Investigation of crystal structures, energetics and isostructurality in halogen-substituted phosphoramidates

A total of 14 compounds, one unsubstituted and 13 halogen-substituted phospho­ramidates, have been synthesized from unsubstituted and halogenated (fluoro-, difluoro-, chloro-, bromo-, iodo-substituted) aniline and di­phenyl phospho­ryl chloride to investigate their molecular assembly in solid-state structures. Amongst them, six groups were formed based on similarities in unit-cell dimensions, space group and molecular assembly of the crystal. The analysis reveals that all the crystal structures contain robust N—H...O hydrogen bonds which are the primary building blocks with ancillary interactions such as C—H...O, C—H...π, C—H...F/Cl/Br/I, F...F, F...π, I...π, Br...π, I...O and Br...O. The role of short and directional C—H...O and C—H...π interactions providing significant stabilization to the densely packed crystalline arrangement is discussed. The contribution of these interactions in stabilizing the crystalline assembly was deduced via computing total interaction energy between dimers and the overall lattice energies using the computer programs Crystal Explorer 17.5 and PIXELC, respectively. Additionally, the occurrence of 3D isostructurality in phosphor­adimates and their halogenated analogs was investigated using the XPac program. A comparison of the magnitudes of the torsion angles in the compounds substantiates the role of conformational flexibility in the solid state.

Computing details

Data collection: Bruker APEX2 for (00), 2Br, 2Cl, (2I), 3Br, 3Cl, (3F), (3I), 4Br, (4F), (4I), (24F), (25F); BRUKER APEX2 for 4Cl. Cell refinement: Bruker SAINT for (00), 2Br, 2Cl, (2I), 3Br, 3Cl, (3F), (3I), 4Br, (4F), (4I), (24F), (25F); SAINT v8.37A (Bruker, 2015) for 4Cl. Data reduction: Bruker SAINT for (00), 2Br, 2Cl, (2I), 3Br, 3Cl, (3F), (3I), 4Br, (4F), (4I), (24F), (25F); SAINT v8.37A (Bruker, 2015) for 4Cl. Program(s) used to solve structure: SIR2014 (Burla et al., 2014) for (00), 3Cl; SHELXS97 (Sheldrick 2008) for 2Br, 2Cl, (2I), 3Br, (3I), 4Br, (4I), (24F), (25F); olex2.solve 1.3 (Bourhis et al., 2015) for (3F); SHELXT 2014/5 (Sheldrick, 2014) for 4Cl. Program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016) for (00); SHELXL 2018/3 (Sheldrick, 2015) for 2Br, 2Cl, (2I), 3Br, 3Cl, (3I), 4Br, (4F), (4I), (24F), (25F); SHELXL2018/3 (Sheldrick, 2018) for (3F), 4Cl. Molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008) for (00), (3F); Olex2 1.3 (Dolomanov et al., 2009) for 2Br, 2Cl, (2I), 3Br, 3Cl, (3I), 4Br, 4Cl, (4F), (4I), (24F), (25F). Software used to prepare material for publication: WinGX (Farrugia, 2014) and PLATON for (00), (3F); Olex2 1.3 (Dolomanov et al., 2009) for 2Br, 2Cl, (2I), 3Br, 3Cl, (3I), 4Br, 4Cl, (4F), (4I), (24F), (25F).

(00)

Crystal data

C18H16NO3P	F(000) = 680
Mr = 325.29	Dx = 1.371 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8195 (4) Å	Cell parameters from 9870 reflections
b = 9.8992 (4) Å	θ = 2.3–30.1°
c = 16.2764 (7) Å	µ = 0.19 mm^−1
β = 94.985 (2)°	T = 100 K
V = 1576.17 (11) Å^3	Block, colourless
Z = 4	0.34 × 0.22 × 0.15 mm

Data collection

Bruker D8 Venture PHOTON 100 CMOS type diffractometer	3507 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.067
Absorption correction: multi-scan SADABS 2014/5	θmax = 29.6°, θmin = 2.3°
Tmin = 0.703, Tmax = 0.746	h = −13→13
36542 measured reflections	k = −13→13
4429 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: dual
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) = 0.100	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 0.9836P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4429 reflections	Δρmax = 0.36 e Å^−3
211 parameters	Δρmin = −0.42 e Å^−3
0 restraints

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	0.05889 (4)	0.18853 (4)	0.43683 (2)	0.00939 (10)
O1	−0.04223 (10)	0.31204 (10)	0.44570 (6)	0.0125 (2)
O2	0.16064 (10)	0.26913 (10)	0.38484 (6)	0.0128 (2)
O3	−0.00572 (10)	0.06778 (10)	0.39826 (6)	0.0127 (2)
N1	0.13674 (13)	0.14996 (13)	0.52600 (8)	0.0120 (2)
H1N	0.1106 (18)	0.0742 (18)	0.5446 (11)	0.014*
C1	−0.16213 (14)	0.28487 (14)	0.48551 (9)	0.0124 (3)
C2	−0.16974 (16)	0.33394 (15)	0.56439 (9)	0.0159 (3)
H2	−0.095202	0.381634	0.591925	0.019*
C3	−0.28888 (17)	0.31193 (16)	0.60254 (10)	0.0196 (3)
H3	−0.296171	0.344991	0.656775	0.023*
C4	−0.39742 (16)	0.24204 (17)	0.56207 (10)	0.0189 (3)
H4	−0.478682	0.227504	0.588522	0.023*
C5	−0.38696 (15)	0.19331 (16)	0.48271 (10)	0.0177 (3)
H5	−0.461207	0.145325	0.455075	0.021*
C6	−0.26858 (15)	0.21444 (15)	0.44370 (9)	0.0153 (3)
H6	−0.260746	0.181337	0.389524	0.018*
C7	0.27063 (14)	0.21355 (14)	0.34665 (8)	0.0112 (3)
C8	0.29072 (15)	0.07618 (15)	0.33770 (9)	0.0155 (3)
H8	0.230616	0.012754	0.359321	0.019*
C9	0.40150 (16)	0.03293 (16)	0.29609 (10)	0.0174 (3)
H9	0.417066	−0.061003	0.289467	0.021*
C10	0.48905 (16)	0.12573 (16)	0.26433 (9)	0.0169 (3)
H10	0.564163	0.095546	0.236146	0.020*
C11	0.46603 (16)	0.26316 (17)	0.27407 (10)	0.0181 (3)
H11	0.525441	0.326903	0.252110	0.022*
C12	0.35709 (15)	0.30795 (15)	0.31555 (9)	0.0150 (3)
H12	0.341870	0.401858	0.322567	0.018*
C13	0.21430 (14)	0.23050 (14)	0.58468 (9)	0.0110 (3)
C14	0.24462 (16)	0.36575 (15)	0.57096 (9)	0.0154 (3)
H14	0.211591	0.408585	0.520920	0.018*
C15	0.32388 (16)	0.43764 (16)	0.63134 (10)	0.0177 (3)
H15	0.345498	0.529519	0.621748	0.021*
C16	0.37155 (16)	0.37737 (16)	0.70499 (9)	0.0162 (3)
H16	0.425211	0.427413	0.745749	0.019*
C17	0.33995 (15)	0.24242 (15)	0.71870 (9)	0.0138 (3)
H17	0.371734	0.200394	0.769236	0.017*
C18	0.26230 (14)	0.16912 (14)	0.65892 (9)	0.0119 (3)
H18	0.241731	0.076982	0.668488	0.014*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.00871 (17)	0.01083 (17)	0.00862 (17)	−0.00084 (13)	0.00066 (12)	0.00142 (13)
O1	0.0102 (5)	0.0131 (5)	0.0143 (5)	0.0005 (4)	0.0026 (4)	0.0023 (4)
O2	0.0123 (5)	0.0125 (5)	0.0143 (5)	−0.0003 (4)	0.0051 (4)	0.0020 (4)
O3	0.0129 (5)	0.0142 (5)	0.0109 (5)	−0.0023 (4)	0.0003 (4)	0.0000 (4)
N1	0.0134 (6)	0.0099 (6)	0.0122 (6)	−0.0029 (5)	−0.0028 (5)	0.0035 (5)
C1	0.0100 (7)	0.0139 (7)	0.0137 (7)	0.0026 (5)	0.0030 (5)	0.0035 (5)
C2	0.0162 (7)	0.0163 (7)	0.0148 (7)	0.0013 (6)	−0.0004 (6)	0.0002 (6)
C3	0.0227 (8)	0.0229 (8)	0.0137 (7)	0.0056 (7)	0.0046 (6)	0.0006 (6)
C4	0.0139 (7)	0.0244 (8)	0.0193 (8)	0.0051 (6)	0.0065 (6)	0.0064 (6)
C5	0.0110 (7)	0.0227 (8)	0.0191 (8)	0.0001 (6)	−0.0004 (6)	0.0027 (6)
C6	0.0137 (7)	0.0197 (7)	0.0122 (7)	0.0015 (6)	−0.0006 (6)	0.0007 (6)
C7	0.0094 (6)	0.0158 (7)	0.0084 (7)	0.0002 (5)	0.0011 (5)	0.0003 (5)
C8	0.0145 (7)	0.0156 (7)	0.0168 (7)	−0.0010 (6)	0.0033 (6)	0.0020 (6)
C9	0.0179 (8)	0.0166 (7)	0.0179 (8)	0.0029 (6)	0.0019 (6)	0.0000 (6)
C10	0.0120 (7)	0.0253 (8)	0.0134 (7)	0.0024 (6)	0.0017 (6)	−0.0021 (6)
C11	0.0151 (8)	0.0221 (8)	0.0176 (8)	−0.0047 (6)	0.0037 (6)	0.0011 (6)
C12	0.0156 (7)	0.0149 (7)	0.0149 (7)	−0.0026 (6)	0.0030 (6)	0.0000 (6)
C13	0.0075 (6)	0.0140 (7)	0.0114 (7)	0.0005 (5)	0.0005 (5)	−0.0004 (5)
C14	0.0179 (8)	0.0139 (7)	0.0135 (7)	0.0000 (6)	−0.0031 (6)	0.0026 (6)
C15	0.0193 (8)	0.0125 (7)	0.0207 (8)	−0.0015 (6)	−0.0017 (6)	−0.0016 (6)
C16	0.0152 (7)	0.0189 (8)	0.0140 (7)	0.0009 (6)	−0.0019 (6)	−0.0046 (6)
C17	0.0125 (7)	0.0199 (7)	0.0091 (7)	0.0033 (6)	0.0018 (5)	−0.0002 (6)
C18	0.0120 (7)	0.0127 (7)	0.0113 (7)	0.0016 (5)	0.0024 (5)	0.0014 (5)

Geometric parameters (Å, º)

P1—O3	1.4685 (10)	C8—C9	1.398 (2)
P1—O2	1.5804 (10)	C8—H8	0.9500
P1—O1	1.5895 (10)	C9—C10	1.388 (2)
P1—N1	1.6260 (13)	C9—H9	0.9500
O1—C1	1.4181 (17)	C10—C11	1.390 (2)
O2—C7	1.4045 (17)	C10—H10	0.9500
N1—C13	1.4148 (18)	C11—C12	1.386 (2)
N1—H1N	0.856 (18)	C11—H11	0.9500
C1—C2	1.381 (2)	C12—H12	0.9500
C1—C6	1.385 (2)	C13—C14	1.394 (2)
C2—C3	1.388 (2)	C13—C18	1.397 (2)
C2—H2	0.9500	C14—C15	1.395 (2)
C3—C4	1.388 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.384 (2)
C4—C5	1.391 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.394 (2)
C5—C6	1.388 (2)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.388 (2)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.384 (2)	C18—H18	0.9500
C7—C12	1.387 (2)
O3—P1—O2	116.86 (6)	C7—C8—H8	120.8
O3—P1—O1	114.51 (6)	C9—C8—H8	120.8
O2—P1—O1	95.12 (5)	C10—C9—C8	120.73 (14)
O3—P1—N1	110.04 (6)	C10—C9—H9	119.6
O2—P1—N1	109.05 (6)	C8—C9—H9	119.6
O1—P1—N1	110.40 (6)	C9—C10—C11	119.53 (14)
C1—O1—P1	116.46 (9)	C9—C10—H10	120.2
C7—O2—P1	125.84 (9)	C11—C10—H10	120.2
C13—N1—P1	130.84 (10)	C12—C11—C10	120.56 (14)
C13—N1—H1N	114.5 (12)	C12—C11—H11	119.7
P1—N1—H1N	112.9 (12)	C10—C11—H11	119.7
C2—C1—C6	122.31 (14)	C11—C12—C7	118.99 (14)
C2—C1—O1	118.19 (13)	C11—C12—H12	120.5
C6—C1—O1	119.47 (13)	C7—C12—H12	120.5
C1—C2—C3	118.45 (14)	C14—C13—C18	119.71 (13)
C1—C2—H2	120.8	C14—C13—N1	122.90 (13)
C3—C2—H2	120.8	C18—C13—N1	117.39 (13)
C4—C3—C2	120.54 (15)	C13—C14—C15	119.42 (14)
C4—C3—H3	119.7	C13—C14—H14	120.3
C2—C3—H3	119.7	C15—C14—H14	120.3
C3—C4—C5	119.86 (15)	C16—C15—C14	121.10 (14)
C3—C4—H4	120.1	C16—C15—H15	119.4
C5—C4—H4	120.1	C14—C15—H15	119.5
C6—C5—C4	120.33 (15)	C15—C16—C17	119.26 (14)
C6—C5—H5	119.8	C15—C16—H16	120.4
C4—C5—H5	119.8	C17—C16—H16	120.4
C1—C6—C5	118.51 (14)	C18—C17—C16	120.35 (14)
C1—C6—H6	120.7	C18—C17—H17	119.8
C5—C6—H6	120.7	C16—C17—H17	119.8
C8—C7—C12	121.75 (14)	C17—C18—C13	120.17 (13)
C8—C7—O2	123.63 (13)	C17—C18—H18	119.9
C12—C7—O2	114.59 (13)	C13—C18—H18	119.9
C7—C8—C9	118.44 (14)
O3—P1—O1—C1	53.11 (11)	P1—O2—C7—C12	−170.52 (10)
O2—P1—O1—C1	175.76 (10)	C12—C7—C8—C9	0.0 (2)
N1—P1—O1—C1	−71.72 (11)	O2—C7—C8—C9	177.88 (13)
O3—P1—O2—C7	−51.28 (13)	C7—C8—C9—C10	−0.2 (2)
O1—P1—O2—C7	−172.10 (11)	C8—C9—C10—C11	0.0 (2)
N1—P1—O2—C7	74.25 (12)	C9—C10—C11—C12	0.4 (2)
O3—P1—N1—C13	178.86 (12)	C10—C11—C12—C7	−0.5 (2)
O2—P1—N1—C13	49.46 (15)	C8—C7—C12—C11	0.3 (2)
O1—P1—N1—C13	−53.79 (15)	O2—C7—C12—C11	−177.72 (13)
P1—O1—C1—C2	106.89 (13)	P1—N1—C13—C14	−4.3 (2)
P1—O1—C1—C6	−75.11 (15)	P1—N1—C13—C18	176.23 (11)
C6—C1—C2—C3	−0.3 (2)	C18—C13—C14—C15	0.7 (2)
O1—C1—C2—C3	177.67 (13)	N1—C13—C14—C15	−178.82 (14)
C1—C2—C3—C4	0.1 (2)	C13—C14—C15—C16	−0.8 (2)
C2—C3—C4—C5	0.1 (2)	C14—C15—C16—C17	0.2 (2)
C3—C4—C5—C6	−0.1 (2)	C15—C16—C17—C18	0.4 (2)
C2—C1—C6—C5	0.3 (2)	C16—C17—C18—C13	−0.5 (2)
O1—C1—C6—C5	−177.65 (13)	C14—C13—C18—C17	−0.1 (2)
C4—C5—C6—C1	−0.1 (2)	N1—C13—C18—C17	179.46 (13)
P1—O2—C7—C8	11.5 (2)

(2Br)

Crystal data

C18H15BrNO3P	Z = 2
Mr = 404.19	F(000) = 408
Triclinic, P1	Dx = 1.632 Mg m^−3
a = 8.4356 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2086 (2) Å	Cell parameters from 7959 reflections
c = 11.2129 (2) Å	θ = 2.5–30.2°
α = 79.719 (1)°	µ = 2.61 mm^−1
β = 86.293 (1)°	T = 100 K
γ = 73.677 (1)°	Block, colourless
V = 822.39 (3) Å^3	0.28 × 0.19 × 0.12 mm

Data collection

Bruker APEX-II CCD diffractometer	3852 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan SADABS-2014/2	θmax = 28.7°, θmin = 1.9°
Tmin = 0.523, Tmax = 0.745	h = −11→11
16599 measured reflections	k = −12→12
4229 independent reflections	l = −15→11

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.059	w = 1/[σ^2(Fo^2) + (0.0269P)^2 + 0.3561P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4229 reflections	Δρmax = 0.40 e Å^−3
217 parameters	Δρmin = −0.37 e Å^−3
0 restraints

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
Br1	−0.14169 (2)	0.81141 (2)	0.24884 (2)	0.01940 (6)
P1	0.25748 (5)	0.83650 (4)	0.48600 (3)	0.01011 (8)
O1	0.36571 (13)	0.71687 (12)	0.58931 (10)	0.0135 (2)
O2	0.39749 (13)	0.80527 (12)	0.38443 (10)	0.0129 (2)
O3	0.19924 (14)	0.99483 (12)	0.50845 (10)	0.0142 (2)
N1	0.10576 (16)	0.77428 (14)	0.45344 (12)	0.0114 (3)
H1	0.005286	0.832989	0.463291	0.014*
C1	0.31604 (19)	0.67630 (17)	0.70892 (14)	0.0127 (3)
C2	0.1871 (2)	0.76956 (18)	0.76606 (15)	0.0157 (3)
H2	0.124090	0.865163	0.723817	0.019*
C3	0.1517 (2)	0.7200 (2)	0.88706 (15)	0.0201 (4)
H3	0.063270	0.782185	0.927783	0.024*
C4	0.2444 (2)	0.5806 (2)	0.94864 (16)	0.0227 (4)
H4	0.219843	0.547778	1.031240	0.027*
C5	0.3728 (2)	0.4895 (2)	0.88930 (15)	0.0207 (4)
H5	0.436445	0.394187	0.931529	0.025*
C6	0.4093 (2)	0.53631 (18)	0.76863 (15)	0.0165 (3)
H6	0.496856	0.473439	0.727623	0.020*
C7	0.11846 (19)	0.63514 (17)	0.41079 (14)	0.0112 (3)
C8	0.01830 (19)	0.63100 (17)	0.31795 (14)	0.0125 (3)
C9	0.0264 (2)	0.49627 (18)	0.27632 (15)	0.0150 (3)
H9	−0.043828	0.496699	0.213295	0.018*
C10	0.1377 (2)	0.36091 (18)	0.32715 (15)	0.0161 (3)
H10	0.144066	0.267819	0.299304	0.019*
C11	0.2396 (2)	0.36204 (18)	0.41889 (15)	0.0160 (3)
H11	0.316382	0.269425	0.453639	0.019*
C12	0.23015 (19)	0.49748 (17)	0.46033 (14)	0.0139 (3)
H12	0.300721	0.496528	0.523315	0.017*
C13	0.37484 (19)	0.90917 (17)	0.27397 (14)	0.0122 (3)
C14	0.4468 (2)	1.02906 (18)	0.25957 (14)	0.0143 (3)
H14	0.509470	1.041320	0.322628	0.017*
C15	0.4252 (2)	1.13124 (18)	0.15052 (15)	0.0169 (3)
H15	0.473587	1.214355	0.138547	0.020*
C16	0.3332 (2)	1.11223 (19)	0.05918 (15)	0.0185 (3)
H16	0.316969	1.183460	−0.014513	0.022*
C17	0.2648 (2)	0.9895 (2)	0.07521 (15)	0.0190 (3)
H17	0.203368	0.976110	0.011911	0.023*
C18	0.2857 (2)	0.88600 (19)	0.18347 (15)	0.0164 (3)
H18	0.239740	0.801333	0.194903	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02218 (10)	0.01430 (8)	0.02073 (9)	−0.00079 (6)	−0.01148 (7)	−0.00314 (6)
P1	0.01010 (18)	0.00961 (17)	0.01067 (18)	−0.00265 (14)	−0.00169 (14)	−0.00134 (14)
O1	0.0127 (5)	0.0148 (5)	0.0117 (5)	−0.0026 (4)	−0.0023 (4)	0.0006 (4)
O2	0.0125 (5)	0.0125 (5)	0.0121 (5)	−0.0022 (4)	−0.0003 (4)	0.0003 (4)
O3	0.0146 (5)	0.0117 (5)	0.0174 (6)	−0.0038 (4)	−0.0017 (4)	−0.0041 (4)
N1	0.0094 (6)	0.0099 (6)	0.0153 (6)	−0.0019 (5)	−0.0020 (5)	−0.0038 (5)
C1	0.0141 (7)	0.0146 (7)	0.0118 (7)	−0.0076 (6)	−0.0035 (6)	−0.0010 (6)
C2	0.0171 (8)	0.0157 (7)	0.0169 (8)	−0.0073 (6)	−0.0031 (6)	−0.0039 (6)
C3	0.0224 (9)	0.0243 (9)	0.0189 (8)	−0.0117 (7)	0.0027 (7)	−0.0098 (7)
C4	0.0289 (10)	0.0305 (9)	0.0136 (8)	−0.0172 (8)	−0.0027 (7)	−0.0009 (7)
C5	0.0241 (9)	0.0210 (8)	0.0174 (8)	−0.0103 (7)	−0.0074 (7)	0.0051 (7)
C6	0.0164 (8)	0.0163 (7)	0.0173 (8)	−0.0056 (6)	−0.0041 (6)	−0.0007 (6)
C7	0.0114 (7)	0.0113 (7)	0.0124 (7)	−0.0054 (6)	0.0014 (6)	−0.0029 (6)
C8	0.0118 (7)	0.0111 (7)	0.0138 (7)	−0.0023 (6)	−0.0003 (6)	−0.0018 (6)
C9	0.0147 (8)	0.0169 (7)	0.0165 (8)	−0.0075 (6)	−0.0001 (6)	−0.0057 (6)
C10	0.0148 (8)	0.0137 (7)	0.0219 (8)	−0.0055 (6)	0.0036 (6)	−0.0078 (6)
C11	0.0120 (7)	0.0122 (7)	0.0229 (8)	−0.0021 (6)	0.0014 (6)	−0.0033 (6)
C12	0.0125 (7)	0.0145 (7)	0.0151 (7)	−0.0047 (6)	−0.0018 (6)	−0.0013 (6)
C13	0.0109 (7)	0.0131 (7)	0.0110 (7)	−0.0014 (6)	0.0018 (6)	−0.0013 (6)
C14	0.0130 (7)	0.0165 (7)	0.0147 (7)	−0.0045 (6)	−0.0001 (6)	−0.0050 (6)
C15	0.0197 (8)	0.0154 (7)	0.0175 (8)	−0.0080 (6)	0.0019 (7)	−0.0035 (6)
C16	0.0222 (9)	0.0182 (8)	0.0145 (8)	−0.0067 (7)	−0.0010 (7)	0.0010 (6)
C17	0.0204 (9)	0.0246 (8)	0.0149 (8)	−0.0100 (7)	−0.0031 (7)	−0.0034 (7)
C18	0.0170 (8)	0.0170 (8)	0.0174 (8)	−0.0085 (6)	0.0006 (6)	−0.0028 (6)

Geometric parameters (Å, º)

Br1—C8	1.8966 (15)	C7—C12	1.396 (2)
P1—O1	1.5827 (11)	C8—C9	1.384 (2)
P1—O2	1.5895 (11)	C9—H9	0.9500
P1—O3	1.4638 (11)	C9—C10	1.385 (2)
P1—N1	1.6270 (13)	C10—H10	0.9500
O1—C1	1.3966 (18)	C10—C11	1.386 (2)
O2—C13	1.4109 (18)	C11—H11	0.9500
N1—H1	0.8800	C11—C12	1.387 (2)
N1—C7	1.4201 (19)	C12—H12	0.9500
C1—C2	1.383 (2)	C13—C14	1.383 (2)
C1—C6	1.385 (2)	C13—C18	1.381 (2)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.393 (2)	C14—C15	1.391 (2)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.388 (3)	C15—C16	1.388 (2)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.384 (3)	C16—C17	1.386 (2)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.387 (2)	C17—C18	1.391 (2)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.395 (2)
O1—P1—O2	94.06 (6)	C9—C8—Br1	117.66 (12)
O1—P1—N1	109.86 (6)	C9—C8—C7	122.02 (14)
O2—P1—N1	108.40 (6)	C8—C9—H9	120.2
O3—P1—O1	115.76 (6)	C8—C9—C10	119.55 (15)
O3—P1—O2	115.90 (6)	C10—C9—H9	120.2
O3—P1—N1	111.52 (7)	C9—C10—H10	120.2
C1—O1—P1	126.78 (10)	C9—C10—C11	119.60 (15)
C13—O2—P1	117.38 (9)	C11—C10—H10	120.2
P1—N1—H1	116.6	C10—C11—H11	119.8
C7—N1—P1	126.82 (11)	C10—C11—C12	120.45 (15)
C7—N1—H1	116.6	C12—C11—H11	119.8
C2—C1—O1	123.23 (14)	C7—C12—H12	119.5
C2—C1—C6	121.80 (15)	C11—C12—C7	120.93 (15)
C6—C1—O1	114.94 (14)	C11—C12—H12	119.5
C1—C2—H2	120.8	C14—C13—O2	118.32 (14)
C1—C2—C3	118.42 (15)	C18—C13—O2	119.26 (13)
C3—C2—H2	120.8	C18—C13—C14	122.40 (14)
C2—C3—H3	119.7	C13—C14—H14	120.8
C4—C3—C2	120.64 (16)	C13—C14—C15	118.40 (15)
C4—C3—H3	119.7	C15—C14—H14	120.8
C3—C4—H4	120.1	C14—C15—H15	119.9
C5—C4—C3	119.75 (16)	C16—C15—C14	120.25 (15)
C5—C4—H4	120.1	C16—C15—H15	119.9
C4—C5—H5	119.7	C15—C16—H16	119.9
C4—C5—C6	120.52 (16)	C17—C16—C15	120.16 (15)
C6—C5—H5	119.7	C17—C16—H16	119.9
C1—C6—C5	118.87 (16)	C16—C17—H17	119.8
C1—C6—H6	120.6	C16—C17—C18	120.34 (16)
C5—C6—H6	120.6	C18—C17—H17	119.8
C8—C7—N1	120.98 (13)	C13—C18—C17	118.43 (15)
C8—C7—C12	117.44 (14)	C13—C18—H18	120.8
C12—C7—N1	121.58 (14)	C17—C18—H18	120.8
C7—C8—Br1	120.27 (11)
Br1—C8—C9—C10	−177.85 (12)	N1—C7—C8—C9	−178.86 (14)
P1—O1—C1—C2	−23.0 (2)	N1—C7—C12—C11	179.09 (14)
P1—O1—C1—C6	158.99 (11)	C1—C2—C3—C4	0.3 (2)
P1—O2—C13—C14	94.93 (15)	C2—C1—C6—C5	−0.5 (2)
P1—O2—C13—C18	−86.59 (16)	C2—C3—C4—C5	−0.3 (3)
P1—N1—C7—C8	−137.50 (13)	C3—C4—C5—C6	−0.1 (3)
P1—N1—C7—C12	43.0 (2)	C4—C5—C6—C1	0.6 (3)
O1—P1—O2—C13	−167.62 (11)	C6—C1—C2—C3	0.1 (2)
O1—P1—N1—C7	−59.46 (14)	C7—C8—C9—C10	−0.4 (2)
O1—C1—C2—C3	−177.79 (14)	C8—C7—C12—C11	−0.4 (2)
O1—C1—C6—C5	177.53 (14)	C8—C9—C10—C11	−0.1 (2)
O2—P1—O1—C1	−176.68 (12)	C9—C10—C11—C12	0.3 (2)
O2—P1—N1—C7	42.05 (14)	C10—C11—C12—C7	0.0 (2)
O2—C13—C14—C15	179.73 (14)	C12—C7—C8—Br1	178.05 (11)
O2—C13—C18—C17	−179.95 (14)	C12—C7—C8—C9	0.7 (2)
O3—P1—O1—C1	61.95 (14)	C13—C14—C15—C16	0.1 (2)
O3—P1—O2—C13	−46.36 (13)	C14—C13—C18—C17	−1.5 (2)
O3—P1—N1—C7	170.81 (12)	C14—C15—C16—C17	−1.2 (3)
N1—P1—O1—C1	−65.46 (13)	C15—C16—C17—C18	1.0 (3)
N1—P1—O2—C13	79.89 (12)	C16—C17—C18—C13	0.4 (3)
N1—C7—C8—Br1	−1.5 (2)	C18—C13—C14—C15	1.3 (2)

