In the title compound, C18H20N+·C12H10O2P-·H2O, the propylaminomethyl side chain lies above the plane of the anthracene moiety. In the crystal structure, the phosphinate O atoms are involved in hydrogen bonds with the water molecule of crystallization and the NH group of the proplyamine side chain of the anthracene moiety.
Supporting information
CCDC reference: 229989
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.103
- wR factor = 0.317
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C18 .. 7.79 su
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.103
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.317
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.67 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.32
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.17
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C11 .. 5.14 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C17
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C17 ... 1.36 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C17 - C18 ... 1.35 Ang.
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
12 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: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
9-Anthracenemethylpropylamine diphenylphosphoride monohydrate
top
Crystal data top
C18H20N+·C12H10O2P−·H2O | Dx = 1.246 Mg m−3 |
Mr = 485.54 | Melting point: 243 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.572 (4) Å | Cell parameters from 620 reflections |
b = 10.370 (3) Å | θ = 2.2–25.0° |
c = 19.435 (6) Å | µ = 0.14 mm−1 |
β = 108.899 (5)° | T = 293 K |
V = 2587.9 (13) Å3 | Prism, yellow |
Z = 4 | 0.25 × 0.15 × 0.08 mm |
F(000) = 1032 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4369 independent reflections |
Radiation source: fine-focus sealed tube | 2163 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→16 |
Tmin = 0.966, Tmax = 0.989 | k = −6→12 |
10002 measured reflections | l = −23→22 |
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)] = 0.103 | H-atom parameters constrained |
wR(F2) = 0.317 | w = 1/[σ2(Fo2) + (0.1614P)2 + 1.9131P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4369 reflections | Δρmax = 1.11 e Å−3 |
317 parameters | Δρmin = −0.35 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (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 | 0.5572 (5) | 0.2641 (6) | 0.3399 (3) | 0.0499 (15) | |
C2 | 0.5224 (6) | 0.3048 (6) | 0.3979 (4) | 0.0636 (18) | |
H2A | 0.4520 | 0.2986 | 0.3927 | 0.076* | |
