Structural and electronic aspects of hydrogen bonding in two polymorphs of butylene-N,N′-bis(O,O′-diarylphosphoramidate)

The bisphosphoramidate (C₆H₅O)₂P(O)NH(CH₂)₄NHP(O)(OC₆H₅)₂ crystallizes in two polymorphs, one (ndl) with a needle habit from tetrahydrofuran (THF)/ethanol and another (prm) which forms prisms from H₂O/ethanol. The molecules in the two forms differ from each other in some torsion angles and the orientation of the diaminobutane bridge, although the differences between the similar bond lengths are not significant for the two polymorphs. The geometry optimizations at the B3LYP/6-31+G* level for isolated molecules show that the two conformers which exist in the crystalline state also represent local gas-phase energy minima. The decrease in the N—H distance from the optimized to the crystal structures has been described in terms of the decrease in electron density (ρ) at the bond-critical point (b.c.p.) of the N—H bond path when the molecule participates in hydrogen bonding, comparing the results of atoms-in-molecules (AIM) and natural bond orbital (NBO) analyses for fully optimized structures ndl and prm with their hydrogen-bonded model clusters.

Computing details

For both compounds, data collection: SMART (Bruker, 1998b); cell refinement: SAINTPlus (Bruker, 1998a); data reduction: SAINTPlus (Bruker, 1998a); program(s) used to solve structure: SHELXTL ver. 5.1 (Sheldrick, 1998b); program(s) used to refine structure: SHELXTL ver. 5.1 (Sheldrick, 1998b); molecular graphics: SHELXTL ver. 5.1 (Sheldrick, 1998b); software used to prepare material for publication: SHELXTL ver. 5.1 (Sheldrick, 1998b).

Figures

(72phcu-needle)

Crystal data

C28H30N2O6P2	F(000) = 580
Mr = 552.48	Dx = 1.389 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3214 reflections
a = 15.7039 (19) Å	θ = 3–30°
b = 5.3299 (7) Å	µ = 0.21 mm^−1
c = 16.932 (2) Å	T = 120 K
β = 111.260 (2)°	Needle, colorless
V = 1320.8 (3) Å^3	0.35 × 0.05 × 0.04 mm
Z = 2

