Buy article online - an online subscription or single-article purchase is required to access this article.
M. Taherzadeh,
M. Pourayoubi,
B. Vahdani Alviri,
S. Shoghpour Bayraq,
M. Ariani,
M. Nečas,
M. Dušek,
V. Eigner,
H. Amiri Rudbari,
G. Bruno,
T. Mancilla Percino,
M. A. Leyva-Ramírez and
K. Damodaran For [C(O)NH](N)
2P(O)-based structures, the magnitude of the differences in the N—H
O, H
O=P and H
O=C angles has been evaluated when the N—H bond lengths, determined by X-ray diffraction, were compared to the neutron normalized values and the maximum percentage difference was obtained,
i.e. about 3% for the angle even if the N—H bond lengths have a difference of about 30% (0.7 Å for the X-ray and 1.03 Å for the neutron-normalized value). The symmetries of the crystals are discussed with respect to the symmetry of the molecules, as well as to the symmetry of hydrogen-bonded motifs, and the role of the most directional hydrogen bond in raising the probability of obtaining centrosymmetric crystal structures is investigated. The work was performed by considering nine new X-ray crystal structures and 204 analogous structures retrieved from the Cambridge Structural Database.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621003371/bm5145sup1.cif Contains datablocks shelx, mt33, mt35, neg_rn24, shelx_1, shelx_2, FK16, global, 8, global_1, 9 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145shelxsup2.hkl Compound 1 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145mt33sup3.hkl Compound 2 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145mt35sup4.hkl Compound 3 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145neg_rn24sup5.hkl Compound 4 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145shelx_1sup6.hkl Compound 5 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145shelx_2sup7.hkl Compound 6 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm5145FK16sup8.hkl Compound 7 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm51458sup9.hkl Compound 8 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621003371/bm51459sup10.hkl Compound 9 |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2052520621003371/bm5145sup11.pdf Figures related to NMR, X-ray and CSD analysis, tables of X-ray and details of spectroscopic measurements |
CCDC references: 1062036; 1033611; 1062033; 851498; 2074592; 1427877; 1062041; 1987638; 1987769
Data collection: COLLECT (Bruker, 2004) for shelx; CrystalClear-SM Expert (Rigaku, 2011) for mt33, mt35; Rigaku CrystalClear-SM Expert (Rigaku, 2014) for neg_rn24, FK16; APEX2 (Bruker, 2008) for shelx_1, shelx_2; CrysAlis PRO (Rigaku OD, 2015) for (8), (9). Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for shelx; CrystalClear-SM Expert (Rigaku, 2011) for mt33, mt35; CrysAlis RED (Oxford Diffraction, 2009) for neg_rn24, FK16; SAINT (Bruker, 2008) for shelx_1, shelx_2; CrysAlis PRO (Rigaku OD, 2015) for (8), (9). Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for shelx; CrystalClear-SM Expert (Rigaku, 2011) for mt33, mt35; CrysAlis RED (Oxford Diffraction, 2009) for neg_rn24, FK16; SAINT (Bruker, 2008) for shelx_1, shelx_2; CrysAlis PRO (Rigaku OD, 2015) for (8), (9). Program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a) for shelx; SHELXT 2014/5 (Sheldrick, 2014) for mt33, mt35; SHELXT2014 (Sheldrick, 2015a) for neg_rn24, FK16; SHELXS97 (Sheldrick, 2008) for shelx_1, shelx_2. Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b for shelx; SHELXL2018/3 (Sheldrick, 2018) for mt33, mt35; SHELXL2018 (Sheldrick, 2015b) for neg_rn24, FK16; SHELXL2016 (Sheldrick, 2015b) for shelx_1, shelx_2.
Crystal data top
C35H33ClN3O2P | F(000) = 2496 |
Mr = 594.06 | Dx = 1.265 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.549 (3) Å | Cell parameters from 600 reflections |
b = 19.601 (4) Å | θ = 1–14° |
c = 19.488 (4) Å | µ = 0.21 mm−1 |
β = 99.21 (3)° | T = 293 K |
V = 6240 (2) Å3 | Block, colourless |
Z = 8 | 0.31 × 0.2 × 0.12 × 0.18 (radius) mm |
Data collection top
Nonius KappaCCD diffractometer | 14247 independent reflections |
Radiation source: Enraf–Nonius FR590 | 8310 reflections with I > 2σ(I) |
Horizonally mounted graphite crystal monochromator | Rint = 0.038 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 4.0° |
CCD rotation images, thick slices scans | h = −21→21 |
Absorption correction: for a sphere [interpolation procedure of Dwiggins (1975) with some modification] | k = 0→25 |
Tmin = 0.861, Tmax = 0.862 | l = −25→25 |
28024 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0747P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
14247 reflections | Δρmax = 0.34 e Å−3 |
765 parameters | Δρmin = −0.30 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C8A | 0.71588 (12) | 0.31258 (10) | 0.53478 (9) | 0.0472 (4) | |
H8D | 0.7413 | 0.2824 | 0.5714 | 0.057* | |
H8C | 0.6666 | 0.3308 | 0.5489 | 0.057* | |
C29 | 0.18607 (13) | 0.55602 (10) | 0.68574 (10) | 0.0527 (5) | |
H29A | 0.1676 | 0.5190 | 0.6541 | 0.063* | |
H29B | 0.2314 | 0.5782 | 0.6688 | 0.063* | |
C29A | 0.70166 (13) | 0.09062 (10) | 0.56404 (10) | 0.0537 (5) | |
H29D | 0.7484 | 0.0775 | 0.5427 | 0.064* | |
H29C | 0.6568 | 0.0602 | 0.5465 | 0.064* | |
C9A | 0.77384 (12) | 0.37110 (10) | 0.52810 (10) | 0.0532 (5) | |
C22A | 0.60890 (12) | 0.18894 (10) | 0.57347 (10) | 0.0497 (5) | |
H22D | 0.5906 | 0.2309 | 0.5496 | 0.060* | |
H22C | 0.6286 | 0.2002 | 0.6217 | 0.060* | |
C2 | −0.00802 (11) | 0.37574 (9) | 0.74407 (9) | 0.0456 (4) | |
C15 | 0.31881 (12) | 0.44505 (11) | 0.66730 (11) | 0.0539 (5) | |
H15B | 0.3255 | 0.4915 | 0.6844 | 0.065* | |
H15A | 0.2965 | 0.4474 | 0.6182 | 0.065* | |
C2A | 0.93834 (11) | 0.14275 (10) | 0.49218 (10) | 0.0483 (4) | |
C23A | 0.53633 (11) | 0.14142 (10) | 0.57046 (10) | 0.0502 (5) | |
C15A | 0.65546 (12) | 0.31197 (11) | 0.40998 (10) | 0.0532 (5) | |
H15D | 0.6511 | 0.2831 | 0.3692 | 0.064* | |
H15C | 0.6911 | 0.3498 | 0.4034 | 0.064* | |
C23 | 0.33275 (12) | 0.60567 (10) | 0.79813 (10) | 0.0510 (5) | |
C7 | −0.02699 (12) | 0.37941 (11) | 0.81021 (10) | 0.0548 (5) | |
H7 | 0.0098 | 0.3995 | 0.8455 | 0.066* | |
C16 | 0.40244 (13) | 0.41228 (11) | 0.67484 (12) | 0.0580 (5) | |
C28A | 0.49816 (14) | 0.11413 (12) | 0.50916 (11) | 0.0627 (6) | |
H28A | 0.5167 | 0.1251 | 0.4679 | 0.075* | |
C1A | 0.86013 (11) | 0.17316 (10) | 0.50658 (10) | 0.0479 (5) | |
C10A | 0.84486 (14) | 0.36265 (13) | 0.50029 (12) | 0.0655 (6) | |
H10A | 0.8570 | 0.3202 | 0.4833 | 0.079* | |
C8 | 0.25349 (15) | 0.33594 (10) | 0.69378 (12) | 0.0650 (6) | |
H8B | 0.2076 | 0.3188 | 0.7140 | 0.078* | |
H8A | 0.3029 | 0.3155 | 0.7190 | 0.078* | |
C7A | 0.94295 (13) | 0.08942 (13) | 0.44750 (13) | 0.0728 (7) | |
H7A | 0.8952 | 0.0703 | 0.4234 | 0.087* | |
C30 | 0.11693 (14) | 0.60702 (11) | 0.68366 (10) | 0.0557 (5) | |
C30A | 0.72307 (13) | 0.08091 (11) | 0.64114 (11) | 0.0570 (5) | |
C16A | 0.57168 (13) | 0.33938 (10) | 0.41614 (10) | 0.0520 (5) | |
C3 | −0.06342 (14) | 0.34507 (13) | 0.69238 (11) | 0.0655 (6) | |
H3 | −0.0518 | 0.3429 | 0.6473 | 0.079* | |
C1 | 0.06886 (12) | 0.40457 (10) | 0.72459 (10) | 0.0474 (4) | |
C6 | −0.10004 (13) | 0.35354 (12) | 0.82472 (12) | 0.0622 (6) | |
H6 | −0.1127 | 0.3566 | 0.8694 | 0.075* | |
C9 | 0.24362 (16) | 0.31347 (11) | 0.61925 (14) | 0.0684 (6) | |
C3A | 1.01022 (13) | 0.16946 (13) | 0.52841 (13) | 0.0668 (6) | |
H3A | 1.0077 | 0.2051 | 0.5595 | 0.080* | |
C26A | 0.40437 (15) | 0.05247 (15) | 0.56723 (14) | 0.0780 (7) | |
H26A | 0.3608 | 0.0223 | 0.5659 | 0.094* | |
C22 | 0.25108 (12) | 0.57631 (10) | 0.80896 (10) | 0.0536 (5) | |
H22A | 0.2578 | 0.5540 | 0.8540 | 0.064* | |
H22B | 0.2125 | 0.6134 | 0.8098 | 0.064* | |
C24 | 0.40113 (15) | 0.56532 (12) | 0.80338 (15) | 0.0788 (7) | |
H24 | 0.3973 | 0.5192 | 0.8136 | 0.095* | |
C14 | 0.29584 (18) | 0.26436 (13) | 0.59996 (17) | 0.0860 (8) | |
H14 | 0.3374 | 0.2464 | 0.6327 | 0.103* | |
C4A | 1.08519 (13) | 0.14418 (14) | 0.51910 (14) | 0.0756 (7) | |
H4A | 1.1331 | 0.1623 | 0.5439 | 0.091* | |
C4 | −0.13528 (15) | 0.31790 (15) | 0.70702 (13) | 0.0808 (8) | |
H4 | −0.1712 | 0.2959 | 0.6725 | 0.097* | |
C35A | 0.78096 (17) | 0.11951 (15) | 0.68099 (13) | 0.0875 (8) | |
H35A | 0.8060 | 0.1550 | 0.6606 | 0.105* | |
C17 | 0.43443 (15) | 0.39733 (14) | 0.61561 (14) | 0.0762 (7) | |
H17 | 0.4028 | 0.4049 | 0.5724 | 0.091* | |
C28 | 0.34093 (15) | 0.67334 (11) | 0.78366 (13) | 0.0679 (6) | |
H28 | 0.2953 | 0.7016 | 0.7798 | 0.081* | |
C25A | 0.44134 (16) | 0.07934 (17) | 0.62848 (14) | 0.0936 (9) | |
H25A | 0.4227 | 0.0678 | 0.6695 | 0.112* | |
C13 | 0.2858 (3) | 0.24221 (18) | 0.5317 (3) | 0.1162 (13) | |
H13 | 0.3202 | 0.2086 | 0.5190 | 0.139* | |
C5 | −0.15362 (13) | 0.32344 (12) | 0.77277 (13) | 0.0660 (6) | |
C31A | 0.6851 (2) | 0.03080 (15) | 0.67355 (14) | 0.0941 (9) | |
H31A | 0.6441 | 0.0049 | 0.6476 | 0.113* | |
C21A | 0.50739 (14) | 0.29525 (13) | 0.41688 (13) | 0.0707 (6) | |
H21A | 0.5161 | 0.2486 | 0.4134 | 0.085* | |
C27A | 0.43249 (15) | 0.07061 (13) | 0.50773 (13) | 0.0752 (7) | |
H27A | 0.4068 | 0.0533 | 0.4654 | 0.090* | |
C21 | 0.44829 (15) | 0.39950 (13) | 0.73891 (14) | 0.0770 (7) | |
H21 | 0.4267 | 0.4078 | 0.7794 | 0.092* | |
C10 | 0.1834 (2) | 0.33972 (14) | 0.56989 (15) | 0.0854 (8) | |
H10 | 0.1482 | 0.3728 | 0.5824 | 0.102* | |
C35 | 0.03744 (15) | 0.58669 (14) | 0.68450 (13) | 0.0740 (7) | |
H35 | 0.0261 | 0.5406 | 0.6889 | 0.089* | |
C26 | 0.48250 (16) | 0.66049 (14) | 0.77989 (15) | 0.0819 (7) | |
H26 | 0.5327 | 0.6790 | 0.7741 | 0.098* | |
C6A | 1.01840 (15) | 0.06382 (16) | 0.43804 (15) | 0.0909 (9) | |
H6A | 1.0215 | 0.0274 | 0.4080 | 0.109* | |
C31 | 0.13168 (18) | 0.67591 (12) | 0.67614 (13) | 0.0767 (7) | |
H31 | 0.1848 | 0.6909 | 0.6751 | 0.092* | |
C24A | 0.50657 (15) | 0.12372 (16) | 0.63023 (13) | 0.0811 (8) | |
H24A | 0.5309 | 0.1420 | 0.6726 | 0.097* | |
C11A | 0.89787 (16) | 0.41635 (16) | 0.49740 (14) | 0.0821 (8) | |
H11A | 0.9457 | 0.4098 | 0.4789 | 0.099* | |
C27 | 0.41510 (17) | 0.70059 (13) | 0.77468 (14) | 0.0787 (7) | |
H27 | 0.4190 | 0.7468 | 0.7650 | 0.094* | |
C20A | 0.43010 (16) | 0.31876 (18) | 0.42267 (15) | 0.0884 (8) | |
H20A | 0.3873 | 0.2880 | 0.4230 | 0.106* | |
C17A | 0.55690 (17) | 0.40854 (13) | 0.42001 (14) | 0.0781 (7) | |
H17A | 0.5991 | 0.4396 | 0.4187 | 0.094* | |
C5A | 1.08855 (13) | 0.09258 (14) | 0.47330 (14) | 0.0746 (7) | |
C19A | 0.4166 (2) | 0.3870 (2) | 0.42795 (15) | 0.0971 (10) | |
H19A | 0.3649 | 0.4030 | 0.4329 | 0.117* | |
C20 | 0.52785 (18) | 0.37390 (16) | 0.74239 (18) | 0.0957 (9) | |
H20 | 0.5599 | 0.3658 | 0.7853 | 0.115* | |
C14A | 0.75768 (19) | 0.43453 (13) | 0.55224 (17) | 0.0945 (9) | |
H14A | 0.7101 | 0.4417 | 0.5709 | 0.113* | |
C34 | −0.02610 (18) | 0.63347 (18) | 0.67893 (15) | 0.0903 (8) | |
H34 | −0.0793 | 0.6187 | 0.6801 | 0.108* | |
C18A | 0.4791 (2) | 0.43157 (17) | 0.42592 (17) | 0.1024 (10) | |
H18A | 0.4695 | 0.4782 | 0.4285 | 0.123* | |
C33 | −0.0106 (2) | 0.70105 (19) | 0.67178 (17) | 0.1023 (10) | |
H33 | −0.0532 | 0.7325 | 0.6680 | 0.123* | |
C25 | 0.47591 (16) | 0.59231 (14) | 0.79373 (17) | 0.0921 (9) | |
H25 | 0.5216 | 0.5642 | 0.7966 | 0.111* | |
C32 | 0.0683 (2) | 0.72282 (15) | 0.67009 (17) | 0.1014 (10) | |
H32 | 0.0789 | 0.7690 | 0.6649 | 0.122* | |
C19 | 0.55862 (19) | 0.36068 (18) | 0.6821 (2) | 0.1073 (11) | |
H19 | 0.6117 | 0.3442 | 0.6846 | 0.129* | |
C11 | 0.1744 (3) | 0.31758 (18) | 0.50143 (17) | 0.1105 (11) | |
H11 | 0.1333 | 0.3357 | 0.4683 | 0.133* | |
C12 | 0.2261 (3) | 0.2690 (2) | 0.4828 (2) | 0.1236 (15) | |
H12 | 0.2205 | 0.2543 | 0.4369 | 0.148* | |
C13A | 0.8113 (3) | 0.48771 (17) | 0.5491 (2) | 0.1357 (15) | |
H13A | 0.7996 | 0.5303 | 0.5662 | 0.163* | |
C32A | 0.7065 (3) | 0.01805 (19) | 0.74384 (17) | 0.1218 (13) | |
H32A | 0.6801 | −0.0161 | 0.7648 | 0.146* | |
C18 | 0.5121 (2) | 0.37146 (18) | 0.61908 (19) | 0.1046 (10) | |
H18 | 0.5327 | 0.3614 | 0.5786 | 0.126* | |
C33A | 0.7663 (2) | 0.0556 (2) | 0.78208 (16) | 0.1205 (13) | |
H33A | 0.7821 | 0.0465 | 0.8291 | 0.145* | |
C34A | 0.8030 (2) | 0.1067 (2) | 0.75114 (15) | 0.1174 (13) | |
H34A | 0.8431 | 0.1332 | 0.7774 | 0.141* | |
C12A | 0.8803 (2) | 0.47926 (18) | 0.52169 (18) | 0.1090 (11) | |
H12A | 0.9157 | 0.5158 | 0.5193 | 0.131* | |
N1 | 0.13580 (9) | 0.40775 (8) | 0.77550 (8) | 0.0466 (4) | |
N2 | 0.21624 (9) | 0.52681 (8) | 0.75515 (8) | 0.0473 (4) | |
N3 | 0.25836 (10) | 0.41065 (8) | 0.70352 (8) | 0.0504 (4) | |
N4 | 0.78991 (10) | 0.15994 (10) | 0.46065 (9) | 0.0487 (4) | |
N5 | 0.69277 (9) | 0.27250 (8) | 0.47123 (7) | 0.0450 (4) | |
N6 | 0.67791 (9) | 0.16099 (8) | 0.54244 (8) | 0.0441 (4) | |
O1 | 0.27626 (8) | 0.43301 (7) | 0.84056 (7) | 0.0541 (3) | |
O3 | 0.64256 (8) | 0.16449 (7) | 0.40313 (7) | 0.0519 (3) | |
O4 | 0.85872 (8) | 0.20950 (8) | 0.55694 (7) | 0.0593 (4) | |
O2 | 0.07036 (9) | 0.42438 (8) | 0.66559 (7) | 0.0648 (4) | |
Cl1 | −0.24555 (4) | 0.29088 (5) | 0.79120 (5) | 0.1142 (3) | |
Cl2 | 1.18305 (4) | 0.06032 (5) | 0.46114 (6) | 0.1322 (4) | |
P1 | 0.22697 (3) | 0.44492 (3) | 0.77143 (2) | 0.04398 (13) | |
P2 | 0.69546 (3) | 0.18890 (3) | 0.46661 (2) | 0.04214 (13) | |
H4AA | 0.7908 (13) | 0.1367 (11) | 0.4321 (11) | 0.049 (7)* | |
H1 | 0.1317 (13) | 0.3879 (11) | 0.8153 (12) | 0.056 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C8A | 0.0500 (11) | 0.0495 (11) | 0.0428 (10) | −0.0025 (9) | 0.0097 (8) | −0.0084 (8) |
C29 | 0.0627 (12) | 0.0518 (11) | 0.0448 (11) | 0.0077 (9) | 0.0124 (9) | 0.0128 (9) |
C29A | 0.0577 (12) | 0.0460 (11) | 0.0574 (12) | 0.0002 (9) | 0.0091 (10) | −0.0049 (9) |
C9A | 0.0537 (12) | 0.0573 (12) | 0.0482 (11) | −0.0090 (10) | 0.0075 (9) | −0.0060 (9) |
C22A | 0.0496 (11) | 0.0536 (11) | 0.0484 (11) | 0.0006 (9) | 0.0152 (9) | −0.0102 (9) |
C2 | 0.0436 (10) | 0.0487 (11) | 0.0419 (10) | 0.0050 (8) | −0.0009 (8) | 0.0019 (8) |
C15 | 0.0554 (12) | 0.0552 (12) | 0.0545 (12) | 0.0030 (10) | 0.0192 (9) | 0.0095 (9) |
C2A | 0.0391 (10) | 0.0573 (12) | 0.0476 (11) | 0.0018 (9) | 0.0044 (8) | 0.0016 (9) |
C23A | 0.0431 (10) | 0.0602 (12) | 0.0491 (11) | 0.0031 (9) | 0.0130 (9) | −0.0032 (9) |
C15A | 0.0563 (12) | 0.0604 (12) | 0.0439 (11) | −0.0063 (10) | 0.0110 (9) | 0.0047 (9) |
C23 | 0.0544 (12) | 0.0478 (11) | 0.0499 (11) | −0.0003 (9) | 0.0057 (9) | −0.0008 (9) |
C7 | 0.0451 (11) | 0.0676 (13) | 0.0496 (12) | −0.0006 (9) | 0.0012 (9) | −0.0044 (10) |
C16 | 0.0542 (12) | 0.0555 (12) | 0.0674 (14) | 0.0034 (10) | 0.0192 (11) | 0.0045 (10) |
C28A | 0.0703 (14) | 0.0696 (14) | 0.0488 (12) | −0.0189 (11) | 0.0118 (10) | −0.0012 (10) |
C1A | 0.0406 (10) | 0.0542 (11) | 0.0481 (11) | −0.0018 (8) | 0.0045 (8) | −0.0041 (9) |
C10A | 0.0651 (14) | 0.0687 (14) | 0.0654 (14) | −0.0115 (11) | 0.0188 (11) | −0.0044 (11) |
C8 | 0.0783 (15) | 0.0458 (12) | 0.0749 (15) | 0.0062 (11) | 0.0248 (12) | 0.0108 (10) |
C7A | 0.0449 (12) | 0.0871 (17) | 0.0814 (16) | 0.0140 (11) | −0.0049 (11) | −0.0285 (13) |
C30 | 0.0657 (14) | 0.0595 (13) | 0.0411 (11) | 0.0144 (10) | 0.0065 (9) | 0.0073 (9) |
C30A | 0.0579 (12) | 0.0562 (12) | 0.0551 (12) | −0.0036 (10) | 0.0035 (10) | 0.0036 (10) |
C16A | 0.0574 (12) | 0.0561 (12) | 0.0413 (10) | 0.0031 (10) | 0.0039 (9) | 0.0066 (9) |
C3 | 0.0626 (14) | 0.0864 (16) | 0.0447 (12) | −0.0110 (12) | −0.0002 (10) | −0.0019 (11) |
C1 | 0.0493 (11) | 0.0503 (11) | 0.0416 (11) | 0.0036 (9) | 0.0046 (8) | 0.0042 (8) |
C6 | 0.0488 (12) | 0.0807 (15) | 0.0578 (13) | 0.0053 (11) | 0.0110 (10) | 0.0018 (11) |
C9 | 0.0852 (17) | 0.0461 (12) | 0.0809 (16) | −0.0078 (12) | 0.0349 (14) | −0.0023 (11) |
C3A | 0.0490 (12) | 0.0761 (15) | 0.0737 (15) | −0.0043 (11) | 0.0053 (11) | −0.0153 (12) |
C26A | 0.0560 (13) | 0.0985 (19) | 0.0811 (18) | −0.0191 (13) | 0.0159 (13) | 0.0044 (14) |
C22 | 0.0608 (12) | 0.0526 (12) | 0.0485 (11) | −0.0002 (9) | 0.0119 (9) | −0.0014 (9) |
C24 | 0.0619 (15) | 0.0541 (14) | 0.119 (2) | −0.0037 (11) | 0.0102 (14) | 0.0083 (13) |
C14 | 0.0925 (18) | 0.0609 (15) | 0.116 (2) | −0.0106 (14) | 0.0522 (17) | −0.0133 (15) |
C4A | 0.0405 (12) | 0.0870 (18) | 0.0968 (19) | −0.0041 (11) | 0.0036 (12) | −0.0063 (15) |
C4 | 0.0619 (15) | 0.110 (2) | 0.0636 (16) | −0.0260 (14) | −0.0116 (12) | 0.0007 (14) |
C35A | 0.0877 (18) | 0.103 (2) | 0.0665 (16) | −0.0392 (16) | −0.0055 (13) | 0.0173 (14) |
C17 | 0.0683 (15) | 0.0912 (18) | 0.0755 (16) | 0.0138 (13) | 0.0305 (13) | 0.0051 (13) |
C28 | 0.0667 (14) | 0.0478 (13) | 0.0863 (17) | −0.0016 (10) | 0.0035 (12) | 0.0001 (11) |
C25A | 0.0662 (16) | 0.153 (3) | 0.0678 (17) | −0.0328 (17) | 0.0296 (13) | 0.0019 (17) |
C13 | 0.138 (3) | 0.082 (2) | 0.151 (4) | −0.033 (2) | 0.089 (3) | −0.049 (2) |
C5 | 0.0400 (11) | 0.0807 (16) | 0.0744 (16) | −0.0044 (10) | 0.0006 (10) | 0.0131 (12) |
C31A | 0.118 (2) | 0.092 (2) | 0.0681 (17) | −0.0460 (18) | 0.0004 (15) | 0.0069 (14) |
C21A | 0.0558 (13) | 0.0694 (15) | 0.0852 (17) | 0.0028 (11) | 0.0061 (12) | 0.0088 (12) |
C27A | 0.0756 (16) | 0.0838 (17) | 0.0637 (15) | −0.0262 (14) | 0.0037 (12) | −0.0007 (12) |
C21 | 0.0729 (16) | 0.0799 (17) | 0.0793 (17) | 0.0210 (13) | 0.0159 (13) | 0.0028 (13) |
C10 | 0.110 (2) | 0.0728 (17) | 0.0756 (18) | 0.0015 (16) | 0.0227 (16) | −0.0102 (14) |