(2Cl)

Crystal data

C18H15ClNO3P	Z = 2
Mr = 359.73	F(000) = 372
Triclinic, P1	Dx = 1.470 Mg m^−3
a = 8.4547 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2155 (2) Å	Cell parameters from 9949 reflections
c = 11.0953 (2) Å	θ = 2.7–30.2°
α = 79.742 (1)°	µ = 0.35 mm^−1
β = 86.939 (1)°	T = 100 K
γ = 72.784 (1)°	Plate, clear colourless
V = 812.55 (3) Å^3	0.34 × 0.08 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	4535 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.014
Absorption correction: multi-scan SADABS-2014/2	θmax = 30.2°, θmin = 2.4°
Tmin = 0.618, Tmax = 0.746	h = −11→11
23195 measured reflections	k = −13→10
4715 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: dual
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) = 0.080	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 0.3613P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
4715 reflections	Δρmax = 0.42 e Å^−3
221 parameters	Δρmin = −0.33 e Å^−3
0 restraints

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	−0.13402 (3)	0.81084 (3)	0.75411 (2)	0.02425 (7)
P1	0.25840 (3)	0.83625 (3)	0.98539 (2)	0.01161 (6)
O1	0.39553 (9)	0.80311 (8)	0.88209 (6)	0.01533 (14)
O2	0.36968 (8)	0.71440 (8)	1.08951 (6)	0.01514 (14)
O3	0.20153 (9)	0.99531 (8)	1.00835 (7)	0.01633 (14)
N1	0.10466 (10)	0.77685 (9)	0.95396 (8)	0.01349 (15)
C1	0.37132 (12)	0.90840 (11)	0.77114 (9)	0.01446 (17)
C2	0.27896 (13)	0.88860 (12)	0.67928 (9)	0.01883 (19)
H2	0.232651	0.807333	0.690355	0.023*
C3	0.25710 (14)	0.99331 (13)	0.56993 (10)	0.0213 (2)
H3	0.195238	0.982261	0.507150	0.026*
C4	0.32698 (14)	1.11402 (13)	0.55397 (10)	0.0210 (2)
H4	0.310589	1.184374	0.481126	0.025*
C5	0.42136 (14)	1.12972 (12)	0.64679 (10)	0.01980 (19)
H5	0.469255	1.209939	0.635418	0.024*
C6	0.44475 (12)	1.02626 (12)	0.75668 (9)	0.01695 (18)
H6	0.508246	1.036018	0.819006	0.020*
C7	0.11568 (11)	0.63898 (11)	0.90985 (8)	0.01297 (16)
C8	0.01138 (12)	0.63992 (11)	0.81587 (9)	0.01549 (17)
C9	0.01728 (13)	0.50665 (12)	0.77191 (10)	0.01856 (19)
H9	−0.053711	0.510114	0.709567	0.022*
C10	0.12988 (13)	0.36806 (12)	0.82159 (10)	0.01948 (19)
H10	0.134728	0.278124	0.792650	0.023*
C11	0.23514 (12)	0.36426 (12)	0.91457 (10)	0.01896 (19)
H11	0.310798	0.271511	0.947791	0.023*
C12	0.22822 (12)	0.49813 (11)	0.95836 (9)	0.01614 (17)
H12	0.299401	0.494024	1.020775	0.019*
C13	0.32105 (12)	0.67266 (11)	1.20950 (9)	0.01443 (17)
C14	0.41536 (13)	0.52993 (12)	1.26893 (9)	0.01825 (18)
H14	0.500978	0.468201	1.228184	0.022*
C15	0.37968 (14)	0.48095 (13)	1.39018 (10)	0.0227 (2)
H15	0.442602	0.386078	1.431412	0.027*
C16	0.25052 (15)	0.57275 (15)	1.45039 (10)	0.0247 (2)
H16	0.226645	0.539200	1.531513	0.030*
C17	0.15751 (14)	0.71439 (14)	1.38914 (10)	0.0228 (2)
H17	0.070890	0.775410	1.429579	0.027*
C18	0.19202 (13)	0.76684 (12)	1.26748 (9)	0.01802 (18)
H18	0.130135	0.862304	1.226500	0.022*
H1	0.008 (2)	0.842 (2)	0.9583 (15)	0.030 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02580 (13)	0.01862 (13)	0.02613 (13)	−0.00057 (9)	−0.01356 (10)	−0.00422 (9)
P1	0.01102 (11)	0.01042 (11)	0.01319 (11)	−0.00275 (8)	−0.00134 (8)	−0.00174 (8)
O1	0.0144 (3)	0.0139 (3)	0.0154 (3)	−0.0023 (2)	0.0009 (2)	0.0003 (2)
O2	0.0132 (3)	0.0166 (3)	0.0136 (3)	−0.0025 (2)	−0.0020 (2)	0.0003 (2)
O3	0.0158 (3)	0.0126 (3)	0.0212 (3)	−0.0039 (2)	−0.0007 (3)	−0.0049 (3)
N1	0.0111 (3)	0.0114 (4)	0.0181 (4)	−0.0021 (3)	−0.0021 (3)	−0.0046 (3)
C1	0.0138 (4)	0.0137 (4)	0.0146 (4)	−0.0029 (3)	0.0019 (3)	−0.0015 (3)
C2	0.0202 (4)	0.0198 (5)	0.0187 (4)	−0.0098 (4)	−0.0003 (3)	−0.0023 (4)
C3	0.0234 (5)	0.0255 (5)	0.0169 (4)	−0.0105 (4)	−0.0033 (4)	−0.0018 (4)
C4	0.0250 (5)	0.0212 (5)	0.0164 (4)	−0.0082 (4)	−0.0005 (4)	0.0005 (4)
C5	0.0242 (5)	0.0180 (5)	0.0192 (4)	−0.0102 (4)	0.0013 (4)	−0.0016 (4)
C6	0.0179 (4)	0.0177 (4)	0.0165 (4)	−0.0069 (3)	0.0003 (3)	−0.0035 (3)
C7	0.0123 (4)	0.0124 (4)	0.0152 (4)	−0.0045 (3)	0.0009 (3)	−0.0035 (3)
C8	0.0144 (4)	0.0154 (4)	0.0167 (4)	−0.0038 (3)	−0.0013 (3)	−0.0032 (3)
C9	0.0175 (4)	0.0208 (5)	0.0208 (4)	−0.0079 (4)	0.0003 (3)	−0.0085 (4)
C10	0.0170 (4)	0.0169 (5)	0.0280 (5)	−0.0072 (4)	0.0043 (4)	−0.0103 (4)
C11	0.0148 (4)	0.0131 (4)	0.0291 (5)	−0.0033 (3)	0.0013 (4)	−0.0056 (4)
C12	0.0137 (4)	0.0134 (4)	0.0212 (4)	−0.0035 (3)	−0.0018 (3)	−0.0031 (3)
C13	0.0151 (4)	0.0160 (4)	0.0136 (4)	−0.0069 (3)	−0.0029 (3)	−0.0014 (3)
C14	0.0175 (4)	0.0180 (5)	0.0184 (4)	−0.0052 (4)	−0.0034 (3)	0.0002 (3)
C15	0.0245 (5)	0.0241 (5)	0.0191 (5)	−0.0101 (4)	−0.0064 (4)	0.0045 (4)
C16	0.0291 (5)	0.0334 (6)	0.0155 (4)	−0.0165 (5)	−0.0010 (4)	−0.0014 (4)
C17	0.0245 (5)	0.0280 (5)	0.0202 (5)	−0.0115 (4)	0.0034 (4)	−0.0095 (4)
C18	0.0189 (4)	0.0170 (4)	0.0195 (4)	−0.0060 (4)	−0.0010 (3)	−0.0049 (3)

Geometric parameters (Å, º)

Cl1—C8	1.7381 (10)	C7—C12	1.3981 (13)
P1—O1	1.5888 (7)	C8—C9	1.3867 (14)
P1—O2	1.5841 (7)	C9—H9	0.9300
P1—O3	1.4654 (7)	C9—C10	1.3881 (15)
P1—N1	1.6274 (8)	C10—H10	0.9300
O1—C1	1.4081 (11)	C10—C11	1.3872 (15)
O2—C13	1.3937 (11)	C11—H11	0.9300
N1—C7	1.4174 (12)	C11—C12	1.3890 (13)
N1—H1	0.859 (18)	C12—H12	0.9300
C1—C2	1.3848 (14)	C13—C14	1.3882 (14)
C1—C6	1.3846 (13)	C13—C18	1.3858 (14)
C2—H2	0.9300	C14—H14	0.9300
C2—C3	1.3923 (14)	C14—C15	1.3877 (14)
C3—H3	0.9300	C15—H15	0.9300
C3—C4	1.3877 (15)	C15—C16	1.3896 (17)
C4—H4	0.9300	C16—H16	0.9300
C4—C5	1.3883 (15)	C16—C17	1.3847 (17)
C5—H5	0.9300	C17—H17	0.9300
C5—C6	1.3911 (14)	C17—C18	1.3964 (15)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.3984 (13)
O1—P1—N1	108.53 (4)	C9—C8—Cl1	118.45 (8)
O2—P1—O1	94.11 (4)	C9—C8—C7	121.81 (9)
O2—P1—N1	109.78 (4)	C8—C9—H9	120.2
O3—P1—O1	115.94 (4)	C8—C9—C10	119.55 (9)
O3—P1—O2	115.58 (4)	C10—C9—H9	120.2
O3—P1—N1	111.58 (4)	C9—C10—H10	120.1
C1—O1—P1	117.53 (6)	C11—C10—C9	119.73 (9)
C13—O2—P1	126.36 (6)	C11—C10—H10	120.1
P1—N1—H1	114.8 (12)	C10—C11—H11	119.8
C7—N1—P1	126.67 (7)	C10—C11—C12	120.40 (10)
C7—N1—H1	118.2 (12)	C12—C11—H11	119.8
C2—C1—O1	119.18 (9)	C7—C12—H12	119.6
C6—C1—O1	118.56 (9)	C11—C12—C7	120.88 (9)
C6—C1—C2	122.25 (9)	C11—C12—H12	119.6
C1—C2—H2	120.8	C14—C13—O2	114.77 (9)
C1—C2—C3	118.39 (9)	C18—C13—O2	123.28 (9)
C3—C2—H2	120.8	C18—C13—C14	121.93 (9)
C2—C3—H3	119.8	C13—C14—H14	120.6
C4—C3—C2	120.47 (10)	C15—C14—C13	118.86 (10)
C4—C3—H3	119.8	C15—C14—H14	120.6
C3—C4—H4	120.0	C14—C15—H15	119.8
C3—C4—C5	119.97 (10)	C14—C15—C16	120.42 (10)
C5—C4—H4	120.0	C16—C15—H15	119.8
C4—C5—H5	119.8	C15—C16—H16	120.1
C4—C5—C6	120.43 (10)	C17—C16—C15	119.74 (10)
C6—C5—H5	119.8	C17—C16—H16	120.1
C1—C6—C5	118.47 (9)	C16—C17—H17	119.6
C1—C6—H6	120.8	C16—C17—C18	120.90 (10)
C5—C6—H6	120.8	C18—C17—H17	119.6
C8—C7—N1	120.37 (8)	C13—C18—C17	118.14 (10)
C12—C7—N1	121.99 (8)	C13—C18—H18	120.9
C12—C7—C8	117.63 (9)	C17—C18—H18	120.9
C7—C8—Cl1	119.72 (7)
Cl1—C8—C9—C10	−178.62 (8)	N1—C7—C8—C9	−179.01 (9)
P1—O1—C1—C2	−86.91 (10)	N1—C7—C12—C11	179.17 (9)
P1—O1—C1—C6	94.74 (9)	C1—C2—C3—C4	0.18 (16)
P1—O2—C13—C14	158.04 (7)	C2—C1—C6—C5	1.40 (15)
P1—O2—C13—C18	−23.76 (13)	C2—C3—C4—C5	0.90 (17)
P1—N1—C7—C8	−136.77 (8)	C3—C4—C5—C6	−0.85 (17)
P1—N1—C7—C12	43.88 (13)	C4—C5—C6—C1	−0.27 (16)
O1—P1—O2—C13	−175.15 (8)	C6—C1—C2—C3	−1.35 (15)
O1—P1—N1—C7	41.12 (9)	C7—C8—C9—C10	−0.29 (15)
O1—C1—C2—C3	−179.64 (9)	C8—C7—C12—C11	−0.20 (14)
O1—C1—C6—C5	179.69 (9)	C8—C9—C10—C11	0.02 (15)
O2—P1—O1—C1	−166.80 (7)	C9—C10—C11—C12	0.15 (16)
O2—P1—N1—C7	−60.46 (9)	C10—C11—C12—C7	−0.06 (15)
O2—C13—C14—C15	177.81 (9)	C12—C7—C8—Cl1	178.68 (7)
O2—C13—C18—C17	−178.25 (9)	C12—C7—C8—C9	0.37 (14)
O3—P1—O1—C1	−45.72 (8)	C13—C14—C15—C16	0.69 (16)
O3—P1—O2—C13	63.48 (9)	C14—C13—C18—C17	−0.17 (15)
O3—P1—N1—C7	170.08 (8)	C14—C15—C16—C17	−0.37 (17)
N1—P1—O1—C1	80.75 (7)	C15—C16—C17—C18	−0.24 (17)
N1—P1—O2—C13	−63.77 (8)	C16—C17—C18—C13	0.50 (16)
N1—C7—C8—Cl1	−0.70 (13)	C18—C13—C14—C15	−0.42 (15)

(2I)

Crystal data

C18H15INO3P	Z = 2
Mr = 451.18	F(000) = 444
Triclinic, P1	Dx = 1.755 Mg m^−3
a = 8.4777 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2823 (6) Å	Cell parameters from 9913 reflections
c = 11.4187 (8) Å	θ = 2.5–30.2°
α = 79.545 (3)°	µ = 1.99 mm^−1
β = 85.778 (3)°	T = 100 K
γ = 75.120 (3)°	Plate, colourless
V = 853.67 (10) Å^3	0.39 × 0.18 × 0.05 mm

Data collection

Bruker APEX-II CCD diffractometer	4291 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan SADABS-2014/5	θmax = 29.1°, θmin = 2.3°
Tmin = 0.592, Tmax = 0.746	h = −11→9
16798 measured reflections	k = −12→11
4563 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0219P)^2 + 0.3496P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
4563 reflections	Δρmax = 0.79 e Å^−3
221 parameters	Δρmin = −0.93 e Å^−3
0 restraints

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
I1	0.35182 (2)	0.30884 (2)	0.24224 (2)	0.01921 (5)
P1	0.75377 (5)	0.33879 (5)	0.48884 (4)	0.01108 (9)
O1	0.89676 (15)	0.31046 (14)	0.39085 (12)	0.0141 (3)
O2	0.85700 (15)	0.22385 (15)	0.59228 (12)	0.0149 (3)
O3	0.69374 (15)	0.49525 (14)	0.50937 (13)	0.0153 (3)
N1	0.60723 (18)	0.27111 (17)	0.45450 (15)	0.0122 (3)
C1	0.8784 (2)	0.4104 (2)	0.28119 (17)	0.0140 (4)
C2	0.9469 (2)	0.5330 (2)	0.26659 (18)	0.0154 (4)
H2	1.004414	0.549615	0.329192	0.018*
C3	0.9297 (2)	0.6312 (2)	0.15817 (19)	0.0184 (4)
H3	0.976590	0.715494	0.146066	0.022*
C4	0.8444 (3)	0.6067 (2)	0.0676 (2)	0.0227 (4)
H4	0.831087	0.675444	−0.005603	0.027*
C5	0.7783 (3)	0.4817 (2)	0.0839 (2)	0.0234 (4)
H5	0.720959	0.464591	0.021439	0.028*
C6	0.7960 (2)	0.3817 (2)	0.19152 (19)	0.0193 (4)
H6	0.752315	0.295415	0.203073	0.023*
C7	0.6234 (2)	0.13165 (19)	0.41372 (17)	0.0116 (3)
C8	0.5284 (2)	0.1214 (2)	0.32217 (17)	0.0130 (3)
C9	0.5410 (2)	−0.0148 (2)	0.28378 (18)	0.0151 (4)
H9	0.474369	−0.019371	0.221874	0.018*
C10	0.6517 (2)	−0.1445 (2)	0.33641 (19)	0.0170 (4)
H10	0.660679	−0.238324	0.311022	0.020*
C11	0.7486 (2)	−0.1362 (2)	0.42589 (19)	0.0167 (4)
H11	0.825437	−0.224485	0.461194	0.020*
C12	0.7346 (2)	0.0003 (2)	0.46471 (18)	0.0150 (4)
H12	0.801578	0.004226	0.526641	0.018*
C13	0.8045 (2)	0.1842 (2)	0.70978 (18)	0.0149 (4)
C14	0.8965 (2)	0.0489 (2)	0.77073 (19)	0.0196 (4)
H14	0.984284	−0.012154	0.731510	0.023*
C15	0.8580 (3)	0.0043 (2)	0.8898 (2)	0.0260 (5)
H15	0.920416	−0.087711	0.932621	0.031*
C16	0.7288 (3)	0.0934 (3)	0.9468 (2)	0.0287 (5)
H16	0.703114	0.062877	1.028428	0.034*
C17	0.6377 (3)	0.2269 (3)	0.8836 (2)	0.0244 (4)
H17	0.548675	0.287288	0.922389	0.029*
C18	0.6745 (2)	0.2740 (2)	0.76430 (19)	0.0187 (4)
H18	0.611835	0.365648	0.721284	0.022*
H1	0.520 (3)	0.327 (3)	0.456 (2)	0.025 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02215 (7)	0.01412 (7)	0.02094 (8)	−0.00093 (5)	−0.01125 (5)	−0.00272 (5)
P1	0.0103 (2)	0.01131 (19)	0.0116 (2)	−0.00292 (15)	−0.00152 (17)	−0.00117 (17)
O1	0.0115 (6)	0.0151 (6)	0.0137 (7)	−0.0024 (5)	0.0004 (5)	0.0008 (5)
O2	0.0133 (6)	0.0180 (6)	0.0125 (7)	−0.0035 (5)	−0.0022 (5)	0.0004 (5)
O3	0.0142 (6)	0.0132 (6)	0.0193 (7)	−0.0035 (5)	−0.0014 (5)	−0.0045 (5)
N1	0.0090 (7)	0.0117 (7)	0.0157 (8)	−0.0007 (5)	−0.0023 (6)	−0.0035 (6)
C1	0.0120 (8)	0.0155 (8)	0.0129 (9)	−0.0025 (6)	0.0014 (7)	−0.0004 (7)
C2	0.0135 (8)	0.0169 (8)	0.0166 (10)	−0.0045 (7)	−0.0009 (7)	−0.0034 (7)
C3	0.0206 (9)	0.0175 (8)	0.0184 (10)	−0.0085 (7)	0.0012 (8)	−0.0020 (8)
C4	0.0262 (10)	0.0270 (10)	0.0156 (10)	−0.0122 (8)	0.0000 (8)	0.0028 (9)
C5	0.0281 (10)	0.0314 (11)	0.0151 (10)	−0.0155 (9)	−0.0048 (8)	−0.0024 (9)
C6	0.0210 (9)	0.0217 (9)	0.0182 (10)	−0.0120 (7)	0.0003 (8)	−0.0019 (8)
C7	0.0104 (7)	0.0111 (7)	0.0138 (9)	−0.0038 (6)	0.0026 (7)	−0.0027 (7)
C8	0.0115 (8)	0.0127 (7)	0.0142 (9)	−0.0030 (6)	0.0004 (7)	−0.0011 (7)
C9	0.0151 (8)	0.0161 (8)	0.0159 (10)	−0.0060 (7)	0.0016 (7)	−0.0052 (7)
C10	0.0155 (8)	0.0140 (8)	0.0227 (11)	−0.0044 (7)	0.0041 (8)	−0.0070 (8)
C11	0.0137 (8)	0.0132 (8)	0.0219 (10)	−0.0018 (6)	0.0023 (7)	−0.0024 (8)
C12	0.0115 (8)	0.0144 (8)	0.0184 (10)	−0.0028 (6)	−0.0013 (7)	−0.0015 (7)
C13	0.0175 (8)	0.0162 (8)	0.0137 (9)	−0.0098 (7)	−0.0034 (7)	−0.0001 (7)
C14	0.0196 (9)	0.0185 (9)	0.0208 (11)	−0.0064 (7)	−0.0062 (8)	0.0009 (8)
C15	0.0338 (12)	0.0258 (10)	0.0200 (11)	−0.0150 (9)	−0.0101 (9)	0.0069 (9)
C16	0.0409 (13)	0.0358 (12)	0.0153 (11)	−0.0231 (10)	−0.0024 (9)	0.0003 (9)
C17	0.0313 (11)	0.0295 (11)	0.0187 (11)	−0.0161 (9)	0.0041 (9)	−0.0099 (9)
C18	0.0233 (9)	0.0177 (8)	0.0183 (10)	−0.0094 (7)	−0.0017 (8)	−0.0047 (8)

Geometric parameters (Å, º)

I1—C8	2.0944 (18)	C7—C12	1.395 (2)
P1—O1	1.5919 (13)	C8—C9	1.389 (3)
P1—O2	1.5858 (14)	C9—H9	0.9500
P1—O3	1.4661 (13)	C9—C10	1.390 (3)
P1—N1	1.6290 (16)	C10—H10	0.9500
O1—C1	1.409 (2)	C10—C11	1.382 (3)
O2—C13	1.397 (2)	C11—H11	0.9500
N1—C7	1.425 (2)	C11—C12	1.392 (3)
N1—H1	0.79 (3)	C12—H12	0.9500
C1—C2	1.384 (3)	C13—C14	1.389 (3)
C1—C6	1.381 (3)	C13—C18	1.382 (3)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.391 (3)	C14—C15	1.388 (3)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.386 (3)	C15—C16	1.390 (3)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.391 (3)	C16—C17	1.385 (3)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.391 (3)	C17—C18	1.392 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.396 (3)
O1—P1—N1	107.97 (8)	C9—C8—I1	116.87 (14)
O2—P1—O1	94.04 (7)	C9—C8—C7	121.60 (16)
O2—P1—N1	109.75 (8)	C8—C9—H9	120.2
O3—P1—O1	115.86 (8)	C8—C9—C10	119.63 (18)
O3—P1—O2	115.90 (8)	C10—C9—H9	120.2
O3—P1—N1	111.88 (8)	C9—C10—H10	120.2
C1—O1—P1	117.64 (11)	C11—C10—C9	119.63 (17)
C13—O2—P1	127.10 (11)	C11—C10—H10	120.2
P1—N1—H1	114.4 (19)	C10—C11—H11	119.7
C7—N1—P1	127.11 (12)	C10—C11—C12	120.53 (17)
C7—N1—H1	118.2 (19)	C12—C11—H11	119.7
C2—C1—O1	118.44 (17)	C7—C12—H12	119.6
C6—C1—O1	119.27 (16)	C11—C12—C7	120.77 (19)
C6—C1—C2	122.28 (18)	C11—C12—H12	119.6
C1—C2—H2	120.8	C14—C13—O2	115.02 (17)
C1—C2—C3	118.47 (19)	C18—C13—O2	123.32 (17)
C3—C2—H2	120.8	C18—C13—C14	121.63 (19)
C2—C3—H3	119.8	C13—C14—H14	120.5
C4—C3—C2	120.38 (18)	C15—C14—C13	118.98 (19)
C4—C3—H3	119.8	C15—C14—H14	120.5
C3—C4—H4	120.0	C14—C15—H15	119.8
C3—C4—C5	120.1 (2)	C14—C15—C16	120.4 (2)
C5—C4—H4	120.0	C16—C15—H15	119.8
C4—C5—H5	119.9	C15—C16—H16	120.2
C6—C5—C4	120.1 (2)	C17—C16—C15	119.5 (2)
C6—C5—H5	119.9	C17—C16—H16	120.2
C1—C6—C5	118.62 (18)	C16—C17—H17	119.5
C1—C6—H6	120.7	C16—C17—C18	121.0 (2)
C5—C6—H6	120.7	C18—C17—H17	119.5
C8—C7—N1	121.32 (15)	C13—C18—C17	118.49 (19)
C12—C7—N1	120.85 (17)	C13—C18—H18	120.8
C12—C7—C8	117.83 (16)	C17—C18—H18	120.8
C7—C8—I1	121.47 (13)
I1—C8—C9—C10	−177.66 (13)	N1—C7—C8—C9	−178.58 (17)
P1—O1—C1—C2	94.47 (17)	N1—C7—C12—C11	179.10 (17)
P1—O1—C1—C6	−86.74 (19)	C1—C2—C3—C4	0.6 (3)
P1—O2—C13—C14	159.92 (14)	C2—C1—C6—C5	−1.5 (3)
P1—O2—C13—C18	−22.2 (3)	C2—C3—C4—C5	−1.3 (3)
P1—N1—C7—C8	−138.56 (16)	C3—C4—C5—C6	0.7 (3)
P1—N1—C7—C12	41.8 (2)	C4—C5—C6—C1	0.7 (3)
O1—P1—O2—C13	−177.49 (15)	C6—C1—C2—C3	0.9 (3)
O1—P1—N1—C7	42.43 (18)	C7—C8—C9—C10	−0.6 (3)
O1—C1—C2—C3	179.65 (16)	C8—C7—C12—C11	−0.6 (3)
O1—C1—C6—C5	179.73 (17)	C8—C9—C10—C11	−0.4 (3)
O2—P1—O1—C1	−168.29 (13)	C9—C10—C11—C12	0.9 (3)
O2—P1—N1—C7	−58.82 (18)	C10—C11—C12—C7	−0.4 (3)
O2—C13—C14—C15	176.87 (17)	C12—C7—C8—I1	178.00 (13)
O2—C13—C18—C17	−176.92 (17)	C12—C7—C8—C9	1.1 (3)
O3—P1—O1—C1	−46.90 (16)	C13—C14—C15—C16	0.4 (3)
O3—P1—O2—C13	61.16 (16)	C14—C13—C18—C17	0.8 (3)
O3—P1—N1—C7	171.07 (15)	C14—C15—C16—C17	0.4 (3)
N1—P1—O1—C1	79.44 (14)	C15—C16—C17—C18	−0.6 (3)
N1—P1—O2—C13	−66.76 (16)	C16—C17—C18—C13	0.0 (3)
N1—C7—C8—I1	−1.7 (2)	C18—C13—C14—C15	−1.0 (3)