C3 | 0.5906 (8) | 0.3534 (8) | 0.4617 (4) | 0.083 (2) | |
H3A | 0.5656 | 0.3806 | 0.4985 | 0.099* | |
C4 | 0.6960 (7) | 0.3619 (7) | 0.4713 (4) | 0.080 (2) | |
H4A | 0.7414 | 0.3927 | 0.5150 | 0.096* | |
C5 | 0.7324 (6) | 0.3269 (6) | 0.4191 (4) | 0.071 (2) | |
H5A | 0.8033 | 0.3349 | 0.4266 | 0.085* | |
C6 | 0.6659 (5) | 0.2764 (6) | 0.3509 (3) | 0.0562 (16) | |
C7 | 0.7045 (5) | 0.2396 (7) | 0.2964 (4) | 0.0658 (19) | |
H7A | 0.7753 | 0.2493 | 0.3038 | 0.079* | |
C8 | 0.6419 (5) | 0.1887 (6) | 0.2309 (3) | 0.0582 (16) | |
C9 | 0.6843 (6) | 0.1527 (8) | 0.1757 (4) | 0.075 (2) | |
H9A | 0.7545 | 0.1673 | 0.1828 | 0.090* | |
C10 | 0.6256 (8) | 0.0989 (8) | 0.1143 (5) | 0.090 (3) | |
H10A | 0.6553 | 0.0733 | 0.0796 | 0.108* | |
C11 | 0.5220 (9) | 0.0808 (8) | 0.1019 (4) | 0.093 (3) | |
H11A | 0.4821 | 0.0454 | 0.0577 | 0.111* | |
C12 | 0.4727 (6) | 0.1131 (6) | 0.1526 (4) | 0.072 (2) | |
H12A | 0.4021 | 0.0974 | 0.1430 | 0.087* | |
C13 | 0.5350 (5) | 0.1719 (5) | 0.2206 (3) | 0.0525 (15) | |
C14 | 0.4915 (4) | 0.2128 (5) | 0.2741 (3) | 0.0499 (15) | |
C15 | 0.3776 (5) | 0.2012 (6) | 0.2606 (4) | 0.0676 (19) | |
H15A | 0.3652 | 0.1893 | 0.3066 | 0.081* | |
H15B | 0.3516 | 0.1255 | 0.2309 | 0.081* | |
C16 | 0.2911 (8) | 0.3373 (11) | 0.1398 (5) | 0.111 (3) | |
H16A | 0.3564 | 0.3367 | 0.1295 | 0.133* | |
H16B | 0.2524 | 0.2615 | 0.1168 | 0.133* | |
C17 | 0.2366 (13) | 0.4429 (11) | 0.1075 (6) | 0.160 (6) | |
H17A | 0.2637 | 0.5164 | 0.1387 | 0.192* | |
H17B | 0.2511 | 0.4577 | 0.0624 | 0.192* | |
C18 | 0.1324 (9) | 0.4415 (12) | 0.0920 (7) | 0.149 (5) | |
H18A | 0.1035 | 0.5203 | 0.0680 | 0.223* | |
H18B | 0.1159 | 0.4334 | 0.1362 | 0.223* | |
H18C | 0.1035 | 0.3698 | 0.0607 | 0.223* | |
C19 | 1.0227 (4) | 0.1482 (6) | 0.3146 (3) | 0.0516 (15) | |
C20 | 1.0412 (5) | 0.2191 (6) | 0.3772 (3) | 0.0616 (17) | |
H20A | 1.0825 | 0.2926 | 0.3839 | 0.074* | |
C21 | 0.9999 (6) | 0.1834 (8) | 0.4300 (4) | 0.078 (2) | |
H21A | 1.0148 | 0.2317 | 0.4725 | 0.094* | |
C22 | 0.9364 (6) | 0.0767 (9) | 0.4209 (4) | 0.085 (2) | |
H22A | 0.9076 | 0.0536 | 0.4566 | 0.102* | |
C23 | 0.9163 (6) | 0.0053 (8) | 0.3586 (5) | 0.080 (2) | |
H23A | 0.8730 | −0.0664 | 0.3518 | 0.096* | |
C24 | 0.9594 (5) | 0.0383 (6) | 0.3060 (4) | 0.0645 (18) | |
H24A | 0.9466 | −0.0124 | 0.2645 | 0.077* | |
C25 | 0.9687 (4) | 0.2459 (6) | 0.1696 (3) | 0.0525 (15) | |
C26 | 0.9205 (6) | 0.3636 (6) | 0.1734 (4) | 0.072 (2) | |
H26A | 0.9437 | 0.4129 | 0.2156 | 0.086* | |