C35 | 0.0721 (16) | 0.0786 (16) | 0.0720 (16) | 0.0177 (13) | 0.0135 (12) | 0.0124 (12) |
C26 | 0.0656 (16) | 0.0826 (18) | 0.097 (2) | −0.0209 (14) | 0.0104 (14) | 0.0059 (15) |
C6A | 0.0616 (15) | 0.104 (2) | 0.103 (2) | 0.0277 (15) | −0.0015 (14) | −0.0391 (17) |
C31 | 0.0893 (18) | 0.0609 (15) | 0.0770 (17) | 0.0147 (13) | 0.0043 (14) | 0.0030 (12) |
C24A | 0.0618 (14) | 0.132 (2) | 0.0533 (14) | −0.0238 (15) | 0.0201 (11) | −0.0130 (14) |
C11A | 0.0699 (16) | 0.106 (2) | 0.0735 (16) | −0.0287 (15) | 0.0202 (13) | 0.0029 (15) |
C27 | 0.0763 (17) | 0.0544 (14) | 0.100 (2) | −0.0155 (13) | −0.0027 (14) | 0.0131 (13) |
C20A | 0.0551 (15) | 0.116 (2) | 0.093 (2) | 0.0063 (15) | 0.0089 (14) | 0.0121 (17) |
C17A | 0.0858 (18) | 0.0613 (15) | 0.0839 (17) | 0.0063 (13) | 0.0035 (14) | 0.0074 (13) |
C5A | 0.0415 (12) | 0.0880 (18) | 0.0935 (18) | 0.0178 (12) | 0.0087 (12) | 0.0041 (15) |
C19A | 0.0743 (19) | 0.138 (3) | 0.0757 (18) | 0.043 (2) | 0.0025 (14) | −0.0022 (18) |
C20 | 0.0826 (19) | 0.097 (2) | 0.102 (2) | 0.0274 (16) | −0.0006 (17) | 0.0104 (17) |
C14A | 0.106 (2) | 0.0611 (16) | 0.129 (2) | −0.0237 (15) | 0.0565 (19) | −0.0312 (16) |
C34 | 0.0737 (17) | 0.113 (2) | 0.0831 (19) | 0.0317 (17) | 0.0075 (14) | 0.0047 (17) |
C18A | 0.115 (3) | 0.082 (2) | 0.104 (2) | 0.042 (2) | −0.004 (2) | −0.0066 (17) |
C33 | 0.100 (2) | 0.103 (3) | 0.097 (2) | 0.051 (2) | −0.0047 (18) | −0.0087 (18) |
C25 | 0.0584 (15) | 0.0738 (18) | 0.142 (3) | −0.0005 (13) | 0.0109 (16) | 0.0006 (17) |
C32 | 0.126 (3) | 0.0657 (17) | 0.105 (2) | 0.0310 (18) | −0.005 (2) | −0.0037 (15) |
C19 | 0.0644 (17) | 0.123 (3) | 0.140 (3) | 0.0310 (17) | 0.034 (2) | 0.006 (2) |
C11 | 0.147 (3) | 0.107 (2) | 0.081 (2) | −0.025 (2) | 0.028 (2) | −0.0246 (18) |
C12 | 0.168 (4) | 0.112 (3) | 0.105 (3) | −0.057 (3) | 0.067 (3) | −0.050 (2) |
C13A | 0.159 (3) | 0.078 (2) | 0.191 (4) | −0.053 (2) | 0.093 (3) | −0.057 (2) |
C32A | 0.165 (3) | 0.118 (3) | 0.077 (2) | −0.058 (2) | 0.005 (2) | 0.0290 (18) |
C18 | 0.084 (2) | 0.131 (3) | 0.107 (2) | 0.0345 (19) | 0.0409 (19) | 0.005 (2) |
C33A | 0.140 (3) | 0.145 (3) | 0.0662 (18) | −0.046 (3) | −0.0142 (19) | 0.0343 (19) |
C34A | 0.118 (3) | 0.156 (3) | 0.0650 (18) | −0.061 (2) | −0.0260 (17) | 0.0213 (19) |
C12A | 0.119 (3) | 0.096 (2) | 0.119 (3) | −0.059 (2) | 0.040 (2) | −0.0231 (19) |
N1 | 0.0426 (9) | 0.0558 (10) | 0.0403 (9) | −0.0039 (7) | 0.0036 (7) | 0.0122 (7) |
N2 | 0.0530 (9) | 0.0487 (9) | 0.0401 (8) | −0.0006 (7) | 0.0074 (7) | 0.0064 (7) |
N3 | 0.0542 (9) | 0.0450 (9) | 0.0548 (10) | 0.0017 (7) | 0.0173 (8) | 0.0081 (7) |
N4 | 0.0384 (9) | 0.0643 (11) | 0.0432 (9) | 0.0034 (8) | 0.0056 (7) | −0.0157 (8) |
N5 | 0.0448 (8) | 0.0505 (9) | 0.0389 (8) | −0.0010 (7) | 0.0045 (7) | −0.0053 (7) |
N6 | 0.0422 (8) | 0.0444 (9) | 0.0466 (9) | −0.0005 (7) | 0.0097 (7) | −0.0067 (7) |
O1 | 0.0469 (7) | 0.0635 (9) | 0.0492 (8) | −0.0069 (6) | −0.0006 (6) | 0.0186 (6) |
O3 | 0.0425 (7) | 0.0647 (8) | 0.0468 (7) | 0.0020 (6) | 0.0013 (6) | −0.0175 (6) |
O4 | 0.0475 (8) | 0.0769 (10) | 0.0522 (8) | −0.0014 (7) | 0.0038 (6) | −0.0217 (7) |
O2 | 0.0620 (9) | 0.0856 (11) | 0.0447 (8) | −0.0020 (8) | 0.0022 (7) | 0.0149 (7) |
Cl1 | 0.0542 (4) | 0.1665 (8) | 0.1189 (6) | −0.0318 (4) | 0.0045 (4) | 0.0299 (6) |
Cl2 | 0.0544 (4) | 0.1423 (8) | 0.2006 (10) | 0.0341 (4) | 0.0226 (5) | −0.0281 (7) |
P1 | 0.0413 (3) | 0.0484 (3) | 0.0422 (3) | −0.0004 (2) | 0.0067 (2) | 0.0112 (2) |
P2 | 0.0354 (2) | 0.0513 (3) | 0.0395 (3) | 0.0001 (2) | 0.00534 (19) | −0.0106 (2) |
Geometric parameters (Å, º) top
C8A—N5 | 1.465 (2) | C4A—C5A | 1.356 (4) |
C8A—C9A | 1.514 (3) | C4A—H4A | 0.9300 |
C8A—H8D | 0.9700 | C4—C5 | 1.368 (3) |
C8A—H8C | 0.9700 | C4—H4 | 0.9300 |
C29—N2 | 1.480 (2) | C35A—C34A | 1.380 (4) |
C29—C30 | 1.515 (3) | C35A—H35A | 0.9300 |
C29—H29A | 0.9700 | C17—C18 | 1.374 (4) |
C29—H29B | 0.9700 | C17—H17 | 0.9300 |
C29A—N6 | 1.477 (2) | C28—C27 | 1.375 (3) |
C29A—C30A | 1.500 (3) | C28—H28 | 0.9300 |
C29A—H29D | 0.9700 | C25A—C24A | 1.383 (4) |
C29A—H29C | 0.9700 | C25A—H25A | 0.9300 |
C9A—C14A | 1.371 (3) | C13—C12 | 1.364 (5) |
C9A—C10A | 1.381 (3) | C13—H13 | 0.9300 |
C22A—N6 | 1.480 (2) | C5—Cl1 | 1.739 (2) |
C22A—C23A | 1.513 (3) | C31A—C32A | 1.382 (4) |
C22A—H22D | 0.9700 | C31A—H31A | 0.9300 |
C22A—H22C | 0.9700 | C21A—C20A | 1.381 (4) |
C2—C7 | 1.376 (3) | C21A—H21A | 0.9300 |
C2—C3 | 1.386 (3) | C27A—H27A | 0.9300 |
C2—C1 | 1.495 (3) | C21—C20 | 1.400 (4) |
C15—N3 | 1.476 (2) | C21—H21 | 0.9300 |
C15—C16 | 1.512 (3) | C10—C11 | 1.388 (4) |
C15—H15B | 0.9700 | C10—H10 | 0.9300 |
C15—H15A | 0.9700 | C35—C34 | 1.386 (3) |
C2A—C7A | 1.370 (3) | C35—H35 | 0.9300 |
C2A—C3A | 1.385 (3) | C26—C27 | 1.355 (4) |
C2A—C1A | 1.492 (3) | C26—C25 | 1.371 (4) |
C23A—C28A | 1.368 (3) | C26—H26 | 0.9300 |
C23A—C24A | 1.380 (3) | C6A—C5A | 1.372 (4) |
C15A—N5 | 1.473 (2) | C6A—H6A | 0.9300 |
C15A—C16A | 1.510 (3) | C31—C32 | 1.386 (4) |
C15A—H15D | 0.9700 | C31—H31 | 0.9300 |
C15A—H15C | 0.9700 | C24A—H24A | 0.9300 |
C23—C28 | 1.367 (3) | C11A—C12A | 1.368 (4) |
C23—C24 | 1.371 (3) | C11A—H11A | 0.9300 |
C23—C22 | 1.515 (3) | C27—H27 | 0.9300 |
C7—C6 | 1.381 (3) | C20A—C19A | 1.363 (4) |
C7—H7 | 0.9300 | C20A—H20A | 0.9300 |
C16—C17 | 1.376 (3) | C17A—C18A | 1.387 (4) |
C16—C21 | 1.376 (3) | C17A—H17A | 0.9300 |
C28A—C27A | 1.378 (3) | C5A—Cl2 | 1.738 (2) |
C28A—H28A | 0.9300 | C19A—C18A | 1.359 (5) |
C1A—O4 | 1.216 (2) | C19A—H19A | 0.9300 |
C1A—N4 | 1.373 (3) | C20—C19 | 1.378 (4) |
C10A—C11A | 1.377 (3) | C20—H20 | 0.9300 |
C10A—H10A | 0.9300 | C14A—C13A | 1.377 (4) |
C8—N3 | 1.477 (3) | C14A—H14A | 0.9300 |
C8—C9 | 1.502 (3) | C34—C33 | 1.360 (5) |
C8—H8B | 0.9700 | C34—H34 | 0.9300 |
C8—H8A | 0.9700 | C18A—H18A | 0.9300 |
C7A—C6A | 1.385 (3) | C33—C32 | 1.379 (5) |
C7A—H7A | 0.9300 | C33—H33 | 0.9300 |
C30—C35 | 1.377 (3) | C25—H25 | 0.9300 |
C30—C31 | 1.384 (3) | C32—H32 | 0.9300 |
C30A—C35A | 1.362 (3) | C19—C18 | 1.357 (5) |
C30A—C31A | 1.373 (3) | C19—H19 | 0.9300 |
C16A—C21A | 1.373 (3) | C11—C12 | 1.367 (5) |
C16A—C17A | 1.382 (3) | C11—H11 | 0.9300 |
C3—C4 | 1.374 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13A—C12A | 1.346 (5) |
C1—O2 | 1.218 (2) | C13A—H13A | 0.9300 |
C1—N1 | 1.365 (2) | C32A—C33A | 1.356 (4) |
C6—C5 | 1.368 (3) | C32A—H32A | 0.9300 |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C9—C10 | 1.369 (4) | C33A—C34A | 1.361 (4) |
C9—C14 | 1.385 (3) | C33A—H33A | 0.9300 |
C3A—C4A | 1.375 (3) | C34A—H34A | 0.9300 |
C3A—H3A | 0.9300 | C12A—H12A | 0.9300 |
C26A—C25A | 1.358 (4) | N1—P1 | 1.6887 (16) |
C26A—C27A | 1.364 (3) | N1—H1 | 0.88 (2) |
C26A—H26A | 0.9300 | N2—P1 | 1.6403 (16) |
C22—N2 | 1.476 (2) | N3—P1 | 1.6408 (17) |
C22—H22A | 0.9700 | N4—P2 | 1.6843 (17) |
C22—H22B | 0.9700 | N4—H4AA | 0.72 (2) |
C24—C25 | 1.386 (4) | N5—P2 | 1.6420 (16) |
C24—H24 | 0.9300 | N6—P2 | 1.6446 (16) |
C14—C13 | 1.384 (5) | O1—P1 | 1.4777 (14) |
C14—H14 | 0.9300 | O3—P2 | 1.4762 (14) |
| | | |
N5—C8A—C9A | 114.63 (15) | C12—C13—C14 | 120.9 (3) |
N5—C8A—H8D | 108.6 | C12—C13—H13 | 119.6 |
C9A—C8A—H8D | 108.6 | C14—C13—H13 | 119.6 |
N5—C8A—H8C | 108.6 | C4—C5—C6 | 120.8 (2) |
C9A—C8A—H8C | 108.6 | C4—C5—Cl1 | 119.80 (19) |
H8D—C8A—H8C | 107.6 | C6—C5—Cl1 | 119.35 (19) |
N2—C29—C30 | 115.00 (16) | C30A—C31A—C32A | 121.5 (3) |
N2—C29—H29A | 108.5 | C30A—C31A—H31A | 119.3 |
C30—C29—H29A | 108.5 | C32A—C31A—H31A | 119.3 |
N2—C29—H29B | 108.5 | C16A—C21A—C20A | 121.3 (2) |
C30—C29—H29B | 108.5 | C16A—C21A—H21A | 119.3 |
H29A—C29—H29B | 107.5 | C20A—C21A—H21A | 119.3 |
N6—C29A—C30A | 114.43 (16) | C26A—C27A—C28A | 121.3 (2) |
N6—C29A—H29D | 108.7 | C26A—C27A—H27A | 119.4 |
C30A—C29A—H29D | 108.7 | C28A—C27A—H27A | 119.4 |
N6—C29A—H29C | 108.7 | C16—C21—C20 | 119.1 (3) |
C30A—C29A—H29C | 108.7 | C16—C21—H21 | 120.4 |
H29D—C29A—H29C | 107.6 | C20—C21—H21 | 120.4 |
C14A—C9A—C10A | 117.9 (2) | C9—C10—C11 | 120.8 (3) |
C14A—C9A—C8A | 119.8 (2) | C9—C10—H10 | 119.6 |
C10A—C9A—C8A | 122.24 (19) | C11—C10—H10 | 119.6 |
N6—C22A—C23A | 114.56 (15) | C30—C35—C34 | 121.4 (3) |
N6—C22A—H22D | 108.6 | C30—C35—H35 | 119.3 |
C23A—C22A—H22D | 108.6 | C34—C35—H35 | 119.3 |
N6—C22A—H22C | 108.6 | C27—C26—C25 | 119.3 (2) |
C23A—C22A—H22C | 108.6 | C27—C26—H26 | 120.3 |
H22D—C22A—H22C | 107.6 | C25—C26—H26 | 120.3 |
C7—C2—C3 | 118.67 (19) | C5A—C6A—C7A | 119.5 (2) |
C7—C2—C1 | 123.28 (17) | C5A—C6A—H6A | 120.2 |
C3—C2—C1 | 118.03 (17) | C7A—C6A—H6A | 120.2 |
N3—C15—C16 | 116.07 (16) | C30—C31—C32 | 120.8 (3) |
N3—C15—H15B | 108.3 | C30—C31—H31 | 119.6 |
C16—C15—H15B | 108.3 | C32—C31—H31 | 119.6 |
N3—C15—H15A | 108.3 | C23A—C24A—C25A | 121.4 (2) |
C16—C15—H15A | 108.3 | C23A—C24A—H24A | 119.3 |
H15B—C15—H15A | 107.4 | C25A—C24A—H24A | 119.3 |
C7A—C2A—C3A | 118.79 (19) | C12A—C11A—C10A | 120.2 (3) |
C7A—C2A—C1A | 124.23 (18) | C12A—C11A—H11A | 119.9 |
C3A—C2A—C1A | 116.95 (18) | C10A—C11A—H11A | 119.9 |
C28A—C23A—C24A | 117.5 (2) | C26—C27—C28 | 120.4 (2) |
C28A—C23A—C22A | 121.82 (18) | C26—C27—H27 | 119.8 |
C24A—C23A—C22A | 120.69 (19) | C28—C27—H27 | 119.8 |
N5—C15A—C16A | 113.20 (15) | C19A—C20A—C21A | 119.9 (3) |
N5—C15A—H15D | 108.9 | C19A—C20A—H20A | 120.0 |
C16A—C15A—H15D | 108.9 | C21A—C20A—H20A | 120.0 |
N5—C15A—H15C | 108.9 | C16A—C17A—C18A | 119.9 (3) |
C16A—C15A—H15C | 108.9 | C16A—C17A—H17A | 120.0 |
H15D—C15A—H15C | 107.8 | C18A—C17A—H17A | 120.0 |
C28—C23—C24 | 117.9 (2) | C4A—C5A—C6A | 121.0 (2) |
C28—C23—C22 | 121.15 (19) | C4A—C5A—Cl2 | 119.59 (19) |
C24—C23—C22 | 120.98 (19) | C6A—C5A—Cl2 | 119.3 (2) |
C2—C7—C6 | 120.72 (19) | C18A—C19A—C20A | 119.6 (3) |
C2—C7—H7 | 119.6 | C18A—C19A—H19A | 120.2 |
C6—C7—H7 | 119.6 | C20A—C19A—H19A | 120.2 |
C17—C16—C21 | 119.5 (2) | C19—C20—C21 | 119.9 (3) |
C17—C16—C15 | 118.6 (2) | C19—C20—H20 | 120.0 |
C21—C16—C15 | 121.9 (2) | C21—C20—H20 | 120.0 |
C23A—C28A—C27A | 120.8 (2) | C9A—C14A—C13A | 120.6 (3) |
C23A—C28A—H28A | 119.6 | C9A—C14A—H14A | 119.7 |
C27A—C28A—H28A | 119.6 | C13A—C14A—H14A | 119.7 |
O4—C1A—N4 | 120.87 (18) | C33—C34—C35 | 119.9 (3) |
O4—C1A—C2A | 121.01 (17) | C33—C34—H34 | 120.0 |
N4—C1A—C2A | 118.11 (17) | C35—C34—H34 | 120.0 |
C11A—C10A—C9A | 120.8 (2) | C19A—C18A—C17A | 121.0 (3) |
C11A—C10A—H10A | 119.6 | C19A—C18A—H18A | 119.5 |
C9A—C10A—H10A | 119.6 | C17A—C18A—H18A | 119.5 |
N3—C8—C9 | 114.23 (17) | C34—C33—C32 | 119.9 (3) |
N3—C8—H8B | 108.7 | C34—C33—H33 | 120.0 |
C9—C8—H8B | 108.7 | C32—C33—H33 | 120.1 |
N3—C8—H8A | 108.7 | C26—C25—C24 | 120.0 (3) |
C9—C8—H8A | 108.7 | C26—C25—H25 | 120.0 |
H8B—C8—H8A | 107.6 | C24—C25—H25 | 120.0 |
C2A—C7A—C6A | 120.3 (2) | C33—C32—C31 | 120.0 (3) |
C2A—C7A—H7A | 119.9 | C33—C32—H32 | 120.0 |
C6A—C7A—H7A | 119.9 | C31—C32—H32 | 120.0 |
C35—C30—C31 | 117.9 (2) | C18—C19—C20 | 120.6 (3) |
C35—C30—C29 | 121.8 (2) | C18—C19—H19 | 119.7 |
C31—C30—C29 | 120.1 (2) | C20—C19—H19 | 119.7 |
C35A—C30A—C31A | 117.8 (2) | C12—C11—C10 | 119.8 (4) |
C35A—C30A—C29A | 122.2 (2) | C12—C11—H11 | 120.1 |
C31A—C30A—C29A | 120.0 (2) | C10—C11—H11 | 120.1 |
C21A—C16A—C17A | 118.2 (2) | C13—C12—C11 | 119.8 (3) |
C21A—C16A—C15A | 119.97 (19) | C13—C12—H12 | 120.1 |
C17A—C16A—C15A | 121.8 (2) | C11—C12—H12 | 120.1 |
C4—C3—C2 | 120.7 (2) | C12A—C13A—C14A | 121.2 (3) |
C4—C3—H3 | 119.6 | C12A—C13A—H13A | 119.4 |
C2—C3—H3 | 119.6 | C14A—C13A—H13A | 119.4 |
O2—C1—N1 | 122.32 (18) | C33A—C32A—C31A | 119.7 (3) |
O2—C1—C2 | 120.47 (17) | C33A—C32A—H32A | 120.2 |
N1—C1—C2 | 117.21 (16) | C31A—C32A—H32A | 120.2 |
C5—C6—C7 | 119.4 (2) | C19—C18—C17 | 119.5 (3) |
C5—C6—H6 | 120.3 | C19—C18—H18 | 120.2 |
C7—C6—H6 | 120.3 | C17—C18—H18 | 120.2 |
C10—C9—C14 | 119.1 (3) | C32A—C33A—C34A | 119.6 (3) |
C10—C9—C8 | 121.6 (2) | C32A—C33A—H33A | 120.2 |
C14—C9—C8 | 119.4 (3) | C34A—C33A—H33A | 120.2 |
C4A—C3A—C2A | 121.1 (2) | C33A—C34A—C35A | 120.4 (3) |
C4A—C3A—H3A | 119.5 | C33A—C34A—H34A | 119.8 |
C2A—C3A—H3A | 119.5 | C35A—C34A—H34A | 119.8 |
C25A—C26A—C27A | 118.6 (2) | C13A—C12A—C11A | 119.2 (3) |
C25A—C26A—H26A | 120.7 | C13A—C12A—H12A | 120.4 |
C27A—C26A—H26A | 120.7 | C11A—C12A—H12A | 120.4 |
N2—C22—C23 | 113.98 (16) | C1—N1—P1 | 127.80 (14) |
N2—C22—H22A | 108.8 | C1—N1—H1 | 116.9 (14) |
C23—C22—H22A | 108.8 | P1—N1—H1 | 115.4 (14) |
N2—C22—H22B | 108.8 | C22—N2—C29 | 115.55 (16) |
C23—C22—H22B | 108.8 | C22—N2—P1 | 119.19 (12) |
H22A—C22—H22B | 107.7 | C29—N2—P1 | 124.43 (13) |
C23—C24—C25 | 120.9 (2) | C15—N3—C8 | 114.74 (16) |
C23—C24—H24 | 119.5 | C15—N3—P1 | 121.66 (14) |
C25—C24—H24 | 119.5 | C8—N3—P1 | 119.45 (13) |
C13—C14—C9 | 119.7 (3) | C1A—N4—P2 | 126.10 (15) |
C13—C14—H14 | 120.2 | C1A—N4—H4AA | 120.1 (17) |
C9—C14—H14 | 120.2 | P2—N4—H4AA | 113.6 (17) |
C5A—C4A—C3A | 119.3 (2) | C8A—N5—C15A | 114.99 (15) |
C5A—C4A—H4A | 120.4 | C8A—N5—P2 | 125.16 (12) |
C3A—C4A—H4A | 120.4 | C15A—N5—P2 | 119.42 (12) |
C5—C4—C3 | 119.5 (2) | C29A—N6—C22A | 114.62 (15) |
C5—C4—H4 | 120.2 | C29A—N6—P2 | 119.32 (12) |
C3—C4—H4 | 120.2 | C22A—N6—P2 | 120.18 (13) |
C30A—C35A—C34A | 120.9 (2) | O1—P1—N2 | 110.96 (8) |
C30A—C35A—H35A | 119.5 | O1—P1—N3 | 118.09 (9) |
C34A—C35A—H35A | 119.5 | N2—P1—N3 | 106.45 (8) |
C18—C17—C16 | 121.3 (3) | O1—P1—N1 | 104.83 (8) |
C18—C17—H17 | 119.3 | N2—P1—N1 | 111.18 (8) |
C16—C17—H17 | 119.3 | N3—P1—N1 | 105.18 (9) |
C23—C28—C27 | 121.5 (2) | O3—P2—N5 | 110.59 (8) |
C23—C28—H28 | 119.2 | O3—P2—N6 | 118.62 (8) |
C27—C28—H28 | 119.2 | N5—P2—N6 | 105.81 (7) |
C26A—C25A—C24A | 120.4 (2) | O3—P2—N4 | 105.39 (8) |
C26A—C25A—H25A | 119.8 | N5—P2—N4 | 111.95 (9) |
C24A—C25A—H25A | 119.8 | N6—P2—N4 | 104.43 (9) |
| | | |
N5—C8A—C9A—C14A | 132.3 (2) | C3A—C4A—C5A—C6A | −2.2 (4) |
N5—C8A—C9A—C10A | −49.9 (3) | C3A—C4A—C5A—Cl2 | 180.0 (2) |
N6—C22A—C23A—C28A | −55.1 (3) | C7A—C6A—C5A—C4A | 2.3 (5) |
N6—C22A—C23A—C24A | 124.5 (2) | C7A—C6A—C5A—Cl2 | −179.9 (2) |
C3—C2—C7—C6 | −0.5 (3) | C21A—C20A—C19A—C18A | 1.4 (4) |
C1—C2—C7—C6 | 178.16 (19) | C16—C21—C20—C19 | −1.2 (5) |
N3—C15—C16—C17 | 127.0 (2) | C10A—C9A—C14A—C13A | −0.5 (5) |
N3—C15—C16—C21 | −55.5 (3) | C8A—C9A—C14A—C13A | 177.5 (3) |
C24A—C23A—C28A—C27A | 0.0 (4) | C30—C35—C34—C33 | 0.6 (4) |
C22A—C23A—C28A—C27A | 179.6 (2) | C20A—C19A—C18A—C17A | −1.4 (5) |
C7A—C2A—C1A—O4 | 163.7 (2) | C16A—C17A—C18A—C19A | 0.0 (4) |
C3A—C2A—C1A—O4 | −14.2 (3) | C35—C34—C33—C32 | 0.0 (5) |
C7A—C2A—C1A—N4 | −17.4 (3) | C27—C26—C25—C24 | −1.1 (5) |
C3A—C2A—C1A—N4 | 164.6 (2) | C23—C24—C25—C26 | 1.1 (5) |
C14A—C9A—C10A—C11A | 0.4 (4) | C34—C33—C32—C31 | −0.4 (5) |
C8A—C9A—C10A—C11A | −177.5 (2) | C30—C31—C32—C33 | 0.2 (4) |
C3A—C2A—C7A—C6A | −1.2 (4) | C21—C20—C19—C18 | −0.8 (5) |
C1A—C2A—C7A—C6A | −179.1 (2) | C9—C10—C11—C12 | 0.0 (5) |
N2—C29—C30—C35 | −77.8 (3) | C14—C13—C12—C11 | −1.1 (5) |
N2—C29—C30—C31 | 106.5 (2) | C10—C11—C12—C13 | 0.5 (5) |
N6—C29A—C30A—C35A | −54.7 (3) | C9A—C14A—C13A—C12A | 0.7 (6) |
N6—C29A—C30A—C31A | 126.8 (2) | C30A—C31A—C32A—C33A | 0.0 (6) |
N5—C15A—C16A—C21A | −67.0 (2) | C20—C19—C18—C17 | 1.6 (6) |
N5—C15A—C16A—C17A | 114.1 (2) | C16—C17—C18—C19 | −0.3 (5) |
C7—C2—C3—C4 | −1.0 (3) | C31A—C32A—C33A—C34A | 1.8 (7) |
C1—C2—C3—C4 | −179.7 (2) | C32A—C33A—C34A—C35A | −1.4 (7) |
C7—C2—C1—O2 | −151.2 (2) | C30A—C35A—C34A—C33A | −0.8 (6) |
C3—C2—C1—O2 | 27.5 (3) | C14A—C13A—C12A—C11A | −0.8 (7) |
C7—C2—C1—N1 | 28.5 (3) | C10A—C11A—C12A—C13A | 0.8 (5) |
C3—C2—C1—N1 | −152.86 (19) | O2—C1—N1—P1 | 6.7 (3) |
C2—C7—C6—C5 | 0.6 (3) | C2—C1—N1—P1 | −172.95 (14) |
N3—C8—C9—C10 | −52.0 (3) | C23—C22—N2—C29 | −70.8 (2) |
N3—C8—C9—C14 | 128.9 (2) | C23—C22—N2—P1 | 99.31 (17) |
C7A—C2A—C3A—C4A | 1.2 (4) | C30—C29—N2—C22 | −61.6 (2) |
C1A—C2A—C3A—C4A | 179.3 (2) | C30—C29—N2—P1 | 128.95 (17) |
C28—C23—C22—N2 | 114.2 (2) | C16—C15—N3—C8 | −46.4 (3) |
C24—C23—C22—N2 | −66.6 (3) | C16—C15—N3—P1 | 110.52 (19) |
C28—C23—C24—C25 | −0.5 (4) | C9—C8—N3—C15 | −50.8 (3) |
C22—C23—C24—C25 | −179.7 (2) | C9—C8—N3—P1 | 151.68 (17) |
C10—C9—C14—C13 | −0.7 (4) | O4—C1A—N4—P2 | −1.1 (3) |
C8—C9—C14—C13 | 178.4 (2) | C2A—C1A—N4—P2 | −179.93 (15) |
C2A—C3A—C4A—C5A | 0.5 (4) | C9A—C8A—N5—C15A | −56.5 (2) |
C2—C3—C4—C5 | 2.4 (4) | C9A—C8A—N5—P2 | 131.06 (16) |
C31A—C30A—C35A—C34A | 2.6 (5) | C16A—C15A—N5—C8A | −68.5 (2) |
C29A—C30A—C35A—C34A | −176.0 (3) | C16A—C15A—N5—P2 | 104.42 (17) |
C21—C16—C17—C18 | −1.7 (4) | C30A—C29A—N6—C22A | −56.2 (2) |
C15—C16—C17—C18 | 175.9 (3) | C30A—C29A—N6—P2 | 150.74 (14) |
C24—C23—C28—C27 | −0.1 (4) | C23A—C22A—N6—C29A | −47.0 (2) |
C22—C23—C28—C27 | 179.1 (2) | C23A—C22A—N6—P2 | 105.80 (17) |
C27A—C26A—C25A—C24A | −0.5 (5) | C22—N2—P1—O1 | −2.79 (16) |
C9—C14—C13—C12 | 1.2 (5) | C29—N2—P1—O1 | 166.34 (14) |
C3—C4—C5—C6 | −2.3 (4) | C22—N2—P1—N3 | −132.50 (14) |
C3—C4—C5—Cl1 | 178.5 (2) | C29—N2—P1—N3 | 36.63 (17) |
C7—C6—C5—C4 | 0.8 (4) | C22—N2—P1—N1 | 113.47 (15) |
C7—C6—C5—Cl1 | 179.98 (18) | C29—N2—P1—N1 | −77.40 (16) |
C35A—C30A—C31A—C32A | −2.2 (5) | C15—N3—P1—O1 | −85.69 (16) |
C29A—C30A—C31A—C32A | 176.5 (3) | C8—N3—P1—O1 | 70.21 (17) |
C17A—C16A—C21A—C20A | −1.2 (4) | C15—N3—P1—N2 | 39.79 (17) |
C15A—C16A—C21A—C20A | 179.8 (2) | C8—N3—P1—N2 | −164.31 (15) |
C25A—C26A—C27A—C28A | 1.4 (4) | C15—N3—P1—N1 | 157.86 (14) |
C23A—C28A—C27A—C26A | −1.1 (4) | C8—N3—P1—N1 | −46.25 (17) |
C17—C16—C21—C20 | 2.4 (4) | C1—N1—P1—O1 | −179.94 (16) |