Data collection

Bruker SMART 1000 CCD area detector diffractometer	3515 independent reflections
Radiation source: fine-focus sealed tube	2097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
phi and ω scans	θmax = 29.0°, θmin = 1.4°
Absorption correction: multi-scan SADABS (Sheldrick, 1998a)	h = −21→21
Tmin = 0.927, Tmax = 0.996	k = −7→7
13832 measured reflections	l = −23→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: mixed
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.530P] where P = (Fo^2 + 2Fc^2)/3
3515 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.28988 (4)	0.13924 (12)	0.38934 (4)	0.01735 (17)
O1	0.30395 (10)	−0.1040 (3)	0.35511 (9)	0.0215 (4)
O2	0.18713 (10)	0.2368 (3)	0.35672 (9)	0.0195 (4)
O3	0.31208 (10)	0.1347 (3)	0.48844 (9)	0.0200 (4)
N1	0.34758 (12)	0.3679 (4)	0.37189 (11)	0.0175 (4)
H1N	0.3298	0.5262	0.3748	0.021*
C1	0.13508 (14)	0.2380 (4)	0.26898 (13)	0.0173 (5)
C2	0.07200 (15)	0.0486 (4)	0.23628 (14)	0.0199 (5)
H2A	0.0652	−0.0819	0.2718	0.024*
C3	0.01882 (15)	0.0529 (5)	0.15065 (15)	0.0227 (5)
H3A	−0.0249	−0.0759	0.1272	0.027*
C4	0.02873 (16)	0.2422 (5)	0.09926 (15)	0.0246 (5)
H4A	−0.0077	0.2434	0.0406	0.030*
C5	0.09207 (16)	0.4309 (5)	0.13348 (15)	0.0249 (6)
H5A	0.0992	0.5606	0.0979	0.030*
C6	0.14518 (15)	0.4323 (4)	0.21929 (14)	0.0207 (5)
H6A	0.1875	0.5640	0.2432	0.025*
C7	0.29168 (15)	−0.0591 (4)	0.53449 (14)	0.0187 (5)
C8	0.22783 (15)	−0.2423 (5)	0.49831 (15)	0.0226 (5)
H8A	0.1939	−0.2418	0.4391	0.027*
C9	0.21378 (16)	−0.4287 (5)	0.54987 (16)	0.0262 (6)
H9A	0.1706	−0.5580	0.5254	0.031*
C10	0.26169 (17)	−0.4277 (5)	0.63592 (16)	0.0288 (6)
H10A	0.2513	−0.5549	0.6707	0.035*
C11	0.32526 (17)	−0.2397 (5)	0.67165 (15)	0.0285 (6)
H11A	0.3584	−0.2387	0.7310	0.034*
C12	0.34072 (16)	−0.0539 (5)	0.62144 (14)	0.0235 (5)
H12A	0.3841	0.0750	0.6458	0.028*
C13	0.44575 (14)	0.3477 (5)	0.38800 (14)	0.0205 (5)
H13A	0.4624	0.4778	0.3544	0.025*	0.80