(3Br)

Crystal data

C18H15BrNO3P	Z = 2
Mr = 404.19	F(000) = 408
Triclinic, P1	Dx = 1.536 Mg m^−3
a = 10.0639 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2306 (1) Å	Cell parameters from 4357 reflections
c = 10.5227 (2) Å	θ = 2.4–30.1°
α = 107.907 (1)°	µ = 2.46 mm^−1
β = 95.159 (1)°	T = 100 K
γ = 118.010 (1)°	Block, colourless
V = 874.05 (2) Å^3	0.44 × 0.28 × 0.18 mm

Data collection

Bruker APEX-II CCD diffractometer	3938 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.027
Absorption correction: multi-scan SADABS-2014/2	θmax = 28.7°, θmin = 2.1°
Tmin = 0.683, Tmax = 0.746	h = −13→13
11517 measured reflections	k = −13→13
4499 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: dual
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) = 0.066	w = 1/[σ^2(Fo^2) + (0.0246P)^2 + 0.5692P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4499 reflections	Δρmax = 0.48 e Å^−3
221 parameters	Δρmin = −0.37 e Å^−3
0 restraints

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
Br1	0.36775 (2)	0.27440 (2)	0.29064 (2)	0.01957 (6)
P1	1.03184 (5)	0.91186 (5)	0.29050 (5)	0.01065 (10)
O1	0.96490 (15)	0.95082 (15)	0.17457 (13)	0.0142 (3)
O2	1.10196 (15)	0.82278 (15)	0.19575 (13)	0.0127 (3)
O3	1.14302 (14)	1.05231 (15)	0.41817 (13)	0.0135 (3)
N1	0.88782 (18)	0.78002 (18)	0.32705 (17)	0.0131 (3)
C10	0.4950 (2)	0.3241 (2)	0.0669 (2)	0.0183 (4)
H10	0.406621	0.220285	0.010049	0.022*
C11	0.6075 (2)	0.4113 (2)	0.0110 (2)	0.0187 (4)
H11	0.595484	0.366315	−0.085913	0.022*
C12	0.7377 (2)	0.5629 (2)	0.09304 (19)	0.0159 (4)
H12	0.813158	0.620985	0.052526	0.019*
C7	0.7563 (2)	0.6288 (2)	0.23543 (18)	0.0122 (3)
C1	0.8939 (2)	1.0428 (2)	0.19806 (19)	0.0129 (3)
C2	0.8494 (2)	1.0836 (2)	0.3176 (2)	0.0189 (4)
H2	0.867119	1.051270	0.389720	0.023*
C3	0.7779 (3)	1.1733 (3)	0.3298 (2)	0.0233 (4)
H3	0.747575	1.203601	0.411581	0.028*
C4	0.7507 (3)	1.2185 (3)	0.2241 (2)	0.0238 (4)
H4	0.701784	1.279591	0.233222	0.029*
C16	1.3482 (2)	0.6506 (2)	0.3576 (2)	0.0204 (4)
H16	1.404411	0.611560	0.394890	0.025*
C15	1.4272 (2)	0.8065 (2)	0.3628 (2)	0.0205 (4)
H15	1.537464	0.873156	0.402678	0.025*
C14	1.3458 (2)	0.8658 (2)	0.31012 (19)	0.0174 (4)
H14	1.399098	0.972344	0.313203	0.021*
C13	1.1850 (2)	0.7652 (2)	0.25305 (18)	0.0133 (3)
C9	0.5155 (2)	0.3933 (2)	0.2088 (2)	0.0145 (4)
C8	0.6439 (2)	0.5436 (2)	0.29398 (19)	0.0140 (4)
H8	0.655350	0.588016	0.390787	0.017*
C5	0.7950 (2)	1.1746 (3)	0.1049 (2)	0.0217 (4)
H5	0.775382	1.204786	0.031834	0.026*
C6	0.8678 (2)	1.0867 (2)	0.09145 (19)	0.0164 (4)
H6	0.899068	1.057211	0.010055	0.020*
C18	1.1047 (2)	0.6093 (2)	0.2453 (2)	0.0203 (4)
H18	0.994513	0.542270	0.204706	0.024*
C17	1.1881 (3)	0.5521 (3)	0.2982 (2)	0.0233 (4)
H17	1.134801	0.444865	0.293433	0.028*
H1	0.881 (3)	0.816 (3)	0.403 (3)	0.023 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01553 (10)	0.01388 (10)	0.02533 (11)	0.00401 (7)	0.00819 (8)	0.00842 (8)
P1	0.0118 (2)	0.0106 (2)	0.0106 (2)	0.00598 (17)	0.00487 (17)	0.00483 (17)
O1	0.0192 (7)	0.0171 (6)	0.0129 (6)	0.0132 (5)	0.0074 (5)	0.0073 (5)
O2	0.0153 (6)	0.0148 (6)	0.0127 (6)	0.0104 (5)	0.0062 (5)	0.0063 (5)
O3	0.0132 (6)	0.0124 (6)	0.0131 (6)	0.0053 (5)	0.0057 (5)	0.0045 (5)
N1	0.0132 (7)	0.0116 (7)	0.0107 (7)	0.0039 (6)	0.0054 (6)	0.0035 (6)
C10	0.0149 (9)	0.0125 (9)	0.0206 (10)	0.0046 (7)	−0.0001 (7)	0.0039 (7)
C11	0.0203 (10)	0.0187 (9)	0.0129 (9)	0.0096 (8)	0.0021 (7)	0.0031 (7)
C12	0.0144 (9)	0.0168 (9)	0.0156 (9)	0.0073 (7)	0.0048 (7)	0.0066 (7)
C7	0.0103 (8)	0.0110 (8)	0.0151 (9)	0.0054 (7)	0.0030 (7)	0.0053 (7)
C1	0.0123 (8)	0.0121 (8)	0.0152 (9)	0.0074 (7)	0.0047 (7)	0.0046 (7)
C2	0.0251 (10)	0.0261 (10)	0.0153 (9)	0.0184 (9)	0.0091 (8)	0.0107 (8)
C3	0.0291 (11)	0.0311 (11)	0.0209 (10)	0.0225 (10)	0.0130 (9)	0.0110 (9)
C4	0.0290 (11)	0.0287 (11)	0.0277 (11)	0.0238 (10)	0.0111 (9)	0.0129 (9)
C16	0.0264 (10)	0.0264 (10)	0.0172 (9)	0.0212 (9)	0.0063 (8)	0.0069 (8)
C15	0.0176 (9)	0.0234 (10)	0.0161 (9)	0.0118 (8)	0.0018 (7)	0.0017 (8)
C14	0.0174 (9)	0.0151 (9)	0.0165 (9)	0.0080 (8)	0.0048 (7)	0.0032 (7)
C13	0.0161 (9)	0.0155 (9)	0.0118 (8)	0.0107 (7)	0.0057 (7)	0.0052 (7)
C9	0.0111 (8)	0.0135 (8)	0.0222 (9)	0.0070 (7)	0.0061 (7)	0.0097 (7)
C8	0.0136 (8)	0.0136 (8)	0.0151 (9)	0.0074 (7)	0.0046 (7)	0.0055 (7)
C5	0.0259 (11)	0.0255 (10)	0.0221 (10)	0.0172 (9)	0.0078 (8)	0.0130 (8)
C6	0.0188 (9)	0.0174 (9)	0.0151 (9)	0.0108 (8)	0.0062 (7)	0.0066 (7)
C18	0.0159 (9)	0.0177 (9)	0.0290 (11)	0.0093 (8)	0.0067 (8)	0.0103 (8)
C17	0.0258 (11)	0.0201 (10)	0.0304 (11)	0.0150 (9)	0.0088 (9)	0.0127 (9)

Geometric parameters (Å, º)

Br1—C9	1.8994 (18)	C3—H3	0.9500
P1—O1	1.5825 (13)	C3—C4	1.380 (3)
P1—O2	1.5793 (13)	C4—H4	0.9500
P1—O3	1.4676 (13)	C4—C5	1.384 (3)
P1—N1	1.6282 (16)	C16—H16	0.9500
O1—C1	1.406 (2)	C16—C15	1.387 (3)
O2—C13	1.414 (2)	C16—C17	1.382 (3)
N1—C7	1.416 (2)	C15—H15	0.9500
N1—H1	0.80 (2)	C15—C14	1.393 (3)
C10—H10	0.9500	C14—H14	0.9500
C10—C11	1.385 (3)	C14—C13	1.385 (3)
C10—C9	1.390 (3)	C13—C18	1.379 (3)
C11—H11	0.9500	C9—C8	1.384 (2)
C11—C12	1.390 (3)	C8—H8	0.9500
C12—H12	0.9500	C5—H5	0.9500
C12—C7	1.394 (3)	C5—C6	1.387 (3)
C7—C8	1.396 (2)	C6—H6	0.9500
C1—C2	1.383 (3)	C18—H18	0.9500
C1—C6	1.377 (3)	C18—C17	1.391 (3)
C2—H2	0.9500	C17—H17	0.9500
C2—C3	1.393 (3)
O1—P1—N1	109.84 (8)	C3—C4—C5	119.74 (19)
O2—P1—O1	95.64 (7)	C5—C4—H4	120.1
O2—P1—N1	108.37 (8)	C15—C16—H16	119.9
O3—P1—O1	115.40 (7)	C17—C16—H16	119.9
O3—P1—O2	116.24 (7)	C17—C16—C15	120.16 (19)
O3—P1—N1	110.39 (8)	C16—C15—H15	119.8
C1—O1—P1	124.04 (11)	C16—C15—C14	120.44 (19)
C13—O2—P1	119.61 (11)	C14—C15—H15	119.8
P1—N1—H1	113.6 (18)	C15—C14—H14	120.9
C7—N1—P1	128.84 (13)	C13—C14—C15	118.16 (18)
C7—N1—H1	115.8 (18)	C13—C14—H14	120.9
C11—C10—H10	121.1	C14—C13—O2	118.59 (16)
C11—C10—C9	117.83 (17)	C18—C13—O2	119.09 (16)
C9—C10—H10	121.1	C18—C13—C14	122.27 (18)
C10—C11—H11	119.2	C10—C9—Br1	119.11 (14)
C10—C11—C12	121.66 (18)	C8—C9—Br1	118.64 (14)
C12—C11—H11	119.2	C8—C9—C10	122.18 (17)
C11—C12—H12	120.3	C7—C8—H8	120.5
C11—C12—C7	119.35 (18)	C9—C8—C7	118.97 (17)
C7—C12—H12	120.3	C9—C8—H8	120.5
C12—C7—N1	122.95 (16)	C4—C5—H5	119.8
C12—C7—C8	120.01 (17)	C4—C5—C6	120.46 (19)
C8—C7—N1	117.03 (16)	C6—C5—H5	119.8
C2—C1—O1	122.93 (17)	C1—C6—C5	118.87 (18)
C6—C1—O1	115.18 (16)	C1—C6—H6	120.6
C6—C1—C2	121.87 (17)	C5—C6—H6	120.6
C1—C2—H2	120.8	C13—C18—H18	120.7
C1—C2—C3	118.39 (18)	C13—C18—C17	118.69 (18)
C3—C2—H2	120.8	C17—C18—H18	120.7
C2—C3—H3	119.7	C16—C17—C18	120.26 (19)
C4—C3—C2	120.66 (19)	C16—C17—H17	119.9
C4—C3—H3	119.7	C18—C17—H17	119.9
C3—C4—H4	120.1
Br1—C9—C8—C7	177.35 (13)	C10—C9—C8—C7	0.3 (3)
P1—O1—C1—C2	−12.3 (2)	C11—C10—C9—Br1	−177.72 (14)
P1—O1—C1—C6	169.28 (13)	C11—C10—C9—C8	−0.7 (3)
P1—O2—C13—C14	−91.04 (18)	C11—C12—C7—N1	177.93 (17)
P1—O2—C13—C18	91.54 (18)	C11—C12—C7—C8	−0.8 (3)
P1—N1—C7—C12	5.4 (3)	C12—C7—C8—C9	0.5 (3)
P1—N1—C7—C8	−175.83 (14)	C1—C2—C3—C4	0.7 (3)
O1—P1—O2—C13	177.60 (13)	C2—C1—C6—C5	0.1 (3)
O1—P1—N1—C7	51.57 (18)	C2—C3—C4—C5	−0.1 (3)
O1—C1—C2—C3	−179.11 (18)	C3—C4—C5—C6	−0.6 (3)
O1—C1—C6—C5	178.59 (17)	C4—C5—C6—C1	0.6 (3)
O2—P1—O1—C1	−175.51 (13)	C16—C15—C14—C13	0.1 (3)
O2—P1—N1—C7	−51.72 (18)	C15—C16—C17—C18	−1.0 (3)
O2—C13—C18—C17	178.07 (17)	C15—C14—C13—O2	−178.26 (16)
O3—P1—O1—C1	−52.92 (16)	C15—C14—C13—C18	−0.9 (3)
O3—P1—O2—C13	55.65 (15)	C14—C13—C18—C17	0.7 (3)
O3—P1—N1—C7	179.93 (15)	C13—C18—C17—C16	0.3 (3)
N1—P1—O1—C1	72.64 (15)	C9—C10—C11—C12	0.3 (3)
N1—P1—O2—C13	−69.31 (14)	C6—C1—C2—C3	−0.8 (3)
N1—C7—C8—C9	−178.35 (16)	C17—C16—C15—C14	0.8 (3)
C10—C11—C12—C7	0.4 (3)

(3Cl)

Crystal data

C18H15ClNO3P	F(000) = 744
Mr = 359.73	Dx = 1.423 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.6702 (9) Å	Cell parameters from 4845 reflections
b = 18.1551 (17) Å	θ = 2.2–27.1°
c = 10.1914 (10) Å	µ = 0.34 mm^−1
β = 110.184 (6)°	T = 100 K
V = 1679.4 (3) Å^3	Needle, colourless
Z = 4	0.33 × 0.09 × 0.05 mm

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.110
φ and ω scans	θmax = 25.7°, θmin = 2.2°
26387 measured reflections	h = −11→11
3184 independent reflections	k = −21→22
2472 reflections with I > 2σ(I)	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.1006P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3184 reflections	Δρmax = 0.58 e Å^−3
221 parameters	Δρmin = −0.66 e Å^−3
0 restraints

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	0.53018 (8)	0.02521 (4)	0.29604 (7)	0.0177 (2)
Cl1	0.13092 (8)	−0.08945 (4)	−0.21446 (7)	0.0274 (2)
O1	0.4978 (2)	0.07968 (10)	0.16861 (19)	0.0204 (5)
O2	0.6062 (2)	−0.03555 (10)	0.23255 (19)	0.0200 (5)
O3	0.6212 (2)	0.05258 (11)	0.43456 (19)	0.0209 (5)
N1	0.3733 (3)	−0.00560 (14)	0.2982 (3)	0.0209 (6)
C1	0.4111 (3)	0.14432 (15)	0.1482 (3)	0.0186 (6)
C2	0.3578 (3)	0.16844 (16)	0.0122 (3)	0.0226 (7)
H2	0.377711	0.141924	−0.059650	0.027*
C3	0.2738 (3)	0.23258 (16)	−0.0181 (3)	0.0254 (7)
H3	0.235168	0.249806	−0.111799	0.031*
C4	0.2464 (3)	0.27116 (17)	0.0861 (3)	0.0266 (7)
H4	0.189772	0.315144	0.065048	0.032*
C5	0.3023 (3)	0.24529 (16)	0.2230 (3)	0.0274 (7)
H5	0.283138	0.271831	0.295240	0.033*
C6	0.3855 (3)	0.18135 (16)	0.2553 (3)	0.0230 (7)
H6	0.423637	0.163628	0.348680	0.028*
C7	0.2542 (3)	−0.03780 (15)	0.1902 (3)	0.0190 (6)
C8	0.2565 (3)	−0.04772 (15)	0.0554 (3)	0.0210 (7)
H8	0.339937	−0.033955	0.032055	0.025*
C9	0.1326 (3)	−0.07840 (16)	−0.0440 (3)	0.0213 (7)
C10	0.0107 (3)	−0.10032 (15)	−0.0133 (3)	0.0226 (7)
H10	−0.072307	−0.121305	−0.083234	0.027*
C11	0.0125 (3)	−0.09092 (16)	0.1223 (3)	0.0232 (7)
H11	−0.070064	−0.105987	0.145779	0.028*
C12	0.1327 (3)	−0.06000 (16)	0.2234 (3)	0.0221 (7)
H12	0.132418	−0.053854	0.315914	0.027*
C13	0.6717 (3)	−0.09740 (15)	0.3160 (3)	0.0207 (7)
C14	0.5821 (4)	−0.15642 (16)	0.3199 (3)	0.0263 (7)
H14	0.478259	−0.153883	0.274792	0.032*
C15	0.6485 (4)	−0.21927 (19)	0.3917 (4)	0.0369 (9)
H15	0.589869	−0.260386	0.396885	0.044*
C16	0.7991 (4)	−0.2222 (2)	0.4554 (4)	0.0411 (9)
H16	0.843862	−0.265913	0.502261	0.049*
C17	0.8857 (4)	−0.1625 (2)	0.4519 (3)	0.0377 (9)
H17	0.989463	−0.164785	0.497321	0.045*
C18	0.8205 (3)	−0.09859 (18)	0.3814 (3)	0.0273 (7)
H18	0.878681	−0.056789	0.379111	0.033*
H1	0.369 (3)	−0.0107 (18)	0.368 (3)	0.016 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0212 (4)	0.0122 (4)	0.0178 (4)	−0.0010 (3)	0.0041 (3)	−0.0003 (3)
Cl1	0.0339 (5)	0.0247 (4)	0.0203 (4)	−0.0061 (3)	0.0050 (3)	−0.0035 (3)
O1	0.0266 (12)	0.0124 (10)	0.0215 (10)	0.0018 (8)	0.0074 (9)	0.0025 (8)
O2	0.0273 (12)	0.0110 (10)	0.0202 (10)	0.0024 (8)	0.0062 (8)	0.0018 (8)
O3	0.0259 (12)	0.0126 (10)	0.0217 (10)	−0.0031 (8)	0.0048 (8)	−0.0004 (8)
N1	0.0259 (15)	0.0221 (14)	0.0144 (13)	−0.0023 (11)	0.0066 (11)	−0.0014 (11)
C1	0.0174 (15)	0.0123 (14)	0.0238 (15)	−0.0026 (11)	0.0042 (12)	−0.0023 (11)
C2	0.0278 (17)	0.0168 (15)	0.0223 (15)	−0.0042 (13)	0.0074 (12)	−0.0006 (12)
C3	0.0283 (17)	0.0202 (16)	0.0244 (15)	−0.0025 (13)	0.0048 (13)	0.0062 (13)
C4	0.0291 (18)	0.0150 (16)	0.0312 (17)	0.0002 (13)	0.0048 (14)	0.0020 (12)
C5	0.0327 (19)	0.0192 (16)	0.0288 (17)	0.0033 (14)	0.0086 (14)	−0.0034 (13)
C6	0.0298 (17)	0.0149 (15)	0.0214 (15)	0.0033 (12)	0.0051 (12)	0.0022 (12)
C7	0.0210 (16)	0.0094 (14)	0.0225 (14)	0.0002 (11)	0.0023 (12)	0.0027 (11)
C8	0.0266 (17)	0.0126 (15)	0.0223 (15)	−0.0021 (12)	0.0066 (12)	0.0012 (11)
C9	0.0273 (17)	0.0123 (14)	0.0220 (15)	0.0028 (12)	0.0056 (12)	0.0007 (11)
C10	0.0208 (16)	0.0137 (15)	0.0282 (16)	−0.0023 (12)	0.0019 (12)	−0.0016 (12)
C11	0.0213 (17)	0.0185 (16)	0.0283 (16)	−0.0023 (12)	0.0067 (13)	0.0018 (12)
C12	0.0258 (17)	0.0161 (15)	0.0232 (15)	0.0025 (12)	0.0068 (12)	0.0013 (12)
C13	0.0291 (17)	0.0143 (15)	0.0176 (14)	0.0037 (12)	0.0066 (12)	0.0008 (11)
C14	0.0345 (19)	0.0145 (16)	0.0330 (17)	−0.0002 (13)	0.0156 (14)	0.0004 (13)
C15	0.057 (2)	0.0188 (18)	0.043 (2)	0.0077 (16)	0.0275 (18)	0.0060 (14)
C16	0.065 (3)	0.028 (2)	0.0353 (19)	0.0218 (19)	0.0229 (18)	0.0107 (15)
C17	0.039 (2)	0.040 (2)	0.0301 (18)	0.0183 (17)	0.0078 (15)	0.0010 (15)
C18	0.0314 (18)	0.0251 (18)	0.0242 (16)	0.0018 (14)	0.0084 (13)	−0.0032 (13)

Geometric parameters (Å, º)

P1—O1	1.575 (2)	C7—C12	1.390 (4)
P1—O2	1.582 (2)	C8—H8	0.9500
P1—O3	1.469 (2)	C8—C9	1.390 (4)
P1—N1	1.624 (3)	C9—C10	1.378 (4)
Cl1—C9	1.744 (3)	C10—H10	0.9500
O1—C1	1.415 (3)	C10—C11	1.386 (4)
O2—C13	1.419 (3)	C11—H11	0.9500
N1—C7	1.416 (4)	C11—C12	1.379 (4)
N1—H1	0.73 (3)	C12—H12	0.9500
C1—C2	1.374 (4)	C13—C14	1.388 (4)
C1—C6	1.375 (4)	C13—C18	1.361 (4)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.392 (4)	C14—C15	1.388 (4)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.373 (4)	C15—C16	1.375 (5)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.392 (4)	C16—C17	1.378 (5)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.386 (4)	C17—C18	1.395 (5)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.394 (4)
O1—P1—O2	95.09 (10)	C9—C8—C7	117.8 (3)
O1—P1—N1	107.85 (12)	C9—C8—H8	121.1
O2—P1—N1	109.47 (12)	C8—C9—Cl1	118.7 (2)
O3—P1—O1	117.56 (11)	C10—C9—Cl1	118.6 (2)
O3—P1—O2	114.84 (11)	C10—C9—C8	122.7 (3)
O3—P1—N1	110.86 (13)	C9—C10—H10	120.9
C1—O1—P1	125.49 (18)	C9—C10—C11	118.2 (3)
C13—O2—P1	118.75 (17)	C11—C10—H10	120.9
P1—N1—H1	115 (2)	C10—C11—H11	119.6
C7—N1—P1	130.1 (2)	C12—C11—C10	120.9 (3)
C7—N1—H1	114 (3)	C12—C11—H11	119.6
C2—C1—O1	114.2 (2)	C7—C12—H12	120.0
C2—C1—C6	122.5 (3)	C11—C12—C7	120.1 (3)
C6—C1—O1	123.3 (2)	C11—C12—H12	120.0
C1—C2—H2	120.7	C14—C13—O2	118.3 (3)
C1—C2—C3	118.6 (3)	C18—C13—O2	119.0 (3)
C3—C2—H2	120.7	C18—C13—C14	122.6 (3)
C2—C3—H3	119.7	C13—C14—H14	121.0
C4—C3—C2	120.6 (3)	C13—C14—C15	118.0 (3)
C4—C3—H3	119.7	C15—C14—H14	121.0
C3—C4—H4	120.3	C14—C15—H15	119.9
C3—C4—C5	119.4 (3)	C16—C15—C14	120.2 (3)
C5—C4—H4	120.3	C16—C15—H15	119.9
C4—C5—H5	119.5	C15—C16—H16	119.6
C6—C5—C4	120.9 (3)	C15—C16—C17	120.7 (3)
C6—C5—H5	119.5	C17—C16—H16	119.6
C1—C6—C5	118.0 (3)	C16—C17—H17	120.1
C1—C6—H6	121.0	C16—C17—C18	119.8 (3)
C5—C6—H6	121.0	C18—C17—H17	120.1
C8—C7—N1	122.3 (3)	C13—C18—C17	118.6 (3)
C12—C7—N1	117.4 (3)	C13—C18—H18	120.7
C12—C7—C8	120.3 (3)	C17—C18—H18	120.7
C7—C8—H8	121.1
P1—O1—C1—C2	−158.9 (2)	N1—C7—C12—C11	179.2 (3)
P1—O1—C1—C6	22.9 (4)	C1—C2—C3—C4	0.6 (4)
P1—O2—C13—C14	83.7 (3)	C2—C1—C6—C5	0.1 (4)
P1—O2—C13—C18	−100.5 (3)	C2—C3—C4—C5	−0.6 (5)
P1—N1—C7—C8	−0.4 (4)	C3—C4—C5—C6	0.2 (5)
P1—N1—C7—C12	179.3 (2)	C4—C5—C6—C1	0.0 (4)
Cl1—C9—C10—C11	−179.6 (2)	C6—C1—C2—C3	−0.4 (4)
O1—P1—O2—C13	174.1 (2)	C7—C8—C9—Cl1	178.6 (2)
O1—P1—N1—C7	51.2 (3)	C7—C8—C9—C10	−1.3 (4)
O1—C1—C2—C3	−178.6 (2)	C8—C7—C12—C11	−1.0 (4)
O1—C1—C6—C5	178.1 (3)	C8—C9—C10—C11	0.2 (4)
O2—P1—O1—C1	171.3 (2)	C9—C10—C11—C12	0.4 (4)
O2—P1—N1—C7	−51.1 (3)	C10—C11—C12—C7	0.0 (4)
O2—C13—C14—C15	174.5 (3)	C12—C7—C8—C9	1.7 (4)
O2—C13—C18—C17	−173.8 (3)	C13—C14—C15—C16	−0.6 (5)
O3—P1—O1—C1	−67.2 (2)	C14—C13—C18—C17	1.8 (5)
O3—P1—O2—C13	50.5 (2)	C14—C15—C16—C17	1.6 (5)
O3—P1—N1—C7	−178.8 (2)	C15—C16—C17—C18	−0.9 (5)
N1—P1—O1—C1	59.0 (2)	C16—C17—C18—C13	−0.8 (5)
N1—P1—O2—C13	−74.9 (2)	C18—C13—C14—C15	−1.2 (4)
N1—C7—C8—C9	−178.6 (3)