C15—C16—C21—C20 | −175.1 (2) | C1—N1—P1—N2 | 60.09 (19) |
C14—C9—C10—C11 | 0.1 (4) | C1—N1—P1—N3 | −54.73 (18) |
C8—C9—C10—C11 | −179.0 (3) | C8A—N5—P2—O3 | 160.06 (14) |
C31—C30—C35—C34 | −0.8 (3) | C15A—N5—P2—O3 | −12.06 (16) |
C29—C30—C35—C34 | −176.6 (2) | C8A—N5—P2—N6 | 30.41 (16) |
C2A—C7A—C6A—C5A | −0.5 (5) | C15A—N5—P2—N6 | −141.71 (13) |
C35—C30—C31—C32 | 0.4 (4) | C8A—N5—P2—N4 | −82.75 (16) |
C29—C30—C31—C32 | 176.2 (2) | C15A—N5—P2—N4 | 105.13 (15) |
C28A—C23A—C24A—C25A | 0.9 (4) | C29A—N6—P2—O3 | 74.61 (16) |
C22A—C23A—C24A—C25A | −178.7 (3) | C22A—N6—P2—O3 | −76.96 (15) |
C26A—C25A—C24A—C23A | −0.6 (5) | C29A—N6—P2—N5 | −160.58 (14) |
C9A—C10A—C11A—C12A | −0.6 (4) | C22A—N6—P2—N5 | 47.85 (15) |
C25—C26—C27—C28 | 0.5 (4) | C29A—N6—P2—N4 | −42.29 (16) |
C23—C28—C27—C26 | 0.1 (4) | C22A—N6—P2—N4 | 166.14 (14) |
C16A—C21A—C20A—C19A | −0.1 (4) | C1A—N4—P2—O3 | 176.50 (17) |
C21A—C16A—C17A—C18A | 1.3 (4) | C1A—N4—P2—N5 | 56.2 (2) |
C15A—C16A—C17A—C18A | −179.7 (2) | C1A—N4—P2—N6 | −57.79 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4AA···O1i | 0.72 (2) | 2.23 (2) | 2.946 (2) | 173 (2) |
N1—H1···O3ii | 0.88 (2) | 1.98 (2) | 2.849 (2) | 169.2 (19) |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2. |
Crystal data top
C21H21ClN3O2P | Z = 2 |
Mr = 413.83 | F(000) = 432 |
Triclinic, P1 | Dx = 1.365 Mg m−3 |
a = 9.9374 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6061 (4) Å | Cell parameters from 6749 reflections |
c = 11.1456 (5) Å | θ = 3.6–33.1° |
α = 80.535 (8)° | µ = 0.29 mm−1 |
β = 71.317 (6)° | T = 120 K |
γ = 64.902 (7)° | Block, colourless |
V = 1007.19 (9) Å3 | 0.30 × 0.20 × 0.20 mm |
Data collection top
AFC11 (Right) Eulerian three-circle CCD diffractometer | 3265 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.025 |
Profile data from ω–scans | θmax = 25.0°, θmin = 3.6° |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011) | h = −11→11 |
Tmin = 0.926, Tmax = 1.000 | k = −12→12 |
11548 measured reflections | l = −13→13 |
3513 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.404P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3513 reflections | Δρmax = 0.31 e Å−3 |
265 parameters | Δρmin = −0.30 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.62186 (5) | 0.24734 (4) | −0.67827 (3) | 0.03166 (13) | |
P1 | 0.24093 (4) | 0.52240 (4) | 0.08089 (3) | 0.01687 (12) | |
O1 | 0.34838 (11) | 0.53956 (11) | 0.13608 (9) | 0.0230 (2) | |
O2 | 0.14696 (11) | 0.45219 (11) | −0.10775 (10) | 0.0225 (2) | |
N1 | 0.34734 (14) | 0.46764 (12) | −0.06920 (11) | 0.0170 (3) | |
N2 | 0.08496 (14) | 0.66036 (13) | 0.07250 (11) | 0.0188 (3) | |
N3 | 0.16741 (14) | 0.41169 (13) | 0.15948 (12) | 0.0208 (3) | |
C1 | 0.28385 (16) | 0.43727 (14) | −0.14610 (13) | 0.0176 (3) | |
C2 | 0.37842 (16) | 0.38531 (14) | −0.27589 (13) | 0.0185 (3) | |
C3 | 0.53162 (17) | 0.37032 (16) | −0.33052 (14) | 0.0220 (3) | |
H3B | 0.584102 | 0.390478 | −0.283281 | 0.026* | |
C4 | 0.60745 (17) | 0.32597 (17) | −0.45390 (15) | 0.0252 (3) | |
H4A | 0.711812 | 0.315523 | −0.491374 | 0.030* | |
C5 | 0.53000 (18) | 0.29725 (16) | −0.52147 (14) | 0.0225 (3) | |
C6 | 0.37917 (19) | 0.30842 (18) | −0.46844 (15) | 0.0286 (4) | |
H6A | 0.328055 | 0.286069 | −0.515475 | 0.034* | |
C7 | 0.30454 (18) | 0.35267 (17) | −0.34586 (15) | 0.0261 (3) | |
H7A | 0.200860 | 0.361027 | −0.308514 | 0.031* | |
C8 | 0.09056 (17) | 0.76842 (15) | −0.02733 (15) | 0.0238 (3) | |
H8A | 0.139251 | 0.724887 | −0.111006 | 0.029* | |
H8B | 0.155463 | 0.813041 | −0.016710 | 0.029* | |
C9 | −0.06916 (17) | 0.87825 (15) | −0.02379 (15) | 0.0218 (3) | |
C10 | −0.09659 (19) | 0.95085 (16) | −0.13504 (16) | 0.0283 (4) | |
H10A | −0.015623 | 0.929286 | −0.212056 | 0.034* | |
C11 | −0.2408 (2) | 1.05448 (18) | −0.13511 (17) | 0.0337 (4) | |
H11A | −0.257259 | 1.104485 | −0.211627 | 0.040* | |
C12 | −0.36022 (19) | 1.08512 (17) | −0.02457 (18) | 0.0333 (4) | |
H12A | −0.459352 | 1.155094 | −0.024915 | 0.040* | |
C13 | −0.33475 (19) | 1.01319 (17) | 0.08707 (17) | 0.0324 (4) | |
H13A | −0.416736 | 1.033845 | 0.163482 | 0.039* | |
C14 | −0.19006 (18) | 0.91121 (16) | 0.08767 (15) | 0.0268 (3) | |
H14A | −0.173218 | 0.863343 | 0.164859 | 0.032* | |
C15 | 0.25718 (17) | 0.27922 (15) | 0.21248 (14) | 0.0235 (3) | |
H15A | 0.355232 | 0.281038 | 0.214446 | 0.028* | |
H15B | 0.283661 | 0.203726 | 0.156486 | 0.028* | |
C16 | 0.17195 (18) | 0.24700 (16) | 0.34517 (14) | 0.0228 (3) | |
C17 | 0.2272 (2) | 0.11334 (18) | 0.39782 (17) | 0.0381 (4) | |
H17A | 0.313735 | 0.041597 | 0.348258 | 0.046* | |
C18 | 0.1575 (3) | 0.0834 (2) | 0.52181 (19) | 0.0494 (5) | |
H18A | 0.196262 | −0.008763 | 0.556125 | 0.059* | |
C19 | 0.0328 (2) | 0.1858 (2) | 0.59575 (17) | 0.0403 (5) | |
H19A | −0.012950 | 0.165244 | 0.681365 | 0.048* | |
C20 | −0.0246 (2) | 0.31771 (19) | 0.54445 (16) | 0.0334 (4) | |
H20A | −0.111512 | 0.388892 | 0.594331 | 0.040* | |
C21 | 0.04419 (18) | 0.34765 (17) | 0.41952 (15) | 0.0278 (4) | |
H21A | 0.002378 | 0.439152 | 0.384698 | 0.033* | |
H2N | 0.008 (2) | 0.6383 (18) | 0.0820 (17) | 0.027 (5)* | |
H1N | 0.448 (2) | 0.4593 (18) | −0.0947 (17) | 0.028 (5)* | |
H3N | 0.093 (2) | 0.415 (2) | 0.1378 (18) | 0.035 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0312 (2) | 0.0424 (3) | 0.0171 (2) | −0.01097 (19) | −0.00264 (16) | −0.00847 (16) |
P1 | 0.0137 (2) | 0.0232 (2) | 0.0141 (2) | −0.00793 (16) | −0.00304 (15) | −0.00173 (14) |
O1 | 0.0168 (5) | 0.0357 (6) | 0.0193 (5) | −0.0126 (5) | −0.0036 (4) | −0.0049 (4) |
O2 | 0.0146 (5) | 0.0325 (6) | 0.0221 (5) | −0.0106 (4) | −0.0030 (4) | −0.0055 (4) |
N1 | 0.0117 (6) | 0.0231 (6) | 0.0152 (6) | −0.0069 (5) | −0.0016 (5) | −0.0026 (5) |
N2 | 0.0151 (6) | 0.0228 (6) | 0.0187 (6) | −0.0090 (5) | −0.0025 (5) | −0.0013 (5) |
N3 | 0.0157 (6) | 0.0282 (7) | 0.0213 (7) | −0.0108 (5) | −0.0083 (5) | 0.0042 (5) |
C1 | 0.0155 (7) | 0.0189 (7) | 0.0188 (7) | −0.0072 (6) | −0.0055 (6) | 0.0008 (5) |
C2 | 0.0175 (7) | 0.0192 (7) | 0.0176 (7) | −0.0062 (6) | −0.0051 (6) | −0.0004 (6) |
C3 | 0.0186 (7) | 0.0290 (8) | 0.0202 (8) | −0.0093 (6) | −0.0062 (6) | −0.0043 (6) |
C4 | 0.0177 (7) | 0.0344 (9) | 0.0218 (8) | −0.0103 (7) | −0.0019 (6) | −0.0047 (6) |
C5 | 0.0228 (8) | 0.0252 (8) | 0.0158 (7) | −0.0066 (6) | −0.0031 (6) | −0.0040 (6) |
C6 | 0.0265 (8) | 0.0413 (9) | 0.0233 (8) | −0.0152 (7) | −0.0081 (7) | −0.0075 (7) |
C7 | 0.0200 (8) | 0.0371 (9) | 0.0242 (8) | −0.0138 (7) | −0.0046 (6) | −0.0049 (7) |
C8 | 0.0196 (7) | 0.0226 (7) | 0.0258 (8) | −0.0090 (6) | −0.0021 (6) | 0.0014 (6) |
C9 | 0.0211 (7) | 0.0194 (7) | 0.0261 (8) | −0.0097 (6) | −0.0056 (6) | −0.0018 (6) |
C10 | 0.0278 (8) | 0.0274 (8) | 0.0282 (9) | −0.0116 (7) | −0.0057 (7) | 0.0006 (7) |
C11 | 0.0355 (9) | 0.0304 (9) | 0.0370 (10) | −0.0123 (8) | −0.0173 (8) | 0.0063 (7) |
C12 | 0.0221 (8) | 0.0265 (8) | 0.0497 (11) | −0.0061 (7) | −0.0135 (8) | −0.0002 (7) |
C13 | 0.0217 (8) | 0.0300 (9) | 0.0385 (10) | −0.0074 (7) | −0.0015 (7) | −0.0044 (7) |
C14 | 0.0231 (8) | 0.0266 (8) | 0.0269 (8) | −0.0081 (7) | −0.0048 (7) | −0.0001 (6) |
C15 | 0.0197 (7) | 0.0229 (8) | 0.0256 (8) | −0.0067 (6) | −0.0061 (6) | −0.0005 (6) |
C16 | 0.0263 (8) | 0.0250 (8) | 0.0230 (8) | −0.0134 (7) | −0.0122 (7) | 0.0033 (6) |
C17 | 0.0504 (11) | 0.0254 (9) | 0.0348 (10) | −0.0112 (8) | −0.0148 (9) | 0.0033 (7) |
C18 | 0.0754 (15) | 0.0342 (10) | 0.0382 (11) | −0.0234 (10) | −0.0222 (11) | 0.0172 (9) |
C19 | 0.0570 (12) | 0.0518 (11) | 0.0246 (9) | −0.0362 (10) | −0.0138 (9) | 0.0121 (8) |
C20 | 0.0305 (9) | 0.0463 (10) | 0.0262 (9) | −0.0211 (8) | −0.0044 (7) | 0.0006 (7) |
C21 | 0.0265 (8) | 0.0304 (8) | 0.0253 (8) | −0.0127 (7) | −0.0069 (7) | 0.0052 (7) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.7435 (15) | C6—C7 | 1.380 (2) |
P1—O1 | 1.4745 (10) | C8—C9 | 1.511 (2) |
P1—N3 | 1.6307 (13) | C9—C10 | 1.389 (2) |
P1—N2 | 1.6358 (12) | C9—C14 | 1.393 (2) |
P1—N1 | 1.7085 (12) | C10—C11 | 1.388 (2) |
O2—C1 | 1.2350 (17) | C11—C12 | 1.378 (3) |
N1—C1 | 1.3587 (18) | C12—C13 | 1.386 (3) |
N2—C8 | 1.4662 (19) | C13—C14 | 1.386 (2) |
N3—C15 | 1.4561 (19) | C15—C16 | 1.516 (2) |
C1—C2 | 1.494 (2) | C16—C21 | 1.380 (2) |
C2—C7 | 1.392 (2) | C16—C17 | 1.389 (2) |
C2—C3 | 1.395 (2) | C17—C18 | 1.385 (3) |
C3—C4 | 1.389 (2) | C18—C19 | 1.375 (3) |
C4—C5 | 1.378 (2) | C19—C20 | 1.371 (3) |
C5—C6 | 1.384 (2) | C20—C21 | 1.391 (2) |
| | | |
O1—P1—N3 | 114.06 (6) | C7—C6—C5 | 118.63 (14) |
O1—P1—N2 | 117.01 (6) | C6—C7—C2 | 121.19 (14) |
N3—P1—N2 | 101.53 (6) | N2—C8—C9 | 111.70 (12) |
O1—P1—N1 | 105.18 (6) | C10—C9—C14 | 118.46 (14) |
N3—P1—N1 | 110.49 (6) | C10—C9—C8 | 119.13 (14) |
N2—P1—N1 | 108.55 (6) | C14—C9—C8 | 122.40 (14) |
C1—N1—P1 | 120.63 (10) | C11—C10—C9 | 120.83 (15) |
C8—N2—P1 | 121.16 (10) | C12—C11—C10 | 120.25 (16) |
C15—N3—P1 | 123.26 (10) | C11—C12—C13 | 119.56 (15) |
O2—C1—N1 | 119.52 (13) | C12—C13—C14 | 120.24 (16) |
O2—C1—C2 | 119.92 (13) | C13—C14—C9 | 120.64 (15) |
N1—C1—C2 | 120.56 (12) | N3—C15—C16 | 112.96 (12) |
C7—C2—C3 | 119.08 (14) | C21—C16—C17 | 117.84 (15) |
C7—C2—C1 | 116.28 (13) | C21—C16—C15 | 122.47 (14) |
C3—C2—C1 | 124.63 (13) | C17—C16—C15 | 119.61 (15) |
C4—C3—C2 | 120.05 (14) | C18—C17—C16 | 120.74 (18) |
C5—C4—C3 | 119.41 (14) | C19—C18—C17 | 120.70 (17) |
C4—C5—C6 | 121.60 (14) | C20—C19—C18 | 119.22 (17) |
C4—C5—Cl1 | 119.79 (12) | C19—C20—C21 | 120.17 (17) |
C6—C5—Cl1 | 118.60 (12) | C16—C21—C20 | 121.30 (16) |
Crystal data top
C21H21ClN3O2P | Z = 2 |
Mr = 413.83 | F(000) = 432 |
Triclinic, P1 | Dx = 1.316 Mg m−3 |
a = 9.9066 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1918 (6) Å | Cell parameters from 6367 reflections |
c = 11.4789 (9) Å | θ = 3.6–32.8° |
α = 86.167 (9)° | µ = 0.28 mm−1 |
β = 79.288 (8)° | T = 120 K |
γ = 66.505 (7)° | Block, colourless |
V = 1044.34 (12) Å3 | 0.25 × 0.15 × 0.10 mm |
Data collection top
AFC11 (Right) Eulerian three-circle CCD diffractometer | 3260 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.030 |
Profile data from ω–scans | θmax = 25.0°, θmin = 3.6° |
Absorption correction: multi-scan CrystalClear-SM Expert; Rigaku, 2011 | h = −10→11 |
Tmin = 0.885, Tmax = 1.000 | k = −12→11 |
11660 measured reflections | l = −13→13 |
3641 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.184P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
3641 reflections | Δρmax = 0.29 e Å−3 |
267 parameters | Δρmin = −0.32 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.66610 (4) | −0.74765 (4) | −0.28418 (4) | 0.03601 (14) | |
P1 | 0.24796 (4) | 0.08282 (4) | 0.01997 (3) | 0.02458 (13) | |
O1 | 0.34878 (11) | 0.15546 (11) | 0.02491 (10) | 0.0292 (3) | |
O2 | 0.15878 (11) | −0.15687 (12) | 0.00005 (10) | 0.0328 (3) | |
N1 | 0.35139 (15) | −0.08839 (13) | −0.02064 (11) | 0.0249 (3) | |
N2 | 0.14124 (15) | 0.07418 (15) | 0.14487 (12) | 0.0296 (3) | |
N3 | 0.13257 (15) | 0.15560 (14) | −0.07339 (12) | 0.0285 (3) | |
C1 | 0.29233 (16) | −0.18537 (16) | −0.03589 (13) | 0.0244 (3) | |
C2 | 0.39173 (16) | −0.32407 (15) | −0.09707 (13) | 0.0232 (3) | |
C3 | 0.53308 (17) | −0.34900 (17) | −0.16290 (13) | 0.0267 (3) | |
H3B | 0.571598 | −0.276652 | −0.168296 | 0.032* | |
C4 | 0.61761 (17) | −0.47925 (17) | −0.22054 (13) | 0.0290 (3) | |
H4A | 0.713718 | −0.496378 | −0.265790 | 0.035* | |
C5 | 0.56036 (17) | −0.58388 (16) | −0.21138 (13) | 0.0269 (3) | |
C6 | 0.42101 (17) | −0.56182 (16) | −0.14577 (14) | 0.0295 (3) | |
H6A | 0.383667 | −0.635070 | −0.139525 | 0.035* | |
C7 | 0.33697 (17) | −0.43139 (17) | −0.08944 (14) | 0.0284 (3) | |
H7A | 0.240584 | −0.414716 | −0.044929 | 0.034* | |
C8 | 0.02796 (16) | 0.18868 (16) | 0.21506 (14) | 0.0267 (3) | |
C9 | 0.02197 (18) | 0.32769 (17) | 0.20750 (15) | 0.0313 (4) | |
H9A | 0.092545 | 0.350326 | 0.151018 | 0.038* | |
C10 | −0.08778 (19) | 0.43325 (17) | 0.28299 (15) | 0.0354 (4) | |
H10A | −0.091204 | 0.527910 | 0.277052 | 0.043* | |
C11 | −0.19269 (19) | 0.40405 (18) | 0.36696 (14) | 0.0351 (4) | |
C12 | −0.18597 (19) | 0.26572 (18) | 0.37160 (15) | 0.0379 (4) | |
H12A | −0.257408 | 0.243330 | 0.427280 | 0.045* | |
C13 | −0.07765 (19) | 0.15891 (18) | 0.29709 (15) | 0.0345 (4) | |
H13A | −0.075740 | 0.064783 | 0.302239 | 0.041* | |
C14 | −0.3101 (2) | 0.5189 (2) | 0.44981 (17) | 0.0491 (5) | |
H14A | −0.261562 | 0.563650 | 0.491716 | 0.074* | |
H14B | −0.366622 | 0.476100 | 0.507452 | 0.074* | |
H14C | −0.378184 | 0.591456 | 0.404039 | 0.074* | |
C15 | 0.16963 (17) | 0.16269 (16) | −0.19758 (14) | 0.0295 (4) | |
C16 | 0.05522 (19) | 0.20649 (17) | −0.26474 (16) | 0.0348 (4) | |
H16A | −0.045693 | 0.235046 | −0.225909 | 0.042* | |
C17 | 0.0874 (2) | 0.20863 (19) | −0.38667 (17) | 0.0430 (5) | |
H17A | 0.007875 | 0.238267 | −0.430504 | 0.052* | |
C18 | 0.2332 (2) | 0.1686 (2) | −0.44722 (16) | 0.0438 (5) | |
C19 | 0.3459 (2) | 0.1286 (2) | −0.37902 (16) | 0.0404 (4) | |
H19A | 0.446483 | 0.102659 | −0.417951 | 0.048* | |
C20 | 0.31598 (18) | 0.12557 (17) | −0.25681 (15) | 0.0330 (4) | |
H20A | 0.395381 | 0.098105 | −0.213012 | 0.040* | |
C21 | 0.2691 (3) | 0.1692 (3) | −0.58100 (18) | 0.0619 (6) | |
H21A | 0.195942 | 0.255410 | −0.611022 | 0.093* | |
H21B | 0.264962 | 0.084198 | −0.612762 | 0.093* | |
H21C | 0.369523 | 0.168328 | −0.606012 | 0.093* | |
H1N | 0.441 (2) | −0.1123 (19) | −0.0279 (16) | 0.036 (5)* | |
H2N | 0.132 (2) | 0.003 (2) | 0.1511 (19) | 0.053 (7)* | |
H3N | 0.049 (2) | 0.1615 (18) | −0.0480 (16) | 0.033 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0331 (2) | 0.0299 (2) | 0.0414 (3) | −0.00670 (17) | −0.00867 (18) | −0.00597 (17) |
P1 | 0.0193 (2) | 0.0258 (2) | 0.0312 (2) | −0.01081 (16) | −0.00601 (16) | 0.00058 (16) |
O1 | 0.0222 (5) | 0.0286 (6) | 0.0406 (7) | −0.0121 (4) | −0.0094 (5) | −0.0005 (5) |
O2 | 0.0210 (6) | 0.0356 (6) | 0.0450 (7) | −0.0151 (5) | −0.0011 (5) | −0.0079 (5) |
N1 | 0.0173 (7) | 0.0289 (7) | 0.0313 (7) | −0.0113 (5) | −0.0053 (5) | −0.0015 (5) |
N2 | 0.0299 (7) | 0.0231 (7) | 0.0357 (8) | −0.0122 (6) | −0.0012 (6) | −0.0005 (6) |
N3 | 0.0177 (7) | 0.0326 (7) | 0.0380 (8) | −0.0126 (5) | −0.0069 (6) | 0.0046 (6) |
C1 | 0.0223 (8) | 0.0309 (8) | 0.0243 (8) | −0.0141 (6) | −0.0070 (6) | 0.0028 (6) |
C2 | 0.0238 (7) | 0.0279 (8) | 0.0211 (8) | −0.0121 (6) | −0.0083 (6) | 0.0023 (6) |
C3 | 0.0267 (8) | 0.0327 (9) | 0.0250 (8) | −0.0161 (6) | −0.0051 (6) | 0.0003 (6) |
C4 | 0.0254 (8) | 0.0366 (9) | 0.0247 (8) | −0.0126 (7) | −0.0022 (6) | −0.0019 (7) |
C5 | 0.0284 (8) | 0.0270 (8) | 0.0245 (8) | −0.0078 (6) | −0.0099 (6) | 0.0002 (6) |
C6 | 0.0302 (8) | 0.0286 (8) | 0.0340 (9) | −0.0144 (7) | −0.0095 (7) | 0.0015 (7) |
C7 | 0.0249 (8) | 0.0338 (9) | 0.0297 (9) | −0.0144 (7) | −0.0060 (6) | 0.0021 (6) |
C8 | 0.0260 (8) | 0.0272 (8) | 0.0275 (8) | −0.0094 (6) | −0.0077 (6) | −0.0014 (6) |
C9 | 0.0313 (8) | 0.0299 (9) | 0.0352 (9) | −0.0141 (7) | −0.0081 (7) | 0.0019 (7) |
C10 | 0.0428 (10) | 0.0251 (9) | 0.0388 (10) | −0.0116 (7) | −0.0123 (8) | 0.0012 (7) |
C11 | 0.0392 (9) | 0.0322 (9) | 0.0292 (9) | −0.0070 (7) | −0.0100 (7) | −0.0010 (7) |
C12 | 0.0390 (9) | 0.0402 (10) | 0.0324 (9) | −0.0159 (8) | 0.0000 (7) | −0.0009 (7) |
C13 | 0.0404 (9) | 0.0304 (9) | 0.0346 (9) | −0.0174 (7) | −0.0023 (7) | −0.0013 (7) |
C14 | 0.0576 (12) | 0.0377 (10) | 0.0384 (11) | −0.0072 (9) | −0.0005 (9) | −0.0059 (8) |
C15 | 0.0297 (8) | 0.0263 (8) | 0.0383 (9) | −0.0147 (6) | −0.0134 (7) | 0.0058 (7) |
C16 | 0.0309 (9) | 0.0334 (9) | 0.0492 (11) | −0.0180 (7) | −0.0195 (8) | 0.0096 (7) |
C17 | 0.0483 (11) | 0.0416 (10) | 0.0529 (12) | −0.0238 (8) | −0.0319 (9) | 0.0132 (8) |
C18 | 0.0554 (12) | 0.0470 (11) | 0.0387 (10) | −0.0256 (9) | −0.0211 (9) | 0.0075 (8) |
C19 | 0.0397 (10) | 0.0475 (11) | 0.0369 (10) | −0.0193 (8) | −0.0100 (8) | 0.0044 (8) |
C20 | 0.0296 (8) | 0.0378 (9) | 0.0356 (9) | −0.0150 (7) | −0.0135 (7) | 0.0056 (7) |
C21 | 0.0779 (16) | 0.0733 (15) | 0.0404 (12) | −0.0299 (13) | −0.0265 (11) | 0.0076 (10) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.7460 (16) | C6—C7 | 1.382 (2) |
P1—O1 | 1.4714 (10) | C8—C13 | 1.386 (2) |
P1—N2 | 1.6355 (14) | C8—C9 | 1.392 (2) |
P1—N3 | 1.6366 (13) | C9—C10 | 1.390 (2) |
P1—N1 | 1.6786 (13) | C10—C11 | 1.391 (2) |
O2—C1 | 1.2296 (17) | C11—C12 | 1.383 (2) |
N1—C1 | 1.3682 (19) | C11—C14 | 1.510 (2) |
N2—C8 | 1.420 (2) | C12—C13 | 1.386 (2) |
N3—C15 | 1.409 (2) | C15—C20 | 1.392 (2) |
C1—C2 | 1.492 (2) | C15—C16 | 1.398 (2) |
C2—C7 | 1.393 (2) | C16—C17 | 1.377 (3) |
C2—C3 | 1.395 (2) | C17—C18 | 1.389 (3) |
C3—C4 | 1.388 (2) | C18—C19 | 1.395 (2) |
C4—C5 | 1.384 (2) | C18—C21 | 1.511 (3) |
C5—C6 | 1.383 (2) | C19—C20 | 1.380 (2) |
| | | |
O1—P1—N2 | 116.17 (7) | C6—C7—C2 | 120.88 (14) |
O1—P1—N3 | 113.41 (7) | C13—C8—C9 | 119.01 (15) |
N2—P1—N3 | 104.77 (7) | C13—C8—N2 | 118.25 (14) |
O1—P1—N1 | 108.72 (6) | C9—C8—N2 | 122.70 (14) |
N2—P1—N1 | 104.73 (7) | C10—C9—C8 | 119.68 (15) |
N3—P1—N1 | 108.48 (7) | C9—C10—C11 | 121.79 (15) |
C1—N1—P1 | 123.83 (11) | C12—C11—C10 | 117.50 (15) |
C8—N2—P1 | 128.20 (11) | C12—C11—C14 | 121.08 (16) |
C15—N3—P1 | 127.11 (11) | C10—C11—C14 | 121.42 (16) |
O2—C1—N1 | 119.79 (14) | C11—C12—C13 | 121.65 (16) |
O2—C1—C2 | 121.10 (13) | C12—C13—C8 | 120.35 (15) |
N1—C1—C2 | 119.10 (12) | C20—C15—C16 | 118.36 (15) |