H13B	0.4577	0.1821	0.3676	0.025*	0.80
H13C	0.4555	0.3915	0.3369	0.025*	0.20
H13D	0.4645	0.1764	0.4012	0.025*	0.20
C14	0.50715 (19)	0.3765 (6)	0.48031 (19)	0.0225 (6)	0.80
H14A	0.5717	0.3659	0.4848	0.027*	0.80
H14B	0.4956	0.2354	0.5131	0.027*	0.80
C14'	0.5038 (8)	0.519 (3)	0.4577 (8)	0.0225 (6)	0.20
H14C	0.5686	0.4955	0.4641	0.027*	0.20
H14D	0.4871	0.6946	0.4399	0.027*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0174 (3)	0.0170 (3)	0.0158 (3)	0.0010 (3)	0.0037 (2)	0.0001 (3)
O1	0.0244 (8)	0.0197 (9)	0.0198 (8)	0.0022 (7)	0.0072 (7)	−0.0008 (7)
O2	0.0167 (8)	0.0230 (9)	0.0162 (8)	0.0016 (7)	0.0027 (6)	0.0004 (7)
O3	0.0235 (8)	0.0186 (9)	0.0152 (8)	−0.0016 (7)	0.0037 (6)	0.0011 (7)
N1	0.0170 (9)	0.0147 (10)	0.0186 (9)	0.0005 (8)	0.0039 (8)	0.0002 (8)
C1	0.0143 (10)	0.0208 (12)	0.0165 (11)	0.0040 (9)	0.0053 (9)	0.0001 (9)
C2	0.0186 (11)	0.0188 (12)	0.0225 (12)	0.0005 (10)	0.0077 (10)	0.0033 (10)
C3	0.0169 (11)	0.0222 (13)	0.0269 (13)	−0.0022 (10)	0.0053 (10)	−0.0036 (10)
C4	0.0207 (12)	0.0325 (15)	0.0187 (12)	0.0036 (11)	0.0049 (10)	0.0016 (11)
C5	0.0237 (12)	0.0250 (14)	0.0242 (13)	0.0024 (10)	0.0066 (10)	0.0075 (11)
C6	0.0183 (11)	0.0188 (13)	0.0231 (12)	0.0010 (10)	0.0050 (10)	−0.0008 (10)
C7	0.0211 (11)	0.0184 (12)	0.0166 (11)	0.0042 (10)	0.0071 (9)	0.0023 (9)
C8	0.0232 (12)	0.0245 (14)	0.0210 (12)	0.0016 (11)	0.0091 (10)	0.0007 (10)
C9	0.0259 (13)	0.0270 (15)	0.0306 (14)	−0.0004 (11)	0.0161 (11)	0.0006 (11)
C10	0.0368 (15)	0.0269 (15)	0.0294 (14)	0.0055 (12)	0.0199 (12)	0.0076 (11)
C11	0.0352 (14)	0.0332 (15)	0.0182 (12)	0.0073 (13)	0.0112 (11)	0.0047 (11)
C12	0.0243 (12)	0.0264 (14)	0.0186 (12)	0.0025 (10)	0.0061 (10)	−0.0015 (10)
C13	0.0143 (11)	0.0229 (13)	0.0238 (12)	0.0003 (10)	0.0063 (9)	−0.0016 (10)
C14	0.0166 (12)	0.0225 (18)	0.0242 (16)	0.0032 (14)	0.0023 (12)	0.0004 (14)
C14'	0.0166 (12)	0.0225 (18)	0.0242 (16)	0.0032 (14)	0.0023 (12)	0.0004 (14)