C27 | 0.8394 (7) | 0.4069 (8) | 0.1154 (6) | 0.094 (3) | |
H27A | 0.8107 | 0.4875 | 0.1180 | 0.113* | |
C28 | 0.8012 (7) | 0.3369 (11) | 0.0560 (6) | 0.103 (3) | |
H28A | 0.7442 | 0.3662 | 0.0181 | 0.124* | |
C29 | 0.8468 (6) | 0.2191 (8) | 0.0506 (4) | 0.080 (2) | |
H29A | 0.8211 | 0.1698 | 0.0086 | 0.097* | |
C30 | 0.9286 (5) | 0.1761 (6) | 0.1066 (3) | 0.0603 (17) | |
H30A | 0.9584 | 0.0970 | 0.1024 | 0.072* | |
N1 | 0.3157 (5) | 0.3234 (6) | 0.2211 (4) | 0.0863 (19) | |
H1A | 0.2550 | 0.3256 | 0.2304 | 0.104* | |
H1B | 0.3521 | 0.3935 | 0.2421 | 0.104* | |
O1 | 1.1517 (4) | 0.2985 (6) | 0.2719 (3) | 0.0906 (17) | |
O2 | 1.1187 (4) | 0.0698 (5) | 0.2197 (3) | 0.0819 (16) | |
O3 | 0.2211 (4) | 0.9695 (5) | 0.1258 (2) | 0.0838 (15) | |
H3C | 0.1786 | 1.0185 | 0.1369 | 0.101* | |
H3B | 0.2754 | 0.9459 | 0.1595 | 0.101* | |
P1 | 1.07698 (12) | 0.19047 (18) | 0.24445 (9) | 0.0561 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.055 (4) | 0.037 (3) | 0.058 (4) | 0.005 (3) | 0.020 (3) | 0.005 (3) |
C2 | 0.078 (4) | 0.048 (4) | 0.069 (4) | 0.007 (4) | 0.031 (4) | 0.012 (3) |
C3 | 0.124 (7) | 0.070 (5) | 0.056 (5) | 0.011 (5) | 0.033 (5) | 0.011 (4) |
C4 | 0.105 (7) | 0.066 (5) | 0.054 (5) | 0.006 (5) | 0.006 (4) | 0.002 (4) |
C5 | 0.071 (4) | 0.053 (4) | 0.074 (5) | −0.003 (4) | 0.004 (4) | 0.014 (4) |
C6 | 0.062 (4) | 0.045 (4) | 0.060 (4) | −0.004 (3) | 0.016 (3) | 0.009 (3) |
C7 | 0.049 (4) | 0.060 (4) | 0.089 (5) | 0.008 (3) | 0.023 (4) | 0.022 (4) |
C8 | 0.063 (4) | 0.051 (4) | 0.061 (4) | 0.017 (3) | 0.020 (3) | 0.010 (3) |
C9 | 0.086 (5) | 0.069 (5) | 0.083 (5) | 0.011 (4) | 0.044 (4) | 0.003 (4) |
C10 | 0.111 (7) | 0.071 (6) | 0.104 (7) | 0.025 (5) | 0.059 (6) | 0.002 (5) |
C11 | 0.152 (9) | 0.062 (5) | 0.058 (5) | 0.001 (6) | 0.026 (5) | −0.011 (4) |
C12 | 0.093 (5) | 0.041 (4) | 0.075 (5) | −0.002 (4) | 0.014 (4) | 0.002 (3) |
C13 | 0.058 (4) | 0.029 (3) | 0.067 (4) | 0.000 (3) | 0.015 (3) | −0.004 (3) |
C14 | 0.042 (3) | 0.039 (3) | 0.067 (4) | 0.002 (3) | 0.016 (3) | 0.002 (3) |
C15 | 0.052 (4) | 0.049 (4) | 0.098 (5) | 0.001 (3) | 0.019 (3) | 0.000 (4) |
C16 | 0.114 (7) | 0.118 (8) | 0.088 (7) | 0.009 (6) | 0.013 (5) | −0.007 (6) |
C17 | 0.210 (15) | 0.090 (8) | 0.115 (9) | −0.016 (9) | −0.037 (9) | 0.025 (6) |
C18 | 0.116 (9) | 0.124 (10) | 0.194 (13) | −0.039 (8) | 0.034 (9) | 0.009 (9) |
C19 | 0.043 (3) | 0.047 (4) | 0.062 (4) | 0.006 (3) | 0.012 (3) | 0.001 (3) |
C20 | 0.063 (4) | 0.057 (4) | 0.061 (4) | −0.011 (3) | 0.015 (3) | −0.016 (3) |