C7—C2—C3 | 119.30 (14) | C20—C15—N3 | 122.81 (14) |
C7—C2—C1 | 117.40 (13) | C16—C15—N3 | 118.82 (14) |
C3—C2—C1 | 123.28 (13) | C17—C16—C15 | 120.62 (16) |
C4—C3—C2 | 120.16 (14) | C16—C17—C18 | 121.70 (16) |
C5—C4—C3 | 119.27 (14) | C17—C18—C19 | 117.08 (17) |
C6—C5—C4 | 121.51 (14) | C17—C18—C21 | 121.85 (17) |
C6—C5—Cl1 | 119.09 (12) | C19—C18—C21 | 121.07 (18) |
C4—C5—Cl1 | 119.41 (12) | C20—C19—C18 | 122.08 (17) |
C7—C6—C5 | 118.88 (14) | C19—C20—C15 | 120.11 (15) |
Crystal data top
C23H25FN3O2P | Z = 2 |
Mr = 425.43 | F(000) = 448 |
Triclinic, P1 | Dx = 1.309 Mg m−3 |
a = 9.8114 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8829 (4) Å | Cell parameters from 5870 reflections |
c = 11.4042 (4) Å | θ = 2.8–27.2° |
α = 91.880 (3)° | µ = 0.16 mm−1 |
β = 99.719 (4)° | T = 120 K |
γ = 115.097 (4)° | Block, colourless |
V = 1079.45 (8) Å3 | 0.40 × 0.30 × 0.30 mm |
Data collection top
AFC11 (Right) Eulerian three-circle CCD diffractometer | 2844 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.022 |
Profile data from ω–scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2009 | h = −11→11 |
Tmin = 0.959, Tmax = 1.000 | k = −12→10 |
12637 measured reflections | l = −13→13 |
3791 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0445P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.001 |
3791 reflections | Δρmax = 0.21 e Å−3 |
277 parameters | Δρmin = −0.38 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.42002 (4) | 0.77637 (4) | 0.42965 (3) | 0.01811 (11) | |
F1 | 0.65568 (11) | 1.11163 (9) | 0.97866 (8) | 0.0357 (3) | |
O1 | 0.48004 (12) | 0.62115 (11) | 0.63547 (9) | 0.0261 (3) | |
O2 | 0.39244 (11) | 0.89210 (10) | 0.38575 (8) | 0.0221 (2) | |
N1 | 0.49906 (14) | 0.82403 (15) | 0.57617 (11) | 0.0195 (3) | |
N2 | 0.25817 (13) | 0.63790 (12) | 0.40530 (10) | 0.0197 (3) | |
N3 | 0.53769 (13) | 0.73366 (12) | 0.37227 (10) | 0.0205 (3) | |
C1 | 0.51563 (16) | 0.74224 (16) | 0.66104 (12) | 0.0190 (3) | |
C2 | 0.58309 (16) | 0.81043 (15) | 0.78713 (12) | 0.0189 (3) | |
C3 | 0.58540 (16) | 0.93394 (16) | 0.82583 (12) | 0.0216 (3) | |
H3A | 0.541010 | 0.978576 | 0.772701 | 0.026* | |
C4 | 0.65301 (17) | 0.98997 (16) | 0.94216 (13) | 0.0244 (4) | |
C5 | 0.71857 (18) | 0.93027 (18) | 1.02275 (14) | 0.0309 (4) | |
H5A | 0.764967 | 0.972317 | 1.102640 | 0.037* | |
C6 | 0.71527 (18) | 0.80727 (18) | 0.98453 (13) | 0.0322 (4) | |
H6A | 0.759751 | 0.763599 | 1.038719 | 0.039* | |
C7 | 0.64768 (17) | 0.74696 (17) | 0.86788 (13) | 0.0251 (4) | |
H7A | 0.645303 | 0.661860 | 0.842728 | 0.030* | |
C8 | 0.11232 (17) | 0.64938 (17) | 0.39299 (13) | 0.0239 (4) | |
H8A | 0.135007 | 0.745181 | 0.417997 | 0.029* | |
H8B | 0.051335 | 0.591468 | 0.447921 | 0.029* | |
C9 | 0.01689 (17) | 0.60754 (16) | 0.26731 (14) | 0.0235 (4) | |
C10 | −0.13044 (18) | 0.50137 (18) | 0.24329 (17) | 0.0368 (4) | |
H10A | −0.170924 | 0.451551 | 0.306039 | 0.044* | |
C11 | −0.2187 (2) | 0.4677 (2) | 0.1283 (2) | 0.0489 (5) | |
H11A | −0.319500 | 0.395083 | 0.112551 | 0.059* | |
C12 | −0.1608 (2) | 0.5390 (2) | 0.03714 (17) | 0.0440 (5) | |
H12A | −0.221462 | 0.515441 | −0.041675 | 0.053* | |
C13 | −0.01501 (19) | 0.64475 (19) | 0.05974 (15) | 0.0358 (4) | |
H13A | 0.024609 | 0.694259 | −0.003417 | 0.043* | |
C14 | 0.07390 (18) | 0.67897 (17) | 0.17439 (13) | 0.0268 (4) | |
H14A | 0.174545 | 0.751786 | 0.189536 | 0.032* | |
C15 | 0.24197 (17) | 0.49803 (15) | 0.39584 (14) | 0.0255 (4) | |
H15A | 0.187614 | 0.449412 | 0.456952 | 0.038* | |
H15B | 0.343994 | 0.499554 | 0.408073 | 0.038* | |
H15C | 0.183421 | 0.451257 | 0.316148 | 0.038* | |
C16 | 0.70068 (16) | 0.77747 (16) | 0.42425 (13) | 0.0234 (4) | |
H16A | 0.726432 | 0.700226 | 0.410471 | 0.028* | |
H16B | 0.717314 | 0.799709 | 0.511908 | 0.028* | |
C17 | 0.80932 (16) | 0.89990 (16) | 0.37413 (12) | 0.0200 (3) | |
C18 | 0.92158 (17) | 0.89038 (17) | 0.31966 (13) | 0.0258 (4) | |
H18A | 0.927511 | 0.805687 | 0.311963 | 0.031* | |
C19 | 1.02526 (17) | 1.00292 (18) | 0.27630 (14) | 0.0302 (4) | |
H19A | 1.102236 | 0.995224 | 0.240268 | 0.036* | |
C20 | 1.01617 (18) | 1.12579 (17) | 0.28570 (14) | 0.0297 (4) | |
H20A | 1.086817 | 1.202926 | 0.256151 | 0.036* | |
C21 | 0.90375 (18) | 1.13633 (17) | 0.33833 (14) | 0.0299 (4) | |
H21A | 0.896841 | 1.220690 | 0.344366 | 0.036* | |
C22 | 0.80143 (17) | 1.02439 (16) | 0.38217 (13) | 0.0257 (4) | |
H22A | 0.724775 | 1.032682 | 0.418227 | 0.031* | |
C23 | 0.49545 (18) | 0.68228 (17) | 0.24452 (13) | 0.0296 (4) | |
H23A | 0.519921 | 0.604823 | 0.232993 | 0.044* | |
H23B | 0.553170 | 0.755125 | 0.199253 | 0.044* | |
H23C | 0.385070 | 0.652560 | 0.215987 | 0.044* | |
H1N | 0.5304 (18) | 0.9057 (16) | 0.5927 (14) | 0.022 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0207 (2) | 0.0140 (2) | 0.01728 (19) | 0.00596 (18) | 0.00233 (15) | 0.00151 (16) |
F1 | 0.0485 (6) | 0.0301 (6) | 0.0279 (5) | 0.0168 (5) | 0.0086 (4) | −0.0038 (4) |
O1 | 0.0347 (7) | 0.0178 (7) | 0.0260 (6) | 0.0124 (5) | 0.0036 (5) | 0.0037 (5) |
O2 | 0.0288 (6) | 0.0138 (6) | 0.0207 (5) | 0.0082 (5) | 0.0002 (4) | 0.0029 (4) |
N1 | 0.0255 (7) | 0.0119 (8) | 0.0196 (7) | 0.0073 (7) | 0.0029 (5) | 0.0020 (6) |
N2 | 0.0191 (7) | 0.0132 (7) | 0.0261 (7) | 0.0069 (6) | 0.0034 (5) | 0.0016 (5) |
N3 | 0.0199 (6) | 0.0175 (8) | 0.0197 (6) | 0.0045 (6) | 0.0027 (5) | 0.0001 (5) |
C1 | 0.0187 (8) | 0.0171 (9) | 0.0221 (8) | 0.0077 (7) | 0.0067 (6) | 0.0053 (7) |
C2 | 0.0157 (7) | 0.0199 (9) | 0.0209 (7) | 0.0061 (7) | 0.0069 (6) | 0.0056 (6) |
C3 | 0.0226 (8) | 0.0239 (10) | 0.0200 (7) | 0.0106 (7) | 0.0070 (6) | 0.0065 (7) |
C4 | 0.0251 (8) | 0.0212 (10) | 0.0254 (8) | 0.0070 (8) | 0.0100 (7) | 0.0016 (7) |
C5 | 0.0293 (9) | 0.0418 (12) | 0.0190 (8) | 0.0143 (9) | 0.0019 (7) | −0.0004 (8) |
C6 | 0.0354 (10) | 0.0444 (12) | 0.0224 (8) | 0.0242 (9) | 0.0007 (7) | 0.0079 (8) |
C7 | 0.0261 (8) | 0.0256 (10) | 0.0271 (8) | 0.0138 (8) | 0.0069 (7) | 0.0068 (7) |
C8 | 0.0225 (8) | 0.0201 (9) | 0.0308 (8) | 0.0093 (7) | 0.0095 (7) | 0.0041 (7) |
C9 | 0.0194 (8) | 0.0185 (9) | 0.0346 (9) | 0.0106 (7) | 0.0045 (7) | −0.0006 (7) |
C10 | 0.0215 (9) | 0.0285 (11) | 0.0573 (12) | 0.0092 (8) | 0.0048 (8) | 0.0053 (9) |
C11 | 0.0228 (10) | 0.0335 (13) | 0.0743 (15) | 0.0056 (9) | −0.0106 (10) | −0.0075 (11) |
C12 | 0.0377 (11) | 0.0444 (13) | 0.0455 (11) | 0.0245 (10) | −0.0176 (9) | −0.0152 (10) |
C13 | 0.0363 (10) | 0.0428 (12) | 0.0330 (9) | 0.0246 (10) | −0.0002 (8) | −0.0014 (8) |
C14 | 0.0213 (8) | 0.0278 (10) | 0.0304 (9) | 0.0117 (8) | 0.0012 (7) | −0.0015 (7) |
C15 | 0.0235 (8) | 0.0151 (9) | 0.0349 (9) | 0.0065 (7) | 0.0038 (7) | 0.0017 (7) |
C16 | 0.0225 (8) | 0.0241 (10) | 0.0259 (8) | 0.0119 (8) | 0.0054 (6) | 0.0057 (7) |
C17 | 0.0169 (8) | 0.0210 (9) | 0.0191 (7) | 0.0074 (7) | −0.0015 (6) | −0.0002 (7) |
C18 | 0.0204 (8) | 0.0258 (10) | 0.0313 (9) | 0.0114 (8) | 0.0022 (7) | 0.0012 (7) |
C19 | 0.0190 (8) | 0.0335 (11) | 0.0360 (9) | 0.0085 (8) | 0.0091 (7) | −0.0007 (8) |
C20 | 0.0228 (9) | 0.0236 (10) | 0.0316 (9) | −0.0002 (8) | 0.0063 (7) | −0.0019 (7) |
C21 | 0.0308 (9) | 0.0203 (10) | 0.0351 (9) | 0.0077 (8) | 0.0079 (7) | −0.0021 (8) |
C22 | 0.0227 (8) | 0.0242 (10) | 0.0290 (8) | 0.0084 (8) | 0.0085 (7) | −0.0016 (7) |
C23 | 0.0281 (9) | 0.0302 (11) | 0.0239 (8) | 0.0066 (8) | 0.0067 (7) | −0.0038 (7) |
Geometric parameters (Å, º) top
P1—O2 | 1.4816 (10) | C10—H10A | 0.9500 |
P1—N2 | 1.6319 (13) | C11—C12 | 1.373 (3) |
P1—N3 | 1.6331 (12) | C11—H11A | 0.9500 |
P1—N1 | 1.6814 (12) | C12—C13 | 1.377 (3) |
F1—C4 | 1.3630 (17) | C12—H12A | 0.9500 |
O1—C1 | 1.2221 (17) | C13—C14 | 1.384 (2) |
N1—C1 | 1.3718 (19) | C13—H13A | 0.9500 |
N1—H1N | 0.811 (15) | C14—H14A | 0.9500 |
N2—C15 | 1.4601 (18) | C15—H15A | 0.9800 |
N2—C8 | 1.4725 (18) | C15—H15B | 0.9800 |
N3—C16 | 1.4666 (18) | C15—H15C | 0.9800 |
N3—C23 | 1.4674 (18) | C16—C17 | 1.513 (2) |
C1—C2 | 1.4995 (19) | C16—H16A | 0.9900 |
C2—C3 | 1.391 (2) | C16—H16B | 0.9900 |
C2—C7 | 1.394 (2) | C17—C22 | 1.390 (2) |
C3—C4 | 1.371 (2) | C17—C18 | 1.390 (2) |
C3—H3A | 0.9500 | C18—C19 | 1.390 (2) |
C4—C5 | 1.369 (2) | C18—H18A | 0.9500 |
C5—C6 | 1.380 (2) | C19—C20 | 1.379 (2) |
C5—H5A | 0.9500 | C19—H19A | 0.9500 |
C6—C7 | 1.384 (2) | C20—C21 | 1.384 (2) |
C6—H6A | 0.9500 | C20—H20A | 0.9500 |
C7—H7A | 0.9500 | C21—C22 | 1.383 (2) |
C8—C9 | 1.510 (2) | C21—H21A | 0.9500 |
C8—H8A | 0.9900 | C22—H22A | 0.9500 |
C8—H8B | 0.9900 | C23—H23A | 0.9800 |
C9—C14 | 1.388 (2) | C23—H23B | 0.9800 |
C9—C10 | 1.389 (2) | C23—H23C | 0.9800 |
C10—C11 | 1.385 (3) | | |
| | | |
O2—P1—N2 | 109.68 (6) | C12—C11—C10 | 120.14 (17) |
O2—P1—N3 | 118.46 (6) | C12—C11—H11A | 119.9 |
N2—P1—N3 | 104.88 (6) | C10—C11—H11A | 119.9 |
O2—P1—N1 | 105.52 (6) | C11—C12—C13 | 120.11 (16) |
N2—P1—N1 | 112.73 (7) | C11—C12—H12A | 119.9 |
N3—P1—N1 | 105.71 (6) | C13—C12—H12A | 119.9 |
C1—N1—P1 | 127.32 (12) | C12—C13—C14 | 120.08 (18) |
C1—N1—H1N | 121.6 (11) | C12—C13—H13A | 120.0 |
P1—N1—H1N | 111.1 (11) | C14—C13—H13A | 120.0 |
C15—N2—C8 | 114.73 (12) | C13—C14—C9 | 120.39 (16) |
C15—N2—P1 | 125.80 (10) | C13—C14—H14A | 119.8 |
C8—N2—P1 | 119.47 (10) | C9—C14—H14A | 119.8 |
C16—N3—C23 | 113.59 (12) | N2—C15—H15A | 109.5 |
C16—N3—P1 | 125.74 (10) | N2—C15—H15B | 109.5 |
C23—N3—P1 | 118.16 (10) | H15A—C15—H15B | 109.5 |
O1—C1—N1 | 122.12 (13) | N2—C15—H15C | 109.5 |
O1—C1—C2 | 121.67 (13) | H15A—C15—H15C | 109.5 |
N1—C1—C2 | 116.20 (13) | H15B—C15—H15C | 109.5 |
C3—C2—C7 | 119.13 (13) | N3—C16—C17 | 114.28 (12) |
C3—C2—C1 | 122.93 (13) | N3—C16—H16A | 108.7 |
C7—C2—C1 | 117.93 (13) | C17—C16—H16A | 108.7 |
C4—C3—C2 | 118.67 (14) | N3—C16—H16B | 108.7 |
C4—C3—H3A | 120.7 | C17—C16—H16B | 108.7 |
C2—C3—H3A | 120.7 | H16A—C16—H16B | 107.6 |
F1—C4—C5 | 118.66 (13) | C22—C17—C18 | 118.29 (15) |
F1—C4—C3 | 118.08 (13) | C22—C17—C16 | 121.49 (14) |
C5—C4—C3 | 123.26 (15) | C18—C17—C16 | 120.22 (14) |
C4—C5—C6 | 118.04 (14) | C19—C18—C17 | 120.99 (16) |
C4—C5—H5A | 121.0 | C19—C18—H18A | 119.5 |
C6—C5—H5A | 121.0 | C17—C18—H18A | 119.5 |
C5—C6—C7 | 120.55 (14) | C20—C19—C18 | 119.88 (15) |
C5—C6—H6A | 119.7 | C20—C19—H19A | 120.1 |
C7—C6—H6A | 119.7 | C18—C19—H19A | 120.1 |
C6—C7—C2 | 120.34 (15) | C19—C20—C21 | 119.77 (16) |
C6—C7—H7A | 119.8 | C19—C20—H20A | 120.1 |
C2—C7—H7A | 119.8 | C21—C20—H20A | 120.1 |
N2—C8—C9 | 113.67 (12) | C22—C21—C20 | 120.21 (16) |
N2—C8—H8A | 108.8 | C22—C21—H21A | 119.9 |
C9—C8—H8A | 108.8 | C20—C21—H21A | 119.9 |
N2—C8—H8B | 108.8 | C21—C22—C17 | 120.86 (15) |
C9—C8—H8B | 108.8 | C21—C22—H22A | 119.6 |
H8A—C8—H8B | 107.7 | C17—C22—H22A | 119.6 |
C14—C9—C10 | 118.91 (15) | N3—C23—H23A | 109.5 |
C14—C9—C8 | 119.96 (14) | N3—C23—H23B | 109.5 |
C10—C9—C8 | 121.08 (15) | H23A—C23—H23B | 109.5 |
C11—C10—C9 | 120.36 (18) | N3—C23—H23C | 109.5 |
C11—C10—H10A | 119.8 | H23A—C23—H23C | 109.5 |
C9—C10—H10A | 119.8 | H23B—C23—H23C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.811 (15) | 1.991 (16) | 2.7985 (17) | 173.7 (15) |
C3—H3A···O2i | 0.95 | 2.34 | 3.0954 (17) | 137 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Crystal data top
C23H24F2N3O2P | F(000) = 1856 |
Mr = 443.42 | Dx = 1.314 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.2590 (4) Å | Cell parameters from 9950 reflections |
b = 9.1240 (2) Å | θ = 2.6–29.9° |
c = 24.4373 (5) Å | µ = 0.16 mm−1 |
β = 96.959 (2)° | T = 296 K |
V = 4483.79 (16) Å3 | Block, colorless |
Z = 8 | 0.56 × 0.48 × 0.40 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5420 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.019 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 30.1°, θmin = 2.0° |
Tmin = 0.705, Tmax = 0.746 | h = −28→28 |
54279 measured reflections | k = −12→12 |
6545 independent reflections | l = −34→34 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0671P)2 + 2.4754P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
6545 reflections | Δρmax = 0.32 e Å−3 |
284 parameters | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.14804 (2) | 0.68343 (4) | 0.02567 (2) | 0.03054 (9) | |
F1 | 0.25066 (7) | 0.8095 (2) | −0.21962 (5) | 0.0965 (5) | |
F2 | 0.07574 (9) | 0.4875 (2) | −0.27409 (5) | 0.1100 (6) | |
O2 | 0.20842 (4) | 0.75955 (12) | 0.05138 (4) | 0.0392 (2) | |
O1 | 0.05504 (5) | 0.59782 (16) | −0.07660 (5) | 0.0580 (3) | |
N3 | 0.08207 (5) | 0.77726 (13) | 0.03566 (5) | 0.0368 (2) | |
C3 | 0.16458 (11) | 0.6457 (3) | −0.24814 (7) | 0.0733 (6) | |
H3 | 0.176385 | 0.644424 | −0.283749 | 0.088* | |
N2 | 0.13286 (6) | 0.51687 (13) | 0.04558 (4) | 0.0379 (2) | |
C21 | 0.07550 (15) | 1.0448 (3) | 0.21674 (11) | 0.0952 (8) | |
H21 | 0.072838 | 1.069942 | 0.253284 | 0.114* | |
C22 | 0.03606 (14) | 1.1131 (3) | 0.17584 (12) | 0.0914 (8) | |
H22 | 0.006725 | 1.185523 | 0.184474 | 0.110* | |
C23 | 0.03904 (10) | 1.0760 (2) | 0.12134 (9) | 0.0646 (5) | |
H23 | 0.011364 | 1.122733 | 0.093556 | 0.077* | |
C18 | 0.08293 (7) | 0.96988 (17) | 0.10802 (7) | 0.0465 (3) | |
C17 | 0.08913 (8) | 0.93340 (16) | 0.04855 (6) | 0.0449 (3) | |
H17A | 0.055399 | 0.987169 | 0.025108 | 0.054* | |
H17B | 0.132216 | 0.966314 | 0.039951 | 0.054* | |
N1 | 0.15826 (5) | 0.67022 (13) | −0.04149 (4) | 0.0352 (2) | |
C7 | 0.11062 (6) | 0.63511 (16) | −0.08396 (5) | 0.0379 (3) | |
C6 | 0.13086 (7) | 0.64452 (17) | −0.14113 (5) | 0.0394 (3) | |
C1 | 0.18429 (8) | 0.7275 (2) | −0.15356 (6) | 0.0488 (4) | |
H1 | 0.209374 | 0.782377 | −0.126490 | 0.059* | |
C2 | 0.19935 (9) | 0.7267 (3) | −0.20713 (7) | 0.0624 (5) | |
C4 | 0.11197 (11) | 0.5673 (3) | −0.23433 (7) | 0.0675 (5) | |
C5 | 0.09298 (8) | 0.5647 (2) | −0.18209 (6) | 0.0511 (4) | |
H5 | 0.056063 | 0.511358 | −0.174457 | 0.061* | |
C14 | 0.16638 (8) | 0.38808 (16) | 0.02562 (6) | 0.0447 (3) | |
H14A | 0.174890 | 0.405645 | −0.012039 | 0.054* | |
H14B | 0.136988 | 0.304108 | 0.025419 | 0.054* | |
C13 | 0.23118 (7) | 0.35252 (15) | 0.06024 (6) | 0.0424 (3) | |
C12 | 0.23433 (10) | 0.2439 (2) | 0.10023 (8) | 0.0608 (4) | |
H12 | 0.196792 | 0.188199 | 0.104277 | 0.073* | |
C11 | 0.29284 (13) | 0.2181 (3) | 0.13405 (10) | 0.0825 (7) | |
H11 | 0.294429 | 0.146352 | 0.161202 | 0.099* | |
C10 | 0.34883 (12) | 0.2986 (3) | 0.12755 (11) | 0.0855 (7) | |
H10 | 0.388251 | 0.281500 | 0.150356 | 0.103* | |
C9 | 0.34637 (10) | 0.4042 (3) | 0.08737 (11) | 0.0744 (6) | |
H9 | 0.384354 | 0.457734 | 0.082743 | 0.089* | |
C8 | 0.28802 (8) | 0.43126 (19) | 0.05385 (8) | 0.0545 (4) | |
H8 | 0.286836 | 0.503038 | 0.026729 | 0.065* | |
C15 | 0.11477 (9) | 0.4983 (2) | 0.10160 (7) | 0.0526 (4) | |
H15A | 0.093153 | 0.585427 | 0.112369 | 0.079* | |
H15B | 0.085155 | 0.416332 | 0.102286 | 0.079* | |
H15C | 0.154196 | 0.480865 | 0.126738 | 0.079* | |
C16 | 0.01432 (7) | 0.72031 (19) | 0.03271 (7) | 0.0469 (3) | |
H16A | 0.014295 | 0.617643 | 0.024105 | 0.070* | |
H16B | −0.002104 | 0.734330 | 0.067571 | 0.070* | |
H16C | −0.013744 | 0.771535 | 0.004510 | 0.070* | |
C20 | 0.11934 (13) | 0.9387 (3) | 0.20452 (9) | 0.0877 (7) | |
H20 | 0.146111 | 0.891239 | 0.232675 | 0.105* | |
C19 | 0.12352 (10) | 0.9028 (3) | 0.15012 (8) | 0.0682 (5) | |
H19 | 0.154044 | 0.832606 | 0.141779 | 0.082* | |
H | 0.1952 (10) | 0.690 (2) | −0.0471 (8) | 0.054 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.02490 (14) | 0.04199 (18) | 0.02471 (14) | 0.00053 (11) | 0.00292 (10) | 0.00068 (11) |
F1 | 0.0854 (9) | 0.1569 (14) | 0.0506 (6) | −0.0287 (9) | 0.0215 (6) | 0.0203 (7) |
F2 | 0.1224 (12) | 0.1543 (15) | 0.0485 (6) | −0.0218 (11) | −0.0085 (7) | −0.0455 (8) |
O2 | 0.0276 (4) | 0.0592 (6) | 0.0306 (4) | −0.0045 (4) | 0.0026 (3) | −0.0056 (4) |
O1 | 0.0371 (5) | 0.0926 (9) | 0.0434 (6) | −0.0178 (6) | 0.0016 (4) | −0.0068 (6) |
N3 | 0.0273 (5) | 0.0424 (6) | 0.0411 (6) | 0.0015 (4) | 0.0052 (4) | −0.0015 (5) |
C3 | 0.0757 (13) | 0.1142 (18) | 0.0299 (7) | 0.0115 (12) | 0.0068 (8) | −0.0043 (9) |
N2 | 0.0379 (5) | 0.0437 (6) | 0.0330 (5) | 0.0049 (5) | 0.0078 (4) | 0.0055 (4) |
C21 | 0.107 (2) | 0.113 (2) | 0.0717 (14) | 0.0037 (16) | 0.0330 (14) | −0.0384 (15) |
C22 | 0.0973 (18) | 0.0834 (16) | 0.1013 (19) | 0.0207 (14) | 0.0439 (16) | −0.0258 (14) |
C23 | 0.0612 (10) | 0.0555 (10) | 0.0811 (13) | 0.0107 (8) | 0.0253 (9) | −0.0045 (9) |
C18 | 0.0419 (7) | 0.0428 (7) | 0.0567 (8) | −0.0013 (6) | 0.0135 (6) | −0.0070 (6) |
C17 | 0.0439 (7) | 0.0412 (7) | 0.0504 (8) | 0.0044 (6) | 0.0096 (6) | 0.0033 (6) |
N1 | 0.0276 (5) | 0.0527 (7) | 0.0252 (5) | −0.0030 (4) | 0.0026 (4) | 0.0003 (4) |
C7 | 0.0332 (6) | 0.0500 (7) | 0.0295 (6) | −0.0005 (5) | −0.0001 (5) | −0.0014 (5) |
C6 | 0.0371 (6) | 0.0521 (7) | 0.0273 (5) | 0.0086 (5) | −0.0026 (5) | −0.0013 (5) |
C1 | 0.0455 (8) | 0.0715 (10) | 0.0284 (6) | −0.0002 (7) | 0.0006 (5) | 0.0032 (6) |
C2 | 0.0564 (10) | 0.0962 (14) | 0.0351 (7) | 0.0025 (9) | 0.0072 (7) | 0.0101 (8) |
C4 | 0.0760 (12) | 0.0896 (14) | 0.0330 (7) | 0.0085 (11) | −0.0093 (7) | −0.0172 (8) |
C5 | 0.0485 (8) | 0.0644 (10) | 0.0378 (7) | 0.0053 (7) | −0.0058 (6) | −0.0095 (7) |
C14 | 0.0479 (8) | 0.0408 (7) | 0.0444 (7) | 0.0025 (6) | 0.0016 (6) | −0.0027 (6) |
C13 | 0.0457 (7) | 0.0379 (6) | 0.0439 (7) | 0.0085 (5) | 0.0069 (6) | −0.0010 (5) |
C12 | 0.0627 (10) | 0.0529 (9) | 0.0678 (11) | 0.0136 (8) | 0.0121 (8) | 0.0168 (8) |