(3F)

Crystal data

C18H15FNO3P	Dx = 1.375 Mg m^−3
Mr = 343.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2073 reflections
a = 35.0174 (17) Å	θ = 2.8–26.1°
b = 7.3265 (3) Å	µ = 0.19 mm^−1
c = 12.9270 (5) Å	T = 100 K
V = 3316.5 (2) Å^3	Needle, colourless
Z = 8	0.40 × 0.06 × 0.06 mm
F(000) = 1424

Data collection

Bruker APEX-II CCD diffractometer	5559 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.095
Absorption correction: multi-scan SADABS-2014/5	θmax = 29.6°, θmin = 2.0°
Tmin = 0.527, Tmax = 0.746	h = −39→48
24220 measured reflections	k = −10→6
9033 independent reflections	l = −17→17

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.064	w = 1/[σ^2(Fo^2) + (0.0671P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.157	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.50 e Å^−3
9033 reflections	Δρmin = −0.53 e Å^−3
439 parameters	Absolute structure: Flack x determined using 1795 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.30 (13)
Primary atom site location: iterative

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	0.11573 (4)	0.00988 (18)	0.41401 (10)	0.0232 (3)
F1	0.09800 (12)	0.7220 (4)	0.6810 (3)	0.0498 (10)
O1	0.07556 (9)	−0.0766 (5)	0.4371 (3)	0.0259 (8)
O2	0.13839 (9)	−0.1168 (5)	0.4908 (3)	0.0247 (8)
O3	0.12842 (11)	0.0069 (5)	0.3065 (3)	0.0301 (9)
N1	0.11651 (12)	0.2178 (6)	0.4581 (3)	0.0242 (9)
H1N	0.1213 (16)	0.291 (8)	0.412 (4)	0.029*
C1	0.04068 (13)	0.0019 (7)	0.4073 (4)	0.0261 (10)
C2	0.01012 (16)	−0.0328 (8)	0.4712 (5)	0.0349 (14)
H2	0.013498	−0.102553	0.532467	0.042*
C3	−0.02545 (17)	0.0342 (8)	0.4458 (5)	0.0419 (15)
H3	−0.046670	0.011252	0.489741	0.050*
C4	−0.03016 (19)	0.1348 (8)	0.3564 (6)	0.0457 (17)
H4	−0.054748	0.179506	0.338460	0.055*
C5	0.00073 (17)	0.1708 (8)	0.2928 (5)	0.0412 (15)
H5	−0.002433	0.242288	0.232093	0.049*
C6	0.03647 (17)	0.1013 (8)	0.3187 (5)	0.0366 (13)
H6	0.057802	0.122893	0.274986	0.044*
C7	0.10668 (14)	0.2857 (7)	0.5565 (4)	0.0223 (11)
C8	0.10770 (15)	0.4719 (7)	0.5722 (4)	0.0265 (12)
H8	0.114972	0.552094	0.517872	0.032*
C9	0.09801 (17)	0.5387 (7)	0.6675 (4)	0.0297 (12)
C10	0.08739 (16)	0.4319 (8)	0.7500 (4)	0.0314 (12)
H10	0.081093	0.483419	0.815274	0.038*
C11	0.08635 (15)	0.2449 (7)	0.7330 (4)	0.0267 (11)
H11	0.079052	0.165999	0.787853	0.032*
C12	0.09577 (14)	0.1705 (7)	0.6373 (4)	0.0243 (11)
H12	0.094784	0.042215	0.626948	0.029*
C13	0.17875 (14)	−0.1050 (7)	0.4949 (4)	0.0261 (11)
C14	0.19525 (16)	0.0016 (8)	0.5691 (5)	0.0347 (13)
H14	0.180022	0.071374	0.615266	0.042*
C15	0.23472 (17)	0.0055 (8)	0.5753 (5)	0.0397 (15)
H15	0.246710	0.077566	0.627082	0.048*
C16	0.25680 (16)	−0.0937 (8)	0.5076 (5)	0.0372 (14)
H16	0.283861	−0.087392	0.511340	0.045*
C17	0.23945 (16)	−0.2023 (8)	0.4341 (5)	0.0376 (13)
H17	0.254633	−0.272117	0.387757	0.045*
C18	0.19988 (14)	−0.2099 (7)	0.4275 (4)	0.0319 (12)
H18	0.187702	−0.285575	0.377785	0.038*
P2	0.13896 (4)	0.50428 (18)	0.20986 (11)	0.0238 (3)
F2	0.13832 (10)	1.2208 (4)	−0.0593 (3)	0.0399 (8)
O4	0.17216 (10)	0.3845 (5)	0.1640 (3)	0.0267 (8)
O5	0.10643 (10)	0.4034 (5)	0.1482 (3)	0.0284 (8)
O6	0.13545 (10)	0.5028 (5)	0.3226 (3)	0.0269 (8)
N2	0.14256 (12)	0.7135 (6)	0.1696 (3)	0.0249 (10)
H2N	0.1395 (16)	0.782 (8)	0.215 (4)	0.030*
C19	0.06960 (14)	0.4771 (7)	0.1341 (4)	0.0259 (11)
C20	0.05263 (15)	0.5894 (7)	0.2063 (5)	0.0329 (12)
H20	0.065632	0.622334	0.268063	0.040*
C21	0.01618 (16)	0.6529 (8)	0.1865 (5)	0.0371 (14)
H21	0.004076	0.731384	0.234893	0.044*
C22	−0.00272 (16)	0.6041 (8)	0.0979 (5)	0.0387 (14)
H22	−0.027760	0.648876	0.085293	0.046*
C23	0.01461 (17)	0.4896 (8)	0.0265 (5)	0.0375 (14)
H23	0.001305	0.453947	−0.034269	0.045*
C24	0.05147 (16)	0.4273 (8)	0.0442 (4)	0.0336 (13)
H24	0.063934	0.351537	−0.005003	0.040*
C25	0.14347 (14)	0.7820 (7)	0.0675 (4)	0.0229 (11)
C26	0.13937 (14)	0.9706 (7)	0.0540 (4)	0.0225 (11)
H26	0.135017	1.049421	0.111108	0.027*
C27	0.14188 (15)	1.0375 (8)	−0.0453 (4)	0.0280 (12)
C28	0.14851 (16)	0.9315 (8)	−0.1312 (4)	0.0299 (12)
H28	0.150702	0.983905	−0.198191	0.036*
C29	0.15186 (15)	0.7460 (8)	−0.1160 (4)	0.0303 (12)
H29	0.155876	0.668732	−0.173970	0.036*
C30	0.14951 (14)	0.6690 (7)	−0.0180 (4)	0.0260 (11)
H30	0.151972	0.540838	−0.009223	0.031*
C31	0.20977 (14)	0.3913 (7)	0.2025 (4)	0.0267 (11)
C32	0.23707 (17)	0.4841 (8)	0.1462 (5)	0.0386 (15)
H32	0.230031	0.550420	0.085994	0.046*
C33	0.27456 (18)	0.4799 (9)	0.1780 (6)	0.0458 (17)
H33	0.293517	0.543410	0.139704	0.055*
C34	0.28456 (18)	0.3839 (9)	0.2651 (5)	0.0436 (15)
H34	0.310494	0.379776	0.286561	0.052*
C35	0.25711 (18)	0.2939 (9)	0.3211 (5)	0.0440 (15)
H35	0.264296	0.228867	0.381658	0.053*
C36	0.21905 (16)	0.2962 (8)	0.2911 (4)	0.0362 (13)
H36	0.200063	0.234361	0.330216	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0252 (6)	0.0179 (7)	0.0264 (7)	−0.0008 (5)	0.0014 (5)	−0.0005 (5)
F1	0.089 (3)	0.0212 (19)	0.039 (2)	−0.0018 (18)	0.0130 (18)	−0.0047 (15)
O1	0.0205 (17)	0.0195 (19)	0.038 (2)	−0.0019 (14)	−0.0030 (14)	0.0020 (15)
O2	0.0195 (16)	0.021 (2)	0.0339 (19)	0.0023 (14)	−0.0004 (14)	−0.0009 (15)
O3	0.036 (2)	0.022 (2)	0.032 (2)	0.0005 (16)	0.0031 (16)	−0.0032 (16)
N1	0.029 (2)	0.018 (2)	0.026 (2)	0.0012 (18)	0.0062 (17)	0.0032 (17)
C1	0.024 (2)	0.020 (3)	0.035 (3)	0.002 (2)	−0.007 (2)	−0.004 (2)
C2	0.031 (3)	0.029 (3)	0.045 (4)	−0.001 (2)	0.001 (3)	0.005 (3)
C3	0.030 (3)	0.034 (4)	0.063 (4)	−0.002 (3)	0.000 (3)	0.002 (3)
C4	0.035 (3)	0.022 (3)	0.080 (5)	0.002 (3)	−0.019 (3)	−0.002 (3)
C5	0.042 (3)	0.028 (3)	0.053 (4)	−0.004 (3)	−0.017 (3)	0.004 (3)
C6	0.036 (3)	0.029 (3)	0.045 (3)	−0.003 (2)	−0.010 (2)	0.001 (3)
C7	0.022 (2)	0.019 (3)	0.027 (3)	0.001 (2)	0.0002 (18)	−0.001 (2)
C8	0.028 (3)	0.024 (3)	0.028 (3)	−0.007 (2)	0.002 (2)	−0.001 (2)
C9	0.046 (3)	0.014 (3)	0.029 (3)	0.003 (2)	0.001 (2)	−0.004 (2)
C10	0.044 (3)	0.025 (3)	0.026 (3)	0.001 (3)	0.003 (2)	−0.001 (2)
C11	0.032 (3)	0.024 (3)	0.024 (3)	0.002 (2)	0.0020 (19)	0.003 (2)
C12	0.028 (3)	0.017 (3)	0.027 (3)	0.002 (2)	−0.001 (2)	−0.001 (2)
C13	0.022 (2)	0.023 (3)	0.033 (3)	−0.001 (2)	0.003 (2)	0.001 (2)
C14	0.030 (3)	0.037 (4)	0.037 (3)	0.004 (3)	−0.001 (2)	−0.006 (3)
C15	0.031 (3)	0.037 (4)	0.051 (4)	−0.005 (3)	−0.010 (3)	−0.016 (3)
C16	0.024 (3)	0.035 (4)	0.053 (4)	−0.001 (3)	−0.003 (3)	0.001 (3)
C17	0.028 (3)	0.036 (3)	0.048 (3)	0.008 (2)	0.001 (2)	−0.002 (3)
C18	0.026 (3)	0.032 (3)	0.039 (3)	0.002 (2)	−0.002 (2)	−0.006 (3)
P2	0.0260 (6)	0.0191 (7)	0.0263 (7)	−0.0002 (6)	0.0014 (5)	−0.0007 (5)
F2	0.064 (2)	0.0218 (18)	0.0338 (17)	0.0034 (15)	−0.0034 (15)	0.0025 (14)
O4	0.0241 (18)	0.023 (2)	0.0328 (19)	0.0038 (15)	−0.0006 (14)	−0.0032 (15)
O5	0.0260 (19)	0.023 (2)	0.036 (2)	0.0008 (15)	−0.0014 (15)	−0.0049 (17)
O6	0.031 (2)	0.024 (2)	0.0255 (19)	−0.0004 (15)	0.0026 (14)	0.0010 (15)
N2	0.030 (2)	0.020 (2)	0.024 (2)	−0.0022 (19)	0.0038 (17)	−0.0045 (18)
C19	0.023 (3)	0.021 (3)	0.034 (3)	0.001 (2)	0.003 (2)	0.000 (2)
C20	0.029 (3)	0.027 (3)	0.043 (3)	−0.001 (2)	−0.001 (2)	−0.005 (3)
C21	0.025 (3)	0.033 (4)	0.053 (4)	0.001 (2)	0.005 (2)	−0.005 (3)
C22	0.027 (3)	0.031 (4)	0.059 (4)	−0.002 (3)	0.000 (3)	0.008 (3)
C23	0.036 (3)	0.038 (4)	0.038 (3)	−0.001 (3)	−0.004 (2)	0.000 (3)
C24	0.029 (3)	0.034 (4)	0.038 (3)	−0.001 (2)	0.003 (2)	−0.001 (3)
C25	0.022 (2)	0.020 (3)	0.027 (3)	0.000 (2)	0.0008 (19)	0.001 (2)
C26	0.024 (3)	0.017 (3)	0.027 (3)	0.001 (2)	0.0008 (19)	−0.004 (2)
C27	0.028 (3)	0.019 (3)	0.036 (3)	0.002 (2)	−0.002 (2)	−0.001 (2)
C28	0.037 (3)	0.026 (3)	0.026 (3)	0.001 (2)	0.004 (2)	0.003 (2)
C29	0.032 (3)	0.027 (3)	0.031 (3)	0.003 (2)	0.002 (2)	−0.005 (2)
C30	0.030 (3)	0.020 (3)	0.029 (3)	0.000 (2)	0.004 (2)	−0.002 (2)
C31	0.025 (3)	0.021 (3)	0.035 (3)	0.001 (2)	−0.002 (2)	−0.002 (2)
C32	0.033 (3)	0.032 (4)	0.050 (4)	−0.004 (3)	−0.006 (3)	0.012 (3)
C33	0.028 (3)	0.036 (4)	0.073 (5)	−0.008 (3)	−0.001 (3)	0.008 (3)
C34	0.032 (3)	0.036 (4)	0.063 (4)	−0.001 (3)	−0.013 (3)	−0.006 (3)
C35	0.042 (4)	0.046 (4)	0.044 (3)	0.012 (3)	−0.011 (3)	−0.002 (3)
C36	0.037 (3)	0.035 (4)	0.037 (3)	0.005 (3)	0.003 (2)	0.008 (2)

Geometric parameters (Å, º)

P1—O3	1.459 (4)	P2—O6	1.463 (4)
P1—O1	1.571 (3)	P2—O4	1.573 (4)
P1—O2	1.574 (4)	P2—O5	1.575 (4)
P1—N1	1.627 (4)	P2—N2	1.624 (5)
F1—C9	1.354 (6)	F2—C27	1.361 (6)
O1—C1	1.404 (6)	O4—C31	1.408 (6)
O2—C13	1.417 (6)	O5—C19	1.410 (6)
N1—C7	1.409 (6)	N2—C25	1.412 (6)
N1—H1N	0.81 (5)	N2—H2N	0.78 (6)
C1—C6	1.366 (8)	C19—C24	1.374 (7)
C1—C2	1.375 (7)	C19—C20	1.379 (7)
C2—C3	1.378 (8)	C20—C21	1.382 (7)
C2—H2	0.9500	C20—H20	0.9500
C3—C4	1.380 (9)	C21—C22	1.370 (8)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.384 (9)	C22—C23	1.387 (8)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.392 (8)	C23—C24	1.388 (8)
C5—H5	0.9500	C23—H23	0.9500
C6—H6	0.9500	C24—H24	0.9500
C7—C8	1.379 (7)	C25—C30	1.397 (7)
C7—C12	1.396 (7)	C25—C26	1.400 (7)
C8—C9	1.369 (8)	C26—C27	1.377 (8)
C8—H8	0.9500	C26—H26	0.9500
C9—C10	1.374 (7)	C27—C28	1.374 (7)
C10—C11	1.388 (7)	C28—C29	1.379 (7)
C10—H10	0.9500	C28—H28	0.9500
C11—C12	1.392 (7)	C29—C30	1.388 (7)
C11—H11	0.9500	C29—H29	0.9500
C12—H12	0.9500	C30—H30	0.9500
C13—C14	1.365 (8)	C31—C36	1.380 (7)
C13—C18	1.377 (7)	C31—C32	1.381 (8)
C14—C15	1.385 (8)	C32—C33	1.376 (9)
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.376 (8)	C33—C34	1.373 (9)
C15—H15	0.9500	C33—H33	0.9500
C16—C17	1.380 (8)	C34—C35	1.372 (9)
C16—H16	0.9500	C34—H34	0.9500
C17—C18	1.389 (7)	C35—C36	1.388 (8)
C17—H17	0.9500	C35—H35	0.9500
C18—H18	0.9500	C36—H36	0.9500
O3—P1—O1	116.6 (2)	O6—P2—O4	115.7 (2)
O3—P1—O2	116.0 (2)	O6—P2—O5	116.1 (2)
O1—P1—O2	95.38 (19)	O4—P2—O5	94.7 (2)
O3—P1—N1	110.0 (2)	O6—P2—N2	109.4 (2)
O1—P1—N1	109.1 (2)	O4—P2—N2	110.4 (2)
O2—P1—N1	108.8 (2)	O5—P2—N2	109.7 (2)
C1—O1—P1	124.2 (3)	C31—O4—P2	122.6 (3)
C13—O2—P1	119.4 (3)	C19—O5—P2	123.2 (3)
C7—N1—P1	130.0 (4)	C25—N2—P2	129.5 (4)
C7—N1—H1N	118 (4)	C25—N2—H2N	118 (4)
P1—N1—H1N	111 (4)	P2—N2—H2N	111 (4)
C6—C1—C2	121.2 (5)	C24—C19—C20	122.1 (5)
C6—C1—O1	122.8 (5)	C24—C19—O5	115.5 (4)
C2—C1—O1	115.9 (5)	C20—C19—O5	122.4 (5)
C1—C2—C3	119.6 (6)	C19—C20—C21	118.2 (5)
C1—C2—H2	120.2	C19—C20—H20	120.9
C3—C2—H2	120.2	C21—C20—H20	120.9
C2—C3—C4	119.8 (6)	C22—C21—C20	120.9 (5)
C2—C3—H3	120.1	C22—C21—H21	119.5
C4—C3—H3	120.1	C20—C21—H21	119.5
C3—C4—C5	120.4 (6)	C21—C22—C23	120.1 (5)
C3—C4—H4	119.8	C21—C22—H22	119.9
C5—C4—H4	119.8	C23—C22—H22	119.9
C4—C5—C6	119.3 (6)	C22—C23—C24	119.8 (6)
C4—C5—H5	120.3	C22—C23—H23	120.1
C6—C5—H5	120.3	C24—C23—H23	120.1
C1—C6—C5	119.6 (6)	C19—C24—C23	118.8 (5)
C1—C6—H6	120.2	C19—C24—H24	120.6
C5—C6—H6	120.2	C23—C24—H24	120.6
C8—C7—C12	119.7 (5)	C30—C25—C26	120.1 (5)
C8—C7—N1	118.4 (5)	C30—C25—N2	122.2 (5)
C12—C7—N1	121.9 (5)	C26—C25—N2	117.7 (4)
C9—C8—C7	118.6 (5)	C27—C26—C25	117.5 (5)
C9—C8—H8	120.7	C27—C26—H26	121.3
C7—C8—H8	120.7	C25—C26—H26	121.3
F1—C9—C8	118.1 (5)	F2—C27—C28	117.7 (5)
F1—C9—C10	117.6 (5)	F2—C27—C26	118.0 (5)
C8—C9—C10	124.2 (5)	C28—C27—C26	124.3 (5)
C9—C10—C11	116.5 (5)	C27—C28—C29	117.1 (5)
C9—C10—H10	121.8	C27—C28—H28	121.5
C11—C10—H10	121.8	C29—C28—H28	121.5
C10—C11—C12	121.4 (5)	C28—C29—C30	121.7 (5)
C10—C11—H11	119.3	C28—C29—H29	119.1
C12—C11—H11	119.3	C30—C29—H29	119.1
C11—C12—C7	119.5 (5)	C29—C30—C25	119.3 (5)
C11—C12—H12	120.2	C29—C30—H30	120.3
C7—C12—H12	120.2	C25—C30—H30	120.3
C14—C13—C18	122.4 (5)	C36—C31—C32	121.5 (5)
C14—C13—O2	118.9 (5)	C36—C31—O4	119.7 (5)
C18—C13—O2	118.6 (4)	C32—C31—O4	118.6 (5)
C13—C14—C15	118.4 (5)	C33—C32—C31	119.5 (6)
C13—C14—H14	120.8	C33—C32—H32	120.3
C15—C14—H14	120.8	C31—C32—H32	120.3
C16—C15—C14	120.8 (5)	C34—C33—C32	120.0 (6)
C16—C15—H15	119.6	C34—C33—H33	120.0
C14—C15—H15	119.6	C32—C33—H33	120.0
C15—C16—C17	119.7 (5)	C35—C34—C33	120.0 (6)
C15—C16—H16	120.1	C35—C34—H34	120.0
C17—C16—H16	120.1	C33—C34—H34	120.0
C16—C17—C18	120.3 (5)	C34—C35—C36	121.3 (6)
C16—C17—H17	119.9	C34—C35—H35	119.4
C18—C17—H17	119.9	C36—C35—H35	119.4
C13—C18—C17	118.4 (5)	C31—C36—C35	117.7 (5)
C13—C18—H18	120.8	C31—C36—H36	121.2
C17—C18—H18	120.8	C35—C36—H36	121.2
O3—P1—O1—C1	−71.0 (4)	O6—P2—O4—C31	−48.2 (4)
O2—P1—O1—C1	166.3 (4)	O5—P2—O4—C31	−170.2 (4)
N1—P1—O1—C1	54.3 (4)	N2—P2—O4—C31	76.8 (4)
O3—P1—O2—C13	51.9 (4)	O6—P2—O5—C19	75.6 (4)
O1—P1—O2—C13	175.0 (3)	O4—P2—O5—C19	−162.7 (4)
N1—P1—O2—C13	−72.7 (4)	N2—P2—O5—C19	−49.0 (4)
O3—P1—N1—C7	179.8 (4)	O6—P2—N2—C25	−174.5 (4)
O1—P1—N1—C7	50.8 (5)	O4—P2—N2—C25	57.1 (5)
O2—P1—N1—C7	−52.0 (5)	O5—P2—N2—C25	−46.0 (5)
P1—O1—C1—C6	33.1 (7)	P2—O5—C19—C24	149.6 (4)
P1—O1—C1—C2	−149.3 (4)	P2—O5—C19—C20	−31.3 (7)
C6—C1—C2—C3	−0.2 (8)	C24—C19—C20—C21	0.0 (8)
O1—C1—C2—C3	−177.9 (5)	O5—C19—C20—C21	−179.0 (5)
C1—C2—C3—C4	0.3 (9)	C19—C20—C21—C22	0.6 (8)
C2—C3—C4—C5	−0.9 (9)	C20—C21—C22—C23	0.0 (9)
C3—C4—C5—C6	1.4 (9)	C21—C22—C23—C24	−1.2 (9)
C2—C1—C6—C5	0.7 (8)	C20—C19—C24—C23	−1.2 (8)
O1—C1—C6—C5	178.2 (5)	O5—C19—C24—C23	177.9 (5)
C4—C5—C6—C1	−1.3 (9)	C22—C23—C24—C19	1.8 (9)
P1—N1—C7—C8	−176.0 (4)	P2—N2—C25—C30	−14.1 (7)
P1—N1—C7—C12	3.4 (7)	P2—N2—C25—C26	167.9 (4)
C12—C7—C8—C9	0.2 (8)	C30—C25—C26—C27	−0.6 (7)
N1—C7—C8—C9	179.7 (5)	N2—C25—C26—C27	177.4 (5)
C7—C8—C9—F1	−178.0 (5)	C25—C26—C27—F2	−179.3 (4)
C7—C8—C9—C10	0.4 (9)	C25—C26—C27—C28	−0.7 (8)
F1—C9—C10—C11	177.8 (5)	F2—C27—C28—C29	−179.7 (5)
C8—C9—C10—C11	−0.6 (9)	C26—C27—C28—C29	1.7 (8)
C9—C10—C11—C12	0.3 (8)	C27—C28—C29—C30	−1.4 (8)
C10—C11—C12—C7	0.3 (7)	C28—C29—C30—C25	0.2 (8)
C8—C7—C12—C11	−0.6 (7)	C26—C25—C30—C29	0.8 (7)
N1—C7—C12—C11	−180.0 (4)	N2—C25—C30—C29	−177.0 (5)
P1—O2—C13—C14	96.2 (5)	P2—O4—C31—C36	80.3 (6)
P1—O2—C13—C18	−87.5 (5)	P2—O4—C31—C32	−103.9 (5)
C18—C13—C14—C15	0.9 (9)	C36—C31—C32—C33	1.0 (9)
O2—C13—C14—C15	177.1 (5)	O4—C31—C32—C33	−174.7 (5)
C13—C14—C15—C16	0.9 (9)	C31—C32—C33—C34	0.0 (10)
C14—C15—C16—C17	−1.7 (9)	C32—C33—C34—C35	−0.8 (10)
C15—C16—C17—C18	0.8 (9)	C33—C34—C35—C36	0.6 (10)
C14—C13—C18—C17	−1.8 (8)	C32—C31—C36—C35	−1.1 (8)
O2—C13—C18—C17	−177.9 (5)	O4—C31—C36—C35	174.5 (5)
C16—C17—C18—C13	0.9 (8)	C34—C35—C36—C31	0.4 (9)