Geometric parameters (Å, º)

P1—O1	1.4690 (17)	C8—C9	1.392 (3)
P1—O3	1.5854 (15)	C8—H8A	0.9500
P1—O2	1.5914 (15)	C9—C10	1.376 (3)
P1—N1	1.6084 (19)	C9—H9A	0.9500
O2—C1	1.412 (2)	C10—C11	1.389 (4)
O3—C7	1.400 (3)	C10—H10A	0.9500
N1—C13	1.469 (3)	C11—C12	1.383 (3)
N1—H1N	0.8961	C11—H11A	0.9500
C1—C6	1.379 (3)	C12—H12A	0.9500
C1—C2	1.381 (3)	C13—C14'	1.509 (13)
C2—C3	1.386 (3)	C13—C14	1.518 (4)
C2—H2A	0.9500	C13—H13A	0.9900
C3—C4	1.377 (3)	C13—H13B	0.9900
C3—H3A	0.9500	C13—H13C	0.9600
C4—C5	1.385 (3)	C13—H13D	0.9600
C4—H4A	0.9500	C14—C14^i	1.529 (6)
C5—C6	1.389 (3)	C14—H14A	0.9900
C5—H5A	0.9500	C14—H14B	0.9900
C6—H6A	0.9500	C14'—C14'^i	1.49 (3)
C7—C8	1.375 (3)	C14'—H14C	0.9900
C7—C12	1.393 (3)	C14'—H14D	0.9900
O1—P1—O3	113.42 (9)	C9—C10—H10A	120.2
O1—P1—O2	115.46 (9)	C11—C10—H10A	120.2
O3—P1—O2	100.28 (8)	C12—C11—C10	120.5 (2)
O1—P1—N1	114.88 (9)	C12—C11—H11A	119.8
O3—P1—N1	106.47 (9)	C10—C11—H11A	119.8
O2—P1—N1	104.87 (9)	C11—C12—C7	118.9 (2)
C1—O2—P1	119.60 (13)	C11—C12—H12A	120.6
C7—O3—P1	126.44 (14)	C7—C12—H12A	120.6
C13—N1—P1	122.24 (16)	N1—C13—C14'	113.4 (5)
C13—N1—H1N	112.7	N1—C13—C14	114.57 (19)
P1—N1—H1N	119.7	N1—C13—H13A	108.6
C6—C1—C2	121.9 (2)	C14'—C13—H13A	79.4
C6—C1—O2	119.6 (2)	C14—C13—H13A	108.6
C2—C1—O2	118.4 (2)	N1—C13—H13B	108.6
C1—C2—C3	118.7 (2)	C14'—C13—H13B	132.4
C1—C2—H2A	120.7	C14—C13—H13B	108.6
C3—C2—H2A	120.7	H13A—C13—H13B	107.6
C4—C3—C2	120.6 (2)	N1—C13—H13C	108.3
C4—C3—H3A	119.7	C14'—C13—H13C	108.0
C2—C3—H3A	119.7	C14—C13—H13C	130.8
C3—C4—C5	119.7 (2)	H13B—C13—H13C	77.9
C3—C4—H4A	120.1	N1—C13—H13D	109.0
C5—C4—H4A	120.1	C14'—C13—H13D	110.2
C4—C5—C6	120.6 (2)	C14—C13—H13D	80.2
C4—C5—H5A	119.7	H13A—C13—H13D	132.6
C6—C5—H5A	119.7	H13C—C13—H13D	107.8
C1—C6—C5	118.4 (2)	C13—C14—C14^i	113.4 (3)
C1—C6—H6A	120.8	C13—C14—H14A	108.9
C5—C6—H6A	120.8	C14^i—C14—H14A	108.9
C8—C7—C12	121.3 (2)	C13—C14—H14B	108.9
C8—C7—O3	123.6 (2)	C14^i—C14—H14B	108.9
C12—C7—O3	115.1 (2)	H14A—C14—H14B	107.7
C7—C8—C9	118.9 (2)	C14'^i—C14'—C13	115.6 (13)
C7—C8—H8A	120.5	C14'^i—C14'—H14C	108.4
C9—C8—H8A	120.5	C13—C14'—H14C	108.4
C10—C9—C8	120.7 (2)	C14'^i—C14'—H14D	108.4
C10—C9—H9A	119.6	C13—C14'—H14D	108.4
C8—C9—H9A	119.6	H14C—C14'—H14D	107.4
C9—C10—C11	119.7 (2)
O1—P1—O2—C1	−49.42 (18)	C4—C5—C6—C1	1.8 (3)
O3—P1—O2—C1	−171.67 (16)	P1—O3—C7—C8	−18.7 (3)
N1—P1—O2—C1	78.07 (17)	P1—O3—C7—C12	161.74 (16)
O1—P1—O3—C7	−39.5 (2)	C12—C7—C8—C9	−1.4 (3)
O2—P1—O3—C7	84.22 (18)	O3—C7—C8—C9	179.1 (2)
N1—P1—O3—C7	−166.78 (17)	C7—C8—C9—C10	1.2 (4)
O1—P1—N1—C13	−47.97 (19)	C8—C9—C10—C11	−0.5 (4)
O3—P1—N1—C13	78.47 (17)	C9—C10—C11—C12	0.0 (4)
O2—P1—N1—C13	−175.80 (15)	C10—C11—C12—C7	−0.2 (4)
P1—O2—C1—C6	−81.4 (2)	C8—C7—C12—C11	0.9 (3)
P1—O2—C1—C2	101.7 (2)	O3—C7—C12—C11	−179.5 (2)
C6—C1—C2—C3	1.3 (3)	P1—N1—C13—C14'	−114.6 (6)
O2—C1—C2—C3	178.13 (19)	P1—N1—C13—C14	−79.2 (3)
C1—C2—C3—C4	0.0 (3)	N1—C13—C14—C14^i	−56.7 (4)
C2—C3—C4—C5	−0.3 (3)	C14'—C13—C14—C14^i	38.6 (9)
C3—C4—C5—C6	−0.6 (4)	N1—C13—C14'—C14'^i	58.8 (16)
C2—C1—C6—C5	−2.1 (3)	C14—C13—C14'—C14'^i	−40.6 (10)
O2—C1—C6—C5	−178.96 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^ii	0.90	2.02	2.887 (3)	164