C11 | 0.0862 (16) | 0.0898 (16) | 0.0711 (13) | 0.0405 (13) | 0.0077 (11) | 0.0273 (12) |
C10 | 0.0634 (13) | 0.1028 (18) | 0.0842 (15) | 0.0357 (13) | −0.0155 (11) | −0.0043 (13) |
C9 | 0.0455 (9) | 0.0724 (12) | 0.1036 (17) | 0.0106 (9) | 0.0019 (10) | −0.0097 (12) |
C8 | 0.0463 (8) | 0.0495 (8) | 0.0687 (10) | 0.0086 (7) | 0.0111 (7) | 0.0035 (8) |
C15 | 0.0569 (9) | 0.0615 (9) | 0.0428 (8) | 0.0088 (7) | 0.0192 (7) | 0.0172 (7) |
C16 | 0.0271 (6) | 0.0565 (9) | 0.0573 (9) | 0.0013 (6) | 0.0065 (6) | 0.0000 (7) |
C20 | 0.0943 (16) | 0.114 (2) | 0.0539 (11) | 0.0194 (15) | 0.0043 (11) | −0.0208 (12) |
C19 | 0.0692 (11) | 0.0802 (13) | 0.0544 (10) | 0.0203 (10) | 0.0047 (8) | −0.0180 (9) |
Geometric parameters (Å, º) top
P1—O2 | 1.4788 (9) | C6—C5 | 1.391 (2) |
P1—N3 | 1.6302 (11) | C1—C2 | 1.380 (2) |
P1—N2 | 1.6361 (12) | C1—H1 | 0.9300 |
P1—N1 | 1.6834 (11) | C4—C5 | 1.378 (2) |
F1—C2 | 1.349 (2) | C5—H5 | 0.9300 |
F2—C4 | 1.357 (2) | C14—C13 | 1.508 (2) |
O1—C7 | 1.2104 (17) | C14—H14A | 0.9700 |
N3—C16 | 1.4612 (17) | C14—H14B | 0.9700 |
N3—C17 | 1.4623 (19) | C13—C8 | 1.382 (2) |
C3—C4 | 1.359 (3) | C13—C12 | 1.388 (2) |
C3—C2 | 1.370 (3) | C12—C11 | 1.381 (3) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
N2—C15 | 1.4691 (17) | C11—C10 | 1.377 (4) |
N2—C14 | 1.4698 (18) | C11—H11 | 0.9300 |
C21—C22 | 1.353 (4) | C10—C9 | 1.372 (4) |
C21—C20 | 1.371 (4) | C10—H10 | 0.9300 |
C21—H21 | 0.9300 | C9—C8 | 1.376 (3) |
C22—C23 | 1.383 (3) | C9—H9 | 0.9300 |
C22—H22 | 0.9300 | C8—H8 | 0.9300 |
C23—C18 | 1.380 (2) | C15—H15A | 0.9600 |
C23—H23 | 0.9300 | C15—H15B | 0.9600 |
C18—C19 | 1.380 (3) | C15—H15C | 0.9600 |
C18—C17 | 1.511 (2) | C16—H16A | 0.9600 |
C17—H17A | 0.9700 | C16—H16B | 0.9600 |
C17—H17B | 0.9700 | C16—H16C | 0.9600 |
N1—C7 | 1.3669 (16) | C20—C19 | 1.382 (3) |
N1—H | 0.80 (2) | C20—H20 | 0.9300 |
C7—C6 | 1.5054 (18) | C19—H19 | 0.9300 |
C6—C1 | 1.384 (2) | | |
| | | |
O2—P1—N3 | 109.92 (6) | F2—C4—C3 | 118.49 (17) |
O2—P1—N2 | 119.04 (6) | F2—C4—C5 | 117.8 (2) |
N3—P1—N2 | 104.85 (6) | C3—C4—C5 | 123.68 (17) |
O2—P1—N1 | 104.75 (5) | C4—C5—C6 | 117.78 (17) |
N3—P1—N1 | 112.55 (6) | C4—C5—H5 | 121.1 |
N2—P1—N1 | 105.86 (6) | C6—C5—H5 | 121.1 |
C16—N3—C17 | 115.07 (11) | N2—C14—C13 | 113.05 (12) |
C16—N3—P1 | 126.02 (10) | N2—C14—H14A | 109.0 |
C17—N3—P1 | 118.90 (9) | C13—C14—H14A | 109.0 |
C4—C3—C2 | 116.83 (16) | N2—C14—H14B | 109.0 |
C4—C3—H3 | 121.6 | C13—C14—H14B | 109.0 |
C2—C3—H3 | 121.6 | H14A—C14—H14B | 107.8 |
C15—N2—C14 | 113.22 (12) | C8—C13—C12 | 118.87 (16) |
C15—N2—P1 | 117.48 (10) | C8—C13—C14 | 120.35 (14) |
C14—N2—P1 | 122.20 (9) | C12—C13—C14 | 120.74 (15) |
C22—C21—C20 | 120.3 (2) | C11—C12—C13 | 120.4 (2) |
C22—C21—H21 | 119.9 | C11—C12—H12 | 119.8 |
C20—C21—H21 | 119.9 | C13—C12—H12 | 119.8 |
C21—C22—C23 | 120.5 (2) | C10—C11—C12 | 120.0 (2) |
C21—C22—H22 | 119.7 | C10—C11—H11 | 120.0 |
C23—C22—H22 | 119.7 | C12—C11—H11 | 120.0 |
C18—C23—C22 | 120.2 (2) | C9—C10—C11 | 119.87 (19) |
C18—C23—H23 | 119.9 | C9—C10—H10 | 120.1 |
C22—C23—H23 | 119.9 | C11—C10—H10 | 120.1 |
C19—C18—C23 | 118.56 (17) | C10—C9—C8 | 120.4 (2) |
C19—C18—C17 | 120.53 (14) | C10—C9—H9 | 119.8 |
C23—C18—C17 | 120.83 (16) | C8—C9—H9 | 119.8 |
N3—C17—C18 | 113.87 (12) | C9—C8—C13 | 120.44 (18) |
N3—C17—H17A | 108.8 | C9—C8—H8 | 119.8 |
C18—C17—H17A | 108.8 | C13—C8—H8 | 119.8 |
N3—C17—H17B | 108.8 | N2—C15—H15A | 109.5 |
C18—C17—H17B | 108.8 | N2—C15—H15B | 109.5 |
H17A—C17—H17B | 107.7 | H15A—C15—H15B | 109.5 |
C7—N1—P1 | 126.74 (9) | N2—C15—H15C | 109.5 |
C7—N1—H | 120.9 (14) | H15A—C15—H15C | 109.5 |
P1—N1—H | 112.3 (14) | H15B—C15—H15C | 109.5 |
O1—C7—N1 | 122.48 (12) | N3—C16—H16A | 109.5 |
O1—C7—C6 | 121.11 (12) | N3—C16—H16B | 109.5 |
N1—C7—C6 | 116.41 (11) | H16A—C16—H16B | 109.5 |
C1—C6—C5 | 120.42 (14) | N3—C16—H16C | 109.5 |
C1—C6—C7 | 122.87 (12) | H16A—C16—H16C | 109.5 |
C5—C6—C7 | 116.71 (14) | H16B—C16—H16C | 109.5 |
C2—C1—C6 | 118.28 (15) | C21—C20—C19 | 119.6 (2) |
C2—C1—H1 | 120.9 | C21—C20—H20 | 120.2 |
C6—C1—H1 | 120.9 | C19—C20—H20 | 120.2 |
F1—C2—C3 | 118.58 (16) | C18—C19—C20 | 120.78 (19) |
F1—C2—C1 | 118.48 (17) | C18—C19—H19 | 119.6 |
C3—C2—C1 | 122.94 (19) | C20—C19—H19 | 119.6 |
| | | |
O2—P1—N3—C16 | −159.29 (12) | C5—C6—C1—C2 | −1.0 (2) |
N2—P1—N3—C16 | −30.22 (13) | C7—C6—C1—C2 | 178.93 (15) |
N1—P1—N3—C16 | 84.37 (13) | C4—C3—C2—F1 | −178.0 (2) |
O2—P1—N3—C17 | 21.08 (12) | C4—C3—C2—C1 | 2.0 (3) |
N2—P1—N3—C17 | 150.15 (11) | C6—C1—C2—F1 | 178.86 (17) |
N1—P1—N3—C17 | −95.26 (11) | C6—C1—C2—C3 | −1.2 (3) |
O2—P1—N2—C15 | 68.95 (12) | C2—C3—C4—F2 | 179.0 (2) |
N3—P1—N2—C15 | −54.45 (12) | C2—C3—C4—C5 | −0.6 (3) |
N1—P1—N2—C15 | −173.64 (10) | F2—C4—C5—C6 | 178.90 (17) |
O2—P1—N2—C14 | −79.57 (12) | C3—C4—C5—C6 | −1.4 (3) |
N3—P1—N2—C14 | 157.03 (11) | C1—C6—C5—C4 | 2.3 (2) |
N1—P1—N2—C14 | 37.85 (12) | C7—C6—C5—C4 | −177.70 (15) |
C20—C21—C22—C23 | 0.6 (5) | C15—N2—C14—C13 | −61.51 (17) |
C21—C22—C23—C18 | −0.8 (4) | P1—N2—C14—C13 | 88.22 (14) |
C22—C23—C18—C19 | −0.2 (3) | N2—C14—C13—C8 | −79.02 (18) |
C22—C23—C18—C17 | −177.00 (19) | N2—C14—C13—C12 | 98.78 (18) |
C16—N3—C17—C18 | 73.69 (16) | C8—C13—C12—C11 | 1.8 (3) |
P1—N3—C17—C18 | −106.64 (13) | C14—C13—C12—C11 | −176.00 (18) |
C19—C18—C17—N3 | 55.8 (2) | C13—C12—C11—C10 | −1.1 (3) |
C23—C18—C17—N3 | −127.50 (16) | C12—C11—C10—C9 | −0.2 (4) |
O2—P1—N1—C7 | −165.96 (12) | C11—C10—C9—C8 | 0.7 (4) |
N3—P1—N1—C7 | −46.57 (14) | C10—C9—C8—C13 | 0.0 (3) |
N2—P1—N1—C7 | 67.41 (13) | C12—C13—C8—C9 | −1.3 (3) |
P1—N1—C7—O1 | −5.9 (2) | C14—C13—C8—C9 | 176.58 (16) |
P1—N1—C7—C6 | 174.38 (10) | C22—C21—C20—C19 | 0.6 (5) |
O1—C7—C6—C1 | 159.14 (16) | C23—C18—C19—C20 | 1.4 (3) |
N1—C7—C6—C1 | −21.1 (2) | C17—C18—C19—C20 | 178.2 (2) |
O1—C7—C6—C5 | −20.9 (2) | C21—C20—C19—C18 | −1.6 (4) |
N1—C7—C6—C5 | 158.88 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2i | 0.93 | 2.36 | 3.1079 (17) | 138 |
N1—H···O2i | 0.80 (2) | 2.02 (2) | 2.8147 (14) | 173 (2) |
Symmetry code: (i) −x+1/2, −y+3/2, −z. |
Crystal data top
C12H16F2N3O2P | Dx = 1.346 Mg m−3 |
Mr = 303.25 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 9708 reflections |
a = 26.9555 (7) Å | θ = 3.0–24.3° |
b = 8.0374 (2) Å | µ = 0.21 mm−1 |
c = 27.6270 (8) Å | T = 296 K |
V = 5985.4 (3) Å3 | Prismatic, colorless |
Z = 16 | 0.53 × 0.43 × 0.25 mm |
F(000) = 2528 | |
Data collection top
Bruker APEXII CCD diffractometer | 5275 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.043 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 27.0°, θmin = 2.1° |
Tmin = 0.703, Tmax = 0.746 | h = −34→34 |
315001 measured reflections | k = −10→10 |
6531 independent reflections | l = −35→35 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.045P)2 + 4.2583P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.001 |
6531 reflections | Δρmax = 0.36 e Å−3 |
377 parameters | Δρmin = −0.31 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1A | 1.02746 (2) | 0.95942 (8) | 0.16693 (2) | 0.04032 (15) | |
P1B | 0.91688 (2) | 0.45980 (8) | 0.28182 (2) | 0.04196 (15) | |
F1A | 0.79223 (7) | 0.9068 (3) | 0.25401 (7) | 0.1058 (7) | |
O2B | 0.96742 (6) | 0.4627 (3) | 0.30274 (6) | 0.0602 (5) | |
F2B | 0.84271 (8) | 0.6852 (4) | 0.03099 (7) | 0.1252 (10) | |
F1B | 0.99527 (6) | 0.4202 (2) | 0.04994 (6) | 0.0765 (5) | |
N3A | 1.04462 (7) | 1.1067 (3) | 0.13105 (7) | 0.0440 (4) | |
O1A | 0.94310 (6) | 0.9886 (3) | 0.10231 (6) | 0.0623 (5) | |
N3B | 0.88161 (6) | 0.6082 (2) | 0.30078 (7) | 0.0449 (4) | |
H3B | 0.894209 | 0.706404 | 0.301823 | 0.054* | |
N2B | 0.88499 (7) | 0.2935 (2) | 0.29297 (7) | 0.0483 (5) | |
H2B | 0.899558 | 0.200008 | 0.287739 | 0.058* | |
F2A | 0.76637 (7) | 1.1610 (5) | 0.10514 (10) | 0.1734 (16) | |
C10A | 1.05183 (8) | 1.0922 (3) | 0.07878 (8) | 0.0436 (5) | |
H10A | 1.071708 | 1.185065 | 0.067509 | 0.052* | |
H10B | 1.019864 | 1.097953 | 0.062744 | 0.052* | |
O2A | 1.05263 (6) | 0.9616 (3) | 0.21444 (6) | 0.0588 (5) | |
C10B | 0.82994 (8) | 0.5900 (3) | 0.31637 (9) | 0.0449 (5) | |
10B1 | 0.808508 | 0.590895 | 0.288170 | 0.054* | |
10B2 | 0.820946 | 0.684015 | 0.336569 | 0.054* | |
C9B | 0.82167 (8) | 0.4298 (3) | 0.34449 (8) | 0.0443 (5) | |
O1B | 0.84450 (6) | 0.4920 (3) | 0.20342 (6) | 0.0601 (5) | |
C5A | 0.79742 (10) | 1.0902 (6) | 0.13760 (12) | 0.0917 (12) | |
C6A | 0.84664 (10) | 1.0780 (5) | 0.12610 (10) | 0.0742 (9) | |
H6A | 0.858508 | 1.117149 | 0.096616 | 0.089* | |
C1A | 0.87829 (8) | 1.0060 (3) | 0.15946 (8) | 0.0452 (5) | |
C7A | 0.93139 (8) | 0.9894 (3) | 0.14493 (8) | 0.0450 (5) | |
N1A | 0.96647 (7) | 0.9757 (3) | 0.18031 (7) | 0.0470 (5) | |
C9A | 1.07733 (8) | 0.9304 (3) | 0.06512 (8) | 0.0446 (5) | |
C11A | 1.08047 (12) | 0.9216 (4) | 0.00985 (9) | 0.0711 (8) | |
H11A | 1.100607 | 1.011515 | −0.001876 | 0.107* | |
H11B | 1.095007 | 0.817533 | 0.000415 | 0.107* | |
H11C | 1.047752 | 0.930370 | −0.003646 | 0.107* | |
C12A | 1.12962 (9) | 0.9227 (3) | 0.08627 (10) | 0.0571 (6) | |
H12A | 1.148764 | 1.014597 | 0.074294 | 0.086* | |
H12B | 1.127825 | 0.928485 | 0.120930 | 0.086* | |
H12C | 1.145130 | 0.820132 | 0.076871 | 0.086* | |
N2A | 1.03703 (8) | 0.7932 (3) | 0.13510 (7) | 0.0466 (5) | |
C8A | 1.04542 (9) | 0.7876 (3) | 0.08290 (8) | 0.0480 (5) | |
H8A1 | 1.013674 | 0.791028 | 0.066394 | 0.058* | |
H8A2 | 1.061397 | 0.683228 | 0.074676 | 0.058* | |
C4A | 0.77744 (10) | 1.0318 (5) | 0.17985 (12) | 0.0805 (10) | |
H4A | 0.743650 | 1.037842 | 0.186428 | 0.097* | |
C3A | 0.81017 (10) | 0.9646 (4) | 0.21140 (10) | 0.0618 (7) | |
C2A | 0.86001 (9) | 0.9502 (3) | 0.20312 (8) | 0.0509 (6) | |
H22A | 0.880948 | 0.904075 | 0.226274 | 0.061* | |
C4B | 0.91925 (11) | 0.5517 (4) | 0.03898 (10) | 0.0651 (7) | |
H4B | 0.925775 | 0.565362 | 0.006168 | 0.078* | |
C5B | 0.87597 (11) | 0.6072 (4) | 0.05960 (10) | 0.0728 (8) | |
C6B | 0.86521 (9) | 0.5868 (4) | 0.10768 (9) | 0.0608 (7) | |
H6B | 0.835153 | 0.623412 | 0.120307 | 0.073* | |
C1B | 0.90009 (8) | 0.5104 (3) | 0.13717 (8) | 0.0436 (5) | |
C7B | 0.88737 (8) | 0.4911 (3) | 0.18966 (8) | 0.0445 (5) | |
N1B | 0.92583 (7) | 0.4751 (3) | 0.22162 (7) | 0.0475 (5) | |
C11B | 0.76672 (9) | 0.4196 (4) | 0.35835 (11) | 0.0644 (7) | |
H11D | 0.760821 | 0.318962 | 0.376166 | 0.097* | |
H11E | 0.758100 | 0.513690 | 0.378034 | 0.097* | |
H11F | 0.746800 | 0.419725 | 0.329546 | 0.097* | |
C12B | 0.85308 (10) | 0.4255 (3) | 0.39050 (9) | 0.0553 (6) | |
H12D | 0.847126 | 0.323254 | 0.407483 | 0.083* | |
H12E | 0.887558 | 0.432918 | 0.382071 | 0.083* | |
H12F | 0.844286 | 0.517724 | 0.410857 | 0.083* | |
C8B | 0.83411 (9) | 0.2853 (3) | 0.31096 (9) | 0.0506 (5) | |
H8C | 0.829456 | 0.181501 | 0.328261 | 0.061* | |
H8D | 0.811418 | 0.286185 | 0.283713 | 0.061* | |
C3B | 0.95215 (9) | 0.4755 (3) | 0.06918 (9) | 0.0522 (6) | |
C2B | 0.94433 (8) | 0.4546 (3) | 0.11786 (8) | 0.0457 (5) | |
H22B | 0.968157 | 0.404277 | 0.137321 | 0.055* | |
H3A | 1.0468 (9) | 1.187 (3) | 0.1419 (9) | 0.043 (7)* | |
H1B | 0.9548 (10) | 0.478 (3) | 0.2124 (9) | 0.047 (7)* | |
H2A | 1.0296 (10) | 0.717 (3) | 0.1473 (10) | 0.054 (8)* | |
H1A | 0.9602 (10) | 0.977 (3) | 0.2087 (10) | 0.056 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1A | 0.0348 (3) | 0.0521 (3) | 0.0341 (3) | −0.0021 (2) | −0.0085 (2) | 0.0040 (2) |
P1B | 0.0322 (3) | 0.0518 (3) | 0.0419 (3) | 0.0037 (2) | −0.0090 (2) | −0.0014 (2) |
F1A | 0.0777 (12) | 0.159 (2) | 0.0806 (12) | 0.0087 (13) | 0.0363 (10) | 0.0415 (13) |
O2B | 0.0355 (8) | 0.0963 (14) | 0.0488 (9) | 0.0082 (9) | −0.0132 (7) | −0.0073 (9) |
F2B | 0.0951 (14) | 0.207 (3) | 0.0730 (12) | 0.0547 (16) | −0.0128 (10) | 0.0512 (15) |
F1B | 0.0743 (10) | 0.0830 (11) | 0.0724 (10) | 0.0187 (9) | 0.0264 (8) | 0.0046 (9) |
N3A | 0.0510 (11) | 0.0381 (10) | 0.0431 (10) | −0.0034 (9) | −0.0053 (8) | −0.0034 (9) |
O1A | 0.0391 (8) | 0.1133 (16) | 0.0344 (8) | 0.0007 (9) | −0.0033 (7) | 0.0053 (9) |
N3B | 0.0376 (9) | 0.0374 (9) | 0.0599 (11) | −0.0042 (8) | −0.0014 (8) | −0.0017 (8) |
N2B | 0.0525 (11) | 0.0384 (10) | 0.0539 (11) | 0.0094 (8) | −0.0013 (9) | −0.0015 (8) |
F2A | 0.0559 (11) | 0.329 (5) | 0.136 (2) | 0.0491 (18) | −0.0051 (12) | 0.115 (3) |
C10A | 0.0447 (12) | 0.0455 (12) | 0.0407 (11) | −0.0035 (9) | −0.0074 (9) | 0.0090 (9) |
O2A | 0.0429 (9) | 0.0955 (14) | 0.0379 (8) | −0.0055 (9) | −0.0131 (7) | 0.0072 (9) |
C10B | 0.0370 (11) | 0.0432 (12) | 0.0546 (13) | 0.0049 (9) | −0.0042 (9) | 0.0007 (10) |
C9B | 0.0383 (11) | 0.0437 (12) | 0.0508 (12) | −0.0022 (9) | −0.0030 (9) | 0.0002 (10) |
O1B | 0.0311 (8) | 0.1001 (14) | 0.0490 (9) | 0.0006 (8) | −0.0052 (7) | 0.0053 (9) |
C5A | 0.0405 (14) | 0.153 (4) | 0.081 (2) | 0.0159 (18) | −0.0087 (14) | 0.039 (2) |
C6A | 0.0428 (13) | 0.123 (3) | 0.0569 (15) | 0.0033 (15) | −0.0020 (11) | 0.0318 (17) |
C1A | 0.0388 (11) | 0.0570 (13) | 0.0397 (11) | −0.0017 (10) | −0.0033 (9) | 0.0031 (10) |
C7A | 0.0373 (11) | 0.0609 (14) | 0.0369 (11) | −0.0016 (10) | −0.0039 (9) | 0.0034 (10) |
N1A | 0.0385 (9) | 0.0714 (14) | 0.0312 (9) | −0.0003 (9) | −0.0039 (7) | 0.0015 (9) |
C9A | 0.0466 (12) | 0.0464 (12) | 0.0408 (11) | −0.0012 (10) | −0.0028 (9) | −0.0003 (9) |
C11A | 0.083 (2) | 0.085 (2) | 0.0455 (14) | −0.0042 (17) | 0.0048 (13) | −0.0052 (14) |
C12A | 0.0441 (13) | 0.0562 (15) | 0.0710 (16) | 0.0045 (11) | −0.0002 (12) | 0.0020 (13) |
N2A | 0.0501 (11) | 0.0390 (10) | 0.0509 (11) | −0.0037 (9) | −0.0020 (9) | 0.0102 (9) |
C8A | 0.0512 (13) | 0.0427 (12) | 0.0500 (13) | −0.0034 (10) | −0.0031 (10) | −0.0061 (10) |
C4A | 0.0398 (13) | 0.123 (3) | 0.078 (2) | 0.0051 (16) | 0.0098 (13) | 0.015 (2) |
C3A | 0.0509 (14) | 0.0814 (19) | 0.0531 (14) | −0.0039 (13) | 0.0118 (11) | 0.0084 (13) |
C2A | 0.0449 (12) | 0.0654 (15) | 0.0424 (12) | 0.0038 (11) | 0.0003 (10) | 0.0055 (11) |
C4B | 0.0704 (17) | 0.0788 (19) | 0.0463 (14) | 0.0013 (15) | 0.0039 (12) | 0.0078 (13) |
C5B | 0.0628 (17) | 0.101 (2) | 0.0550 (15) | 0.0135 (16) | −0.0105 (13) | 0.0207 (16) |
C6B | 0.0438 (13) | 0.086 (2) | 0.0527 (14) | 0.0115 (13) | −0.0062 (11) | 0.0087 (13) |
C1B | 0.0359 (10) | 0.0495 (12) | 0.0452 (11) | −0.0028 (9) | −0.0063 (9) | 0.0023 (10) |
C7B | 0.0330 (10) | 0.0560 (13) | 0.0446 (11) | −0.0008 (9) | −0.0072 (9) | 0.0018 (10) |
N1B | 0.0281 (9) | 0.0703 (13) | 0.0441 (10) | 0.0014 (9) | −0.0052 (8) | 0.0010 (9) |
C11B | 0.0481 (14) | 0.0679 (17) | 0.0772 (18) | −0.0082 (13) | 0.0059 (12) | 0.0050 (14) |
C12B | 0.0608 (15) | 0.0553 (14) | 0.0499 (13) | 0.0032 (12) | −0.0059 (11) | 0.0012 (11) |
C8B | 0.0499 (13) | 0.0424 (12) | 0.0594 (14) | −0.0066 (10) | −0.0051 (11) | −0.0018 (11) |
C3B | 0.0515 (13) | 0.0485 (13) | 0.0566 (14) | −0.0006 (11) | 0.0082 (11) | −0.0025 (11) |
C2B | 0.0413 (11) | 0.0470 (12) | 0.0488 (12) | −0.0003 (10) | −0.0050 (9) | 0.0031 (10) |
Geometric parameters (Å, º) top
P1A—O2A | 1.4777 (15) | C9A—C8A | 1.516 (3) |
P1A—N3A | 1.612 (2) | C9A—C12A | 1.527 (3) |
P1A—N2A | 1.620 (2) | C9A—C11A | 1.531 (3) |
P1A—N1A | 1.690 (2) | C11A—H11A | 0.9600 |
P1B—O2B | 1.4802 (15) | C11A—H11B | 0.9600 |
P1B—N3B | 1.6125 (19) | C11A—H11C | 0.9600 |
P1B—N2B | 1.619 (2) | C12A—H12A | 0.9600 |
P1B—N1B | 1.685 (2) | C12A—H12B | 0.9600 |
F1A—C3A | 1.355 (3) | C12A—H12C | 0.9600 |
F2B—C5B | 1.350 (3) | N2A—C8A | 1.460 (3) |
F1B—C3B | 1.353 (3) | N2A—H2A | 0.73 (3) |
N3A—C10A | 1.462 (3) | C8A—H8A1 | 0.9700 |
N3A—H3A | 0.72 (2) | C8A—H8A2 | 0.9700 |
O1A—C7A | 1.219 (3) | C4A—C3A | 1.353 (4) |
N3B—C10B | 1.465 (3) | C4A—H4A | 0.9300 |
N3B—H3B | 0.8600 | C3A—C2A | 1.368 (3) |
N2B—C8B | 1.460 (3) | C2A—H22A | 0.9300 |
N2B—H2B | 0.8600 | C4B—C3B | 1.363 (4) |
F2A—C5A | 1.352 (3) | C4B—C5B | 1.373 (4) |
C10A—C9A | 1.519 (3) | C4B—H4B | 0.9300 |
C10A—H10A | 0.9700 | C5B—C6B | 1.369 (4) |
C10A—H10B | 0.9700 | C6B—C1B | 1.387 (3) |
C10B—C9B | 1.520 (3) | C6B—H6B | 0.9300 |
C10B—10B1 | 0.9700 | C1B—C2B | 1.381 (3) |
C10B—10B2 | 0.9700 | C1B—C7B | 1.498 (3) |
C9B—C8B | 1.523 (3) | C7B—N1B | 1.368 (3) |
C9B—C12B | 1.528 (3) | N1B—H1B | 0.82 (3) |
C9B—C11B | 1.532 (3) | C11B—H11D | 0.9600 |
O1B—C7B | 1.217 (3) | C11B—H11E | 0.9600 |
C5A—C6A | 1.368 (4) | C11B—H11F | 0.9600 |
C5A—C4A | 1.369 (4) | C12B—H12D | 0.9600 |
C6A—C1A | 1.383 (3) | C12B—H12E | 0.9600 |
C6A—H6A | 0.9300 | C12B—H12F | 0.9600 |
C1A—C2A | 1.378 (3) | C8B—H8C | 0.9700 |
C1A—C7A | 1.493 (3) | C8B—H8D | 0.9700 |
C7A—N1A | 1.364 (3) | C3B—C2B | 1.372 (3) |
N1A—H1A | 0.80 (3) | C2B—H22B | 0.9300 |
| | | |
O2A—P1A—N3A | 113.96 (11) | C9A—C12A—H12A | 109.5 |
O2A—P1A—N2A | 114.75 (11) | C9A—C12A—H12B | 109.5 |
N3A—P1A—N2A | 103.07 (11) | H12A—C12A—H12B | 109.5 |
O2A—P1A—N1A | 104.56 (10) | C9A—C12A—H12C | 109.5 |
N3A—P1A—N1A | 110.89 (11) | H12A—C12A—H12C | 109.5 |
N2A—P1A—N1A | 109.73 (11) | H12B—C12A—H12C | 109.5 |
O2B—P1B—N3B | 113.83 (10) | C8A—N2A—P1A | 125.88 (17) |
O2B—P1B—N2B | 115.31 (11) | C8A—N2A—H2A | 118 (2) |
N3B—P1B—N2B | 103.64 (10) | P1A—N2A—H2A | 113 (2) |
O2B—P1B—N1B | 104.63 (10) | N2A—C8A—C9A | 112.62 (19) |
N3B—P1B—N1B | 110.56 (10) | N2A—C8A—H8A1 | 109.1 |
N2B—P1B—N1B | 108.91 (10) | C9A—C8A—H8A1 | 109.1 |
C10A—N3A—P1A | 125.96 (17) | N2A—C8A—H8A2 | 109.1 |
C10A—N3A—H3A | 118 (2) | C9A—C8A—H8A2 | 109.1 |
P1A—N3A—H3A | 116 (2) | H8A1—C8A—H8A2 | 107.8 |
C10B—N3B—P1B | 125.61 (15) | C3A—C4A—C5A | 115.5 (2) |