(3I)

Crystal data

C18H15INO3P	Z = 2
Mr = 451.18	F(000) = 444
Triclinic, P1	Dx = 1.668 Mg m^−3
a = 10.0600 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4577 (2) Å	Cell parameters from 4653 reflections
c = 10.6104 (2) Å	θ = 2.4–28.0°
α = 109.098 (1)°	µ = 1.89 mm^−1
β = 95.734 (1)°	T = 100 K
γ = 116.967 (1)°	Block, colourless
V = 898.35 (3) Å^3	0.35 × 0.13 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	3639 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.029
Absorption correction: multi-scan SADABS-2014/5	θmax = 28.3°, θmin = 2.1°
Tmin = 0.649, Tmax = 0.746	h = −13→13
11038 measured reflections	k = −13→13
4192 independent reflections	l = −11→14

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0141P)^2 + 0.9249P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4192 reflections	Δρmax = 0.67 e Å^−3
220 parameters	Δρmin = −0.90 e Å^−3
0 restraints

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
I1	0.36293 (2)	0.26885 (2)	0.29159 (2)	0.01635 (7)
P1	1.02586 (8)	0.90785 (9)	0.28786 (8)	0.01144 (17)
O1	1.0962 (2)	0.8191 (2)	0.1927 (2)	0.0124 (4)
O2	0.9550 (2)	0.9415 (2)	0.1711 (2)	0.0131 (5)
O3	1.1373 (2)	1.0480 (2)	0.4158 (2)	0.0135 (5)
N1	0.8857 (3)	0.7807 (3)	0.3238 (3)	0.0124 (6)
H1	0.881 (3)	0.815 (4)	0.399 (3)	0.015*
C1	1.1818 (3)	0.7645 (3)	0.2509 (3)	0.0137 (7)
C2	1.1033 (4)	0.6117 (4)	0.2405 (3)	0.0203 (7)
H2	0.993658	0.545534	0.198265	0.024*
C3	1.1878 (4)	0.5574 (4)	0.2929 (4)	0.0243 (8)
H3	1.136056	0.452648	0.286524	0.029*
C4	1.3475 (4)	0.6546 (4)	0.3548 (3)	0.0190 (7)
H4	1.404848	0.617328	0.392179	0.023*
C5	1.4232 (4)	0.8061 (4)	0.3621 (3)	0.0201 (7)
H5	1.532933	0.872364	0.403670	0.024*
C6	1.3402 (3)	0.8621 (4)	0.3091 (3)	0.0180 (7)
H6	1.391953	0.965756	0.313096	0.022*
C7	0.7565 (3)	0.6302 (3)	0.2319 (3)	0.0114 (6)
C8	0.6470 (3)	0.5464 (3)	0.2887 (3)	0.0120 (6)
H8	0.658593	0.591193	0.385658	0.014*
C9	0.5214 (3)	0.3971 (3)	0.2022 (3)	0.0135 (7)
C10	0.5013 (3)	0.3280 (3)	0.0609 (3)	0.0158 (7)
H10	0.415189	0.225000	0.003145	0.019*
C11	0.6103 (3)	0.4132 (3)	0.0059 (3)	0.0165 (7)
H11	0.598103	0.367683	−0.091131	0.020*
C12	0.7366 (3)	0.5631 (3)	0.0891 (3)	0.0156 (7)
H12	0.809313	0.620082	0.049098	0.019*
C13	0.8878 (3)	1.0368 (3)	0.1966 (3)	0.0131 (7)
C14	0.8403 (4)	1.0755 (4)	0.3139 (3)	0.0198 (7)
H14	0.852878	1.039602	0.383235	0.024*
C15	0.7731 (4)	1.1687 (4)	0.3281 (4)	0.0258 (8)
H15	0.740118	1.197381	0.408237	0.031*
C16	0.7543 (4)	1.2195 (4)	0.2263 (4)	0.0247 (8)
H16	0.708524	1.282807	0.236495	0.030*
C17	0.8022 (4)	1.1779 (4)	0.1097 (4)	0.0224 (8)
H17	0.788418	1.212265	0.039477	0.027*
C18	0.8701 (3)	1.0869 (3)	0.0943 (3)	0.0147 (7)
H18	0.903981	1.059211	0.014562	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01394 (10)	0.01179 (11)	0.01986 (13)	0.00337 (8)	0.00716 (8)	0.00697 (9)
P1	0.0114 (4)	0.0104 (4)	0.0128 (5)	0.0052 (3)	0.0056 (3)	0.0052 (3)
O1	0.0151 (10)	0.0141 (10)	0.0120 (12)	0.0099 (9)	0.0065 (9)	0.0057 (9)
O2	0.0168 (11)	0.0161 (11)	0.0129 (12)	0.0117 (9)	0.0077 (9)	0.0077 (9)
O3	0.0136 (10)	0.0124 (10)	0.0111 (12)	0.0047 (9)	0.0047 (9)	0.0038 (9)
N1	0.0126 (13)	0.0129 (13)	0.0063 (15)	0.0039 (11)	0.0047 (11)	0.0016 (12)
C1	0.0179 (16)	0.0187 (16)	0.0116 (18)	0.0143 (14)	0.0081 (13)	0.0060 (14)
C2	0.0154 (16)	0.0184 (17)	0.027 (2)	0.0086 (14)	0.0068 (15)	0.0097 (16)
C3	0.0265 (19)	0.0199 (18)	0.033 (2)	0.0146 (16)	0.0117 (16)	0.0140 (17)
C4	0.0276 (18)	0.0260 (18)	0.0123 (19)	0.0211 (16)	0.0058 (14)	0.0075 (15)
C5	0.0178 (16)	0.0225 (18)	0.0146 (19)	0.0108 (15)	0.0027 (14)	0.0019 (15)
C6	0.0170 (16)	0.0137 (16)	0.0190 (19)	0.0066 (13)	0.0067 (14)	0.0035 (14)
C7	0.0130 (15)	0.0076 (14)	0.0125 (18)	0.0053 (12)	0.0037 (13)	0.0029 (13)
C8	0.0158 (15)	0.0129 (15)	0.0102 (17)	0.0092 (13)	0.0060 (13)	0.0049 (13)
C9	0.0108 (14)	0.0103 (15)	0.021 (2)	0.0055 (12)	0.0062 (13)	0.0085 (14)
C10	0.0138 (15)	0.0108 (15)	0.0164 (19)	0.0032 (13)	0.0013 (13)	0.0041 (14)
C11	0.0204 (17)	0.0173 (16)	0.0092 (18)	0.0099 (14)	0.0017 (13)	0.0033 (14)
C12	0.0142 (15)	0.0137 (15)	0.0172 (19)	0.0056 (13)	0.0059 (14)	0.0067 (14)
C13	0.0119 (15)	0.0101 (15)	0.0150 (18)	0.0055 (12)	0.0031 (13)	0.0030 (13)
C14	0.0243 (18)	0.0251 (18)	0.020 (2)	0.0172 (15)	0.0112 (15)	0.0136 (16)
C15	0.032 (2)	0.034 (2)	0.025 (2)	0.0260 (18)	0.0159 (17)	0.0123 (18)
C16	0.0313 (19)	0.031 (2)	0.031 (2)	0.0259 (17)	0.0152 (17)	0.0176 (18)
C17	0.0262 (18)	0.0258 (18)	0.024 (2)	0.0160 (16)	0.0082 (16)	0.0161 (17)
C18	0.0167 (16)	0.0146 (16)	0.0161 (19)	0.0084 (13)	0.0077 (14)	0.0091 (14)

Geometric parameters (Å, º)

I1—C9	2.106 (3)	C7—C12	1.394 (4)
P1—O1	1.5838 (19)	C8—H8	0.9500
P1—O2	1.582 (2)	C8—C9	1.385 (4)
P1—O3	1.467 (2)	C9—C10	1.381 (4)
P1—N1	1.625 (2)	C10—H10	0.9500
O1—C1	1.421 (3)	C10—C11	1.386 (4)
O2—C13	1.412 (3)	C11—H11	0.9500
N1—H1	0.78 (3)	C11—C12	1.384 (4)
N1—C7	1.416 (4)	C12—H12	0.9500
C1—C2	1.383 (4)	C13—C14	1.381 (4)
C1—C6	1.371 (4)	C13—C18	1.380 (4)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.379 (4)	C14—C15	1.397 (4)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.384 (4)	C15—C16	1.382 (4)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.382 (4)	C16—C17	1.382 (4)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.385 (4)	C17—C18	1.382 (4)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.396 (4)
O1—P1—N1	108.31 (12)	C9—C8—C7	119.3 (3)
O2—P1—O1	95.44 (11)	C9—C8—H8	120.4
O2—P1—N1	109.77 (12)	C8—C9—I1	118.6 (2)
O3—P1—O1	116.13 (11)	C10—C9—I1	119.4 (2)
O3—P1—O2	115.46 (11)	C10—C9—C8	121.9 (3)
O3—P1—N1	110.70 (12)	C9—C10—H10	120.9
C1—O1—P1	119.34 (18)	C9—C10—C11	118.2 (3)
C13—O2—P1	123.55 (18)	C11—C10—H10	120.9
P1—N1—H1	114 (2)	C10—C11—H11	119.3
C7—N1—P1	129.0 (2)	C12—C11—C10	121.5 (3)
C7—N1—H1	116 (2)	C12—C11—H11	119.3
C2—C1—O1	118.8 (3)	C7—C12—H12	120.2
C6—C1—O1	118.9 (3)	C11—C12—C7	119.7 (3)
C6—C1—C2	122.2 (3)	C11—C12—H12	120.2
C1—C2—H2	120.7	C14—C13—O2	122.9 (3)
C3—C2—C1	118.5 (3)	C18—C13—O2	115.2 (2)
C3—C2—H2	120.7	C18—C13—C14	121.9 (3)
C2—C3—H3	119.8	C13—C14—H14	120.8
C2—C3—C4	120.4 (3)	C13—C14—C15	118.3 (3)
C4—C3—H3	119.8	C15—C14—H14	120.8
C3—C4—H4	120.1	C14—C15—H15	119.8
C5—C4—C3	119.8 (3)	C16—C15—C14	120.4 (3)
C5—C4—H4	120.1	C16—C15—H15	119.8
C4—C5—H5	119.8	C15—C16—H16	120.1
C4—C5—C6	120.5 (3)	C15—C16—C17	119.9 (3)
C6—C5—H5	119.8	C17—C16—H16	120.1
C1—C6—C5	118.5 (3)	C16—C17—H17	119.7
C1—C6—H6	120.7	C18—C17—C16	120.5 (3)
C5—C6—H6	120.7	C18—C17—H17	119.7
C8—C7—N1	117.8 (3)	C13—C18—C17	118.9 (3)
C12—C7—N1	122.6 (3)	C13—C18—H18	120.5
C12—C7—C8	119.5 (3)	C17—C18—H18	120.5
C7—C8—H8	120.4
I1—C9—C10—C11	−177.9 (2)	N1—C7—C12—C11	177.8 (3)
P1—O1—C1—C2	92.3 (3)	C1—C2—C3—C4	0.2 (5)
P1—O1—C1—C6	−91.0 (3)	C2—C1—C6—C5	−1.6 (5)
P1—O2—C13—C14	−17.6 (4)	C2—C3—C4—C5	−1.1 (5)
P1—O2—C13—C18	163.6 (2)	C3—C4—C5—C6	0.7 (5)
P1—N1—C7—C8	−176.8 (2)	C4—C5—C6—C1	0.6 (5)
P1—N1—C7—C12	4.1 (4)	C6—C1—C2—C3	1.1 (5)
O1—P1—O2—C13	−172.7 (2)	C7—C8—C9—I1	177.4 (2)
O1—P1—N1—C7	−50.7 (3)	C7—C8—C9—C10	0.3 (4)
O1—C1—C2—C3	177.8 (3)	C8—C7—C12—C11	−1.2 (4)
O1—C1—C6—C5	−178.2 (3)	C8—C9—C10—C11	−0.8 (4)
O2—P1—O1—C1	178.10 (19)	C9—C10—C11—C12	0.2 (4)
O2—P1—N1—C7	52.4 (3)	C10—C11—C12—C7	0.8 (4)
O2—C13—C14—C15	−179.1 (3)	C12—C7—C8—C9	0.7 (4)
O2—C13—C18—C17	178.6 (3)	C13—C14—C15—C16	0.4 (5)
O3—P1—O1—C1	56.3 (2)	C14—C13—C18—C17	−0.2 (4)
O3—P1—O2—C13	−50.3 (2)	C14—C15—C16—C17	0.0 (5)
O3—P1—N1—C7	−179.0 (2)	C15—C16—C17—C18	−0.5 (5)
N1—P1—O1—C1	−69.0 (2)	C16—C17—C18—C13	0.6 (5)
N1—P1—O2—C13	75.6 (2)	C18—C13—C14—C15	−0.3 (5)
N1—C7—C8—C9	−178.4 (3)

(4Br)

Crystal data

C18H15BrNO3P	F(000) = 1632
Mr = 404.19	Dx = 1.543 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.8534 (5) Å	Cell parameters from 4501 reflections
b = 7.2695 (1) Å	θ = 2.4–27.7°
c = 19.7913 (4) Å	µ = 2.47 mm^−1
β = 103.346 (1)°	T = 100 K
V = 3479.16 (11) Å^3	Block, colourless
Z = 8	0.23 × 0.21 × 0.20 mm

Data collection

Bruker APEX-II CCD diffractometer	3868 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan SADABS-2014/2	θmax = 30.1°, θmin = 2.1°
Tmin = 0.542, Tmax = 0.746	h = −34→31
15103 measured reflections	k = −9→10
5008 independent reflections	l = −26→27

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 2.2644P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5008 reflections	Δρmax = 0.76 e Å^−3
217 parameters	Δρmin = −0.50 e Å^−3
0 restraints

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
Br1	−0.00789 (2)	0.61444 (3)	0.37251 (2)	0.02530 (8)
P1	0.19314 (2)	0.01762 (7)	0.26800 (3)	0.01414 (12)
O1	0.19385 (6)	−0.09723 (19)	0.33608 (7)	0.0171 (3)
O2	0.13731 (6)	−0.07085 (19)	0.22550 (7)	0.0168 (3)
O3	0.24133 (6)	−0.0003 (2)	0.23803 (7)	0.0187 (3)
N1	0.18167 (7)	0.2331 (2)	0.28157 (8)	0.0156 (4)
H1	0.201652	0.300032	0.272801	0.019*
C1	0.23441 (9)	−0.0664 (3)	0.39764 (11)	0.0169 (4)
C2	0.21673 (10)	−0.0094 (3)	0.45490 (12)	0.0271 (5)
H2	0.178603	0.013446	0.451819	0.033*
C3	0.25497 (11)	0.0145 (4)	0.51722 (12)	0.0318 (6)
H3	0.243084	0.053792	0.557185	0.038*
C4	0.31014 (10)	−0.0184 (3)	0.52149 (12)	0.0279 (5)
H4	0.336318	−0.001284	0.564307	0.034*
C5	0.32751 (11)	−0.0764 (3)	0.46355 (12)	0.0284 (5)
H5	0.365692	−0.098173	0.466637	0.034*
C6	0.28951 (10)	−0.1033 (3)	0.40075 (12)	0.0243 (5)
H6	0.301104	−0.145877	0.360994	0.029*
C7	0.13608 (8)	0.3145 (3)	0.30127 (10)	0.0144 (4)
C8	0.12915 (9)	0.5043 (3)	0.29312 (10)	0.0175 (4)
H8	0.154266	0.573425	0.273634	0.021*
C9	0.08607 (9)	0.5927 (3)	0.31313 (11)	0.0196 (5)
H9	0.081435	0.721789	0.307075	0.024*
C10	0.04984 (8)	0.4923 (3)	0.34194 (10)	0.0168 (4)
C11	0.05530 (9)	0.3031 (3)	0.34908 (11)	0.0200 (5)
H11	0.029566	0.234552	0.367748	0.024*
C12	0.09835 (9)	0.2141 (3)	0.32894 (11)	0.0185 (4)
H12	0.102209	0.084482	0.333974	0.022*
C13	0.11755 (9)	−0.0356 (3)	0.15383 (10)	0.0173 (4)
C14	0.12890 (9)	−0.1616 (3)	0.10744 (11)	0.0208 (5)
H14	0.151656	−0.265273	0.122999	0.025*
C15	0.10629 (10)	−0.1339 (3)	0.03702 (12)	0.0244 (5)
H15	0.113687	−0.219419	0.004015	0.029*
C16	0.07329 (9)	0.0166 (3)	0.01485 (11)	0.0235 (5)
H16	0.057856	0.034275	−0.033285	0.028*
C17	0.06265 (9)	0.1415 (3)	0.06249 (12)	0.0228 (5)
H17	0.040098	0.245695	0.046917	0.027*
C18	0.08464 (9)	0.1165 (3)	0.13327 (11)	0.0200 (5)
H18	0.077212	0.201676	0.166386	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01957 (13)	0.02575 (14)	0.03302 (14)	0.00578 (10)	0.01109 (9)	−0.00545 (10)
P1	0.0148 (3)	0.0102 (3)	0.0191 (3)	0.0001 (2)	0.0074 (2)	−0.0002 (2)
O1	0.0188 (8)	0.0134 (8)	0.0195 (7)	−0.0031 (6)	0.0054 (6)	0.0023 (6)
O2	0.0190 (8)	0.0142 (8)	0.0181 (7)	−0.0032 (6)	0.0060 (6)	0.0002 (6)
O3	0.0163 (8)	0.0155 (8)	0.0267 (8)	0.0030 (6)	0.0102 (6)	0.0019 (6)
N1	0.0160 (9)	0.0090 (9)	0.0252 (9)	−0.0026 (7)	0.0116 (7)	−0.0018 (7)
C1	0.0209 (11)	0.0093 (10)	0.0205 (10)	−0.0007 (8)	0.0049 (8)	0.0027 (8)
C2	0.0250 (13)	0.0296 (14)	0.0291 (12)	0.0020 (11)	0.0110 (10)	−0.0020 (10)
C3	0.0394 (15)	0.0341 (15)	0.0238 (12)	−0.0003 (12)	0.0111 (11)	−0.0057 (11)
C4	0.0344 (14)	0.0221 (13)	0.0250 (12)	−0.0013 (11)	0.0019 (10)	0.0018 (10)
C5	0.0246 (13)	0.0300 (14)	0.0292 (12)	0.0050 (10)	0.0031 (10)	0.0019 (10)
C6	0.0259 (12)	0.0252 (13)	0.0226 (11)	0.0065 (10)	0.0070 (9)	0.0012 (9)
C7	0.0145 (10)	0.0135 (10)	0.0161 (9)	0.0003 (8)	0.0053 (7)	−0.0014 (8)
C8	0.0209 (11)	0.0131 (10)	0.0205 (10)	−0.0013 (9)	0.0086 (8)	−0.0001 (8)
C9	0.0221 (11)	0.0141 (11)	0.0232 (11)	0.0049 (9)	0.0063 (9)	−0.0001 (9)
C10	0.0135 (10)	0.0194 (11)	0.0173 (10)	0.0042 (8)	0.0032 (8)	−0.0043 (8)
C11	0.0171 (11)	0.0213 (12)	0.0241 (11)	−0.0022 (9)	0.0098 (8)	−0.0011 (9)
C12	0.0190 (11)	0.0130 (11)	0.0258 (11)	0.0003 (9)	0.0101 (9)	0.0013 (9)
C13	0.0161 (11)	0.0183 (11)	0.0182 (10)	−0.0042 (9)	0.0053 (8)	0.0005 (8)
C14	0.0216 (11)	0.0164 (11)	0.0264 (11)	0.0013 (9)	0.0098 (9)	−0.0012 (9)
C15	0.0271 (13)	0.0243 (13)	0.0247 (11)	−0.0054 (10)	0.0117 (9)	−0.0071 (9)
C16	0.0217 (12)	0.0284 (13)	0.0212 (11)	−0.0060 (10)	0.0064 (9)	0.0008 (10)
C17	0.0180 (11)	0.0219 (13)	0.0286 (12)	0.0011 (9)	0.0052 (9)	0.0032 (9)
C18	0.0171 (11)	0.0184 (11)	0.0254 (11)	−0.0011 (9)	0.0069 (9)	−0.0031 (9)

Geometric parameters (Å, º)

Br1—C10	1.901 (2)	C7—C12	1.396 (3)
P1—O1	1.5817 (15)	C8—H8	0.9500
P1—O2	1.5837 (15)	C8—C9	1.382 (3)
P1—O3	1.4597 (15)	C9—H9	0.9500
P1—N1	1.6257 (18)	C9—C10	1.381 (3)
O1—C1	1.408 (3)	C10—C11	1.386 (3)
O2—C13	1.413 (2)	C11—H11	0.9500
N1—H1	0.7436	C11—C12	1.385 (3)
N1—C7	1.410 (2)	C12—H12	0.9500
C1—C2	1.371 (3)	C13—C14	1.371 (3)
C1—C6	1.383 (3)	C13—C18	1.380 (3)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.383 (3)	C14—C15	1.392 (3)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.375 (4)	C15—C16	1.377 (3)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.381 (3)	C16—C17	1.378 (3)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.390 (3)	C17—C18	1.393 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.395 (3)
O1—P1—O2	94.26 (8)	C9—C8—C7	120.65 (19)
O1—P1—N1	109.63 (8)	C9—C8—H8	119.7
O2—P1—N1	108.27 (8)	C8—C9—H9	120.2
O3—P1—O1	116.75 (8)	C10—C9—C8	119.6 (2)
O3—P1—O2	116.63 (8)	C10—C9—H9	120.2
O3—P1—N1	110.18 (9)	C9—C10—Br1	119.78 (16)
C1—O1—P1	121.18 (13)	C9—C10—C11	120.60 (19)
C13—O2—P1	121.22 (13)	C11—C10—Br1	119.63 (15)
P1—N1—H1	116.1	C10—C11—H11	120.1
C7—N1—P1	129.23 (14)	C12—C11—C10	119.85 (19)
C7—N1—H1	114.4	C12—C11—H11	120.1
C2—C1—O1	117.5 (2)	C7—C12—H12	119.9
C2—C1—C6	121.7 (2)	C11—C12—C7	120.1 (2)
C6—C1—O1	120.76 (19)	C11—C12—H12	119.9
C1—C2—H2	120.3	C14—C13—O2	118.25 (19)
C1—C2—C3	119.3 (2)	C14—C13—C18	122.5 (2)
C3—C2—H2	120.3	C18—C13—O2	119.09 (18)
C2—C3—H3	119.9	C13—C14—H14	120.8
C4—C3—C2	120.2 (2)	C13—C14—C15	118.4 (2)
C4—C3—H3	119.9	C15—C14—H14	120.8
C3—C4—H4	120.0	C14—C15—H15	119.8
C3—C4—C5	120.0 (2)	C16—C15—C14	120.5 (2)
C5—C4—H4	120.0	C16—C15—H15	119.8
C4—C5—H5	119.8	C15—C16—H16	120.0
C4—C5—C6	120.5 (2)	C15—C16—C17	120.0 (2)
C6—C5—H5	119.8	C17—C16—H16	120.0
C1—C6—C5	118.3 (2)	C16—C17—H17	119.7
C1—C6—H6	120.9	C16—C17—C18	120.6 (2)
C5—C6—H6	120.9	C18—C17—H17	119.7
C8—C7—N1	117.93 (17)	C13—C18—C17	118.0 (2)
C8—C7—C12	119.08 (18)	C13—C18—H18	121.0
C12—C7—N1	122.99 (19)	C17—C18—H18	121.0
C7—C8—H8	119.7
Br1—C10—C11—C12	−177.94 (16)	N1—C7—C12—C11	178.18 (19)
P1—O1—C1—C2	118.60 (19)	C1—C2—C3—C4	0.1 (4)
P1—O1—C1—C6	−65.2 (2)	C2—C1—C6—C5	−1.7 (3)
P1—O2—C13—C14	96.9 (2)	C2—C3—C4—C5	−0.3 (4)
P1—O2—C13—C18	−87.4 (2)	C3—C4—C5—C6	−0.5 (4)
P1—N1—C7—C8	−164.45 (15)	C4—C5—C6—C1	1.5 (4)
P1—N1—C7—C12	16.2 (3)	C6—C1—C2—C3	1.0 (4)
O1—P1—O2—C13	−172.34 (15)	C7—C8—C9—C10	0.5 (3)
O1—P1—N1—C7	−59.09 (19)	C8—C7—C12—C11	−1.1 (3)
O1—C1—C2—C3	177.1 (2)	C8—C9—C10—Br1	177.80 (16)
O1—C1—C6—C5	−177.7 (2)	C8—C9—C10—C11	−1.9 (3)
O2—P1—O1—C1	−175.19 (15)	C9—C10—C11—C12	1.8 (3)
O2—P1—N1—C7	42.49 (19)	C10—C11—C12—C7	−0.2 (3)
O2—C13—C14—C15	175.60 (19)	C12—C7—C8—C9	1.0 (3)
O2—C13—C18—C17	−175.77 (18)	C13—C14—C15—C16	−0.1 (3)
O3—P1—O1—C1	62.07 (17)	C14—C13—C18—C17	−0.3 (3)
O3—P1—O2—C13	−49.51 (18)	C14—C15—C16—C17	0.3 (3)
O3—P1—N1—C7	171.11 (17)	C15—C16—C17—C18	−0.5 (3)
N1—P1—O1—C1	−64.07 (17)	C16—C17—C18—C13	0.5 (3)
N1—P1—O2—C13	75.37 (16)	C18—C13—C14—C15	0.1 (3)
N1—C7—C8—C9	−178.34 (19)

(4Cl)