C21 | 0.084 (5) | 0.097 (6) | 0.052 (4) | 0.005 (5) | 0.019 (4) | −0.007 (4) |
C22 | 0.087 (6) | 0.096 (6) | 0.075 (5) | −0.008 (5) | 0.029 (4) | 0.021 (5) |
C23 | 0.093 (6) | 0.056 (5) | 0.099 (6) | −0.007 (4) | 0.042 (5) | 0.007 (4) |
C24 | 0.064 (4) | 0.051 (4) | 0.082 (5) | −0.003 (3) | 0.029 (4) | −0.007 (3) |
C25 | 0.047 (3) | 0.045 (3) | 0.068 (4) | −0.003 (3) | 0.022 (3) | −0.005 (3) |
C26 | 0.087 (5) | 0.035 (4) | 0.094 (5) | 0.011 (4) | 0.028 (4) | −0.004 (3) |
C27 | 0.096 (6) | 0.061 (5) | 0.119 (7) | 0.039 (5) | 0.024 (5) | 0.013 (5) |
C28 | 0.076 (6) | 0.107 (8) | 0.110 (7) | 0.009 (5) | 0.007 (5) | 0.035 (6) |
C29 | 0.088 (5) | 0.077 (6) | 0.063 (5) | −0.002 (5) | 0.005 (4) | 0.001 (4) |
C30 | 0.067 (4) | 0.050 (4) | 0.060 (4) | 0.006 (3) | 0.014 (3) | −0.002 (3) |
N1 | 0.068 (4) | 0.081 (5) | 0.108 (5) | 0.001 (3) | 0.025 (3) | −0.010 (4) |
O1 | 0.067 (3) | 0.122 (5) | 0.083 (3) | −0.052 (3) | 0.024 (3) | −0.017 (3) |
O2 | 0.084 (3) | 0.088 (4) | 0.082 (3) | 0.054 (3) | 0.038 (3) | 0.017 (3) |
O3 | 0.096 (4) | 0.087 (4) | 0.065 (3) | 0.020 (3) | 0.022 (3) | 0.017 (3) |
P1 | 0.0441 (9) | 0.0655 (12) | 0.0589 (10) | −0.0002 (9) | 0.0169 (7) | −0.0030 (8) |
Geometric parameters (Å, º) top
C1—C14 | 1.404 (8) | C17—H17B | 0.9700 |
C1—C2 | 1.420 (9) | C18—H18A | 0.9600 |
C1—C6 | 1.427 (8) | C18—H18B | 0.9600 |
C2—C3 | 1.380 (10) | C18—H18C | 0.9600 |
C2—H2A | 0.9300 | C19—C20 | 1.373 (9) |
C3—C4 | 1.383 (12) | C19—C24 | 1.404 (9) |
C3—H3A | 0.9300 | C19—P1 | 1.801 (7) |
C4—C5 | 1.315 (11) | C20—C21 | 1.371 (10) |
C4—H4A | 0.9300 | C20—H20A | 0.9300 |
C5—C6 | 1.440 (9) | C21—C22 | 1.378 (10) |
C5—H5A | 0.9300 | C21—H21A | 0.9300 |
C6—C7 | 1.379 (9) | C22—C23 | 1.369 (11) |
C7—C8 | 1.385 (9) | C22—H22A | 0.9300 |
C7—H7A | 0.9300 | C23—C24 | 1.377 (10) |
C8—C13 | 1.409 (9) | C23—H23A | 0.9300 |
C8—C9 | 1.423 (9) | C24—H24A | 0.9300 |
C9—C10 | 1.324 (11) | C25—C30 | 1.373 (8) |
C9—H9A | 0.9300 | C25—C26 | 1.398 (9) |
C10—C11 | 1.361 (13) | C25—P1 | 1.795 (6) |
C10—H10A | 0.9300 | C26—C27 | 1.371 (11) |
C11—C12 | 1.398 (12) | C26—H26A | 0.9300 |
C11—H11A | 0.9300 | C27—C28 | 1.319 (12) |
C12—C13 | 1.453 (9) | C27—H27A | 0.9300 |
C12—H12A | 0.9300 | C28—C29 | 1.389 (12) |
C13—C14 | 1.418 (8) | C28—H28A | 0.9300 |
C14—C15 | 1.487 (8) | C29—C30 | 1.354 (9) |
C15—N1 | 1.575 (9) | C29—H29A | 0.9300 |
C15—H15A | 0.9700 | C30—H30A | 0.9300 |
C15—H15B | 0.9700 | N1—H1A | 0.9000 |
C16—C17 | 1.356 (13) | N1—H1B | 0.9000 |
C16—N1 | 1.512 (10) | O1—P1 | 1.489 (5) |