C10B—N3B—H3B | 117.2 | C3A—C4A—H4A | 122.3 |
P1B—N3B—H3B | 117.2 | C5A—C4A—H4A | 122.3 |
C8B—N2B—P1B | 126.90 (16) | C4A—C3A—F1A | 117.6 (2) |
C8B—N2B—H2B | 116.5 | C4A—C3A—C2A | 124.5 (2) |
P1B—N2B—H2B | 116.5 | F1A—C3A—C2A | 117.8 (2) |
N3A—C10A—C9A | 111.96 (18) | C3A—C2A—C1A | 118.0 (2) |
N3A—C10A—H10A | 109.2 | C3A—C2A—H22A | 121.0 |
C9A—C10A—H10A | 109.2 | C1A—C2A—H22A | 121.0 |
N3A—C10A—H10B | 109.2 | C3B—C4B—C5B | 116.4 (2) |
C9A—C10A—H10B | 109.2 | C3B—C4B—H4B | 121.8 |
H10A—C10A—H10B | 107.9 | C5B—C4B—H4B | 121.8 |
N3B—C10B—C9B | 111.96 (17) | F2B—C5B—C6B | 118.9 (3) |
N3B—C10B—10B1 | 109.2 | F2B—C5B—C4B | 118.2 (3) |
C9B—C10B—10B1 | 109.2 | C6B—C5B—C4B | 122.9 (3) |
N3B—C10B—10B2 | 109.2 | C5B—C6B—C1B | 118.6 (2) |
C9B—C10B—10B2 | 109.2 | C5B—C6B—H6B | 120.7 |
10B1—C10B—10B2 | 107.9 | C1B—C6B—H6B | 120.7 |
C10B—C9B—C8B | 107.62 (19) | C2B—C1B—C6B | 120.1 (2) |
C10B—C9B—C12B | 111.28 (19) | C2B—C1B—C7B | 122.5 (2) |
C8B—C9B—C12B | 111.53 (19) | C6B—C1B—C7B | 117.3 (2) |
C10B—C9B—C11B | 108.35 (19) | O1B—C7B—N1B | 121.2 (2) |
C8B—C9B—C11B | 108.9 (2) | O1B—C7B—C1B | 121.29 (19) |
C12B—C9B—C11B | 109.1 (2) | N1B—C7B—C1B | 117.46 (19) |
F2A—C5A—C6A | 118.5 (3) | C7B—N1B—P1B | 122.37 (16) |
F2A—C5A—C4A | 117.8 (3) | C7B—N1B—H1B | 121.2 (18) |
C6A—C5A—C4A | 123.7 (3) | P1B—N1B—H1B | 116.3 (17) |
C5A—C6A—C1A | 118.3 (3) | C9B—C11B—H11D | 109.5 |
C5A—C6A—H6A | 120.9 | C9B—C11B—H11E | 109.5 |
C1A—C6A—H6A | 120.9 | H11D—C11B—H11E | 109.5 |
C2A—C1A—C6A | 119.9 (2) | C9B—C11B—H11F | 109.5 |
C2A—C1A—C7A | 123.3 (2) | H11D—C11B—H11F | 109.5 |
C6A—C1A—C7A | 116.7 (2) | H11E—C11B—H11F | 109.5 |
O1A—C7A—N1A | 120.8 (2) | C9B—C12B—H12D | 109.5 |
O1A—C7A—C1A | 120.55 (19) | C9B—C12B—H12E | 109.5 |
N1A—C7A—C1A | 118.63 (19) | H12D—C12B—H12E | 109.5 |
C7A—N1A—P1A | 121.58 (16) | C9B—C12B—H12F | 109.5 |
C7A—N1A—H1A | 124 (2) | H12D—C12B—H12F | 109.5 |
P1A—N1A—H1A | 115 (2) | H12E—C12B—H12F | 109.5 |
C8A—C9A—C10A | 108.12 (18) | N2B—C8B—C9B | 112.32 (18) |
C8A—C9A—C12A | 111.7 (2) | N2B—C8B—H8C | 109.1 |
C10A—C9A—C12A | 110.93 (19) | C9B—C8B—H8C | 109.1 |
C8A—C9A—C11A | 108.7 (2) | N2B—C8B—H8D | 109.1 |
C10A—C9A—C11A | 108.2 (2) | C9B—C8B—H8D | 109.1 |
C12A—C9A—C11A | 109.2 (2) | H8C—C8B—H8D | 107.9 |
C9A—C11A—H11A | 109.5 | F1B—C3B—C4B | 117.8 (2) |
C9A—C11A—H11B | 109.5 | F1B—C3B—C2B | 118.5 (2) |
H11A—C11A—H11B | 109.5 | C4B—C3B—C2B | 123.7 (2) |
C9A—C11A—H11C | 109.5 | C3B—C2B—C1B | 118.1 (2) |
H11A—C11A—H11C | 109.5 | C3B—C2B—H22B | 120.9 |
H11B—C11A—H11C | 109.5 | C1B—C2B—H22B | 120.9 |
| | | |
O2A—P1A—N3A—C10A | 141.51 (18) | C12A—C9A—C8A—N2A | 64.0 (3) |
N2A—P1A—N3A—C10A | 16.5 (2) | C11A—C9A—C8A—N2A | −175.5 (2) |
N1A—P1A—N3A—C10A | −100.8 (2) | F2A—C5A—C4A—C3A | −179.0 (4) |
O2B—P1B—N3B—C10B | −135.06 (18) | C6A—C5A—C4A—C3A | 2.4 (6) |
N2B—P1B—N3B—C10B | −9.0 (2) | C5A—C4A—C3A—F1A | 179.2 (3) |
N1B—P1B—N3B—C10B | 107.52 (19) | C5A—C4A—C3A—C2A | −1.2 (6) |
O2B—P1B—N2B—C8B | 131.13 (19) | C4A—C3A—C2A—C1A | −0.8 (5) |
N3B—P1B—N2B—C8B | 6.1 (2) | F1A—C3A—C2A—C1A | 178.8 (3) |
N1B—P1B—N2B—C8B | −111.7 (2) | C6A—C1A—C2A—C3A | 1.7 (4) |
P1A—N3A—C10A—C9A | −41.1 (3) | C7A—C1A—C2A—C3A | −176.7 (3) |
P1B—N3B—C10B—C9B | 38.3 (3) | C3B—C4B—C5B—F2B | 179.2 (3) |
N3B—C10B—C9B—C8B | −61.2 (2) | C3B—C4B—C5B—C6B | −0.8 (5) |
N3B—C10B—C9B—C12B | 61.3 (3) | F2B—C5B—C6B—C1B | −178.3 (3) |
N3B—C10B—C9B—C11B | −178.8 (2) | C4B—C5B—C6B—C1B | 1.6 (5) |
F2A—C5A—C6A—C1A | 179.8 (4) | C5B—C6B—C1B—C2B | −0.8 (4) |
C4A—C5A—C6A—C1A | −1.5 (6) | C5B—C6B—C1B—C7B | 179.6 (3) |
C5A—C6A—C1A—C2A | −0.6 (5) | C2B—C1B—C7B—O1B | −157.1 (2) |
C5A—C6A—C1A—C7A | 177.9 (3) | C6B—C1B—C7B—O1B | 22.5 (4) |
C2A—C1A—C7A—O1A | 156.0 (3) | C2B—C1B—C7B—N1B | 24.0 (3) |
C6A—C1A—C7A—O1A | −22.5 (4) | C6B—C1B—C7B—N1B | −156.4 (2) |
C2A—C1A—C7A—N1A | −24.3 (4) | O1B—C7B—N1B—P1B | −1.3 (4) |
C6A—C1A—C7A—N1A | 157.3 (3) | C1B—C7B—N1B—P1B | 177.63 (17) |
O1A—C7A—N1A—P1A | 0.7 (4) | O2B—P1B—N1B—C7B | −174.2 (2) |
C1A—C7A—N1A—P1A | −179.06 (18) | N3B—P1B—N1B—C7B | −51.3 (2) |
O2A—P1A—N1A—C7A | 175.5 (2) | N2B—P1B—N1B—C7B | 62.0 (2) |
N3A—P1A—N1A—C7A | 52.2 (2) | P1B—N2B—C8B—C9B | −32.3 (3) |
N2A—P1A—N1A—C7A | −61.0 (2) | C10B—C9B—C8B—N2B | 58.2 (2) |
N3A—C10A—C9A—C8A | 59.2 (2) | C12B—C9B—C8B—N2B | −64.1 (3) |
N3A—C10A—C9A—C12A | −63.6 (2) | C11B—C9B—C8B—N2B | 175.5 (2) |
N3A—C10A—C9A—C11A | 176.7 (2) | C5B—C4B—C3B—F1B | −179.7 (3) |
O2A—P1A—N2A—C8A | −139.68 (19) | C5B—C4B—C3B—C2B | −0.9 (4) |
N3A—P1A—N2A—C8A | −15.2 (2) | F1B—C3B—C2B—C1B | −179.6 (2) |
N1A—P1A—N2A—C8A | 103.0 (2) | C4B—C3B—C2B—C1B | 1.6 (4) |
P1A—N2A—C8A—C9A | 38.7 (3) | C6B—C1B—C2B—C3B | −0.7 (4) |
C10A—C9A—C8A—N2A | −58.3 (2) | C7B—C1B—C2B—C3B | 178.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O2Bi | 0.82 (3) | 2.14 (3) | 2.957 (2) | 172 (2) |
N1A—H1A···O2Ai | 0.80 (3) | 2.15 (3) | 2.955 (3) | 175 (3) |
N2A—H2A···O2Bi | 0.73 (3) | 2.47 (3) | 3.165 (3) | 161 (3) |
N3A—H3A···O2Bii | 0.72 (2) | 2.72 (3) | 3.412 (3) | 164 (3) |
N3B—H3B···O2Ai | 0.86 | 2.54 | 3.374 (3) | 163 |
N2B—H2B···O2Aiii | 0.86 | 2.31 | 3.160 (3) | 170 |
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+2, y+1, −z+1/2; (iii) −x+2, y−1, −z+1/2. |
Crystal data top
C23H24F2N3O2P | Z = 2 |
Mr = 443.42 | F(000) = 464 |
Triclinic, P1 | Dx = 1.375 Mg m−3 |
a = 10.2700 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.7913 (7) Å | Cell parameters from 4282 reflections |
c = 11.0678 (5) Å | θ = 3.1–27.7° |
α = 99.789 (4)° | µ = 0.17 mm−1 |
β = 92.876 (4)° | T = 120 K |
γ = 116.470 (6)° | Block, colourless |
V = 1070.94 (12) Å3 | 0.40 × 0.30 × 0.30 mm |
Data collection top
AFC11 (Right) Eulerian three-circle CCD diffractometer | 3058 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.013 |
Profile data from ω–scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2009 | h = −12→11 |
Tmin = 0.997, Tmax = 1.000 | k = −12→12 |
7063 measured reflections | l = −13→8 |
3754 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0407P)2 + 0.1338P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3754 reflections | Δρmax = 0.22 e Å−3 |
286 parameters | Δρmin = −0.39 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.36505 (4) | 0.26271 (4) | 0.47764 (4) | 0.01571 (11) | |
F1 | 0.70213 (9) | 0.49484 (9) | 0.27329 (8) | 0.0239 (2) | |
F2 | 0.98183 (10) | 0.64639 (9) | 0.24439 (9) | 0.0322 (2) | |
O1 | 0.31856 (11) | 0.37369 (10) | 0.47638 (9) | 0.0185 (2) | |
O2 | 0.55518 (12) | 0.12461 (10) | 0.38060 (10) | 0.0256 (3) | |
N1 | 0.53695 (13) | 0.32783 (13) | 0.44049 (12) | 0.0172 (3) | |
N2 | 0.25178 (13) | 0.11614 (12) | 0.38006 (11) | 0.0181 (3) | |
N3 | 0.37734 (13) | 0.22192 (13) | 0.61179 (11) | 0.0196 (3) | |
C1 | 0.60742 (16) | 0.25295 (15) | 0.39308 (14) | 0.0179 (3) | |
C2 | 0.75909 (16) | 0.33708 (15) | 0.36318 (13) | 0.0172 (3) | |
C3 | 0.80096 (16) | 0.45415 (15) | 0.31051 (13) | 0.0180 (3) | |
C4 | 0.94512 (17) | 0.52954 (16) | 0.29208 (14) | 0.0220 (4) | |
C5 | 1.04972 (17) | 0.48984 (17) | 0.32210 (14) | 0.0252 (4) | |
H5A | 1.148232 | 0.542471 | 0.308252 | 0.030* | |
C6 | 1.00925 (17) | 0.37119 (17) | 0.37318 (14) | 0.0247 (4) | |
H6A | 1.080212 | 0.341839 | 0.394754 | 0.030* | |
C7 | 0.86559 (17) | 0.29603 (16) | 0.39253 (14) | 0.0213 (4) | |
H7A | 0.838628 | 0.214349 | 0.426662 | 0.026* | |
C8 | 0.22624 (18) | −0.02467 (15) | 0.39440 (15) | 0.0243 (4) | |
H8A | 0.247139 | −0.072804 | 0.320319 | 0.036* | |
H8B | 0.123516 | −0.080040 | 0.405388 | 0.036* | |
H8C | 0.290921 | −0.015632 | 0.467116 | 0.036* | |
C9 | 0.16886 (17) | 0.11705 (16) | 0.26830 (14) | 0.0220 (3) | |
H9A | 0.190713 | 0.216054 | 0.267836 | 0.026* | |
H9B | 0.062472 | 0.063128 | 0.272067 | 0.026* | |
C10 | 0.20293 (17) | 0.05434 (15) | 0.14876 (14) | 0.0206 (3) | |
C11 | 0.34135 (18) | 0.12064 (17) | 0.11339 (15) | 0.0266 (4) | |
H11A | 0.415897 | 0.204230 | 0.166298 | 0.032* | |
C12 | 0.3721 (2) | 0.06671 (19) | 0.00240 (16) | 0.0355 (4) | |
H12A | 0.467239 | 0.113366 | −0.020531 | 0.043* | |
C13 | 0.2646 (2) | −0.0552 (2) | −0.07556 (16) | 0.0382 (5) | |
H13A | 0.285506 | −0.091978 | −0.152172 | 0.046* | |
C14 | 0.1274 (2) | −0.12260 (18) | −0.04133 (16) | 0.0359 (5) | |
H14A | 0.053434 | −0.206540 | −0.094301 | 0.043* | |
C15 | 0.09655 (19) | −0.06844 (16) | 0.07036 (15) | 0.0279 (4) | |
H15A | 0.001568 | −0.115971 | 0.093344 | 0.033* | |
C16 | 0.24734 (18) | 0.17971 (17) | 0.67572 (15) | 0.0283 (4) | |
H16A | 0.276031 | 0.232980 | 0.761850 | 0.042* | |
H16B | 0.204300 | 0.077996 | 0.674070 | 0.042* | |
H16C | 0.174870 | 0.199974 | 0.633953 | 0.042* | |
C17 | 0.49627 (17) | 0.20230 (16) | 0.66890 (14) | 0.0214 (3) | |
H17A | 0.559237 | 0.196199 | 0.605662 | 0.026* | |
H17B | 0.453124 | 0.110857 | 0.695608 | 0.026* | |
C18 | 0.59173 (16) | 0.31878 (15) | 0.77931 (14) | 0.0184 (3) | |
C19 | 0.59605 (18) | 0.45063 (16) | 0.80117 (15) | 0.0258 (4) | |
H19A | 0.534409 | 0.469058 | 0.747898 | 0.031* | |
C20 | 0.6899 (2) | 0.55614 (17) | 0.90044 (16) | 0.0361 (5) | |
H20A | 0.691358 | 0.646123 | 0.915327 | 0.043* | |
C21 | 0.7811 (2) | 0.53126 (18) | 0.97777 (17) | 0.0392 (5) | |
H21A | 0.845947 | 0.604175 | 1.045170 | 0.047* | |
C22 | 0.77784 (19) | 0.40047 (19) | 0.95687 (16) | 0.0329 (4) | |
H22A | 0.840847 | 0.383127 | 1.009666 | 0.040* | |
C23 | 0.68304 (17) | 0.29437 (17) | 0.85921 (14) | 0.0242 (4) | |
H23A | 0.679960 | 0.203733 | 0.846277 | 0.029* | |
H1N | 0.5826 (18) | 0.4138 (18) | 0.4552 (15) | 0.024 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0133 (2) | 0.0134 (2) | 0.0192 (2) | 0.00555 (16) | 0.00269 (15) | 0.00200 (15) |
F1 | 0.0232 (5) | 0.0272 (5) | 0.0275 (5) | 0.0154 (4) | 0.0048 (4) | 0.0101 (4) |
F2 | 0.0300 (6) | 0.0274 (5) | 0.0333 (6) | 0.0053 (4) | 0.0091 (4) | 0.0130 (4) |
O1 | 0.0153 (6) | 0.0152 (5) | 0.0243 (6) | 0.0074 (4) | 0.0022 (4) | 0.0018 (4) |
O2 | 0.0246 (6) | 0.0161 (6) | 0.0375 (7) | 0.0103 (5) | 0.0094 (5) | 0.0049 (5) |
N1 | 0.0142 (7) | 0.0101 (6) | 0.0250 (7) | 0.0046 (6) | 0.0036 (5) | 0.0012 (5) |
N2 | 0.0174 (7) | 0.0146 (6) | 0.0200 (7) | 0.0058 (5) | 0.0010 (5) | 0.0026 (5) |
N3 | 0.0171 (7) | 0.0209 (7) | 0.0203 (7) | 0.0081 (5) | 0.0037 (5) | 0.0049 (5) |
C1 | 0.0187 (8) | 0.0178 (8) | 0.0188 (8) | 0.0100 (7) | 0.0016 (6) | 0.0038 (6) |
C2 | 0.0167 (8) | 0.0174 (7) | 0.0150 (8) | 0.0077 (6) | 0.0020 (6) | −0.0019 (6) |
C3 | 0.0176 (8) | 0.0211 (8) | 0.0164 (8) | 0.0113 (7) | 0.0008 (6) | 0.0004 (6) |
C4 | 0.0224 (9) | 0.0204 (8) | 0.0173 (8) | 0.0053 (7) | 0.0034 (7) | 0.0020 (6) |
C5 | 0.0149 (8) | 0.0336 (9) | 0.0196 (8) | 0.0071 (7) | 0.0038 (7) | −0.0021 (7) |
C6 | 0.0212 (9) | 0.0355 (9) | 0.0204 (8) | 0.0185 (8) | 0.0006 (7) | −0.0017 (7) |
C7 | 0.0241 (9) | 0.0235 (8) | 0.0200 (8) | 0.0147 (7) | 0.0044 (7) | 0.0026 (7) |
C8 | 0.0258 (9) | 0.0147 (8) | 0.0275 (9) | 0.0056 (7) | 0.0032 (7) | 0.0037 (7) |
C9 | 0.0187 (8) | 0.0225 (8) | 0.0236 (9) | 0.0098 (7) | 0.0002 (7) | 0.0021 (7) |
C10 | 0.0246 (9) | 0.0192 (8) | 0.0205 (8) | 0.0129 (7) | 0.0001 (7) | 0.0037 (6) |
C11 | 0.0289 (10) | 0.0260 (9) | 0.0263 (9) | 0.0135 (7) | 0.0033 (7) | 0.0066 (7) |
C12 | 0.0432 (11) | 0.0423 (11) | 0.0323 (10) | 0.0261 (9) | 0.0159 (9) | 0.0150 (9) |
C13 | 0.0643 (14) | 0.0444 (11) | 0.0209 (9) | 0.0382 (11) | 0.0084 (9) | 0.0060 (8) |
C14 | 0.0538 (13) | 0.0274 (9) | 0.0248 (9) | 0.0218 (9) | −0.0083 (9) | −0.0035 (8) |
C15 | 0.0295 (10) | 0.0249 (9) | 0.0267 (9) | 0.0120 (8) | −0.0016 (7) | 0.0027 (7) |
C16 | 0.0228 (9) | 0.0329 (9) | 0.0274 (9) | 0.0093 (8) | 0.0091 (7) | 0.0108 (8) |
C17 | 0.0252 (9) | 0.0210 (8) | 0.0220 (8) | 0.0140 (7) | 0.0036 (7) | 0.0052 (7) |
C18 | 0.0168 (8) | 0.0217 (8) | 0.0186 (8) | 0.0087 (6) | 0.0072 (6) | 0.0080 (6) |
C19 | 0.0284 (9) | 0.0241 (8) | 0.0251 (9) | 0.0128 (7) | −0.0017 (7) | 0.0056 (7) |
C20 | 0.0484 (12) | 0.0204 (9) | 0.0332 (10) | 0.0127 (8) | −0.0056 (9) | 0.0021 (8) |
C21 | 0.0440 (12) | 0.0286 (10) | 0.0287 (10) | 0.0059 (9) | −0.0125 (8) | 0.0025 (8) |
C22 | 0.0290 (10) | 0.0401 (10) | 0.0287 (10) | 0.0137 (8) | −0.0027 (8) | 0.0132 (8) |
C23 | 0.0265 (9) | 0.0270 (9) | 0.0246 (9) | 0.0152 (7) | 0.0077 (7) | 0.0105 (7) |
Geometric parameters (Å, º) top
P1—O1 | 1.4756 (10) | C10—C15 | 1.388 (2) |
P1—N3 | 1.6331 (13) | C10—C11 | 1.389 (2) |
P1—N2 | 1.6353 (12) | C11—C12 | 1.381 (2) |
P1—N1 | 1.6866 (13) | C11—H11A | 0.9500 |
F1—C3 | 1.3452 (17) | C12—C13 | 1.385 (3) |
F2—C4 | 1.3540 (17) | C12—H12A | 0.9500 |
O2—C1 | 1.2207 (17) | C13—C14 | 1.376 (3) |
N1—C1 | 1.3665 (19) | C13—H13A | 0.9500 |
N1—H1N | 0.812 (16) | C14—C15 | 1.389 (2) |
N2—C8 | 1.4607 (18) | C14—H14A | 0.9500 |
N2—C9 | 1.4701 (19) | C15—H15A | 0.9500 |
N3—C17 | 1.4610 (19) | C16—H16A | 0.9800 |
N3—C16 | 1.467 (2) | C16—H16B | 0.9800 |
C1—C2 | 1.501 (2) | C16—H16C | 0.9800 |
C2—C3 | 1.383 (2) | C17—C18 | 1.514 (2) |
C2—C7 | 1.394 (2) | C17—H17A | 0.9900 |
C3—C4 | 1.381 (2) | C17—H17B | 0.9900 |
C4—C5 | 1.368 (2) | C18—C19 | 1.382 (2) |
C5—C6 | 1.388 (2) | C18—C23 | 1.395 (2) |
C5—H5A | 0.9500 | C19—C20 | 1.386 (2) |
C6—C7 | 1.380 (2) | C19—H19A | 0.9500 |
C6—H6A | 0.9500 | C20—C21 | 1.380 (2) |
C7—H7A | 0.9500 | C20—H20A | 0.9500 |
C8—H8A | 0.9800 | C21—C22 | 1.376 (2) |
C8—H8B | 0.9800 | C21—H21A | 0.9500 |
C8—H8C | 0.9800 | C22—C23 | 1.381 (2) |
C9—C10 | 1.511 (2) | C22—H22A | 0.9500 |
C9—H9A | 0.9900 | C23—H23A | 0.9500 |
C9—H9B | 0.9900 | | |
| | | |
O1—P1—N3 | 115.48 (6) | C15—C10—C11 | 118.35 (15) |
O1—P1—N2 | 110.62 (6) | C15—C10—C9 | 121.14 (14) |
N3—P1—N2 | 107.01 (6) | C11—C10—C9 | 120.50 (13) |
O1—P1—N1 | 106.62 (6) | C12—C11—C10 | 120.92 (16) |
N3—P1—N1 | 105.31 (6) | C12—C11—H11A | 119.5 |
N2—P1—N1 | 111.75 (6) | C10—C11—H11A | 119.5 |
C1—N1—P1 | 127.48 (11) | C11—C12—C13 | 120.18 (17) |
C1—N1—H1N | 117.6 (12) | C11—C12—H12A | 119.9 |
P1—N1—H1N | 114.9 (12) | C13—C12—H12A | 119.9 |
C8—N2—C9 | 114.57 (12) | C14—C13—C12 | 119.56 (17) |
C8—N2—P1 | 123.63 (10) | C14—C13—H13A | 120.2 |
C9—N2—P1 | 121.79 (10) | C12—C13—H13A | 120.2 |
C17—N3—C16 | 114.58 (12) | C13—C14—C15 | 120.25 (16) |
C17—N3—P1 | 127.21 (10) | C13—C14—H14A | 119.9 |
C16—N3—P1 | 117.58 (11) | C15—C14—H14A | 119.9 |
O2—C1—N1 | 122.86 (14) | C10—C15—C14 | 120.73 (16) |
O2—C1—C2 | 120.27 (13) | C10—C15—H15A | 119.6 |
N1—C1—C2 | 116.77 (12) | C14—C15—H15A | 119.6 |
C3—C2—C7 | 117.78 (14) | N3—C16—H16A | 109.5 |
C3—C2—C1 | 124.39 (13) | N3—C16—H16B | 109.5 |
C7—C2—C1 | 117.82 (13) | H16A—C16—H16B | 109.5 |
F1—C3—C4 | 118.64 (13) | N3—C16—H16C | 109.5 |
F1—C3—C2 | 120.96 (13) | H16A—C16—H16C | 109.5 |
C4—C3—C2 | 120.38 (14) | H16B—C16—H16C | 109.5 |
F2—C4—C5 | 120.14 (14) | N3—C17—C18 | 114.43 (12) |
F2—C4—C3 | 118.16 (14) | N3—C17—H17A | 108.7 |
C5—C4—C3 | 121.69 (14) | C18—C17—H17A | 108.7 |
C4—C5—C6 | 118.76 (15) | N3—C17—H17B | 108.7 |
C4—C5—H5A | 120.6 | C18—C17—H17B | 108.7 |
C6—C5—H5A | 120.6 | H17A—C17—H17B | 107.6 |
C7—C6—C5 | 119.78 (15) | C19—C18—C23 | 118.67 (14) |
C7—C6—H6A | 120.1 | C19—C18—C17 | 122.31 (13) |
C5—C6—H6A | 120.1 | C23—C18—C17 | 118.97 (14) |
C6—C7—C2 | 121.58 (14) | C18—C19—C20 | 120.34 (15) |
C6—C7—H7A | 119.2 | C18—C19—H19A | 119.8 |
C2—C7—H7A | 119.2 | C20—C19—H19A | 119.8 |
N2—C8—H8A | 109.5 | C21—C20—C19 | 120.42 (16) |
N2—C8—H8B | 109.5 | C21—C20—H20A | 119.8 |
H8A—C8—H8B | 109.5 | C19—C20—H20A | 119.8 |
N2—C8—H8C | 109.5 | C22—C21—C20 | 119.75 (16) |
H8A—C8—H8C | 109.5 | C22—C21—H21A | 120.1 |
H8B—C8—H8C | 109.5 | C20—C21—H21A | 120.1 |
N2—C9—C10 | 113.86 (12) | C21—C22—C23 | 120.06 (16) |
N2—C9—H9A | 108.8 | C21—C22—H22A | 120.0 |
C10—C9—H9A | 108.8 | C23—C22—H22A | 120.0 |
N2—C9—H9B | 108.8 | C22—C23—C18 | 120.75 (15) |
C10—C9—H9B | 108.8 | C22—C23—H23A | 119.6 |
H9A—C9—H9B | 107.7 | C18—C23—H23A | 119.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.812 (16) | 2.030 (17) | 2.8316 (16) | 168.9 (16) |
N1—H1N···F1 | 0.812 (16) | 2.493 (16) | 2.8765 (15) | 110.2 (14) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Crystal data top
C23H25ClN3O2P | Z = 1 |
Mr = 441.9 | F(000) = 232 |
Triclinic, P1 | Dx = 1.317 Mg m−3 |
Hall symbol: P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 4.8880 (3) Å | Cell parameters from 7454 reflections |
b = 10.5428 (5) Å | θ = 4.3–67.2° |
c = 11.2104 (6) Å | µ = 2.39 mm−1 |
α = 99.273 (4)° | T = 120 K |
β = 100.628 (5)° | Prism, colourless |
γ = 94.226 (4)° | 0.42 × 0.16 × 0.03 mm |
V = 557.18 (5) Å3 | |
Data collection top
Rigaku Xcalibur AtlasS2 Gemini ultra diffractometer | 3835 independent reflections |
Radiation source: X-ray tube | 3703 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.042 |
Detector resolution: 5.1783 pixels mm-1 | θmax = 67.2°, θmin = 4.1° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −12→12 |
Tmin = 0.232, Tmax = 1 | l = −13→13 |
9772 measured reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.041 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.104 | (Δ/σ)max = 0.028 |
S = 1.59 | Δρmax = 0.31 e Å−3 |
3835 reflections | Δρmin = −0.32 e Å−3 |
233 parameters | Absolute structure: 1847 of Friedel pairs used in the refinement |
3 restraints | Absolute structure parameter: −0.017 (16) |
56 constraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.2756 (4) | 0.30895 (10) | 0.79676 (9) | 0.0436 (3) | |
P1 | −0.0964 (4) | 0.73248 (9) | 0.62271 (7) | 0.01454 (17) | |