Crystal data

C18H15ClNO3P	F(000) = 744
Mr = 359.73	Dx = 1.386 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.3815 (2) Å	Cell parameters from 5772 reflections
b = 9.3201 (2) Å	θ = 2.5–29.6°
c = 17.8130 (3) Å	µ = 0.33 mm^−1
β = 90.725 (1)°	T = 100 K
V = 1723.39 (6) Å^3	Needle, colourless
Z = 4	0.40 × 0.09 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	3926 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.034
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0492 before and 0.0373 after correction. The Ratio of minimum to maximum transmission is 0.9241. The λ/2 correction factor is 0.00150.	θmax = 30.1°, θmin = 2.0°
Tmin = 0.689, Tmax = 0.746	h = −13→14
19630 measured reflections	k = −11→13
4947 independent reflections	l = −21→25

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 0.5293P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4947 reflections	Δρmax = 0.50 e Å^−3
221 parameters	Δρmin = −0.38 e Å^−3
0 restraints

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	0.68144 (4)	0.55884 (4)	0.56257 (2)	0.01609 (11)
Cl1	0.97004 (4)	−0.12570 (5)	0.59391 (3)	0.02751 (12)
O1	0.74035 (11)	0.57807 (12)	0.64425 (6)	0.0197 (3)
O2	0.81052 (10)	0.59234 (12)	0.51961 (6)	0.0179 (2)
O3	0.57284 (11)	0.65280 (12)	0.54273 (6)	0.0207 (3)
N1	0.64460 (13)	0.39075 (15)	0.55080 (8)	0.0179 (3)
C7	0.72435 (15)	0.26979 (17)	0.56188 (8)	0.0149 (3)
C14	0.88964 (16)	0.46568 (18)	0.41341 (10)	0.0209 (4)
H14	0.934402	0.402778	0.446612	0.025*
C13	0.81314 (15)	0.57407 (17)	0.44100 (9)	0.0174 (3)
C8	0.67794 (16)	0.13503 (18)	0.54050 (9)	0.0194 (3)
H8	0.594097	0.126796	0.518945	0.023*
C1	0.67426 (16)	0.53285 (18)	0.70867 (9)	0.0195 (3)
C11	0.92276 (16)	0.15810 (18)	0.60303 (9)	0.0201 (3)
H11	1.006797	0.165407	0.624415	0.024*
C10	0.87470 (16)	0.02637 (17)	0.58153 (9)	0.0184 (3)
C18	0.74620 (17)	0.66708 (19)	0.39437 (10)	0.0247 (4)
H18	0.694418	0.741350	0.414565	0.030*
C12	0.84769 (15)	0.28004 (17)	0.59328 (9)	0.0189 (3)
H12	0.880541	0.371020	0.608088	0.023*
C9	0.75273 (17)	0.01322 (18)	0.55034 (9)	0.0210 (3)
H9	0.720553	−0.078218	0.535833	0.025*
C2	0.54817 (17)	0.5731 (2)	0.72079 (10)	0.0255 (4)
H2	0.501743	0.627852	0.684489	0.031*
C6	0.74416 (19)	0.4546 (2)	0.76074 (10)	0.0295 (4)
H6	0.831248	0.429498	0.751571	0.035*
C15	0.89996 (17)	0.4503 (2)	0.33625 (10)	0.0264 (4)
H15	0.952579	0.376617	0.316171	0.032*
C16	0.83347 (19)	0.5424 (2)	0.28842 (11)	0.0300 (4)
H16	0.840854	0.531877	0.235604	0.036*
C17	0.7565 (2)	0.6494 (2)	0.31747 (11)	0.0321 (4)
H17	0.710216	0.711233	0.284418	0.039*
C3	0.49119 (18)	0.5316 (2)	0.78728 (11)	0.0320 (4)
H3	0.404817	0.559031	0.796919	0.038*
C4	0.5583 (2)	0.4509 (2)	0.83974 (11)	0.0326 (4)
H4	0.517689	0.421374	0.884651	0.039*
C5	0.6853 (2)	0.4133 (2)	0.82656 (11)	0.0365 (5)
H5	0.732059	0.358912	0.862867	0.044*
H1	0.577 (2)	0.377 (2)	0.5270 (11)	0.022 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0155 (2)	0.0149 (2)	0.0178 (2)	−0.00136 (15)	−0.00338 (16)	−0.00204 (15)
Cl1	0.0339 (2)	0.0185 (2)	0.0301 (2)	0.00736 (17)	0.00196 (19)	−0.00162 (17)
O1	0.0195 (6)	0.0215 (6)	0.0181 (6)	−0.0037 (5)	−0.0041 (5)	−0.0024 (5)
O2	0.0170 (5)	0.0181 (6)	0.0185 (5)	−0.0038 (4)	−0.0027 (5)	−0.0011 (4)
O3	0.0201 (6)	0.0187 (6)	0.0231 (6)	0.0020 (4)	−0.0050 (5)	−0.0038 (5)
N1	0.0144 (6)	0.0172 (7)	0.0220 (7)	−0.0020 (5)	−0.0058 (6)	−0.0018 (5)
C7	0.0168 (7)	0.0153 (8)	0.0125 (7)	−0.0016 (6)	0.0010 (6)	−0.0001 (6)
C14	0.0178 (7)	0.0217 (9)	0.0231 (8)	−0.0002 (6)	−0.0031 (7)	0.0032 (7)
C13	0.0164 (7)	0.0169 (8)	0.0187 (7)	−0.0043 (6)	−0.0022 (6)	0.0012 (6)
C8	0.0212 (8)	0.0207 (8)	0.0163 (7)	−0.0059 (6)	−0.0009 (6)	−0.0017 (6)
C1	0.0221 (8)	0.0192 (8)	0.0172 (7)	−0.0020 (6)	−0.0028 (7)	−0.0050 (6)
C11	0.0185 (8)	0.0208 (8)	0.0210 (8)	−0.0007 (6)	−0.0006 (7)	0.0009 (7)
C10	0.0253 (8)	0.0153 (8)	0.0147 (7)	0.0035 (6)	0.0053 (7)	0.0013 (6)
C18	0.0280 (9)	0.0187 (9)	0.0275 (9)	0.0028 (7)	−0.0011 (8)	0.0055 (7)
C12	0.0194 (7)	0.0140 (8)	0.0232 (8)	−0.0042 (6)	−0.0028 (7)	−0.0013 (6)
C9	0.0292 (9)	0.0153 (8)	0.0186 (8)	−0.0051 (7)	0.0028 (7)	−0.0034 (6)
C2	0.0224 (8)	0.0318 (10)	0.0222 (8)	0.0021 (7)	−0.0043 (7)	−0.0035 (7)
C6	0.0294 (9)	0.0356 (11)	0.0234 (9)	0.0098 (8)	−0.0019 (8)	0.0000 (8)
C15	0.0254 (9)	0.0290 (10)	0.0248 (9)	0.0007 (7)	0.0027 (8)	−0.0010 (7)
C16	0.0337 (10)	0.0362 (11)	0.0201 (8)	−0.0045 (8)	0.0013 (8)	0.0053 (8)
C17	0.0381 (11)	0.0308 (11)	0.0273 (9)	0.0017 (8)	−0.0044 (9)	0.0120 (8)
C3	0.0232 (9)	0.0464 (13)	0.0264 (9)	0.0023 (8)	−0.0009 (8)	−0.0054 (8)
C4	0.0354 (10)	0.0414 (12)	0.0212 (9)	−0.0016 (9)	0.0023 (8)	−0.0002 (8)
C5	0.0430 (12)	0.0428 (12)	0.0238 (9)	0.0123 (10)	−0.0009 (9)	0.0049 (9)

Geometric parameters (Å, º)

P1—O3	1.4673 (12)	C11—H11	0.9500
P1—O1	1.5813 (11)	C10—C9	1.382 (2)
P1—O2	1.5826 (12)	C18—C17	1.385 (3)
P1—N1	1.6256 (14)	C18—H18	0.9500
Cl1—C10	1.7412 (17)	C12—H12	0.9500
O1—C1	1.409 (2)	C9—H9	0.9500
O2—C13	1.4111 (19)	C2—C3	1.386 (3)
N1—C7	1.411 (2)	C2—H2	0.9500
N1—H1	0.83 (2)	C6—C5	1.384 (3)
C7—C12	1.394 (2)	C6—H6	0.9500
C7—C8	1.396 (2)	C15—C16	1.387 (3)
C14—C13	1.379 (2)	C15—H15	0.9500
C14—C15	1.387 (2)	C16—C17	1.383 (3)
C14—H14	0.9500	C16—H16	0.9500
C13—C18	1.382 (2)	C17—H17	0.9500
C8—C9	1.385 (2)	C3—C4	1.381 (3)
C8—H8	0.9500	C3—H3	0.9500
C1—C6	1.379 (2)	C4—C5	1.387 (3)
C1—C2	1.381 (2)	C4—H4	0.9500
C11—C10	1.378 (2)	C5—H5	0.9500
C11—C12	1.388 (2)
O3—P1—O1	116.17 (7)	C13—C18—H18	120.8
O3—P1—O2	114.74 (7)	C17—C18—H18	120.8
O1—P1—O2	95.89 (6)	C11—C12—C7	120.37 (15)
O3—P1—N1	111.43 (7)	C11—C12—H12	119.8
O1—P1—N1	108.39 (7)	C7—C12—H12	119.8
O2—P1—N1	109.09 (7)	C10—C9—C8	119.18 (15)
C1—O1—P1	121.93 (10)	C10—C9—H9	120.4
C13—O2—P1	118.89 (9)	C8—C9—H9	120.4
C7—N1—P1	127.97 (11)	C1—C2—C3	118.25 (17)
C7—N1—H1	116.3 (13)	C1—C2—H2	120.9
P1—N1—H1	114.3 (13)	C3—C2—H2	120.9
C12—C7—C8	118.89 (15)	C1—C6—C5	118.88 (18)
C12—C7—N1	122.39 (14)	C1—C6—H6	120.6
C8—C7—N1	118.72 (14)	C5—C6—H6	120.6
C13—C14—C15	118.74 (15)	C16—C15—C14	120.02 (18)
C13—C14—H14	120.6	C16—C15—H15	120.0
C15—C14—H14	120.6	C14—C15—H15	120.0
C14—C13—C18	122.19 (16)	C17—C16—C15	120.13 (18)
C14—C13—O2	117.41 (14)	C17—C16—H16	119.9
C18—C13—O2	120.32 (15)	C15—C16—H16	119.9
C9—C8—C7	120.78 (15)	C16—C17—C18	120.53 (17)
C9—C8—H8	119.6	C16—C17—H17	119.7
C7—C8—H8	119.6	C18—C17—H17	119.7
C6—C1—C2	122.02 (17)	C4—C3—C2	120.86 (18)
C6—C1—O1	116.65 (15)	C4—C3—H3	119.6
C2—C1—O1	121.21 (15)	C2—C3—H3	119.6
C10—C11—C12	119.62 (15)	C3—C4—C5	119.73 (19)
C10—C11—H11	120.2	C3—C4—H4	120.1
C12—C11—H11	120.2	C5—C4—H4	120.1
C11—C10—C9	121.17 (15)	C6—C5—C4	120.24 (18)
C11—C10—Cl1	119.13 (13)	C6—C5—H5	119.9
C9—C10—Cl1	119.69 (13)	C4—C5—H5	119.9
C13—C18—C17	118.38 (17)
O3—P1—O1—C1	71.70 (14)	C14—C13—C18—C17	0.3 (3)
O2—P1—O1—C1	−167.00 (12)	O2—C13—C18—C17	176.93 (15)
N1—P1—O1—C1	−54.62 (13)	C10—C11—C12—C7	0.0 (2)
O3—P1—O2—C13	−64.31 (13)	C8—C7—C12—C11	0.0 (2)
O1—P1—O2—C13	173.30 (11)	N1—C7—C12—C11	−179.93 (15)
N1—P1—O2—C13	61.50 (12)	C11—C10—C9—C8	0.1 (2)
O3—P1—N1—C7	178.10 (13)	Cl1—C10—C9—C8	−179.76 (12)
O1—P1—N1—C7	−52.87 (16)	C7—C8—C9—C10	−0.2 (2)
O2—P1—N1—C7	50.40 (15)	C6—C1—C2—C3	−0.6 (3)
P1—N1—C7—C12	7.0 (2)	O1—C1—C2—C3	−176.44 (16)
P1—N1—C7—C8	−172.93 (13)	C2—C1—C6—C5	1.1 (3)
C15—C14—C13—C18	0.3 (3)	O1—C1—C6—C5	177.09 (17)
C15—C14—C13—O2	−176.38 (14)	C13—C14—C15—C16	−0.4 (3)
P1—O2—C13—C14	−112.72 (14)	C14—C15—C16—C17	−0.2 (3)
P1—O2—C13—C18	70.54 (18)	C15—C16—C17—C18	0.9 (3)
C12—C7—C8—C9	0.1 (2)	C13—C18—C17—C16	−0.9 (3)
N1—C7—C8—C9	−179.95 (15)	C1—C2—C3—C4	−0.6 (3)
P1—O1—C1—C6	132.84 (14)	C2—C3—C4—C5	1.3 (3)
P1—O1—C1—C2	−51.1 (2)	C1—C6—C5—C4	−0.3 (3)
C12—C11—C10—C9	0.0 (2)	C3—C4—C5—C6	−0.9 (3)
C12—C11—C10—Cl1	179.87 (13)

(4F)

Crystal data

C18H15FNO3P	Z = 4
Mr = 343.28	F(000) = 712
Triclinic, P1	Dx = 1.380 Mg m^−3
a = 10.1285 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1480 (7) Å	Cell parameters from 9947 reflections
c = 17.8798 (14) Å	θ = 2.4–30.1°
α = 86.225 (3)°	µ = 0.19 mm^−1
β = 90.171 (3)°	T = 100 K
γ = 91.354 (3)°	Block, clear colourless
V = 1652.6 (2) Å^3	0.32 × 0.25 × 0.07 mm

Data collection

Bruker D8 Venture diffractometer	6078 reflections with I > 2σ(I)
φ and ω scans	θmax = 30.2°, θmin = 2.2°
Absorption correction: multi-scan SADABS-2014/2	h = −14→14
Tmin = 0.597, Tmax = 0.746	k = −12→12
9620 measured reflections	l = −20→25
9620 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.076	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.226	w = 1/[σ^2(Fo^2) + (0.1157P)^2 + 1.3293P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
9620 reflections	Δρmax = 0.78 e Å^−3
442 parameters	Δρmin = −0.69 e Å^−3
0 restraints

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.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P2	0.69864 (7)	1.05048 (8)	0.54953 (4)	0.02457 (19)
P1	0.69511 (7)	0.45152 (7)	0.05533 (4)	0.02266 (18)
F1	0.9289 (2)	1.1347 (2)	0.08679 (12)	0.0433 (5)
F2	0.9400 (2)	0.3743 (2)	0.57970 (12)	0.0445 (5)
O4	0.82886 (19)	1.0784 (2)	0.50176 (12)	0.0268 (4)
O1	0.82725 (19)	0.4274 (2)	0.01138 (11)	0.0254 (4)
O3	0.58649 (19)	0.3492 (2)	0.03905 (12)	0.0268 (4)
O5	0.76597 (19)	1.0697 (2)	0.62820 (12)	0.0277 (5)
O2	0.75788 (19)	0.4323 (2)	0.13606 (12)	0.0269 (4)
O6	0.5905 (2)	1.1500 (2)	0.52999 (13)	0.0308 (5)
N2	0.6516 (2)	0.8797 (3)	0.54570 (15)	0.0266 (5)
N1	0.6520 (2)	0.6207 (3)	0.04067 (15)	0.0257 (5)
C18	0.6638 (3)	0.8834 (3)	0.04306 (16)	0.0250 (6)
H18	0.573403	0.885286	0.028864	0.030*
C1	0.8271 (3)	0.4407 (3)	−0.06719 (17)	0.0251 (6)
C24	0.8972 (3)	0.9336 (3)	0.40303 (17)	0.0273 (6)
H24	0.940131	0.870268	0.439110	0.033*
C32	0.6739 (3)	0.6214 (3)	0.53320 (17)	0.0277 (6)
H32	0.587133	0.618988	0.512933	0.033*
C13	0.7263 (3)	0.7498 (3)	0.05242 (15)	0.0217 (5)
C31	0.7282 (3)	0.7534 (3)	0.55473 (16)	0.0226 (6)
C19	0.8278 (3)	1.0517 (3)	0.42543 (17)	0.0263 (6)
C25	0.7014 (3)	1.0327 (3)	0.69613 (18)	0.0297 (7)
C2	0.8942 (3)	0.5591 (3)	−0.10250 (19)	0.0314 (7)
H2A	0.933886	0.632611	−0.074102	0.038*
C7	0.6895 (3)	0.4678 (3)	0.20080 (17)	0.0278 (6)
C16	0.8619 (3)	1.0077 (3)	0.07452 (17)	0.0288 (6)
C17	0.7310 (3)	1.0141 (3)	0.05405 (17)	0.0297 (6)
H17	0.688025	1.105233	0.047649	0.036*
C36	0.8559 (3)	0.7553 (3)	0.58528 (17)	0.0261 (6)
H36	0.893514	0.844142	0.601263	0.031*
C23	0.9034 (3)	0.9088 (4)	0.32815 (19)	0.0358 (7)
H23	0.951653	0.828590	0.312348	0.043*
C33	0.7448 (3)	0.4929 (3)	0.54093 (18)	0.0323 (7)
H33	0.707722	0.402999	0.526050	0.039*
C14	0.8589 (3)	0.7473 (3)	0.07333 (19)	0.0294 (7)
H14	0.902710	0.656725	0.080479	0.035*
C34	0.8698 (3)	0.4995 (3)	0.57063 (18)	0.0309 (7)
C6	0.7660 (3)	0.3337 (4)	−0.10731 (19)	0.0375 (8)
H6	0.719278	0.253541	−0.082312	0.045*
C35	0.9274 (3)	0.6274 (3)	0.59217 (18)	0.0306 (7)
H35	1.014835	0.628473	0.611504	0.037*
C26	0.5743 (3)	1.0770 (4)	0.7096 (2)	0.0416 (9)
H26	0.525706	1.130119	0.671708	0.050*
C15	0.9269 (3)	0.8790 (3)	0.08367 (18)	0.0310 (7)
H15	1.017724	0.878890	0.096997	0.037*
C8	0.5617 (3)	0.4174 (4)	0.2148 (2)	0.0405 (8)
H8	0.515489	0.361386	0.179823	0.049*
C20	0.7639 (4)	1.1455 (4)	0.3738 (2)	0.0402 (8)
H20	0.716739	1.226521	0.389554	0.048*
C30	0.7734 (4)	0.9546 (4)	0.7510 (2)	0.0422 (8)
H30	0.860337	0.924638	0.740906	0.051*
C29	0.7169 (4)	0.9212 (4)	0.8201 (2)	0.0494 (10)
H29	0.765613	0.868903	0.858244	0.059*
C3	0.9024 (4)	0.5687 (4)	−0.1793 (2)	0.0409 (8)
H3	0.949602	0.648421	−0.204309	0.049*
C12	0.7583 (4)	0.5482 (4)	0.2509 (2)	0.0456 (9)
H12	0.845885	0.582346	0.240132	0.055*
C5	0.7745 (4)	0.3462 (5)	−0.1841 (2)	0.0497 (10)
H5	0.733406	0.273811	−0.212580	0.060*
C9	0.5030 (4)	0.4504 (5)	0.2809 (2)	0.0492 (9)
H9	0.415284	0.416510	0.291512	0.059*
C28	0.5893 (4)	0.9635 (5)	0.8345 (2)	0.0490 (9)
H28	0.550017	0.938584	0.881901	0.059*
C27	0.5197 (4)	1.0419 (5)	0.7796 (2)	0.0523 (11)
H27	0.432994	1.072363	0.789920	0.063*
C22	0.8401 (4)	0.9998 (5)	0.2760 (2)	0.0475 (9)
H22	0.843874	0.981721	0.224311	0.057*
C4	0.8423 (4)	0.4630 (5)	−0.2203 (2)	0.0522 (10)
H4	0.847591	0.470615	−0.273468	0.063*
C10	0.5695 (4)	0.5319 (5)	0.3317 (2)	0.0508 (10)
H10	0.527381	0.555777	0.376561	0.061*
C11	0.6983 (5)	0.5785 (5)	0.3169 (2)	0.0557 (11)
H11	0.745642	0.631838	0.352576	0.067*
C21	0.7707 (4)	1.1181 (5)	0.2988 (2)	0.0550 (11)
H21	0.727461	1.180802	0.262595	0.066*
H1	0.582 (4)	0.627 (4)	0.0195 (19)	0.031 (9)*
H2	0.579 (4)	0.874 (4)	0.526 (2)	0.048 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P2	0.0161 (3)	0.0183 (3)	0.0399 (4)	−0.0007 (3)	−0.0086 (3)	−0.0078 (3)
P1	0.0160 (3)	0.0168 (3)	0.0356 (4)	0.0030 (2)	−0.0088 (3)	−0.0044 (3)
F1	0.0485 (12)	0.0232 (9)	0.0583 (13)	−0.0145 (8)	−0.0023 (10)	−0.0077 (8)
F2	0.0499 (13)	0.0254 (10)	0.0589 (13)	0.0157 (9)	−0.0016 (10)	−0.0027 (9)
O4	0.0181 (9)	0.0242 (10)	0.0387 (12)	−0.0031 (8)	−0.0081 (8)	−0.0080 (8)
O1	0.0167 (9)	0.0246 (10)	0.0356 (11)	0.0049 (8)	−0.0090 (8)	−0.0052 (8)
O3	0.0183 (9)	0.0182 (9)	0.0440 (12)	0.0008 (7)	−0.0109 (9)	−0.0043 (8)
O5	0.0197 (10)	0.0265 (10)	0.0376 (12)	−0.0013 (8)	−0.0058 (9)	−0.0090 (9)
O2	0.0184 (10)	0.0272 (10)	0.0356 (11)	0.0047 (8)	−0.0095 (8)	−0.0059 (8)
O6	0.0198 (10)	0.0207 (10)	0.0529 (14)	0.0023 (8)	−0.0126 (9)	−0.0090 (9)
N2	0.0158 (11)	0.0192 (12)	0.0455 (15)	−0.0015 (9)	−0.0085 (11)	−0.0081 (10)
N1	0.0154 (11)	0.0191 (11)	0.0431 (15)	0.0031 (9)	−0.0112 (11)	−0.0052 (10)
C18	0.0259 (14)	0.0209 (13)	0.0283 (14)	0.0041 (11)	−0.0043 (11)	−0.0015 (11)
C1	0.0187 (13)	0.0217 (13)	0.0358 (16)	0.0046 (10)	−0.0074 (11)	−0.0072 (11)
C24	0.0188 (13)	0.0275 (15)	0.0350 (16)	−0.0005 (11)	−0.0091 (12)	0.0015 (12)
C32	0.0265 (14)	0.0220 (14)	0.0350 (16)	−0.0034 (11)	−0.0018 (12)	−0.0060 (11)
C13	0.0207 (13)	0.0195 (13)	0.0254 (14)	0.0038 (10)	−0.0026 (11)	−0.0043 (10)
C31	0.0196 (13)	0.0197 (13)	0.0287 (14)	−0.0009 (10)	−0.0018 (11)	−0.0038 (10)
C19	0.0165 (12)	0.0234 (14)	0.0382 (16)	−0.0037 (10)	−0.0082 (11)	0.0006 (11)
C25	0.0234 (14)	0.0265 (15)	0.0405 (17)	−0.0019 (11)	−0.0038 (13)	−0.0125 (13)
C2	0.0213 (14)	0.0247 (15)	0.0481 (19)	0.0028 (11)	−0.0086 (13)	−0.0019 (13)
C7	0.0239 (14)	0.0230 (14)	0.0363 (16)	0.0014 (11)	−0.0041 (12)	−0.0007 (12)
C16	0.0338 (16)	0.0200 (13)	0.0326 (16)	−0.0067 (12)	0.0030 (13)	−0.0055 (11)
C17	0.0373 (17)	0.0177 (13)	0.0339 (16)	0.0033 (12)	−0.0021 (13)	0.0002 (11)
C36	0.0199 (13)	0.0225 (14)	0.0361 (16)	−0.0009 (11)	−0.0052 (12)	−0.0037 (11)
C23	0.0297 (16)	0.0403 (18)	0.0375 (18)	−0.0008 (14)	−0.0024 (14)	−0.0036 (14)
C33	0.0368 (17)	0.0212 (14)	0.0394 (17)	−0.0021 (12)	−0.0005 (14)	−0.0066 (12)
C14	0.0185 (13)	0.0202 (14)	0.0504 (19)	0.0035 (11)	−0.0069 (13)	−0.0093 (12)
C34	0.0380 (17)	0.0174 (13)	0.0373 (17)	0.0080 (12)	0.0059 (14)	0.0005 (11)
C6	0.0380 (18)	0.0338 (17)	0.0412 (18)	−0.0080 (14)	−0.0014 (15)	−0.0107 (14)
C35	0.0235 (15)	0.0302 (16)	0.0376 (17)	0.0041 (12)	−0.0029 (13)	0.0016 (13)
C26	0.0241 (16)	0.061 (2)	0.0422 (19)	0.0081 (15)	−0.0089 (14)	−0.0208 (17)
C15	0.0211 (14)	0.0312 (16)	0.0417 (18)	−0.0039 (12)	−0.0026 (13)	−0.0114 (13)
C8	0.0245 (16)	0.054 (2)	0.0434 (19)	−0.0011 (15)	−0.0111 (14)	−0.0053 (16)
C20	0.0377 (19)	0.0314 (17)	0.051 (2)	0.0050 (14)	−0.0112 (16)	0.0048 (15)
C30	0.0399 (19)	0.0415 (19)	0.045 (2)	0.0134 (16)	0.0079 (16)	−0.0010 (15)
C29	0.061 (3)	0.043 (2)	0.044 (2)	0.0123 (19)	0.0079 (19)	0.0026 (16)
C3	0.0340 (18)	0.042 (2)	0.045 (2)	0.0021 (15)	−0.0001 (15)	0.0053 (15)
C12	0.044 (2)	0.047 (2)	0.047 (2)	−0.0184 (17)	0.0049 (17)	−0.0151 (16)
C5	0.057 (2)	0.055 (2)	0.039 (2)	−0.0116 (19)	−0.0029 (18)	−0.0193 (17)
C9	0.0282 (18)	0.072 (3)	0.046 (2)	−0.0017 (18)	0.0001 (16)	0.0043 (19)
C28	0.043 (2)	0.058 (2)	0.046 (2)	−0.0061 (18)	0.0087 (18)	−0.0123 (18)
C27	0.0251 (17)	0.085 (3)	0.050 (2)	0.0017 (18)	0.0011 (16)	−0.027 (2)
C22	0.050 (2)	0.063 (3)	0.0290 (18)	−0.0007 (19)	−0.0082 (16)	0.0037 (16)
C4	0.052 (2)	0.075 (3)	0.0287 (18)	0.002 (2)	−0.0040 (17)	−0.0016 (18)
C10	0.054 (2)	0.057 (2)	0.042 (2)	−0.001 (2)	0.0127 (18)	−0.0051 (18)
C11	0.069 (3)	0.055 (2)	0.044 (2)	−0.022 (2)	0.010 (2)	−0.0158 (18)
C21	0.060 (3)	0.057 (3)	0.046 (2)	0.012 (2)	−0.0193 (19)	0.0164 (18)

