2 | −1.2 (4) | C15—C32—C33—C34 | −179.1 (4) |
C14—C9—C10—C11 | −0.1 (5) | C32—C33—C34—C29 | −1.6 (6) |
N1—C9—C10—C11 | 177.8 (3) | C30—C29—C34—C33 | −0.5 (5) |
C9—C10—C11—C12 | 0.5 (6) | N2—C29—C34—C33 | 177.3 (3) |
C10—C11—C12—C13 | −0.3 (5) | O2—C8—N1—C9 | 71.6 (4) |
C10—C11—C12—C15 | 178.1 (3) | C7—C8—N1—C9 | −171.9 (3) |
C11—C12—C13—C14 | −0.4 (5) | C14—C9—N1—C8 | 179.1 (3) |
C15—C12—C13—C14 | −178.8 (3) | C10—C9—N1—C8 | 1.2 (6) |
C10—C9—C14—C13 | −0.6 (5) | C30—C29—N2—C28 | 9.3 (5) |
N1—C9—C14—C13 | −178.6 (4) | C34—C29—N2—C28 | −168.4 (3) |
C12—C13—C14—C9 | 0.8 (6) | C27—C28—N2—C29 | 167.0 (3) |
C11—C12—C15—C32 | −102.8 (4) | O4—C28—N2—C29 | −77.2 (4) |
C13—C12—C15—C32 | 75.6 (5) | O5—C35—N3—C36 | −5.6 (12) |
O3—C21—C22—C27 | −179.2 (4) | O5—C35—N3—C37 | −177.2 (7) |
O4—C21—C22—C27 | 1.1 (4) | O1—C1—O2—C8 | 175.6 (4) |
O3—C21—C22—C23 | 1.5 (7) | C2—C1—O2—C8 | −3.0 (4) |
O4—C21—C22—C23 | −178.2 (4) | N1—C8—O2—C1 | 125.2 (3) |
C27—C22—C23—C24 | 1.3 (6) | C7—C8—O2—C1 | 2.6 (4) |
C21—C22—C23—C24 | −179.5 (4) | O3—C21—O4—C28 | −179.8 (4) |
C22—C23—C24—C25 | 0.0 (6) | C22—C21—O4—C28 | −0.1 (4) |
C23—C24—C25—C26 | −1.2 (7) | N2—C28—O4—C21 | −124.1 (3) |
C24—C25—C26—C27 | 0.9 (6) | C27—C28—O4—C21 | −0.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O5 | 0.85 (2) | 2.06 (2) | 2.886 (5) | 165 (4) |
C34—H34···O5 | 0.93 | 2.81 | 3.505 (6) | 133 |
N1—H1···O3i | 0.87 (2) | 2.10 (2) | 2.956 (4) | 168 (4) |
C5—H5···O2ii | 0.93 | 2.53 | 3.413 (6) | 160 |
C8—H8···O1iii | 0.98 | 2.88 | 3.573 (5) | 129 |
C25—H25···O4iv | 0.93 | 2.54 | 3.408 (4) | 155 |
C36—H36b···O3v | 0.96 | 2.85 | 3.669 (13) | 143 |
C37—H37c···O1vi | 0.96 | 2.60 | 3.208 (10) | 121 |
C14—H14···Cg1iv | 0.93 | 3.00 | 3.735 (4) | 137 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) −x, −y+2, −z+2; (iv) x+1, y, z; (v) −x+1, −y, −z+1; (vi) x+1, y−1, z. |