O1 | −0.3626 (5) | 0.79062 (17) | 0.62328 (17) | 0.0197 (5) | |
O2 | 0.2390 (5) | 0.5078 (2) | 0.6241 (2) | 0.0349 (7) | |
N1 | −0.1907 (5) | 0.57273 (19) | 0.6219 (2) | 0.0185 (6) | |
N2 | 0.1566 (6) | 0.7907 (2) | 0.7383 (2) | 0.0189 (6) | |
N3 | 0.0474 (5) | 0.7460 (2) | 0.5056 (2) | 0.0192 (6) | |
C1 | −0.0105 (6) | 0.4808 (3) | 0.6203 (3) | 0.0216 (8) | |
C2 | −0.1380 (6) | 0.3447 (2) | 0.6102 (3) | 0.0235 (8) | |
C3 | −0.0199 (7) | 0.2592 (3) | 0.6821 (3) | 0.0288 (9) | |
C4 | −0.1428 (8) | 0.1326 (3) | 0.6669 (3) | 0.0353 (10) | |
C5 | −0.3822 (8) | 0.0907 (3) | 0.5810 (3) | 0.0398 (11) | |
C6 | −0.5067 (8) | 0.1745 (3) | 0.5087 (3) | 0.0392 (10) | |
C7 | −0.3834 (7) | 0.3000 (3) | 0.5228 (3) | 0.0302 (9) | |
H1c4 | −0.058587 | 0.074563 | 0.716978 | 0.0423* | |
H1c5 | −0.465026 | 0.003175 | 0.570551 | 0.0478* | |
H1c6 | −0.676998 | 0.145474 | 0.449295 | 0.0471* | |
H1c7 | −0.467746 | 0.357167 | 0.471774 | 0.0362* | |
H1n1 | −0.3637 (18) | 0.545 (3) | 0.615 (3) | 0.0222* | |
H1n2 | 0.320 (3) | 0.784 (3) | 0.721 (3) | 0.0227* | |
H1n3 | 0.2274 (6) | 0.756 (3) | 0.520 (3) | 0.023* | |
C8a | −0.1004 (8) | 0.7305 (4) | 0.3808 (3) | 0.0232 (8) | 0.569 (6) |
C9a | −0.0514 (14) | 0.8558 (5) | 0.3310 (5) | 0.0359 (11) | 0.569 (6) |
C10a | −0.0353 (11) | 0.6149 (5) | 0.2949 (5) | 0.0229 (7) | 0.569 (6) |
C11a | 0.1881 (14) | 0.5455 (6) | 0.3263 (5) | 0.0284 (10) | 0.569 (6) |
C12a | 0.2445 (18) | 0.4428 (7) | 0.2423 (6) | 0.0437 (14) | 0.569 (6) |
C13a | 0.0773 (19) | 0.4106 (7) | 0.1252 (6) | 0.0425 (11) | 0.569 (6) |
C14a | −0.1463 (18) | 0.4771 (8) | 0.0947 (6) | 0.0460 (14) | 0.569 (6) |
C15a | −0.2020 (14) | 0.5795 (7) | 0.1778 (5) | 0.0389 (13) | 0.569 (6) |
H1c8a | −0.310 (6) | 0.715 (3) | 0.387 (3) | 0.026 (7)* | 0.569 (6) |
H1c9a | −0.093869 | 0.927341 | 0.386787 | 0.0431* | 0.569 (6) |
H2c9a | 0.140801 | 0.868986 | 0.323692 | 0.0431* | 0.569 (6) |
H3c9a | −0.170438 | 0.849475 | 0.251521 | 0.0431* | 0.569 (6) |
H1c11a | 0.305803 | 0.568218 | 0.406847 | 0.0341* | 0.569 (6) |
H1c12a | 0.398662 | 0.394519 | 0.265486 | 0.0524* | 0.569 (6) |
H1c13a | 0.119016 | 0.341957 | 0.0661 | 0.051* | 0.569 (6) |
H1c14a | −0.266504 | 0.452773 | 0.014897 | 0.0552* | 0.569 (6) |
H1c15a | −0.357868 | 0.626628 | 0.154057 | 0.0467* | 0.569 (6) |
C8b | −0.1211 (17) | 0.7536 (5) | 0.3800 (6) | 0.0232 (8) | 0.431 (6) |
C9b | −0.010 (3) | 0.8828 (6) | 0.3512 (10) | 0.0359 (11) | 0.431 (6) |
C10b | −0.0782 (11) | 0.6412 (5) | 0.2846 (4) | 0.0229 (7) | 0.431 (6) |
C11b | 0.1058 (17) | 0.5514 (8) | 0.3112 (7) | 0.0284 (10) | 0.431 (6) |
C12b | 0.145 (3) | 0.4524 (10) | 0.2191 (11) | 0.0437 (14) | 0.431 (6) |
C13b | 0.000 (3) | 0.4445 (10) | 0.0989 (10) | 0.0425 (11) | 0.431 (6) |
C14b | −0.185 (3) | 0.5312 (12) | 0.0727 (8) | 0.0460 (14) | 0.431 (6) |
C15b | −0.223 (2) | 0.6299 (9) | 0.1639 (6) | 0.0389 (13) | 0.431 (6) |
H1c8b | −0.335 (7) | 0.752 (3) | 0.378 (3) | 0.026 (7)* | 0.431 (6) |
H1c9b | −0.039106 | 0.952264 | 0.412648 | 0.0431* | 0.431 (6) |
H2c9b | 0.186953 | 0.883339 | 0.351414 | 0.0431* | 0.431 (6) |
H3c9b | −0.106965 | 0.893569 | 0.27149 | 0.0431* | 0.431 (6) |
H1c11b | 0.20795 | 0.557196 | 0.394092 | 0.0341* | 0.431 (6) |
H1c12b | 0.271087 | 0.389883 | 0.23888 | 0.0524* | 0.431 (6) |
H1c13b | 0.03119 | 0.378343 | 0.034579 | 0.051* | 0.431 (6) |
H1c14b | −0.290642 | 0.523812 | −0.009803 | 0.0552* | 0.431 (6) |
H1c15b | −0.351625 | 0.691419 | 0.143383 | 0.0467* | 0.431 (6) |
C8c | 0.1484 (14) | 0.7811 (5) | 0.8705 (5) | 0.0232 (8) | 0.516 (5) |
C9c | 0.291 (3) | 0.6640 (6) | 0.9066 (9) | 0.0359 (12) | 0.516 (5) |
C10c | 0.2949 (11) | 0.9058 (5) | 0.9515 (4) | 0.0229 (8) | 0.516 (5) |
C11c | 0.4436 (16) | 0.9987 (7) | 0.9076 (7) | 0.0284 (11) | 0.516 (5) |
C12c | 0.583 (2) | 1.1097 (9) | 0.9869 (9) | 0.0437 (15) | 0.516 (5) |
C13c | 0.576 (3) | 1.1268 (10) | 1.1116 (9) | 0.0425 (12) | 0.516 (5) |
C14c | 0.425 (3) | 1.0368 (11) | 1.1548 (8) | 0.0460 (15) | 0.516 (5) |
C15c | 0.2874 (17) | 0.9262 (8) | 1.0764 (6) | 0.0389 (13) | 0.516 (5) |
H1c8c | −0.058 (7) | 0.773 (3) | 0.882 (3) | 0.026 (7)* | 0.516 (5) |
H1c9c | 0.194473 | 0.586433 | 0.854257 | 0.0431* | 0.516 (5) |
H2c9c | 0.482077 | 0.672792 | 0.897279 | 0.0431* | 0.516 (5) |
H3c9c | 0.284407 | 0.659602 | 0.990967 | 0.0431* | 0.516 (5) |
H1c11c | 0.451272 | 0.986705 | 0.821601 | 0.0341* | 0.516 (5) |
H1c12c | 0.683248 | 1.174129 | 0.955225 | 0.0524* | 0.516 (5) |
H1c13c | 0.676143 | 1.20156 | 1.16704 | 0.051* | 0.516 (5) |
H1c14c | 0.413384 | 1.050105 | 1.240433 | 0.0552* | 0.516 (5) |
H1c15c | 0.185763 | 0.862769 | 1.108738 | 0.0467* | 0.516 (5) |
C8d | 0.1212 (13) | 0.8087 (5) | 0.8633 (5) | 0.0232 (8) | 0.484 (5) |
C9d | 0.151 (2) | 0.6882 (6) | 0.9234 (8) | 0.0359 (12) | 0.484 (5) |
C10d | 0.2917 (11) | 0.9267 (5) | 0.9469 (5) | 0.0229 (8) | 0.484 (5) |
C11d | 0.5256 (15) | 0.9886 (7) | 0.9194 (7) | 0.0284 (11) | 0.484 (5) |
C12d | 0.681 (2) | 1.0940 (8) | 1.0015 (9) | 0.0437 (15) | 0.484 (5) |
C13d | 0.603 (3) | 1.1366 (8) | 1.1129 (8) | 0.0425 (12) | 0.484 (5) |
C14d | 0.369 (3) | 1.0775 (9) | 1.1392 (7) | 0.0460 (15) | 0.484 (5) |
C15d | 0.2155 (17) | 0.9724 (8) | 1.0581 (6) | 0.0389 (13) | 0.484 (5) |
H1c8d | −0.087 (7) | 0.828 (3) | 0.848 (3) | 0.026 (7)* | 0.484 (5) |
H1c9d | 0.041163 | 0.61505 | 0.86893 | 0.0431* | 0.484 (5) |
H2c9d | 0.343747 | 0.672305 | 0.939174 | 0.0431* | 0.484 (5) |
H3c9d | 0.085531 | 0.702027 | 0.999716 | 0.0431* | 0.484 (5) |
H1c11d | 0.581774 | 0.958679 | 0.842976 | 0.0341* | 0.484 (5) |
H1c12d | 0.841225 | 1.136987 | 0.980986 | 0.0524* | 0.484 (5) |
H1c13d | 0.712332 | 1.207205 | 1.170912 | 0.051* | 0.484 (5) |
H1c14d | 0.310716 | 1.109012 | 1.214742 | 0.0552* | 0.484 (5) |
H1c15d | 0.054154 | 0.930673 | 1.07905 | 0.0467* | 0.484 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0380 (4) | 0.0407 (4) | 0.0528 (5) | 0.0107 (3) | −0.0010 (4) | 0.0197 (3) |
P1 | 0.0122 (3) | 0.0133 (2) | 0.0185 (3) | 0.00186 (17) | 0.0037 (2) | 0.0030 (2) |
O1 | 0.0143 (8) | 0.0178 (7) | 0.0287 (10) | 0.0032 (6) | 0.0074 (7) | 0.0049 (6) |
O2 | 0.0168 (10) | 0.0314 (10) | 0.0645 (15) | 0.0085 (8) | 0.0153 (9) | 0.0210 (9) |
N1 | 0.0132 (10) | 0.0147 (9) | 0.0284 (11) | 0.0028 (7) | 0.0062 (9) | 0.0034 (8) |
N2 | 0.0172 (11) | 0.0213 (10) | 0.0180 (10) | −0.0010 (8) | 0.0042 (9) | 0.0037 (8) |
N3 | 0.0115 (9) | 0.0248 (10) | 0.0214 (11) | 0.0011 (7) | 0.0042 (8) | 0.0041 (8) |
C1 | 0.0166 (13) | 0.0223 (11) | 0.0286 (13) | 0.0040 (9) | 0.0077 (10) | 0.0079 (10) |
C2 | 0.0257 (13) | 0.0192 (12) | 0.0315 (14) | 0.0094 (10) | 0.0161 (11) | 0.0073 (10) |
C3 | 0.0282 (15) | 0.0287 (14) | 0.0355 (16) | 0.0110 (12) | 0.0153 (13) | 0.0098 (12) |
C4 | 0.0496 (18) | 0.0219 (13) | 0.0435 (17) | 0.0160 (12) | 0.0229 (15) | 0.0117 (11) |
C5 | 0.054 (2) | 0.0203 (13) | 0.0496 (19) | 0.0046 (12) | 0.0218 (16) | 0.0044 (12) |
C6 | 0.0501 (19) | 0.0242 (13) | 0.0393 (17) | −0.0019 (13) | 0.0075 (15) | −0.0020 (12) |
C7 | 0.0347 (15) | 0.0214 (12) | 0.0361 (15) | 0.0048 (10) | 0.0127 (12) | 0.0027 (11) |
C8a | 0.0259 (12) | 0.0271 (15) | 0.0189 (10) | 0.0120 (10) | 0.0022 (9) | 0.0099 (9) |
C9a | 0.056 (2) | 0.0297 (16) | 0.0225 (14) | 0.0084 (16) | 0.0035 (16) | 0.0081 (12) |
C10a | 0.0212 (11) | 0.0261 (12) | 0.0204 (10) | 0.0004 (9) | 0.0033 (9) | 0.0034 (9) |
C11a | 0.029 (2) | 0.0309 (11) | 0.0244 (13) | 0.0076 (13) | 0.0045 (12) | 0.0004 (9) |
C12a | 0.062 (3) | 0.0386 (14) | 0.0353 (17) | 0.0254 (18) | 0.0163 (17) | 0.0024 (12) |
C13a | 0.064 (2) | 0.0275 (13) | 0.0338 (14) | 0.0009 (13) | 0.0170 (15) | −0.0070 (10) |
C14a | 0.050 (2) | 0.051 (3) | 0.0263 (17) | −0.0076 (19) | −0.0008 (15) | −0.0092 (17) |
C15a | 0.0343 (16) | 0.051 (3) | 0.0269 (15) | 0.0090 (16) | −0.0019 (12) | 0.0006 (16) |
C8b | 0.0296 (12) | 0.0230 (16) | 0.0208 (9) | 0.0113 (10) | 0.0055 (8) | 0.0114 (9) |
C9b | 0.057 (2) | 0.0280 (17) | 0.0239 (14) | 0.0040 (16) | 0.0074 (15) | 0.0090 (12) |
C10b | 0.0210 (12) | 0.0268 (13) | 0.0203 (10) | 0.0015 (9) | 0.0032 (9) | 0.0043 (9) |
C11b | 0.031 (2) | 0.0305 (12) | 0.0235 (12) | 0.0086 (13) | 0.0051 (12) | 0.0017 (9) |
C12b | 0.067 (3) | 0.0336 (15) | 0.0359 (16) | 0.0212 (18) | 0.0200 (16) | 0.0024 (12) |
C13b | 0.060 (2) | 0.0320 (14) | 0.0314 (13) | −0.0038 (14) | 0.0156 (14) | −0.0093 (10) |
C14b | 0.049 (2) | 0.058 (3) | 0.0222 (16) | −0.004 (2) | −0.0020 (14) | −0.0047 (17) |
C15b | 0.0390 (17) | 0.051 (3) | 0.0255 (15) | 0.0133 (16) | 0.0000 (12) | 0.0056 (16) |
C8c | 0.0280 (14) | 0.0230 (15) | 0.0195 (9) | −0.0021 (11) | 0.0025 (9) | 0.0116 (9) |
C9c | 0.053 (3) | 0.0289 (17) | 0.0239 (14) | 0.0062 (17) | −0.0012 (15) | 0.0079 (12) |
C10c | 0.0217 (14) | 0.0269 (13) | 0.0201 (10) | 0.0033 (10) | 0.0046 (9) | 0.0036 (8) |
C11c | 0.030 (2) | 0.0284 (13) | 0.0241 (12) | −0.0038 (14) | 0.0042 (12) | 0.0017 (9) |
C12c | 0.053 (3) | 0.0292 (16) | 0.0394 (16) | −0.0138 (19) | −0.0057 (17) | 0.0033 (12) |
C13c | 0.050 (3) | 0.0297 (14) | 0.0370 (14) | 0.0043 (15) | −0.0051 (14) | −0.0105 (10) |
C14c | 0.053 (2) | 0.056 (3) | 0.0235 (16) | 0.008 (2) | 0.0074 (15) | −0.0084 (17) |
C15c | 0.043 (2) | 0.048 (3) | 0.0244 (14) | −0.0048 (18) | 0.0094 (13) | 0.0045 (15) |
C8d | 0.0241 (14) | 0.0284 (14) | 0.0185 (11) | −0.0044 (11) | 0.0076 (10) | 0.0084 (9) |
C9d | 0.055 (2) | 0.0305 (15) | 0.0226 (15) | −0.0022 (16) | 0.0094 (18) | 0.0069 (13) |
C10d | 0.0226 (13) | 0.0257 (12) | 0.0206 (11) | 0.0049 (10) | 0.0048 (10) | 0.0032 (9) |
C11d | 0.027 (2) | 0.0305 (11) | 0.0250 (13) | −0.0024 (13) | 0.0050 (14) | −0.0005 (9) |
C12d | 0.048 (4) | 0.0397 (13) | 0.0345 (18) | −0.0196 (18) | −0.0001 (19) | 0.0005 (12) |
C13d | 0.058 (3) | 0.0259 (12) | 0.0337 (15) | −0.0006 (14) | −0.0038 (16) | −0.0062 (10) |
C14d | 0.058 (2) | 0.047 (3) | 0.0293 (18) | 0.013 (2) | 0.0105 (17) | −0.0100 (17) |
C15d | 0.0367 (19) | 0.050 (3) | 0.0289 (16) | 0.0003 (17) | 0.0130 (14) | −0.0016 (16) |
Geometric parameters (Å, º) top
P1—O1 | 1.479 (3) | C9b—H3c9b | 0.96 |
P1—N1 | 1.711 (2) | C10b—C11b | 1.383 (10) |
P1—N2 | 1.621 (2) | C10b—C15b | 1.389 (9) |
P1—N3 | 1.620 (3) | C11b—C12b | 1.395 (14) |
O2—C1 | 1.223 (4) | C11b—H1c11b | 0.96 |
N1—C1 | 1.357 (4) | C12b—C13b | 1.388 (16) |
N1—H1n1 | 0.860 (12) | C12b—H1c12b | 0.96 |
N2—H1n2 | 0.860 (19) | C13b—C14b | 1.36 (2) |
N2—C8c | 1.509 (6) | C13b—H1c13b | 0.96 |
N2—C8d | 1.427 (6) | C14b—C15b | 1.385 (14) |
N3—H1n3 | 0.860 (4) | C14b—H1c14b | 0.96 |
N3—C8a | 1.429 (4) | C15b—H1c15b | 0.96 |
N3—C8b | 1.512 (7) | C8c—C9c | 1.534 (10) |
C1—C2 | 1.500 (4) | C8c—C10c | 1.518 (6) |
C2—C3 | 1.391 (4) | C8c—H1c8c | 1.04 (4) |
C2—C7 | 1.399 (4) | C9c—H1c9c | 0.96 |
C3—C4 | 1.394 (4) | C9c—H2c9c | 0.96 |
C4—C5 | 1.364 (5) | C9c—H3c9c | 0.96 |
C4—H1c4 | 0.96 | C10c—C11c | 1.383 (10) |
C5—C6 | 1.392 (5) | C10c—C15c | 1.389 (8) |
C5—H1c5 | 0.9601 | C11c—C12c | 1.395 (11) |
C6—C7 | 1.385 (4) | C11c—H1c11c | 0.96 |
C6—H1c6 | 0.96 | C12c—C13c | 1.388 (15) |
C7—H1c7 | 0.96 | C12c—H1c12c | 0.96 |
C8a—C9a | 1.534 (8) | C13c—C14c | 1.362 (17) |
C8a—C10a | 1.518 (7) | C13c—H1c13c | 0.96 |
C8a—H1c8a | 1.04 (3) | C14c—C15c | 1.385 (12) |
C9a—H1c9a | 0.96 | C14c—H1c14c | 0.96 |
C9a—H2c9a | 0.96 | C15c—H1c15c | 0.96 |
C9a—H3c9a | 0.96 | C8d—C9d | 1.534 (9) |
C10a—C11a | 1.383 (9) | C8d—C10d | 1.518 (6) |
C10a—C15a | 1.389 (7) | C8d—H1c8d | 1.04 (3) |
C11a—C12a | 1.395 (10) | C9d—H1c9d | 0.96 |
C11a—H1c11a | 0.96 | C9d—H2c9d | 0.96 |
C12a—C13a | 1.388 (10) | C9d—H3c9d | 0.96 |
C12a—H1c12a | 0.96 | C10d—C11d | 1.383 (10) |
C13a—C14a | 1.362 (12) | C10d—C15d | 1.389 (9) |
C13a—H1c13a | 0.96 | C11d—C12d | 1.395 (10) |
C14a—C15a | 1.385 (10) | C11d—H1c11d | 0.96 |
C14a—H1c14a | 0.96 | C12d—C13d | 1.388 (15) |
C15a—H1c15a | 0.96 | C12d—H1c12d | 0.96 |
C8b—C9b | 1.534 (11) | C13d—C14d | 1.362 (18) |
C8b—C10b | 1.518 (8) | C13d—H1c13d | 0.96 |
C8b—H1c8b | 1.04 (3) | C14d—C15d | 1.385 (11) |
C9b—H1c9b | 0.96 | C14d—H1c14d | 0.96 |
C9b—H2c9b | 0.96 | C15d—H1c15d | 0.96 |
| | | |
O1—P1—N1 | 103.07 (14) | H2c9b—C9b—H3c9b | 109.47 |
O1—P1—N2 | 115.74 (13) | C8b—C10b—C11b | 123.0 (5) |
O1—P1—N3 | 115.75 (13) | C8b—C10b—C15b | 118.7 (6) |
N1—P1—N2 | 110.60 (13) | C11b—C10b—C15b | 118.2 (6) |
N1—P1—N3 | 109.51 (12) | C10b—C11b—C12b | 120.8 (8) |
N2—P1—N3 | 102.26 (16) | C10b—C11b—H1c11b | 119.62 |
P1—N1—C1 | 124.0 (2) | C12b—C11b—H1c11b | 119.62 |
P1—N1—H1n1 | 120.3 (19) | C11b—C12b—C13b | 119.9 (11) |
C1—N1—H1n1 | 115.4 (18) | C11b—C12b—H1c12b | 120.06 |
P1—N2—H1n2 | 113.5 (19) | C13b—C12b—H1c12b | 120.06 |
P1—N2—C8c | 124.0 (3) | C12b—C13b—C14b | 119.5 (10) |
P1—N2—C8d | 122.8 (3) | C12b—C13b—H1c13b | 120.23 |
H1n2—N2—C8c | 113 (2) | C14b—C13b—H1c13b | 120.23 |
H1n2—N2—C8d | 120 (2) | C13b—C14b—C15b | 120.6 (9) |
P1—N3—H1n3 | 116 (2) | C13b—C14b—H1c14b | 119.68 |
P1—N3—C8a | 124.9 (2) | C15b—C14b—H1c14b | 119.68 |
P1—N3—C8b | 122.5 (4) | C10b—C15b—C14b | 120.9 (9) |
H1n3—N3—C8a | 119 (2) | C10b—C15b—H1c15b | 119.55 |
H1n3—N3—C8b | 121 (2) | C14b—C15b—H1c15b | 119.55 |
O2—C1—N1 | 121.6 (3) | N2—C8c—C9c | 110.5 (5) |
O2—C1—C2 | 122.5 (3) | N2—C8c—C10c | 107.9 (4) |
N1—C1—C2 | 115.8 (3) | N2—C8c—H1c8c | 110.0 (17) |
C1—C2—C3 | 123.0 (2) | C9c—C8c—C10c | 111.0 (5) |
C1—C2—C7 | 118.9 (3) | C9c—C8c—H1c8c | 110 (2) |
C3—C2—C7 | 118.1 (3) | C10c—C8c—H1c8c | 107.5 (17) |
C2—C3—C4 | 120.8 (3) | C8c—C9c—H1c9c | 109.47 |
C3—C4—C5 | 120.3 (3) | C8c—C9c—H2c9c | 109.47 |
C3—C4—H1c4 | 119.86 | C8c—C9c—H3c9c | 109.47 |
C5—C4—H1c4 | 119.85 | H1c9c—C9c—H2c9c | 109.47 |
C4—C5—C6 | 120.2 (3) | H1c9c—C9c—H3c9c | 109.47 |
C4—C5—H1c5 | 119.9 | H2c9c—C9c—H3c9c | 109.47 |
C6—C5—H1c5 | 119.89 | C8c—C10c—C11c | 123.0 (5) |
C5—C6—C7 | 119.6 (3) | C8c—C10c—C15c | 118.7 (6) |
C5—C6—H1c6 | 120.21 | C11c—C10c—C15c | 118.2 (5) |
C7—C6—H1c6 | 120.22 | C10c—C11c—C12c | 120.8 (7) |
C2—C7—C6 | 121.1 (3) | C10c—C11c—H1c11c | 119.62 |
C2—C7—H1c7 | 119.48 | C12c—C11c—H1c11c | 119.62 |
C6—C7—H1c7 | 119.47 | C11c—C12c—C13c | 119.9 (10) |
N3—C8a—C9a | 109.6 (3) | C11c—C12c—H1c12c | 120.06 |
N3—C8a—C10a | 114.8 (4) | C13c—C12c—H1c12c | 120.06 |
N3—C8a—H1c8a | 103.8 (16) | C12c—C13c—C14c | 119.5 (8) |
C9a—C8a—C10a | 111.0 (4) | C12c—C13c—H1c13c | 120.23 |
C9a—C8a—H1c8a | 109.8 (19) | C14c—C13c—H1c13c | 120.23 |
C10a—C8a—H1c8a | 107.5 (16) | C13c—C14c—C15c | 120.6 (8) |
C8a—C9a—H1c9a | 109.47 | C13c—C14c—H1c14c | 119.68 |
C8a—C9a—H2c9a | 109.47 | C15c—C14c—H1c14c | 119.68 |
C8a—C9a—H3c9a | 109.47 | C10c—C15c—C14c | 120.9 (8) |
H1c9a—C9a—H2c9a | 109.47 | C10c—C15c—H1c15c | 119.55 |
H1c9a—C9a—H3c9a | 109.47 | C14c—C15c—H1c15c | 119.55 |
H2c9a—C9a—H3c9a | 109.47 | N2—C8d—C9d | 114.5 (5) |
C8a—C10a—C11a | 123.0 (4) | N2—C8d—C10d | 115.0 (5) |
C8a—C10a—C15a | 118.7 (5) | N2—C8d—H1c8d | 97.9 (18) |
C11a—C10a—C15a | 118.2 (5) | C9d—C8d—C10d | 111.0 (5) |
C10a—C11a—C12a | 120.8 (5) | C9d—C8d—H1c8d | 110 (2) |
C10a—C11a—H1c11a | 119.62 | C10d—C8d—H1c8d | 107.5 (16) |
C12a—C11a—H1c11a | 119.62 | C8d—C9d—H1c9d | 109.47 |
C11a—C12a—C13a | 119.9 (7) | C8d—C9d—H2c9d | 109.47 |
C11a—C12a—H1c12a | 120.06 | C8d—C9d—H3c9d | 109.47 |
C13a—C12a—H1c12a | 120.06 | H1c9d—C9d—H2c9d | 109.47 |
C12a—C13a—C14a | 119.5 (7) | H1c9d—C9d—H3c9d | 109.47 |
C12a—C13a—H1c13a | 120.23 | H2c9d—C9d—H3c9d | 109.47 |
C14a—C13a—H1c13a | 120.23 | C8d—C10d—C11d | 123.0 (5) |
C13a—C14a—C15a | 120.6 (6) | C8d—C10d—C15d | 118.7 (6) |
C13a—C14a—H1c14a | 119.68 | C11d—C10d—C15d | 118.2 (5) |
C15a—C14a—H1c14a | 119.68 | C10d—C11d—C12d | 120.8 (8) |
C10a—C15a—C14a | 120.9 (6) | C10d—C11d—H1c11d | 119.62 |
C10a—C15a—H1c15a | 119.55 | C12d—C11d—H1c11d | 119.62 |
C14a—C15a—H1c15a | 119.55 | C11d—C12d—C13d | 119.9 (10) |
N3—C8b—C9b | 105.0 (6) | C11d—C12d—H1c12d | 120.06 |
N3—C8b—C10b | 110.5 (5) | C13d—C12d—H1c12d | 120.06 |
N3—C8b—H1c8b | 113.1 (18) | C12d—C13d—C14d | 119.5 (8) |
C9b—C8b—C10b | 111.0 (7) | C12d—C13d—H1c13d | 120.23 |
C9b—C8b—H1c8b | 110 (2) | C14d—C13d—H1c13d | 120.23 |
C10b—C8b—H1c8b | 107.5 (17) | C13d—C14d—C15d | 120.6 (9) |
C8b—C9b—H1c9b | 109.47 | C13d—C14d—H1c14d | 119.68 |
C8b—C9b—H2c9b | 109.47 | C15d—C14d—H1c14d | 119.68 |
C8b—C9b—H3c9b | 109.47 | C10d—C15d—C14d | 120.9 (8) |
H1c9b—C9b—H2c9b | 109.47 | C10d—C15d—H1c15d | 119.55 |
H1c9b—C9b—H3c9b | 109.47 | C14d—C15d—H1c15d | 119.55 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H1c5···O1i | 0.96 | 2.47 | 3.279 (4) | 141.77 |
N1—H1n1···O2ii | 0.860 (12) | 1.977 (13) | 2.826 (4) | 169 (3) |
N2—H1n2···O1iii | 0.860 (19) | 2.06 (3) | 2.882 (4) | 159 (3) |
N3—H1n3···O1iii | 0.860 (11) | 2.094 (12) | 2.911 (3) | 158 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x+1, y, z. |
Crystal data top
C23H25ClN3O2P | Z = 1 |
Mr = 441.9 | F(000) = 232 |
Triclinic, P1 | Dx = 1.317 Mg m−3 |
Hall symbol: P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 4.8901 (2) Å | Cell parameters from 7881 reflections |
b = 10.5424 (3) Å | θ = 5.3–67.0° |
c = 11.2098 (4) Å | µ = 2.39 mm−1 |
α = 99.235 (3)° | T = 120 K |
β = 100.658 (3)° | Prism, colourless |
γ = 94.249 (3)° | 0.38 × 0.24 × 0.06 mm |
V = 557.36 (4) Å3 | |
Data collection top
Rigaku Xcalibur AtlasS2 Gemini ultra diffractometer | 3839 independent reflections |
Radiation source: X-ray tube | 3761 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.038 |