C16—H16A | 0.9700 | O2—P1 | 1.514 (5) |
C16—H16B | 0.9700 | O3—H3C | 0.8475 |
C17—C18 | 1.347 (17) | O3—H3B | 0.8468 |
C17—H17A | 0.9700 | | |
| | | |
C14—C1—C2 | 123.9 (6) | C16—C17—H17B | 107.8 |
C14—C1—C6 | 119.4 (6) | H17A—C17—H17B | 107.1 |
C2—C1—C6 | 116.6 (6) | C17—C18—H18A | 109.5 |
C3—C2—C1 | 121.5 (7) | C17—C18—H18B | 109.5 |
C3—C2—H2A | 119.2 | H18A—C18—H18B | 109.5 |
C1—C2—H2A | 119.2 | C17—C18—H18C | 109.5 |
C2—C3—C4 | 120.5 (7) | H18A—C18—H18C | 109.5 |
C2—C3—H3A | 119.7 | H18B—C18—H18C | 109.5 |
C4—C3—H3A | 119.7 | C20—C19—C24 | 118.0 (6) |
C5—C4—C3 | 120.5 (7) | C20—C19—P1 | 122.5 (5) |
C5—C4—H4A | 119.7 | C24—C19—P1 | 119.4 (5) |
C3—C4—H4A | 119.7 | C21—C20—C19 | 121.1 (7) |
C4—C5—C6 | 122.1 (7) | C21—C20—H20A | 119.5 |
C4—C5—H5A | 118.9 | C19—C20—H20A | 119.5 |
C6—C5—H5A | 118.9 | C20—C21—C22 | 120.8 (7) |
C7—C6—C1 | 119.4 (6) | C20—C21—H21A | 119.6 |
C7—C6—C5 | 121.9 (6) | C22—C21—H21A | 119.6 |
C1—C6—C5 | 118.7 (6) | C23—C22—C21 | 119.0 (7) |
C6—C7—C8 | 122.6 (6) | C23—C22—H22A | 120.5 |
C6—C7—H7A | 118.7 | C21—C22—H22A | 120.5 |
C8—C7—H7A | 118.7 | C22—C23—C24 | 120.8 (8) |
C7—C8—C13 | 118.4 (6) | C22—C23—H23A | 119.6 |
C7—C8—C9 | 121.0 (7) | C24—C23—H23A | 119.6 |
C13—C8—C9 | 120.6 (6) | C23—C24—C19 | 120.3 (7) |
C10—C9—C8 | 121.2 (8) | C23—C24—H24A | 119.9 |
C10—C9—H9A | 119.4 | C19—C24—H24A | 119.9 |
C8—C9—H9A | 119.4 | C30—C25—C26 | 116.8 (6) |
C9—C10—C11 | 120.2 (8) | C30—C25—P1 | 122.5 (5) |
C9—C10—H10A | 119.9 | C26—C25—P1 | 120.7 (5) |
C11—C10—H10A | 119.9 | C27—C26—C25 | 120.5 (7) |
C10—C11—C12 | 123.0 (8) | C27—C26—H26A | 119.8 |
C10—C11—H11A | 118.5 | C25—C26—H26A | 119.8 |
C12—C11—H11A | 118.5 | C28—C27—C26 | 121.5 (8) |
C11—C12—C13 | 118.1 (8) | C28—C27—H27A | 119.3 |
C11—C12—H12A | 121.0 | C26—C27—H27A | 119.3 |
C13—C12—H12A | 121.0 | C27—C28—C29 | 119.4 (8) |
C8—C13—C14 | 120.9 (5) | C27—C28—H28A | 120.3 |
C8—C13—C12 | 116.8 (6) | C29—C28—H28A | 120.3 |
C14—C13—C12 | 122.4 (6) | C30—C29—C28 | 119.9 (8) |
C1—C14—C13 | 119.2 (5) | C30—C29—H29A | 120.0 |
C1—C14—C15 | 120.6 (6) | C28—C29—H29A | 120.0 |
C13—C14—C15 | 120.2 (6) | C29—C30—C25 | 121.8 (7) |
C14—C15—N1 | 112.4 (5) | C29—C30—H30A | 119.1 |
C14—C15—H15A | 109.1 | C25—C30—H30A | 119.1 |
N1—C15—H15A | 109.1 | C16—N1—C15 | 119.2 (6) |
C14—C15—H15B | 109.1 | C16—N1—H1A | 107.5 |
N1—C15—H15B | 109.1 | C15—N1—H1A | 107.5 |
H15A—C15—H15B | 107.9 | C16—N1—H1B | 107.5 |
C17—C16—N1 | 117.6 (10) | C15—N1—H1B | 107.5 |
C17—C16—H16A | 107.9 | H1A—N1—H1B | 107.0 |
N1—C16—H16A | 107.9 | H3C—O3—H3B | 118.0 |