Geometric parameters (Å, º)

P2—O4	1.580 (2)	C36—H36	0.9500
P2—O5	1.580 (2)	C36—C35	1.389 (4)
P2—O6	1.467 (2)	C23—H23	0.9500
P2—N2	1.628 (2)	C23—C22	1.376 (5)
P1—O1	1.581 (2)	C33—H33	0.9500
P1—O3	1.4684 (19)	C33—C34	1.373 (5)
P1—O2	1.576 (2)	C14—H14	0.9500
P1—N1	1.623 (2)	C14—C15	1.396 (4)
F1—C16	1.362 (3)	C34—C35	1.372 (4)
F2—C34	1.363 (3)	C6—H6	0.9500
O4—C19	1.402 (4)	C6—C5	1.372 (5)
O1—C1	1.402 (4)	C35—H35	0.9500
O5—C25	1.399 (4)	C26—H26	0.9500
O2—C7	1.410 (4)	C26—C27	1.384 (5)
N2—C31	1.407 (4)	C15—H15	0.9500
N2—H2	0.82 (4)	C8—H8	0.9500
N1—C13	1.413 (3)	C8—C9	1.378 (5)
N1—H1	0.80 (4)	C20—H20	0.9500
C18—H18	0.9500	C20—C21	1.381 (5)
C18—C13	1.390 (4)	C30—H30	0.9500
C18—C17	1.386 (4)	C30—C29	1.376 (5)
C1—C2	1.382 (4)	C29—H29	0.9500
C1—C6	1.385 (4)	C29—C28	1.387 (6)
C24—H24	0.9500	C3—H3	0.9500
C24—C19	1.384 (4)	C3—C4	1.380 (6)
C24—C23	1.375 (4)	C12—H12	0.9500
C32—H32	0.9500	C12—C11	1.377 (5)
C32—C31	1.392 (4)	C5—H5	0.9500
C32—C33	1.390 (4)	C5—C4	1.382 (6)
C13—C14	1.394 (4)	C9—H9	0.9500
C31—C36	1.403 (4)	C9—C10	1.377 (6)
C19—C20	1.387 (4)	C28—H28	0.9500
C25—C26	1.386 (4)	C28—C27	1.379 (6)
C25—C30	1.390 (5)	C27—H27	0.9500
C2—H2A	0.9500	C22—H22	0.9500
C2—C3	1.373 (5)	C22—C21	1.388 (6)
C7—C8	1.382 (4)	C4—H4	0.9500
C7—C12	1.374 (4)	C10—H10	0.9500
C16—C17	1.375 (4)	C10—C11	1.383 (6)
C16—C15	1.363 (4)	C11—H11	0.9500
C17—H17	0.9500	C21—H21	0.9500
O4—P2—N2	108.85 (12)	C34—C33—C32	118.3 (3)
O5—P2—O4	95.90 (11)	C34—C33—H33	120.9
O5—P2—N2	108.41 (13)	C13—C14—H14	120.3
O6—P2—O4	115.38 (13)	C13—C14—C15	119.4 (3)
O6—P2—O5	115.64 (12)	C15—C14—H14	120.3
O6—P2—N2	111.49 (12)	F2—C34—C33	119.1 (3)
O1—P1—N1	109.31 (12)	F2—C34—C35	118.3 (3)
O3—P1—O1	114.47 (11)	C35—C34—C33	122.7 (3)
O3—P1—O2	116.32 (12)	C1—C6—H6	120.8
O3—P1—N1	111.56 (12)	C5—C6—C1	118.4 (3)
O2—P1—O1	95.80 (11)	C5—C6—H6	120.8
O2—P1—N1	108.23 (12)	C36—C35—H35	120.5
C19—O4—P2	119.55 (17)	C34—C35—C36	119.0 (3)
C1—O1—P1	119.47 (17)	C34—C35—H35	120.5
C25—O5—P2	122.70 (18)	C25—C26—H26	120.8
C7—O2—P1	122.18 (18)	C27—C26—C25	118.4 (4)
P2—N2—H2	110 (3)	C27—C26—H26	120.8
C31—N2—P2	128.6 (2)	C16—C15—C14	119.5 (3)
C31—N2—H2	119 (3)	C16—C15—H15	120.2
P1—N1—H1	112 (3)	C14—C15—H15	120.2
C13—N1—P1	128.6 (2)	C7—C8—H8	120.8
C13—N1—H1	119 (3)	C9—C8—C7	118.3 (3)
C13—C18—H18	119.4	C9—C8—H8	120.8
C17—C18—H18	119.4	C19—C20—H20	120.8
C17—C18—C13	121.2 (3)	C21—C20—C19	118.3 (3)
C2—C1—O1	118.1 (3)	C21—C20—H20	120.8
C2—C1—C6	121.7 (3)	C25—C30—H30	120.4
C6—C1—O1	120.1 (3)	C29—C30—C25	119.1 (3)
C19—C24—H24	120.3	C29—C30—H30	120.4
C23—C24—H24	120.3	C30—C29—H29	119.8
C23—C24—C19	119.4 (3)	C30—C29—C28	120.3 (4)
C31—C32—H32	119.5	C28—C29—H29	119.8
C33—C32—H32	119.5	C2—C3—H3	119.9
C33—C32—C31	121.0 (3)	C2—C3—C4	120.3 (3)
C18—C13—N1	118.4 (2)	C4—C3—H3	119.9
C18—C13—C14	119.3 (3)	C7—C12—H12	120.5
C14—C13—N1	122.3 (2)	C7—C12—C11	119.0 (3)
C32—C31—N2	118.4 (2)	C11—C12—H12	120.5
C32—C31—C36	119.0 (3)	C6—C5—H5	119.6
C36—C31—N2	122.6 (2)	C6—C5—C4	120.7 (3)
C24—C19—O4	118.0 (3)	C4—C5—H5	119.6
C24—C19—C20	121.3 (3)	C8—C9—H9	119.5
C20—C19—O4	120.6 (3)	C10—C9—C8	121.1 (3)
C26—C25—O5	121.9 (3)	C10—C9—H9	119.5
C26—C25—C30	121.4 (3)	C29—C28—H28	120.1
C30—C25—O5	116.6 (3)	C27—C28—C29	119.8 (4)
C1—C2—H2A	120.6	C27—C28—H28	120.1
C3—C2—C1	118.9 (3)	C26—C27—H27	119.5
C3—C2—H2A	120.6	C28—C27—C26	121.0 (3)
C8—C7—O2	121.4 (3)	C28—C27—H27	119.5
C12—C7—O2	116.8 (3)	C23—C22—H22	120.0
C12—C7—C8	121.7 (3)	C23—C22—C21	120.0 (3)
F1—C16—C17	118.8 (3)	C21—C22—H22	120.0
F1—C16—C15	118.7 (3)	C3—C4—C5	120.0 (3)
C15—C16—C17	122.6 (3)	C3—C4—H4	120.0
C18—C17—H17	121.0	C5—C4—H4	120.0
C16—C17—C18	118.0 (3)	C9—C10—H10	120.3
C16—C17—H17	121.0	C9—C10—C11	119.4 (4)
C31—C36—H36	120.0	C11—C10—H10	120.3
C35—C36—C31	120.0 (3)	C12—C11—C10	120.5 (4)
C35—C36—H36	120.0	C12—C11—H11	119.8
C24—C23—H23	119.9	C10—C11—H11	119.8
C24—C23—C22	120.3 (3)	C20—C21—C22	120.7 (3)
C22—C23—H23	119.9	C20—C21—H21	119.7
C32—C33—H33	120.9	C22—C21—H21	119.7
P2—O4—C19—C24	−110.0 (3)	N1—C13—C14—C15	179.7 (3)
P2—O4—C19—C20	73.0 (3)	C18—C13—C14—C15	−0.7 (5)
P2—O5—C25—C26	−47.8 (4)	C1—C2—C3—C4	1.2 (5)
P2—O5—C25—C30	135.0 (3)	C1—C6—C5—C4	−0.1 (6)
P2—N2—C31—C32	−166.2 (2)	C24—C19—C20—C21	0.2 (5)
P2—N2—C31—C36	14.6 (4)	C24—C23—C22—C21	0.7 (6)
P1—O1—C1—C2	110.4 (3)	C32—C31—C36—C35	1.4 (4)
P1—O1—C1—C6	−72.4 (3)	C32—C33—C34—F2	179.0 (3)
P1—O2—C7—C8	49.4 (4)	C32—C33—C34—C35	−0.6 (5)
P1—O2—C7—C12	−133.8 (3)	C13—C18—C17—C16	0.1 (4)
P1—N1—C13—C18	−173.5 (2)	C13—C14—C15—C16	1.2 (5)
P1—N1—C13—C14	6.1 (4)	C31—C32—C33—C34	0.2 (5)
F1—C16—C17—C18	−178.9 (3)	C31—C36—C35—C34	−1.8 (5)
F1—C16—C15—C14	178.3 (3)	C19—C24—C23—C22	−0.6 (5)
F2—C34—C35—C36	−178.2 (3)	C19—C20—C21—C22	−0.2 (6)
O4—P2—O5—C25	−168.9 (2)	C25—C26—C27—C28	−0.7 (6)
O4—P2—N2—C31	46.2 (3)	C25—C30—C29—C28	0.8 (6)
O4—C19—C20—C21	177.2 (3)	C2—C1—C6—C5	0.8 (5)
O1—P1—O2—C7	168.7 (2)	C2—C3—C4—C5	−0.6 (6)
O1—P1—N1—C13	−55.0 (3)	C7—C8—C9—C10	0.1 (6)
O1—C1—C2—C3	175.7 (3)	C7—C12—C11—C10	−1.6 (6)
O1—C1—C6—C5	−176.3 (3)	C17—C18—C13—N1	179.7 (3)
O3—P1—O1—C1	60.7 (2)	C17—C18—C13—C14	0.1 (4)
O3—P1—O2—C7	−70.3 (2)	C17—C16—C15—C14	−1.1 (5)
O3—P1—N1—C13	177.4 (2)	C23—C24—C19—O4	−176.8 (3)
O5—P2—O4—C19	170.3 (2)	C23—C24—C19—C20	0.2 (4)
O5—P2—N2—C31	−57.0 (3)	C23—C22—C21—C20	−0.2 (7)
O5—C25—C26—C27	−176.9 (3)	C33—C32—C31—N2	−179.9 (3)
O5—C25—C30—C29	177.0 (3)	C33—C32—C31—C36	−0.6 (5)
O2—P1—O1—C1	−176.89 (19)	C33—C34—C35—C36	1.4 (5)
O2—P1—N1—C13	48.2 (3)	C6—C1—C2—C3	−1.4 (5)
O2—C7—C8—C9	177.0 (3)	C6—C5—C4—C3	0.0 (7)
O2—C7—C12—C11	−176.4 (3)	C26—C25—C30—C29	−0.2 (5)
O6—P2—O4—C19	−67.6 (2)	C15—C16—C17—C18	0.5 (5)
O6—P2—O5—C25	69.2 (2)	C8—C7—C12—C11	0.3 (6)
O6—P2—N2—C31	174.6 (3)	C8—C9—C10—C11	−1.4 (7)
N2—P2—O4—C19	58.6 (2)	C30—C25—C26—C27	0.2 (5)
N2—P2—O5—C25	−56.8 (2)	C30—C29—C28—C27	−1.3 (6)
N2—C31—C36—C35	−179.4 (3)	C29—C28—C27—C26	1.2 (6)
N1—P1—O1—C1	−65.3 (2)	C12—C7—C8—C9	0.4 (5)
N1—P1—O2—C7	56.2 (2)	C9—C10—C11—C12	2.1 (7)

(4I)

Crystal data

C18H15INO3P	F(000) = 1776
Mr = 451.18	Dx = 1.677 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.2005 (5) Å	Cell parameters from 8444 reflections
b = 7.3428 (2) Å	θ = 2.9–30.1°
c = 19.8275 (4) Å	µ = 1.90 mm^−1
β = 103.083 (1)°	T = 100 K
V = 3573.69 (14) Å^3	Plate, colourless
Z = 8	0.47 × 0.17 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	4838 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.022
Absorption correction: multi-scan SADABS-2014/2	θmax = 30.1°, θmin = 1.7°
Tmin = 0.652, Tmax = 0.746	h = −24→35
18234 measured reflections	k = −10→10
5238 independent reflections	l = −27→28

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.0241P)^2 + 6.8304P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.004
5238 reflections	Δρmax = 1.38 e Å^−3
221 parameters	Δρmin = −0.68 e Å^−3
0 restraints

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
I1	1.00937 (2)	0.61390 (2)	0.12487 (2)	0.02255 (5)
P1	0.80568 (2)	0.00273 (6)	0.23160 (2)	0.01316 (9)
O1	0.80484 (6)	−0.10972 (17)	0.16330 (7)	0.0172 (3)
O2	0.86073 (5)	−0.08474 (17)	0.27359 (7)	0.0164 (2)
O3	0.75805 (5)	−0.01587 (18)	0.26200 (7)	0.0176 (3)
N1	0.81668 (6)	0.2175 (2)	0.21830 (8)	0.0151 (3)
C1	0.76438 (8)	−0.0763 (2)	0.10274 (10)	0.0172 (3)
C2	0.71033 (9)	−0.1180 (3)	0.10012 (11)	0.0235 (4)
H2	0.699472	−0.165993	0.139417	0.028*
C3	0.67237 (9)	−0.0876 (3)	0.03822 (12)	0.0283 (5)
H3	0.634931	−0.112192	0.035491	0.034*
C4	0.68861 (10)	−0.0219 (3)	−0.01933 (11)	0.0285 (5)
H4	0.662390	−0.002406	−0.061366	0.034*
C5	0.74259 (10)	0.0153 (3)	−0.01579 (11)	0.0309 (5)
H5	0.753629	0.059740	−0.055489	0.037*
C6	0.78121 (9)	−0.0119 (3)	0.04582 (11)	0.0263 (4)
H6	0.818585	0.013640	0.048502	0.032*
C7	0.86109 (7)	0.2994 (2)	0.19806 (9)	0.0137 (3)
C8	0.89939 (8)	0.2002 (2)	0.17200 (10)	0.0178 (4)
H8	0.896205	0.071596	0.167773	0.021*
C9	0.94220 (8)	0.2895 (3)	0.15222 (10)	0.0181 (4)
H9	0.968290	0.221874	0.134705	0.022*
C10	0.94666 (7)	0.4776 (2)	0.15815 (9)	0.0154 (3)
C11	0.90919 (8)	0.5770 (3)	0.18477 (10)	0.0178 (3)
H11	0.912566	0.705520	0.189219	0.021*
C12	0.86688 (7)	0.4875 (2)	0.20478 (9)	0.0156 (3)
H12	0.841446	0.555500	0.223358	0.019*
C13	0.88008 (7)	−0.0487 (3)	0.34466 (10)	0.0160 (3)
C14	0.91434 (8)	0.0984 (3)	0.36491 (10)	0.0197 (4)
H14	0.922499	0.180331	0.331568	0.024*
C15	0.93656 (8)	0.1236 (3)	0.43522 (11)	0.0230 (4)
H15	0.960095	0.223869	0.450259	0.028*
C16	0.92445 (9)	0.0026 (3)	0.48346 (11)	0.0235 (4)
H16	0.939895	0.020126	0.531362	0.028*
C17	0.89009 (9)	−0.1428 (3)	0.46212 (11)	0.0233 (4)
H17	0.881952	−0.224866	0.495412	0.028*
C18	0.86721 (8)	−0.1700 (3)	0.39183 (11)	0.0209 (4)
H18	0.843378	−0.269560	0.376801	0.025*
H1	0.7947 (12)	0.285 (4)	0.2249 (14)	0.036 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01698 (6)	0.02233 (7)	0.03068 (8)	−0.00547 (5)	0.01033 (5)	0.00538 (5)
P1	0.01207 (19)	0.01024 (19)	0.0192 (2)	−0.00021 (15)	0.00773 (16)	−0.00019 (15)
O1	0.0187 (6)	0.0138 (6)	0.0200 (6)	0.0025 (5)	0.0065 (5)	−0.0026 (5)
O2	0.0164 (6)	0.0142 (6)	0.0195 (6)	0.0028 (5)	0.0057 (5)	−0.0007 (5)
O3	0.0146 (6)	0.0150 (6)	0.0260 (7)	−0.0029 (5)	0.0108 (5)	−0.0007 (5)
N1	0.0138 (7)	0.0097 (6)	0.0256 (8)	0.0016 (6)	0.0123 (6)	0.0007 (6)
C1	0.0207 (9)	0.0125 (8)	0.0190 (8)	0.0015 (7)	0.0060 (7)	−0.0020 (6)
C2	0.0244 (10)	0.0247 (10)	0.0225 (9)	−0.0062 (8)	0.0074 (8)	−0.0019 (7)
C3	0.0239 (10)	0.0304 (11)	0.0296 (11)	−0.0062 (9)	0.0039 (9)	−0.0050 (8)
C4	0.0350 (12)	0.0248 (10)	0.0230 (10)	0.0020 (9)	0.0008 (9)	−0.0017 (8)
C5	0.0393 (13)	0.0319 (12)	0.0235 (10)	−0.0005 (10)	0.0111 (9)	0.0053 (8)
C6	0.0249 (10)	0.0296 (11)	0.0269 (10)	−0.0009 (9)	0.0109 (8)	0.0031 (8)
C7	0.0124 (7)	0.0121 (7)	0.0179 (8)	−0.0001 (6)	0.0064 (6)	0.0011 (6)
C8	0.0170 (8)	0.0119 (8)	0.0280 (9)	−0.0007 (7)	0.0120 (7)	−0.0013 (7)
C9	0.0155 (8)	0.0178 (8)	0.0241 (9)	0.0001 (7)	0.0108 (7)	−0.0007 (7)
C10	0.0134 (8)	0.0163 (8)	0.0175 (8)	−0.0031 (6)	0.0052 (6)	0.0018 (6)
C11	0.0191 (8)	0.0127 (8)	0.0226 (9)	−0.0026 (7)	0.0069 (7)	−0.0007 (6)
C12	0.0163 (8)	0.0122 (8)	0.0204 (8)	0.0005 (6)	0.0085 (7)	−0.0005 (6)
C13	0.0138 (8)	0.0154 (8)	0.0198 (8)	0.0034 (6)	0.0058 (7)	−0.0005 (6)
C14	0.0176 (8)	0.0181 (9)	0.0244 (9)	0.0010 (7)	0.0071 (7)	0.0022 (7)
C15	0.0194 (9)	0.0214 (9)	0.0276 (10)	−0.0004 (7)	0.0043 (8)	−0.0014 (7)
C16	0.0221 (9)	0.0277 (10)	0.0211 (9)	0.0038 (8)	0.0059 (8)	−0.0005 (8)
C17	0.0254 (10)	0.0237 (10)	0.0237 (9)	0.0021 (8)	0.0117 (8)	0.0040 (7)
C18	0.0201 (9)	0.0171 (8)	0.0278 (10)	0.0001 (7)	0.0099 (8)	0.0006 (7)

Geometric parameters (Å, º)

I1—C10	2.0992 (17)	C7—C12	1.393 (2)
P1—O1	1.5820 (14)	C8—H8	0.9500
P1—O2	1.5834 (14)	C8—C9	1.392 (3)
P1—O3	1.4663 (14)	C9—H9	0.9500
P1—N1	1.6326 (16)	C9—C10	1.388 (3)
O1—C1	1.410 (2)	C10—C11	1.389 (3)
O2—C13	1.408 (2)	C11—H11	0.9500
N1—C7	1.407 (2)	C11—C12	1.385 (3)
N1—H1	0.78 (3)	C12—H12	0.9500
C1—C2	1.386 (3)	C13—C14	1.385 (3)
C1—C6	1.376 (3)	C13—C18	1.382 (3)
C2—H2	0.9500	C14—H14	0.9500
C2—C3	1.393 (3)	C14—C15	1.392 (3)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.383 (3)	C15—C16	1.389 (3)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.373 (3)	C16—C17	1.380 (3)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.393 (3)	C17—C18	1.397 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.398 (2)
O1—P1—O2	94.51 (7)	C9—C8—C7	120.18 (16)
O1—P1—N1	109.62 (8)	C9—C8—H8	119.9
O2—P1—N1	108.42 (8)	C8—C9—H9	120.1
O3—P1—O1	116.73 (8)	C10—C9—C8	119.82 (17)
O3—P1—O2	116.57 (8)	C10—C9—H9	120.1
O3—P1—N1	109.94 (8)	C9—C10—I1	120.00 (13)
C1—O1—P1	120.33 (11)	C9—C10—C11	120.40 (16)
C13—O2—P1	120.91 (11)	C11—C10—I1	119.59 (13)
P1—N1—H1	116 (2)	C10—C11—H11	120.2
C7—N1—P1	129.36 (13)	C12—C11—C10	119.58 (16)
C7—N1—H1	115 (2)	C12—C11—H11	120.2
C2—C1—O1	120.59 (17)	C7—C12—H12	119.5
C6—C1—O1	117.42 (18)	C11—C12—C7	120.93 (17)
C6—C1—C2	121.88 (19)	C11—C12—H12	119.5
C1—C2—H2	121.0	C14—C13—O2	119.26 (17)
C1—C2—C3	118.09 (19)	C18—C13—O2	118.36 (17)
C3—C2—H2	121.0	C18—C13—C14	122.22 (18)
C2—C3—H3	119.7	C13—C14—H14	120.8
C4—C3—C2	120.7 (2)	C13—C14—C15	118.50 (18)
C4—C3—H3	119.7	C15—C14—H14	120.8
C3—C4—H4	119.9	C14—C15—H15	119.9
C5—C4—C3	120.1 (2)	C16—C15—C14	120.23 (19)
C5—C4—H4	119.9	C16—C15—H15	119.9
C4—C5—H5	119.9	C15—C16—H16	119.9
C4—C5—C6	120.2 (2)	C17—C16—C15	120.28 (19)
C6—C5—H5	119.9	C17—C16—H16	119.9
C1—C6—C5	119.0 (2)	C16—C17—H17	119.8
C1—C6—H6	120.5	C16—C17—C18	120.38 (19)
C5—C6—H6	120.5	C18—C17—H17	119.8
C8—C7—N1	122.91 (16)	C13—C18—C17	118.40 (19)
C12—C7—N1	118.02 (15)	C13—C18—H18	120.8
C12—C7—C8	119.07 (16)	C17—C18—H18	120.8
C7—C8—H8	119.9
I1—C10—C11—C12	178.07 (14)	N1—C7—C12—C11	−178.96 (17)
P1—O1—C1—C2	−67.3 (2)	C1—C2—C3—C4	1.6 (3)
P1—O1—C1—C6	116.61 (17)	C2—C1—C6—C5	1.2 (3)
P1—O2—C13—C14	−89.96 (19)	C2—C3—C4—C5	−0.4 (3)
P1—O2—C13—C18	94.67 (18)	C3—C4—C5—C6	−0.4 (4)
P1—N1—C7—C8	13.6 (3)	C4—C5—C6—C1	0.0 (3)
P1—N1—C7—C12	−166.16 (15)	C6—C1—C2—C3	−2.0 (3)
O1—P1—O2—C13	−172.92 (14)	C7—C8—C9—C10	−0.3 (3)
O1—P1—N1—C7	−58.86 (18)	C8—C7—C12—C11	1.3 (3)
O1—C1—C2—C3	−177.94 (18)	C8—C9—C10—I1	−177.66 (14)
O1—C1—C6—C5	177.29 (19)	C8—C9—C10—C11	1.1 (3)
O2—P1—O1—C1	−175.21 (13)	C9—C10—C11—C12	−0.7 (3)
O2—P1—N1—C7	43.07 (19)	C10—C11—C12—C7	−0.5 (3)
O2—C13—C14—C15	−174.94 (17)	C12—C7—C8—C9	−0.9 (3)
O2—C13—C18—C17	174.74 (17)	C13—C14—C15—C16	0.2 (3)
O3—P1—O1—C1	61.97 (15)	C14—C13—C18—C17	−0.5 (3)
O3—P1—O2—C13	−49.98 (16)	C14—C15—C16—C17	−0.3 (3)
O3—P1—N1—C7	171.56 (16)	C15—C16—C17—C18	0.1 (3)
N1—P1—O1—C1	−63.82 (15)	C16—C17—C18—C13	0.3 (3)
N1—P1—O2—C13	74.67 (15)	C18—C13—C14—C15	0.2 (3)
N1—C7—C8—C9	179.39 (18)

(24F)

Crystal data

C18H14F2NO3P	F(000) = 744
Mr = 361.27	Dx = 1.446 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.1665 (6) Å	Cell parameters from 8409 reflections
b = 9.3374 (5) Å	θ = 2.3–29.8°
c = 17.5495 (10) Å	µ = 0.20 mm^−1
β = 94.912 (2)°	T = 100 K
V = 1659.83 (16) Å^3	Plate, colourless
Z = 4	0.55 × 0.10 × 0.02 mm

Data collection

Bruker APEX-II CCD diffractometer	2703 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.094
Absorption correction: multi-scan SADABS-2014/5	θmax = 27.1°, θmin = 2.3°
Tmin = 0.657, Tmax = 0.746	h = −13→13
32876 measured reflections	k = −11→11
3652 independent reflections	l = −21→22

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0299P)^2 + 1.6612P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3652 reflections	Δρmax = 0.28 e Å^−3
226 parameters	Δρmin = −0.41 e Å^−3
0 restraints

