Hydrogen-bond directionality and symmetry in [C(O)NH](N)₂P(O)-based structures: a comparison between X-ray crystallography data and neutron-normalized values, and evaluation of reliability

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.

Computing details

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.

(shelx)

Crystal data

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) Å^3	Block, colourless
Z = 8	0.31 × 0.2 × 0.12 × 0.18 (radius) mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0747P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4AA···O1^i	0.72 (2)	2.23 (2)	2.946 (2)	173 (2)
N1—H1···O3^ii	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.

(mt33)

Crystal data

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) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.404P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(mt35)

Crystal data

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) Å^3	0.25 × 0.15 × 0.10 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.184P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

(neg_rn24)

Crystal data

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) Å^3	0.40 × 0.30 × 0.30 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0445P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.811 (15)	1.991 (16)	2.7985 (17)	173.7 (15)
C3—H3A···O2^i	0.95	2.34	3.0954 (17)	137

Symmetry code: (i) −x+1, −y+2, −z+1.

(shelx_1)

Crystal data

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) Å^3	Block, colorless
Z = 8	0.56 × 0.48 × 0.40 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0671P)^2 + 2.4754P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2^i	0.93	2.36	3.1079 (17)	138
N1—H···O2^i	0.80 (2)	2.02 (2)	2.8147 (14)	173 (2)

Symmetry code: (i) −x+1/2, −y+3/2, −z.

(shelx_2)

Crystal data

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) Å^3	Prismatic, colorless
Z = 16	0.53 × 0.43 × 0.25 mm
F(000) = 2528

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 4.2583P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O2B^i	0.82 (3)	2.14 (3)	2.957 (2)	172 (2)
N1A—H1A···O2A^i	0.80 (3)	2.15 (3)	2.955 (3)	175 (3)
N2A—H2A···O2B^i	0.73 (3)	2.47 (3)	3.165 (3)	161 (3)
N3A—H3A···O2B^ii	0.72 (2)	2.72 (3)	3.412 (3)	164 (3)
N3B—H3B···O2A^i	0.86	2.54	3.374 (3)	163
N2B—H2B···O2A^iii	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.

(FK16)

Crystal data

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) Å^3	0.40 × 0.30 × 0.30 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 0.1338P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	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.

(8)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	Weighting scheme based on measured s.u.'s w = 1/(σ^2(I) + 0.0016I^2)
wR(F^2) = 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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1c5···O1^i	0.96	2.47	3.279 (4)	141.77
N1—H1n1···O2^ii	0.860 (12)	1.977 (13)	2.826 (4)	169 (3)
N2—H1n2···O1^iii	0.860 (19)	2.06 (3)	2.882 (4)	159 (3)
N3—H1n3···O1^iii	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.

(9)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	Weighting scheme based on measured s.u.'s w = 1/(σ^2(I) + 0.0016I^2)
wR(F^2) = 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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n1···O2^i	0.860 (12)	1.968 (13)	2.825 (4)	174 (3)
N2—H1n2···O1^ii	0.860 (18)	2.07 (3)	2.886 (4)	158 (3)
N3—H1n3···O1^ii	0.860 (10)	2.090 (12)	2.911 (3)	159 (3)
C5—H1c5···O1^iii	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.