C17—C16—H16B | 107.9 | O1—P1—O2 | 117.0 (3) |
N1—C16—H16B | 107.9 | O1—P1—C25 | 109.5 (3) |
H16A—C16—H16B | 107.2 | O2—P1—C25 | 107.4 (3) |
C18—C17—C16 | 118.1 (13) | O1—P1—C19 | 108.0 (3) |
C18—C17—H17A | 107.8 | O2—P1—C19 | 109.0 (3) |
C16—C17—H17A | 107.8 | C25—P1—C19 | 105.3 (3) |
C18—C17—H17B | 107.8 | | |
| | | |
C14—C1—C2—C3 | 179.3 (6) | C1—C14—C15—N1 | 91.8 (7) |
C6—C1—C2—C3 | −0.2 (9) | C13—C14—C15—N1 | −88.2 (7) |
C1—C2—C3—C4 | −1.0 (11) | N1—C16—C17—C18 | −80.8 (15) |
C2—C3—C4—C5 | 1.7 (12) | C24—C19—C20—C21 | 0.4 (10) |
C3—C4—C5—C6 | −1.1 (11) | P1—C19—C20—C21 | −179.1 (5) |
C14—C1—C6—C7 | 1.1 (9) | C19—C20—C21—C22 | −1.5 (11) |
C2—C1—C6—C7 | −179.4 (6) | C20—C21—C22—C23 | 1.0 (12) |
C14—C1—C6—C5 | −178.8 (5) | C21—C22—C23—C24 | 0.6 (12) |
C2—C1—C6—C5 | 0.7 (8) | C22—C23—C24—C19 | −1.7 (11) |
C4—C5—C6—C7 | −179.9 (7) | C20—C19—C24—C23 | 1.2 (10) |
C4—C5—C6—C1 | −0.1 (10) | P1—C19—C24—C23 | −179.3 (6) |
C1—C6—C7—C8 | −1.0 (9) | C30—C25—C26—C27 | −2.0 (10) |
C5—C6—C7—C8 | 178.8 (6) | P1—C25—C26—C27 | 178.5 (6) |
C6—C7—C8—C13 | −1.3 (9) | C25—C26—C27—C28 | 3.3 (14) |
C6—C7—C8—C9 | 179.5 (6) | C26—C27—C28—C29 | −2.8 (15) |
C7—C8—C9—C10 | 177.0 (7) | C27—C28—C29—C30 | 1.2 (14) |
C13—C8—C9—C10 | −2.2 (11) | C28—C29—C30—C25 | 0.0 (11) |
C8—C9—C10—C11 | 2.2 (12) | C26—C25—C30—C29 | 0.4 (10) |
C9—C10—C11—C12 | −2.1 (13) | P1—C25—C30—C29 | 179.9 (6) |
C10—C11—C12—C13 | 1.8 (11) | C17—C16—N1—C15 | 179.2 (10) |
C7—C8—C13—C14 | 3.6 (9) | C14—C15—N1—C16 | 79.8 (8) |
C9—C8—C13—C14 | −177.2 (6) | C30—C25—P1—O1 | 135.3 (6) |
C7—C8—C13—C12 | −177.4 (5) | C26—C25—P1—O1 | −45.3 (6) |
C9—C8—C13—C12 | 1.8 (9) | C30—C25—P1—O2 | 7.2 (6) |
C11—C12—C13—C8 | −1.6 (9) | C26—C25—P1—O2 | −173.3 (5) |
C11—C12—C13—C14 | 177.4 (6) | C30—C25—P1—C19 | −108.8 (6) |
C2—C1—C14—C13 | −178.3 (6) | C26—C25—P1—C19 | 70.6 (6) |
C6—C1—C14—C13 | 1.2 (8) | C20—C19—P1—O1 | 7.3 (6) |
C2—C1—C14—C15 | 1.7 (9) | C24—C19—P1—O1 | −172.2 (5) |
C6—C1—C14—C15 | −178.8 (5) | C20—C19—P1—O2 | 135.5 (5) |
C8—C13—C14—C1 | −3.5 (9) | C24—C19—P1—O2 | −44.0 (6) |
C12—C13—C14—C1 | 177.5 (5) | C20—C19—P1—C25 | −109.6 (5) |
C8—C13—C14—C15 | 176.5 (5) | C24—C19—P1—C25 | 70.9 (5) |
C12—C13—C14—C15 | −2.5 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O2i | 0.85 | 2.09 | 2.827 (7) | 145 |
O3—H3B···O1ii | 0.85 | 2.06 | 2.802 (7) | 146 |
N1—H1B···O2ii | 0.90 | 1.96 | 2.826 (8) | 160 |
N1—H1A···O1iii | 0.90 | 1.85 | 2.725 (8) | 163 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1, y, z. |