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	0.20142 (5)	0.52469 (6)	0.56332 (3)	0.01209 (14)
F1	0.02276 (11)	0.11326 (13)	0.55061 (7)	0.0193 (3)
F2	0.41396 (12)	−0.15317 (13)	0.59683 (8)	0.0226 (3)
O1	0.32857 (14)	0.56017 (15)	0.52076 (8)	0.0147 (3)
O2	0.27572 (14)	0.51997 (15)	0.64623 (8)	0.0151 (3)
O3	0.09297 (14)	0.62757 (15)	0.55031 (8)	0.0157 (3)
N1	0.15280 (17)	0.36224 (18)	0.54189 (10)	0.0140 (4)
H1	0.073094	0.353203	0.518567	0.017*
C1	0.3163 (2)	0.5832 (2)	0.44079 (12)	0.0149 (5)
C2	0.2525 (2)	0.7036 (2)	0.41087 (13)	0.0195 (5)
H2	0.212115	0.769146	0.443096	0.023*
C3	0.2487 (2)	0.7269 (3)	0.33269 (13)	0.0255 (6)
H3	0.204864	0.808854	0.310864	0.031*
C4	0.3085 (2)	0.6312 (3)	0.28626 (14)	0.0294 (6)
H4	0.306684	0.648395	0.232827	0.035*
C5	0.3709 (2)	0.5103 (3)	0.31759 (14)	0.0278 (6)
H5	0.410712	0.444030	0.285471	0.033*
C6	0.3756 (2)	0.4857 (2)	0.39570 (13)	0.0208 (5)
H6	0.418655	0.403364	0.417674	0.025*
C7	0.2247 (2)	0.2342 (2)	0.55669 (11)	0.0125 (4)
C8	0.1563 (2)	0.1061 (2)	0.56025 (12)	0.0135 (4)
C9	0.2159 (2)	−0.0246 (2)	0.57278 (12)	0.0148 (4)
H9	0.166087	−0.110593	0.573732	0.018*
C10	0.3519 (2)	−0.0249 (2)	0.58394 (12)	0.0156 (5)
C11	0.4258 (2)	0.0974 (2)	0.58288 (13)	0.0190 (5)
H11	0.519260	0.093508	0.591566	0.023*
C12	0.3617 (2)	0.2272 (2)	0.56885 (13)	0.0178 (5)
H12	0.412113	0.312640	0.567542	0.021*
C13	0.2176 (2)	0.4657 (2)	0.71040 (12)	0.0155 (5)
C14	0.3042 (2)	0.4112 (2)	0.76783 (13)	0.0206 (5)
H14	0.396131	0.406934	0.761888	0.025*
C15	0.2550 (2)	0.3626 (3)	0.83440 (14)	0.0252 (6)
H15	0.313833	0.325913	0.874707	0.030*
C16	0.1212 (3)	0.3671 (3)	0.84259 (14)	0.0300 (6)
H16	0.087601	0.332554	0.888004	0.036*
C17	0.0367 (3)	0.4224 (3)	0.78402 (14)	0.0368 (7)
H17	−0.055344	0.425624	0.789572	0.044*
C18	0.0840 (2)	0.4733 (3)	0.71715 (13)	0.0271 (6)
H18	0.025730	0.512201	0.677249	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0124 (3)	0.0099 (3)	0.0135 (3)	−0.0013 (2)	−0.0019 (2)	−0.0001 (2)
F1	0.0118 (6)	0.0154 (7)	0.0304 (7)	−0.0018 (5)	−0.0008 (5)	−0.0012 (5)
F2	0.0210 (7)	0.0131 (7)	0.0334 (8)	0.0048 (5)	−0.0001 (6)	0.0019 (6)
O1	0.0142 (8)	0.0153 (8)	0.0140 (8)	−0.0031 (6)	−0.0024 (6)	0.0020 (6)
O2	0.0148 (8)	0.0160 (8)	0.0139 (7)	−0.0035 (6)	−0.0019 (6)	0.0008 (6)
O3	0.0158 (8)	0.0117 (7)	0.0189 (8)	−0.0010 (6)	−0.0017 (6)	−0.0009 (6)
N1	0.0110 (9)	0.0126 (9)	0.0176 (9)	−0.0007 (7)	−0.0035 (7)	−0.0001 (7)
C1	0.0108 (10)	0.0180 (11)	0.0155 (11)	−0.0073 (9)	−0.0010 (8)	0.0014 (9)
C2	0.0206 (12)	0.0181 (12)	0.0200 (12)	−0.0025 (9)	0.0027 (10)	0.0002 (9)
C3	0.0283 (14)	0.0250 (13)	0.0228 (13)	−0.0050 (11)	−0.0001 (11)	0.0096 (10)
C4	0.0282 (14)	0.0442 (16)	0.0160 (12)	−0.0139 (12)	0.0025 (11)	0.0009 (11)
C5	0.0222 (13)	0.0347 (15)	0.0274 (14)	−0.0090 (11)	0.0076 (10)	−0.0125 (11)
C6	0.0119 (11)	0.0209 (12)	0.0294 (13)	−0.0025 (9)	0.0009 (9)	−0.0029 (10)
C7	0.0150 (11)	0.0097 (10)	0.0127 (11)	0.0003 (8)	0.0005 (8)	−0.0017 (8)
C8	0.0090 (10)	0.0187 (12)	0.0127 (11)	−0.0014 (9)	−0.0003 (8)	−0.0020 (9)
C9	0.0177 (11)	0.0111 (10)	0.0155 (11)	−0.0032 (9)	0.0006 (9)	−0.0004 (9)
C10	0.0190 (11)	0.0122 (10)	0.0153 (11)	0.0051 (9)	0.0005 (9)	0.0013 (9)
C11	0.0120 (11)	0.0187 (12)	0.0260 (13)	−0.0001 (9)	−0.0002 (9)	−0.0009 (10)
C12	0.0153 (11)	0.0139 (11)	0.0238 (12)	−0.0036 (9)	−0.0008 (9)	0.0004 (9)
C13	0.0195 (11)	0.0132 (11)	0.0140 (10)	−0.0025 (9)	0.0017 (9)	−0.0037 (9)
C14	0.0182 (12)	0.0212 (12)	0.0226 (12)	0.0050 (10)	0.0030 (10)	0.0033 (10)
C15	0.0292 (14)	0.0238 (13)	0.0225 (13)	0.0037 (11)	0.0018 (11)	0.0069 (10)
C16	0.0325 (15)	0.0396 (16)	0.0186 (13)	−0.0078 (12)	0.0066 (11)	0.0018 (11)
C17	0.0192 (13)	0.071 (2)	0.0208 (14)	−0.0073 (13)	0.0031 (11)	−0.0056 (13)
C18	0.0169 (12)	0.0495 (16)	0.0140 (12)	0.0009 (12)	−0.0031 (9)	−0.0025 (11)

Geometric parameters (Å, º)

P1—O1	1.5824 (15)	C7—C8	1.388 (3)
P1—O2	1.5816 (15)	C7—C12	1.392 (3)
P1—O3	1.4655 (15)	C8—C9	1.372 (3)
P1—N1	1.6294 (18)	C9—H9	0.9500
F1—C8	1.355 (2)	C9—C10	1.380 (3)
F2—C10	1.364 (2)	C10—C11	1.367 (3)
O1—C1	1.415 (2)	C11—H11	0.9500
O2—C13	1.410 (2)	C11—C12	1.388 (3)
N1—H1	0.8800	C12—H12	0.9500
N1—C7	1.414 (3)	C13—C14	1.378 (3)
C1—C2	1.380 (3)	C13—C18	1.375 (3)
C1—C6	1.378 (3)	C14—H14	0.9500
C2—H2	0.9500	C14—C15	1.386 (3)
C2—C3	1.386 (3)	C15—H15	0.9500
C3—H3	0.9500	C15—C16	1.381 (3)
C3—C4	1.384 (4)	C16—H16	0.9500
C4—H4	0.9500	C16—C17	1.382 (4)
C4—C5	1.386 (4)	C17—H17	0.9500
C5—H5	0.9500	C17—C18	1.389 (3)
C5—C6	1.387 (3)	C18—H18	0.9500
C6—H6	0.9500
O1—P1—N1	109.27 (8)	F1—C8—C9	119.19 (18)
O2—P1—O1	95.45 (8)	C9—C8—C7	123.88 (19)
O2—P1—N1	107.34 (9)	C8—C9—H9	121.7
O3—P1—O1	115.05 (8)	C8—C9—C10	116.59 (19)
O3—P1—O2	117.08 (8)	C10—C9—H9	121.7
O3—P1—N1	111.40 (9)	F2—C10—C9	117.95 (19)
C1—O1—P1	119.60 (12)	F2—C10—C11	119.23 (19)
C13—O2—P1	123.03 (13)	C11—C10—C9	122.8 (2)
P1—N1—H1	116.5	C10—C11—H11	120.6
C7—N1—P1	127.06 (15)	C10—C11—C12	118.7 (2)
C7—N1—H1	116.5	C12—C11—H11	120.6
C2—C1—O1	119.98 (19)	C7—C12—H12	119.4
C6—C1—O1	117.63 (19)	C11—C12—C7	121.1 (2)
C6—C1—C2	122.3 (2)	C11—C12—H12	119.4
C1—C2—H2	120.8	C14—C13—O2	115.58 (19)
C1—C2—C3	118.5 (2)	C18—C13—O2	122.3 (2)
C3—C2—H2	120.8	C18—C13—C14	122.0 (2)
C2—C3—H3	119.8	C13—C14—H14	120.5
C4—C3—C2	120.3 (2)	C13—C14—C15	118.9 (2)
C4—C3—H3	119.8	C15—C14—H14	120.5
C3—C4—H4	119.9	C14—C15—H15	119.8
C3—C4—C5	120.1 (2)	C16—C15—C14	120.5 (2)
C5—C4—H4	119.9	C16—C15—H15	119.8
C4—C5—H5	119.9	C15—C16—H16	120.4
C4—C5—C6	120.2 (2)	C15—C16—C17	119.3 (2)
C6—C5—H5	119.9	C17—C16—H16	120.4
C1—C6—C5	118.6 (2)	C16—C17—H17	119.4
C1—C6—H6	120.7	C16—C17—C18	121.2 (2)
C5—C6—H6	120.7	C18—C17—H17	119.4
C8—C7—N1	118.90 (18)	C13—C18—C17	118.1 (2)
C8—C7—C12	116.82 (19)	C13—C18—H18	121.0
C12—C7—N1	124.28 (18)	C17—C18—H18	121.0
F1—C8—C7	116.93 (18)
P1—O1—C1—C2	68.7 (2)	N1—C7—C8—C9	178.72 (19)
P1—O1—C1—C6	−114.42 (18)	N1—C7—C12—C11	−179.8 (2)
P1—O2—C13—C14	152.84 (16)	C1—C2—C3—C4	−0.3 (3)
P1—O2—C13—C18	−30.4 (3)	C2—C1—C6—C5	0.2 (3)
P1—N1—C7—C8	157.20 (16)	C2—C3—C4—C5	0.9 (4)
P1—N1—C7—C12	−22.2 (3)	C3—C4—C5—C6	−1.0 (4)
F1—C8—C9—C10	−178.55 (18)	C4—C5—C6—C1	0.4 (3)
F2—C10—C11—C12	179.29 (19)	C6—C1—C2—C3	−0.2 (3)
O1—P1—O2—C13	−167.75 (15)	C7—C8—C9—C10	1.4 (3)
O1—P1—N1—C7	60.94 (19)	C8—C7—C12—C11	0.8 (3)
O1—C1—C2—C3	176.46 (19)	C8—C9—C10—F2	179.75 (18)
O1—C1—C6—C5	−176.56 (19)	C8—C9—C10—C11	0.0 (3)
O2—P1—O1—C1	−177.22 (14)	C9—C10—C11—C12	−1.0 (3)
O2—P1—N1—C7	−41.44 (19)	C10—C11—C12—C7	0.5 (3)
O2—C13—C14—C15	176.74 (19)	C12—C7—C8—F1	178.15 (18)
O2—C13—C18—C17	−177.3 (2)	C12—C7—C8—C9	−1.8 (3)
O3—P1—O1—C1	−53.89 (17)	C13—C14—C15—C16	0.8 (4)
O3—P1—O2—C13	70.48 (17)	C14—C13—C18—C17	−0.7 (4)
O3—P1—N1—C7	−170.83 (16)	C14—C15—C16—C17	−0.8 (4)
N1—P1—O1—C1	72.27 (16)	C15—C16—C17—C18	0.1 (4)
N1—P1—O2—C13	−55.60 (17)	C16—C17—C18—C13	0.7 (4)
N1—C7—C8—F1	−1.3 (3)	C18—C13—C14—C15	0.0 (3)

(25F)

Crystal data

C18H14F2NO3P	Z = 2
Mr = 361.27	F(000) = 372
Triclinic, P1	Dx = 1.483 Mg m^−3
a = 9.2189 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0245 (7) Å	Cell parameters from 6562 reflections
c = 10.0445 (7) Å	θ = 2.4–29.4°
α = 68.276 (3)°	µ = 0.21 mm^−1
β = 84.831 (3)°	T = 100 K
γ = 69.889 (3)°	Needle, colourless
V = 809.02 (10) Å^3	0.36 × 0.05 × 0.02 mm

Data collection

Bruker APEX-II CCD diffractometer	2972 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.094
Absorption correction: multi-scan SADABS-2014/5	θmax = 28.3°, θmin = 2.3°
Tmin = 0.678, Tmax = 0.746	h = −12→12
22878 measured reflections	k = −13→13
4012 independent reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0304P)^2 + 0.5222P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4012 reflections	Δρmax = 0.33 e Å^−3
230 parameters	Δρmin = −0.54 e Å^−3
0 restraints

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	0.05565 (6)	0.18760 (5)	0.02516 (5)	0.01272 (12)
F1	−0.08886 (14)	0.23889 (14)	−0.38945 (12)	0.0239 (3)
F2	−0.21078 (14)	0.77583 (13)	−0.31823 (13)	0.0256 (3)
O1	0.17258 (15)	0.27812 (15)	−0.00478 (14)	0.0156 (3)
O2	−0.06092 (15)	0.28456 (14)	0.10800 (14)	0.0152 (3)
O3	0.11482 (15)	0.02359 (15)	0.10545 (14)	0.0172 (3)
N1	−0.02350 (19)	0.22597 (19)	−0.12917 (17)	0.0155 (3)
C1	0.2972 (2)	0.2645 (2)	−0.09561 (19)	0.0145 (4)
C2	0.3519 (2)	0.3855 (2)	−0.1419 (2)	0.0173 (4)
H2	0.303849	0.471283	−0.114480	0.021*
C3	0.4777 (2)	0.3806 (2)	−0.2289 (2)	0.0215 (4)
H3	0.515880	0.463640	−0.261962	0.026*
C4	0.5478 (2)	0.2550 (2)	−0.2676 (2)	0.0225 (5)
H4	0.633974	0.251582	−0.327294	0.027*
C5	0.4918 (2)	0.1345 (2)	−0.2192 (2)	0.0217 (4)
H5	0.540694	0.048125	−0.245493	0.026*
C6	0.3655 (2)	0.1375 (2)	−0.1329 (2)	0.0181 (4)
H6	0.326848	0.054771	−0.100249	0.022*
C7	−0.0875 (2)	0.3692 (2)	−0.2384 (2)	0.0146 (4)
C8	−0.1231 (2)	0.3745 (2)	−0.3722 (2)	0.0174 (4)
C9	−0.1878 (2)	0.5076 (3)	−0.4850 (2)	0.0226 (5)
H9	−0.211927	0.505342	−0.573992	0.027*
C10	−0.2178 (2)	0.6456 (2)	−0.4682 (2)	0.0229 (5)
H10	−0.262092	0.739731	−0.544645	0.027*
C11	−0.1811 (2)	0.6409 (2)	−0.3370 (2)	0.0183 (4)
C12	−0.1174 (2)	0.5081 (2)	−0.2213 (2)	0.0165 (4)
H12	−0.094642	0.511183	−0.132341	0.020*
C13	−0.1737 (2)	0.2289 (2)	0.1909 (2)	0.0138 (4)
C14	−0.1473 (2)	0.1623 (2)	0.3378 (2)	0.0180 (4)
H14	−0.052062	0.146304	0.380647	0.022*
C15	−0.2637 (2)	0.1194 (2)	0.4212 (2)	0.0208 (4)
H15	−0.248018	0.072731	0.522496	0.025*
C16	−0.4026 (2)	0.1442 (2)	0.3575 (2)	0.0222 (5)
H16	−0.482129	0.115646	0.415449	0.027*
C17	−0.4258 (2)	0.2103 (2)	0.2099 (2)	0.0220 (5)
H17	−0.520910	0.226223	0.166872	0.026*
C18	−0.3108 (2)	0.2533 (2)	0.1247 (2)	0.0194 (4)
H18	−0.325618	0.298562	0.023288	0.023*
H1	−0.041 (3)	0.154 (3)	−0.138 (3)	0.041 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0160 (2)	0.0133 (2)	0.0115 (2)	−0.00751 (19)	0.00137 (18)	−0.00519 (19)
F1	0.0294 (7)	0.0338 (7)	0.0189 (6)	−0.0162 (6)	0.0037 (5)	−0.0164 (5)
F2	0.0280 (7)	0.0163 (6)	0.0271 (7)	−0.0071 (5)	−0.0032 (5)	−0.0012 (5)
O1	0.0179 (7)	0.0184 (7)	0.0164 (7)	−0.0108 (6)	0.0036 (5)	−0.0093 (6)
O2	0.0184 (7)	0.0162 (7)	0.0144 (7)	−0.0095 (6)	0.0045 (5)	−0.0068 (6)
O3	0.0192 (7)	0.0156 (7)	0.0177 (7)	−0.0077 (5)	−0.0003 (6)	−0.0050 (6)
N1	0.0220 (9)	0.0149 (8)	0.0133 (8)	−0.0095 (7)	0.0000 (7)	−0.0058 (7)
C1	0.0146 (9)	0.0186 (10)	0.0092 (9)	−0.0057 (8)	−0.0020 (7)	−0.0033 (8)
C2	0.0191 (10)	0.0146 (10)	0.0187 (10)	−0.0061 (8)	−0.0021 (8)	−0.0054 (8)
C3	0.0204 (10)	0.0251 (11)	0.0224 (11)	−0.0146 (9)	0.0009 (8)	−0.0061 (9)
C4	0.0171 (10)	0.0320 (12)	0.0226 (11)	−0.0126 (9)	0.0043 (8)	−0.0111 (9)
C5	0.0209 (10)	0.0236 (11)	0.0249 (11)	−0.0073 (9)	0.0036 (9)	−0.0144 (9)
C6	0.0207 (10)	0.0167 (10)	0.0203 (10)	−0.0102 (8)	0.0017 (8)	−0.0070 (8)
C7	0.0129 (9)	0.0210 (10)	0.0119 (9)	−0.0097 (8)	0.0021 (7)	−0.0049 (8)
C8	0.0156 (9)	0.0256 (11)	0.0173 (10)	−0.0120 (8)	0.0045 (8)	−0.0107 (9)
C9	0.0164 (10)	0.0386 (13)	0.0133 (10)	−0.0114 (9)	−0.0004 (8)	−0.0078 (9)
C10	0.0155 (10)	0.0275 (12)	0.0168 (10)	−0.0063 (8)	−0.0018 (8)	0.0013 (9)
C11	0.0150 (9)	0.0184 (10)	0.0197 (10)	−0.0066 (8)	0.0008 (8)	−0.0039 (8)
C12	0.0171 (9)	0.0206 (10)	0.0134 (10)	−0.0091 (8)	0.0002 (8)	−0.0050 (8)
C13	0.0177 (9)	0.0113 (9)	0.0145 (9)	−0.0069 (7)	0.0045 (7)	−0.0060 (7)
C14	0.0188 (10)	0.0174 (10)	0.0175 (10)	−0.0052 (8)	−0.0008 (8)	−0.0063 (8)
C15	0.0271 (11)	0.0173 (10)	0.0150 (10)	−0.0072 (8)	0.0044 (8)	−0.0037 (8)
C16	0.0215 (10)	0.0185 (10)	0.0276 (12)	−0.0099 (8)	0.0096 (9)	−0.0084 (9)
C17	0.0192 (10)	0.0221 (11)	0.0281 (12)	−0.0095 (8)	−0.0004 (9)	−0.0099 (9)
C18	0.0237 (10)	0.0206 (10)	0.0153 (10)	−0.0097 (8)	0.0000 (8)	−0.0059 (8)

Geometric parameters (Å, º)

P1—O1	1.5773 (13)	C7—C8	1.390 (3)
P1—O2	1.5846 (14)	C7—C12	1.396 (3)
P1—O3	1.4602 (14)	C8—C9	1.370 (3)
P1—N1	1.6287 (16)	C9—H9	0.9500
F1—C8	1.359 (2)	C9—C10	1.386 (3)
F2—C11	1.366 (2)	C10—H10	0.9500
O1—C1	1.403 (2)	C10—C11	1.370 (3)
O2—C13	1.409 (2)	C11—C12	1.381 (3)
N1—C7	1.407 (2)	C12—H12	0.9500
N1—H1	0.82 (3)	C13—C14	1.380 (3)
C1—C2	1.380 (3)	C13—C18	1.384 (3)
C1—C6	1.384 (3)	C14—H14	0.9500
C2—H2	0.9500	C14—C15	1.388 (3)
C2—C3	1.386 (3)	C15—H15	0.9500
C3—H3	0.9500	C15—C16	1.386 (3)
C3—C4	1.382 (3)	C16—H16	0.9500
C4—H4	0.9500	C16—C17	1.384 (3)
C4—C5	1.383 (3)	C17—H17	0.9500
C5—H5	0.9500	C17—C18	1.386 (3)
C5—C6	1.386 (3)	C18—H18	0.9500
C6—H6	0.9500
O1—P1—O2	95.06 (7)	F1—C8—C9	119.64 (17)
O1—P1—N1	106.99 (8)	C9—C8—C7	123.41 (19)
O2—P1—N1	109.50 (8)	C8—C9—H9	120.3
O3—P1—O1	117.63 (8)	C8—C9—C10	119.37 (19)
O3—P1—O2	114.97 (8)	C10—C9—H9	120.3
O3—P1—N1	111.38 (8)	C9—C10—H10	121.3
C1—O1—P1	125.54 (12)	C11—C10—C9	117.41 (19)
C13—O2—P1	119.39 (11)	C11—C10—H10	121.3
P1—N1—H1	114.9 (18)	F2—C11—C10	118.20 (17)
C7—N1—P1	128.27 (14)	F2—C11—C12	117.60 (17)
C7—N1—H1	116.0 (18)	C10—C11—C12	124.20 (19)
C2—C1—O1	114.97 (17)	C7—C12—H12	120.8
C2—C1—C6	121.73 (18)	C11—C12—C7	118.31 (18)
C6—C1—O1	123.25 (17)	C11—C12—H12	120.8
C1—C2—H2	120.4	C14—C13—O2	117.90 (16)
C1—C2—C3	119.23 (19)	C14—C13—C18	122.47 (18)
C3—C2—H2	120.4	C18—C13—O2	119.43 (17)
C2—C3—H3	120.0	C13—C14—H14	120.9
C4—C3—C2	120.09 (18)	C13—C14—C15	118.25 (18)
C4—C3—H3	120.0	C15—C14—H14	120.9
C3—C4—H4	120.2	C14—C15—H15	119.8
C3—C4—C5	119.70 (19)	C16—C15—C14	120.36 (19)
C5—C4—H4	120.2	C16—C15—H15	119.8
C4—C5—H5	119.4	C15—C16—H16	119.9
C4—C5—C6	121.16 (19)	C17—C16—C15	120.27 (19)
C6—C5—H5	119.4	C17—C16—H16	119.9
C1—C6—C5	118.08 (18)	C16—C17—H17	119.9
C1—C6—H6	121.0	C16—C17—C18	120.24 (19)
C5—C6—H6	121.0	C18—C17—H17	119.9
C8—C7—N1	118.73 (17)	C13—C18—C17	118.41 (19)
C8—C7—C12	117.28 (17)	C13—C18—H18	120.8
C12—C7—N1	123.99 (17)	C17—C18—H18	120.8
F1—C8—C7	116.94 (17)
P1—O1—C1—C2	159.85 (13)	N1—C7—C8—C9	178.97 (18)
P1—O1—C1—C6	−22.4 (2)	N1—C7—C12—C11	−179.75 (17)
P1—O2—C13—C14	101.79 (17)	C1—C2—C3—C4	−0.4 (3)
P1—O2—C13—C18	−83.35 (19)	C2—C1—C6—C5	−0.1 (3)
P1—N1—C7—C8	168.17 (14)	C2—C3—C4—C5	0.0 (3)
P1—N1—C7—C12	−11.6 (3)	C3—C4—C5—C6	0.4 (3)
F1—C8—C9—C10	−177.88 (17)	C4—C5—C6—C1	−0.4 (3)
F2—C11—C12—C7	179.54 (16)	C6—C1—C2—C3	0.5 (3)
O1—P1—O2—C13	−164.86 (13)	C7—C8—C9—C10	1.2 (3)
O1—P1—N1—C7	−47.42 (18)	C8—C7—C12—C11	0.4 (3)
O1—C1—C2—C3	178.23 (16)	C8—C9—C10—C11	−0.3 (3)
O1—C1—C6—C5	−177.62 (17)	C9—C10—C11—F2	−179.60 (17)
O2—P1—O1—C1	−170.05 (14)	C9—C10—C11—C12	−0.4 (3)
O2—P1—N1—C7	54.48 (18)	C10—C11—C12—C7	0.3 (3)
O2—C13—C14—C15	174.41 (16)	C12—C7—C8—F1	177.86 (16)
O2—C13—C18—C17	−174.04 (17)	C12—C7—C8—C9	−1.2 (3)
O3—P1—O1—C1	68.30 (16)	C13—C14—C15—C16	−0.4 (3)
O3—P1—O2—C13	−41.16 (15)	C14—C13—C18—C17	0.6 (3)
O3—P1—N1—C7	−177.24 (16)	C14—C15—C16—C17	0.8 (3)
N1—P1—O1—C1	−57.87 (16)	C15—C16—C17—C18	−0.5 (3)
N1—P1—O2—C13	85.11 (14)	C16—C17—C18—C13	−0.2 (3)
N1—C7—C8—F1	−1.9 (2)	C18—C13—C14—C15	−0.3 (3)