Detector resolution: 5.1783 pixels mm-1 | θmax = 67.2°, θmin = 4.1° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −12→12 |
Tmin = 0.596, Tmax = 1 | l = −13→13 |
9949 measured reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.109 | (Δ/σ)max = 0.028 |
S = 1.73 | Δρmax = 0.43 e Å−3 |
3839 reflections | Δρmin = −0.32 e Å−3 |
233 parameters | Absolute structure: 1852 of Friedel pairs used in the refinement |
3 restraints | Absolute structure parameter: 0.001 (16) |
56 constraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.7242 (4) | 0.69137 (11) | 0.20306 (9) | 0.0429 (3) | |
P1 | 1.0962 (4) | 0.26793 (9) | 0.37713 (7) | 0.01367 (17) | |
O1 | 1.3625 (5) | 0.20981 (17) | 0.37679 (17) | 0.0191 (5) | |
O2 | 0.7604 (5) | 0.4926 (2) | 0.3760 (2) | 0.0345 (8) | |
N1 | 1.1909 (5) | 0.42744 (19) | 0.3784 (2) | 0.0184 (7) | |
N2 | 0.8430 (6) | 0.2096 (2) | 0.2612 (2) | 0.0183 (7) | |
N3 | 0.9522 (6) | 0.2549 (2) | 0.49453 (19) | 0.0183 (6) | |
C1 | 1.0083 (6) | 0.5194 (2) | 0.3792 (2) | 0.0204 (8) | |
C2 | 1.1379 (7) | 0.6557 (2) | 0.3895 (3) | 0.0220 (8) | |
C3 | 1.0189 (7) | 0.7407 (3) | 0.3177 (3) | 0.0276 (10) | |
C4 | 1.1435 (8) | 0.8679 (3) | 0.3331 (3) | 0.0333 (10) | |
C5 | 1.3813 (8) | 0.9098 (3) | 0.4191 (3) | 0.0382 (11) | |
C6 | 1.5071 (9) | 0.8257 (3) | 0.4917 (3) | 0.0376 (11) | |
C7 | 1.3827 (7) | 0.7001 (3) | 0.4767 (3) | 0.0293 (9) | |
H1n1 | 1.3651 (18) | 0.451 (3) | 0.383 (3) | 0.022* | |
H1n2 | 0.677 (3) | 0.214 (3) | 0.276 (3) | 0.0219* | |
H1n3 | 0.7724 (7) | 0.242 (3) | 0.479 (3) | 0.022* | |
H1c4 | 1.060377 | 0.925833 | 0.282521 | 0.04* | |
H1c5 | 1.463174 | 0.997529 | 0.430022 | 0.0458* | |
H1c6 | 1.677294 | 0.854547 | 0.551143 | 0.0452* | |
H1c7 | 1.466827 | 0.642516 | 0.527413 | 0.0352* | |
C8a | 1.0988 (8) | 0.2702 (4) | 0.6197 (3) | 0.0204 (8) | 0.573 (6) |
C9a | 1.0486 (14) | 0.1453 (5) | 0.6687 (5) | 0.0350 (11) | 0.573 (6) |
C10a | 1.0326 (11) | 0.3860 (5) | 0.7056 (5) | 0.0215 (7) | 0.573 (6) |
C11a | 0.8118 (14) | 0.4561 (6) | 0.6741 (5) | 0.0269 (9) | 0.573 (6) |
C12a | 0.7538 (18) | 0.5580 (7) | 0.7586 (6) | 0.0415 (13) | 0.573 (6) |
C13a | 0.9245 (19) | 0.5900 (7) | 0.8755 (6) | 0.0411 (11) | 0.573 (6) |
C14a | 1.1446 (18) | 0.5227 (7) | 0.9066 (6) | 0.0450 (14) | 0.573 (6) |
C15a | 1.2006 (14) | 0.4215 (7) | 0.8227 (5) | 0.0392 (13) | 0.573 (6) |
H1c8a | 1.302 (6) | 0.287 (3) | 0.615 (2) | 0.016 (7)* | 0.573 (6) |
H1c9a | 1.103851 | 0.074783 | 0.616101 | 0.042* | 0.573 (6) |
H2c9a | 0.853559 | 0.129029 | 0.670066 | 0.042* | 0.573 (6) |
H3c9a | 1.156903 | 0.153595 | 0.750784 | 0.042* | 0.573 (6) |
H1c11a | 0.696199 | 0.434526 | 0.593049 | 0.0322* | 0.573 (6) |
H1c12a | 0.597906 | 0.605593 | 0.736301 | 0.0498* | 0.573 (6) |
H1c13a | 0.886173 | 0.659898 | 0.934166 | 0.0493* | 0.573 (6) |
H1c14a | 1.262126 | 0.545448 | 0.987135 | 0.054* | 0.573 (6) |
H1c15a | 1.357727 | 0.374877 | 0.84575 | 0.047* | 0.573 (6) |
C8b | 1.1242 (17) | 0.2455 (5) | 0.6203 (6) | 0.0204 (8) | 0.427 (6) |
C9b | 1.014 (3) | 0.1168 (6) | 0.6491 (10) | 0.0350 (11) | 0.427 (6) |
C10b | 1.0794 (11) | 0.3584 (5) | 0.7155 (4) | 0.0215 (7) | 0.427 (6) |
C11b | 0.8966 (17) | 0.4479 (8) | 0.6888 (7) | 0.0269 (10) | 0.427 (6) |
C12b | 0.855 (3) | 0.5462 (10) | 0.7811 (10) | 0.0415 (13) | 0.427 (6) |
C13b | 1.004 (3) | 0.5545 (10) | 0.9011 (10) | 0.0411 (11) | 0.427 (6) |
C14b | 1.187 (3) | 0.4678 (11) | 0.9278 (8) | 0.0450 (14) | 0.427 (6) |
C15b | 1.227 (2) | 0.3702 (9) | 0.8361 (6) | 0.0392 (13) | 0.427 (6) |
H1c8b | 1.332 (6) | 0.249 (3) | 0.623 (2) | 0.016 (7)* | 0.427 (6) |
H1c9b | 1.056328 | 0.047151 | 0.591194 | 0.042* | 0.427 (6) |
H2c9b | 0.815412 | 0.113417 | 0.642972 | 0.042* | 0.427 (6) |
H3c9b | 1.102177 | 0.109027 | 0.731171 | 0.042* | 0.427 (6) |
H1c11b | 0.796218 | 0.442593 | 0.605761 | 0.0322* | 0.427 (6) |
H1c12b | 0.725303 | 0.607498 | 0.761995 | 0.0498* | 0.427 (6) |
H1c13b | 0.976913 | 0.621684 | 0.965181 | 0.0493* | 0.427 (6) |
H1c14b | 1.290291 | 0.474211 | 1.010589 | 0.054* | 0.427 (6) |
H1c15b | 1.358235 | 0.309791 | 0.856124 | 0.047* | 0.427 (6) |
C8c | 0.8509 (14) | 0.2197 (5) | 0.1290 (5) | 0.0204 (8) | 0.527 (5) |
C9c | 0.710 (3) | 0.3360 (6) | 0.0923 (9) | 0.0350 (12) | 0.527 (5) |
C10c | 0.7032 (11) | 0.0941 (5) | 0.0488 (4) | 0.0215 (7) | 0.527 (5) |
C11c | 0.5558 (16) | 0.0017 (7) | 0.0929 (7) | 0.0269 (10) | 0.527 (5) |
C12c | 0.414 (2) | −0.1092 (9) | 0.0138 (9) | 0.0415 (13) | 0.527 (5) |
C13c | 0.426 (3) | −0.1268 (9) | −0.1108 (9) | 0.0411 (11) | 0.527 (5) |
C14c | 0.574 (3) | −0.0371 (10) | −0.1547 (8) | 0.0450 (14) | 0.527 (5) |
C15c | 0.7130 (17) | 0.0728 (8) | −0.0761 (6) | 0.0392 (13) | 0.527 (5) |
H1c8c | 1.051 (7) | 0.226 (3) | 0.117 (2) | 0.016 (7)* | 0.527 (5) |
H1c9c | 0.814086 | 0.414093 | 0.140343 | 0.042* | 0.527 (5) |
H2c9c | 0.522623 | 0.330598 | 0.107293 | 0.042* | 0.527 (5) |
H3c9c | 0.704114 | 0.336387 | 0.006344 | 0.042* | 0.527 (5) |
H1c11c | 0.550254 | 0.013592 | 0.179063 | 0.0322* | 0.527 (5) |
H1c12c | 0.309917 | −0.172559 | 0.045126 | 0.0498* | 0.527 (5) |
H1c13c | 0.329581 | −0.20263 | −0.165848 | 0.0493* | 0.527 (5) |
H1c14c | 0.582427 | −0.049945 | −0.240597 | 0.054* | 0.527 (5) |
H1c15c | 0.817908 | 0.135343 | −0.108219 | 0.047* | 0.527 (5) |
C8d | 0.8816 (14) | 0.1906 (5) | 0.1364 (5) | 0.0204 (8) | 0.473 (5) |
C9d | 0.854 (2) | 0.3109 (6) | 0.0772 (8) | 0.0350 (11) | 0.473 (5) |
C10d | 0.7079 (11) | 0.0728 (5) | 0.0527 (5) | 0.0215 (7) | 0.473 (5) |
C11d | 0.4754 (15) | 0.0111 (7) | 0.0802 (7) | 0.0269 (10) | 0.473 (5) |
C12d | 0.317 (2) | −0.0932 (8) | −0.0026 (9) | 0.0415 (14) | 0.473 (5) |
C13d | 0.398 (3) | −0.1359 (8) | −0.1136 (8) | 0.0411 (12) | 0.473 (5) |
C14d | 0.629 (3) | −0.0768 (9) | −0.1407 (7) | 0.0450 (14) | 0.473 (5) |
C15d | 0.7847 (18) | 0.0268 (8) | −0.0585 (6) | 0.0392 (13) | 0.473 (5) |
H1c8d | 1.083 (7) | 0.170 (3) | 0.150 (3) | 0.016 (7)* | 0.473 (5) |
H1c9d | 0.974634 | 0.382294 | 0.12912 | 0.042* | 0.473 (5) |
H2c9d | 0.663351 | 0.331012 | 0.067249 | 0.042* | 0.473 (5) |
H3c9d | 0.905245 | 0.295009 | −0.002005 | 0.042* | 0.473 (5) |
H1c11d | 0.421565 | 0.040059 | 0.15732 | 0.0322* | 0.473 (5) |
H1c12d | 0.153698 | −0.134928 | 0.016788 | 0.0498* | 0.473 (5) |
H1c13d | 0.290559 | −0.207475 | −0.171137 | 0.0493* | 0.473 (5) |
H1c14d | 0.684667 | −0.106964 | −0.217131 | 0.054* | 0.473 (5) |
H1c15d | 0.948381 | 0.067472 | −0.078585 | 0.047* | 0.473 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0385 (5) | 0.0376 (4) | 0.0522 (5) | 0.0067 (3) | −0.0009 (4) | 0.0169 (3) |
P1 | 0.0106 (3) | 0.0113 (2) | 0.0183 (3) | −0.00244 (17) | 0.0033 (2) | 0.00156 (19) |
O1 | 0.0128 (9) | 0.0140 (8) | 0.0308 (9) | −0.0011 (6) | 0.0070 (7) | 0.0026 (6) |
O2 | 0.0168 (11) | 0.0284 (10) | 0.0656 (15) | 0.0046 (8) | 0.0164 (10) | 0.0198 (9) |
N1 | 0.0118 (11) | 0.0139 (9) | 0.0293 (11) | −0.0040 (7) | 0.0076 (9) | 0.0020 (8) |
N2 | 0.0133 (11) | 0.0199 (10) | 0.0201 (11) | −0.0057 (8) | 0.0041 (9) | 0.0015 (8) |
N3 | 0.0117 (10) | 0.0224 (10) | 0.0205 (10) | −0.0032 (8) | 0.0056 (9) | 0.0021 (8) |
C1 | 0.0176 (14) | 0.0167 (11) | 0.0286 (13) | 0.0009 (9) | 0.0079 (11) | 0.0056 (9) |
C2 | 0.0236 (14) | 0.0159 (11) | 0.0314 (13) | 0.0044 (10) | 0.0153 (12) | 0.0060 (10) |
C3 | 0.0295 (17) | 0.0237 (13) | 0.0354 (15) | 0.0074 (11) | 0.0159 (14) | 0.0092 (11) |
C4 | 0.0444 (19) | 0.0188 (13) | 0.0437 (17) | 0.0100 (12) | 0.0207 (15) | 0.0093 (11) |
C5 | 0.049 (2) | 0.0170 (12) | 0.0503 (19) | 0.0009 (12) | 0.0186 (16) | 0.0027 (12) |
C6 | 0.048 (2) | 0.0190 (13) | 0.0407 (17) | −0.0055 (12) | 0.0059 (15) | −0.0030 (11) |
C7 | 0.0365 (17) | 0.0167 (12) | 0.0352 (15) | 0.0011 (11) | 0.0125 (13) | 0.0007 (10) |
C8a | 0.0245 (12) | 0.0204 (14) | 0.0191 (9) | 0.0108 (10) | 0.0046 (8) | 0.0074 (9) |
C9a | 0.056 (2) | 0.0255 (16) | 0.0241 (14) | 0.0080 (16) | 0.0061 (15) | 0.0059 (12) |
C10a | 0.0193 (11) | 0.0216 (12) | 0.0224 (10) | 0.0007 (9) | 0.0052 (8) | 0.0003 (9) |
C11a | 0.027 (2) | 0.0281 (11) | 0.0253 (12) | 0.0073 (12) | 0.0074 (11) | −0.0004 (9) |
C12a | 0.060 (3) | 0.0335 (12) | 0.0356 (16) | 0.0241 (16) | 0.0168 (14) | 0.0023 (11) |
C13a | 0.064 (2) | 0.0256 (13) | 0.0316 (14) | −0.0003 (13) | 0.0180 (13) | −0.0070 (10) |
C14a | 0.0426 (19) | 0.050 (3) | 0.0306 (16) | −0.0082 (18) | −0.0007 (13) | −0.0126 (17) |
C15a | 0.0335 (17) | 0.050 (3) | 0.0276 (15) | 0.0090 (15) | −0.0032 (11) | −0.0030 (16) |
C8b | 0.0271 (13) | 0.0172 (15) | 0.0204 (9) | 0.0094 (10) | 0.0068 (8) | 0.0076 (9) |
C9b | 0.056 (2) | 0.0243 (17) | 0.0249 (13) | 0.0032 (16) | 0.0090 (14) | 0.0058 (12) |
C10b | 0.0188 (11) | 0.0228 (13) | 0.0215 (9) | 0.0015 (9) | 0.0041 (8) | 0.0002 (8) |
C11b | 0.028 (2) | 0.0280 (12) | 0.0244 (11) | 0.0079 (12) | 0.0074 (10) | 0.0000 (9) |
C12b | 0.064 (3) | 0.0291 (14) | 0.0361 (15) | 0.0195 (17) | 0.0199 (14) | 0.0014 (11) |
C13b | 0.060 (2) | 0.0303 (14) | 0.0296 (13) | −0.0053 (14) | 0.0166 (13) | −0.0094 (10) |
C14b | 0.041 (2) | 0.058 (3) | 0.0253 (15) | −0.0032 (18) | −0.0035 (13) | −0.0086 (17) |
C15b | 0.0385 (18) | 0.051 (3) | 0.0250 (14) | 0.0138 (16) | −0.0020 (11) | 0.0020 (16) |
C8c | 0.0242 (14) | 0.0169 (15) | 0.0200 (9) | −0.0026 (11) | 0.0014 (8) | 0.0082 (9) |
C9c | 0.051 (2) | 0.0248 (17) | 0.0258 (14) | 0.0053 (17) | −0.0019 (14) | 0.0052 (12) |
C10c | 0.0191 (14) | 0.0220 (13) | 0.0222 (9) | 0.0010 (10) | 0.0049 (9) | 0.0002 (8) |
C11c | 0.026 (2) | 0.0255 (12) | 0.0258 (11) | −0.0046 (13) | 0.0031 (11) | 0.0002 (9) |
C12c | 0.051 (3) | 0.0249 (15) | 0.0397 (15) | −0.0128 (18) | −0.0053 (15) | 0.0028 (12) |
C13c | 0.048 (3) | 0.0282 (14) | 0.0355 (13) | 0.0053 (14) | −0.0070 (13) | −0.0110 (10) |
C14c | 0.049 (2) | 0.054 (3) | 0.0270 (15) | 0.005 (2) | 0.0114 (14) | −0.0115 (17) |
C15c | 0.045 (2) | 0.047 (3) | 0.0243 (13) | −0.0066 (17) | 0.0113 (12) | 0.0012 (15) |
C8d | 0.0211 (14) | 0.0217 (14) | 0.0186 (10) | −0.0054 (10) | 0.0045 (9) | 0.0065 (9) |
C9d | 0.053 (2) | 0.0263 (15) | 0.0240 (15) | −0.0035 (16) | 0.0068 (17) | 0.0053 (12) |
C10d | 0.0191 (13) | 0.0210 (12) | 0.0227 (11) | 0.0029 (9) | 0.0027 (9) | 0.0005 (9) |
C11d | 0.023 (2) | 0.0278 (10) | 0.0256 (12) | −0.0029 (12) | 0.0019 (12) | −0.0009 (9) |
C12d | 0.046 (3) | 0.0351 (12) | 0.0347 (17) | −0.0193 (17) | −0.0008 (16) | 0.0009 (12) |
C13d | 0.058 (3) | 0.0241 (13) | 0.0313 (15) | −0.0001 (13) | −0.0056 (15) | −0.0060 (10) |
C14d | 0.050 (2) | 0.046 (3) | 0.0341 (17) | 0.0128 (19) | 0.0103 (15) | −0.0131 (17) |
C15d | 0.036 (2) | 0.049 (3) | 0.0303 (16) | −0.0006 (17) | 0.0137 (13) | −0.0053 (16) |
Geometric parameters (Å, º) top
P1—O1 | 1.480 (3) | C9b—H3c9b | 0.96 |
P1—N1 | 1.708 (2) | C10b—C11b | 1.377 (10) |
P1—N2 | 1.624 (2) | C10b—C15b | 1.392 (8) |
P1—N3 | 1.623 (3) | C11b—C12b | 1.396 (13) |
O2—C1 | 1.217 (4) | C11b—H1c11b | 0.96 |
N1—C1 | 1.366 (4) | C12b—C13b | 1.392 (16) |
N1—H1n1 | 0.860 (12) | C12b—H1c12b | 0.96 |
N2—H1n2 | 0.860 (18) | C13b—C14b | 1.36 (2) |
N2—C8c | 1.509 (6) | C13b—H1c13b | 0.96 |
N2—C8d | 1.430 (6) | C14b—C15b | 1.384 (14) |
N3—H1n3 | 0.860 (4) | C14b—H1c14b | 0.96 |
N3—C8a | 1.431 (4) | C15b—H1c15b | 0.96 |
N3—C8b | 1.524 (7) | C8c—C9c | 1.526 (10) |
C1—C2 | 1.505 (4) | C8c—C10c | 1.523 (6) |
C2—C3 | 1.387 (4) | C8c—H1c8c | 1.01 (3) |
C2—C7 | 1.395 (4) | C9c—H1c9c | 0.96 |
C3—C4 | 1.401 (4) | C9c—H2c9c | 0.96 |
C4—C5 | 1.360 (5) | C9c—H3c9c | 0.96 |
C4—H1c4 | 0.9601 | C10c—C11c | 1.377 (10) |
C5—C6 | 1.398 (5) | C10c—C15c | 1.392 (8) |
C5—H1c5 | 0.9601 | C11c—C12c | 1.396 (11) |
C6—C7 | 1.387 (4) | C11c—H1c11c | 0.96 |
C6—H1c6 | 0.96 | C12c—C13c | 1.392 (15) |
C7—H1c7 | 0.9599 | C12c—H1c12c | 0.96 |
C8a—C9a | 1.526 (7) | C13c—C14c | 1.355 (16) |
C8a—C10a | 1.523 (7) | C13c—H1c13c | 0.96 |
C8a—H1c8a | 1.01 (3) | C14c—C15c | 1.384 (12) |
C9a—H1c9a | 0.96 | C14c—H1c14c | 0.96 |
C9a—H2c9a | 0.96 | C15c—H1c15c | 0.96 |
C9a—H3c9a | 0.96 | C8d—C9d | 1.526 (9) |
C10a—C11a | 1.377 (9) | C8d—C10d | 1.523 (6) |
C10a—C15a | 1.392 (7) | C8d—H1c8d | 1.01 (3) |
C11a—C12a | 1.396 (9) | C9d—H1c9d | 0.96 |
C11a—H1c11a | 0.96 | C9d—H2c9d | 0.96 |
C12a—C13a | 1.392 (9) | C9d—H3c9d | 0.96 |
C12a—H1c12a | 0.96 | C10d—C11d | 1.377 (10) |
C13a—C14a | 1.355 (12) | C10d—C15d | 1.392 (9) |
C13a—H1c13a | 0.96 | C11d—C12d | 1.396 (10) |
C14a—C15a | 1.384 (10) | C11d—H1c11d | 0.96 |
C14a—H1c14a | 0.96 | C12d—C13d | 1.392 (15) |
C15a—H1c15a | 0.96 | C12d—H1c12d | 0.96 |
C8b—C9b | 1.526 (11) | C13d—C14d | 1.355 (18) |
C8b—C10b | 1.523 (8) | C13d—H1c13d | 0.96 |
C8b—H1c8b | 1.01 (3) | C14d—C15d | 1.384 (11) |
C9b—H1c9b | 0.96 | C14d—H1c14d | 0.96 |
C9b—H2c9b | 0.96 | C15d—H1c15d | 0.96 |
| | | |
O1—P1—N1 | 103.01 (15) | H2c9b—C9b—H3c9b | 109.47 |
O1—P1—N2 | 115.73 (13) | C8b—C10b—C11b | 123.4 (5) |
O1—P1—N3 | 115.78 (13) | C8b—C10b—C15b | 118.3 (6) |
N1—P1—N2 | 110.77 (13) | C11b—C10b—C15b | 118.3 (6) |
N1—P1—N3 | 109.23 (12) | C10b—C11b—C12b | 120.9 (8) |
N2—P1—N3 | 102.40 (16) | C10b—C11b—H1c11b | 119.57 |
P1—N1—C1 | 123.6 (2) | C12b—C11b—H1c11b | 119.57 |
P1—N1—H1n1 | 118 (2) | C11b—C12b—C13b | 119.3 (11) |
C1—N1—H1n1 | 119 (2) | C11b—C12b—H1c12b | 120.34 |
P1—N2—H1n2 | 115.1 (19) | C13b—C12b—H1c12b | 120.34 |
P1—N2—C8c | 124.0 (3) | C12b—C13b—C14b | 120.2 (10) |
P1—N2—C8d | 122.4 (3) | C12b—C13b—H1c13b | 119.91 |
H1n2—N2—C8c | 112 (2) | C14b—C13b—H1c13b | 119.91 |
H1n2—N2—C8d | 120 (2) | C13b—C14b—C15b | 120.3 (9) |
P1—N3—H1n3 | 116 (2) | C13b—C14b—H1c14b | 119.85 |
P1—N3—C8a | 125.2 (2) | C15b—C14b—H1c14b | 119.85 |
P1—N3—C8b | 122.0 (4) | C10b—C15b—C14b | 121.0 (9) |
H1n3—N3—C8a | 119 (2) | C10b—C15b—H1c15b | 119.48 |
H1n3—N3—C8b | 122 (2) | C14b—C15b—H1c15b | 119.48 |
O2—C1—N1 | 122.0 (2) | N2—C8c—C9c | 111.0 (5) |
O2—C1—C2 | 122.8 (3) | N2—C8c—C10c | 107.3 (4) |
N1—C1—C2 | 115.2 (3) | N2—C8c—H1c8c | 110.2 (16) |
C1—C2—C3 | 122.5 (2) | C9c—C8c—C10c | 111.1 (5) |
C1—C2—C7 | 119.1 (3) | C9c—C8c—H1c8c | 110.4 (19) |
C3—C2—C7 | 118.4 (3) | C10c—C8c—H1c8c | 106.8 (16) |
C2—C3—C4 | 120.4 (3) | C8c—C9c—H1c9c | 109.47 |
C3—C4—C5 | 120.4 (3) | C8c—C9c—H2c9c | 109.47 |
C3—C4—H1c4 | 119.8 | C8c—C9c—H3c9c | 109.47 |
C5—C4—H1c4 | 119.79 | H1c9c—C9c—H2c9c | 109.47 |
C4—C5—C6 | 120.3 (3) | H1c9c—C9c—H3c9c | 109.47 |
C4—C5—H1c5 | 119.83 | H2c9c—C9c—H3c9c | 109.47 |
C6—C5—H1c5 | 119.83 | C8c—C10c—C11c | 123.4 (5) |
C5—C6—C7 | 119.1 (3) | C8c—C10c—C15c | 118.3 (5) |
C5—C6—H1c6 | 120.43 | C11c—C10c—C15c | 118.3 (5) |
C7—C6—H1c6 | 120.44 | C10c—C11c—C12c | 120.9 (7) |
C2—C7—C6 | 121.3 (3) | C10c—C11c—H1c11c | 119.57 |
C2—C7—H1c7 | 119.35 | C12c—C11c—H1c11c | 119.57 |
C6—C7—H1c7 | 119.34 | C11c—C12c—C13c | 119.3 (9) |
N3—C8a—C9a | 109.5 (3) | C11c—C12c—H1c12c | 120.34 |
N3—C8a—C10a | 114.7 (3) | C13c—C12c—H1c12c | 120.34 |
N3—C8a—H1c8a | 104.2 (15) | C12c—C13c—C14c | 120.2 (8) |
C9a—C8a—C10a | 111.1 (4) | C12c—C13c—H1c13c | 119.91 |
C9a—C8a—H1c8a | 110.4 (18) | C14c—C13c—H1c13c | 119.91 |
C10a—C8a—H1c8a | 106.8 (16) | C13c—C14c—C15c | 120.3 (8) |
C8a—C9a—H1c9a | 109.47 | C13c—C14c—H1c14c | 119.85 |
C8a—C9a—H2c9a | 109.47 | C15c—C14c—H1c14c | 119.85 |
C8a—C9a—H3c9a | 109.47 | C10c—C15c—C14c | 121.0 (8) |
H1c9a—C9a—H2c9a | 109.47 | C10c—C15c—H1c15c | 119.48 |
H1c9a—C9a—H3c9a | 109.47 | C14c—C15c—H1c15c | 119.48 |
H2c9a—C9a—H3c9a | 109.47 | N2—C8d—C9d | 113.8 (5) |
C8a—C10a—C11a | 123.4 (4) | N2—C8d—C10d | 114.7 (5) |
C8a—C10a—C15a | 118.3 (5) | N2—C8d—H1c8d | 99.3 (17) |
C11a—C10a—C15a | 118.3 (5) | C9d—C8d—C10d | 111.1 (5) |
C10a—C11a—C12a | 120.9 (5) | C9d—C8d—H1c8d | 110.4 (19) |
C10a—C11a—H1c11a | 119.57 | C10d—C8d—H1c8d | 106.8 (16) |
C12a—C11a—H1c11a | 119.57 | C8d—C9d—H1c9d | 109.47 |
C11a—C12a—C13a | 119.3 (7) | C8d—C9d—H2c9d | 109.47 |
C11a—C12a—H1c12a | 120.34 | C8d—C9d—H3c9d | 109.47 |
C13a—C12a—H1c12a | 120.34 | H1c9d—C9d—H2c9d | 109.47 |
C12a—C13a—C14a | 120.2 (7) | H1c9d—C9d—H3c9d | 109.47 |
C12a—C13a—H1c13a | 119.91 | H2c9d—C9d—H3c9d | 109.47 |
C14a—C13a—H1c13a | 119.91 | C8d—C10d—C11d | 123.4 (5) |
C13a—C14a—C15a | 120.3 (6) | C8d—C10d—C15d | 118.3 (6) |
C13a—C14a—H1c14a | 119.85 | C11d—C10d—C15d | 118.3 (5) |
C15a—C14a—H1c14a | 119.85 | C10d—C11d—C12d | 120.9 (8) |
C10a—C15a—C14a | 121.0 (6) | C10d—C11d—H1c11d | 119.57 |
C10a—C15a—H1c15a | 119.48 | C12d—C11d—H1c11d | 119.57 |
C14a—C15a—H1c15a | 119.48 | C11d—C12d—C13d | 119.3 (10) |
N3—C8b—C9b | 105.4 (6) | C11d—C12d—H1c12d | 120.34 |
N3—C8b—C10b | 109.3 (5) | C13d—C12d—H1c12d | 120.34 |
N3—C8b—H1c8b | 114.0 (17) | C12d—C13d—C14d | 120.2 (8) |
C9b—C8b—C10b | 111.1 (7) | C12d—C13d—H1c13d | 119.91 |
C9b—C8b—H1c8b | 110 (2) | C14d—C13d—H1c13d | 119.91 |
C10b—C8b—H1c8b | 106.8 (16) | C13d—C14d—C15d | 120.3 (9) |
C8b—C9b—H1c9b | 109.47 | C13d—C14d—H1c14d | 119.85 |
C8b—C9b—H2c9b | 109.47 | C15d—C14d—H1c14d | 119.85 |
C8b—C9b—H3c9b | 109.47 | C10d—C15d—C14d | 121.0 (8) |
H1c9b—C9b—H2c9b | 109.47 | C10d—C15d—H1c15d | 119.48 |
H1c9b—C9b—H3c9b | 109.47 | C14d—C15d—H1c15d | 119.48 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O2i | 0.860 (12) | 1.968 (13) | 2.825 (4) | 174 (3) |
N2—H1n2···O1ii | 0.860 (18) | 2.07 (3) | 2.886 (4) | 158 (3) |
N3—H1n3···O1ii | 0.860 (10) | 2.090 (12) | 2.911 (3) | 159 (3) |
C5—H1c5···O1iii | 0.96 | 2.47 | 3.278 (4) | 142.02 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, y+1, z. |
Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.