Symmetry code: (ii) x, y+1, z.

(72phcu-prism)

Crystal data

C28H30N2O6P2	F(000) = 580
Mr = 552.48	Dx = 1.396 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2568 reflections
a = 9.6437 (9) Å	θ = 3–30°
b = 14.3801 (13) Å	µ = 0.21 mm^−1
c = 10.3503 (9) Å	T = 120 K
β = 113.659 (2)°	Prism, colorless
V = 1314.7 (2) Å^3	0.35 × 0.30 × 0.30 mm
Z = 2

Data collection

Bruker SMART 1000 CCD area detector diffractometer	3473 independent reflections
Radiation source: fine-focus sealed tube	2580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
phi and ω scans	θmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan SADABS (Sheldrick, 1998a)	h = −13→13
Tmin = 0.924, Tmax = 0.931	k = −19→19
10920 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: mixed
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.880P] where P = (Fo^2 + 2Fc^2)/3
3473 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
P1	0.52065 (5)	0.92701 (3)	0.81441 (5)	0.01914 (13)
O1	0.38529 (14)	0.93875 (8)	0.84432 (13)	0.0229 (3)
O2	0.52895 (14)	0.83814 (8)	0.72675 (13)	0.0231 (3)
O3	0.53081 (15)	0.99897 (9)	0.70059 (13)	0.0244 (3)
N1	0.67619 (16)	0.92751 (10)	0.95473 (16)	0.0201 (3)
H1N	0.6763	0.9553	1.0335	0.024*
C1	0.5370 (2)	0.74795 (12)	0.78237 (18)	0.0218 (4)
C2	0.4057 (2)	0.70493 (14)	0.7737 (2)	0.0293 (4)
H2A	0.3117	0.7370	0.7359	0.035*
C3	0.4130 (2)	0.61406 (14)	0.8210 (2)	0.0329 (5)
H3A	0.3234	0.5835	0.8154	0.040*
C4	0.5503 (3)	0.56777 (14)	0.8763 (2)	0.0328 (5)
H4A	0.5550	0.5057	0.9092	0.039*
C5	0.6804 (2)	0.61178 (13)	0.8835 (2)	0.0322 (4)
H5A	0.7743	0.5796	0.9211	0.039*
C6	0.6752 (2)	0.70289 (13)	0.8363 (2)	0.0272 (4)
H6A	0.7645	0.7334	0.8410	0.033*
C7	0.4966 (2)	1.09314 (12)	0.70346 (19)	0.0220 (4)
C8	0.4287 (2)	1.13668 (13)	0.5740 (2)	0.0266 (4)
H8A	0.4057	1.1029	0.4890	0.032*
C9	0.3947 (2)	1.23095 (14)	0.5708 (2)	0.0311 (4)
H9A	0.3490	1.2619	0.4827	0.037*
C10	0.4265 (2)	1.27997 (13)	0.6941 (2)	0.0315 (4)
H10A	0.4004	1.3439	0.6908	0.038*
C11	0.4968 (2)	1.23525 (13)	0.8227 (2)	0.0273 (4)
H11A	0.5206	1.2692	0.9077	0.033*
C12	0.5329 (2)	1.14138 (13)	0.82859 (19)	0.0244 (4)
H12A	0.5814	1.1108	0.9168	0.029*
C13	0.82656 (19)	0.91889 (12)	0.95086 (19)	0.0216 (4)
H13A	0.8138	0.9034	0.8535	0.026*
H13B	0.8817	0.8669	1.0129	0.026*
C14	0.92056 (19)	1.00647 (12)	0.99734 (19)	0.0225 (4)
H14A	0.9275	1.0247	1.0920	0.027*
H14B	0.8695	1.0575	0.9311	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0211 (2)	0.0194 (2)	0.0182 (2)	0.00061 (16)	0.00912 (18)	−0.00038 (16)
O1	0.0213 (6)	0.0262 (6)	0.0223 (6)	0.0007 (5)	0.0097 (5)	−0.0014 (5)
O2	0.0283 (7)	0.0204 (6)	0.0219 (6)	0.0010 (5)	0.0113 (5)	−0.0024 (5)
O3	0.0340 (7)	0.0217 (6)	0.0215 (6)	0.0028 (5)	0.0153 (6)	0.0031 (5)
N1	0.0194 (7)	0.0228 (7)	0.0196 (7)	−0.0002 (5)	0.0093 (6)	−0.0026 (6)
C1	0.0273 (9)	0.0201 (8)	0.0212 (8)	−0.0024 (7)	0.0129 (7)	−0.0038 (7)
C2	0.0244 (9)	0.0350 (10)	0.0291 (10)	−0.0035 (8)	0.0114 (8)	−0.0047 (8)
C3	0.0362 (11)	0.0332 (10)	0.0374 (11)	−0.0122 (8)	0.0231 (10)	−0.0055 (9)
C4	0.0493 (12)	0.0236 (9)	0.0353 (11)	−0.0056 (8)	0.0272 (10)	−0.0007 (8)
C5	0.0338 (11)	0.0233 (9)	0.0432 (12)	0.0042 (8)	0.0194 (10)	0.0013 (8)
C6	0.0252 (9)	0.0228 (9)	0.0365 (11)	−0.0014 (7)	0.0154 (8)	−0.0010 (8)
C7	0.0224 (9)	0.0211 (8)	0.0258 (9)	0.0005 (6)	0.0132 (8)	0.0024 (7)
C8	0.0260 (9)	0.0303 (9)	0.0244 (9)	−0.0008 (7)	0.0112 (8)	0.0046 (7)
C9	0.0301 (10)	0.0321 (10)	0.0327 (10)	0.0026 (8)	0.0143 (9)	0.0136 (8)
C10	0.0352 (11)	0.0225 (9)	0.0434 (12)	0.0034 (8)	0.0227 (10)	0.0081 (8)
C11	0.0298 (10)	0.0241 (9)	0.0287 (10)	−0.0026 (7)	0.0125 (8)	−0.0002 (7)
C12	0.0255 (9)	0.0241 (9)	0.0244 (9)	0.0000 (7)	0.0109 (8)	0.0032 (7)
C13	0.0203 (8)	0.0214 (8)	0.0251 (9)	−0.0004 (6)	0.0111 (7)	−0.0024 (7)
C14	0.0222 (9)	0.0198 (8)	0.0264 (9)	−0.0003 (7)	0.0108 (7)	−0.0033 (7)

Geometric parameters (Å, º)

P1—O1	1.4672 (13)	C6—H6A	0.9500
P1—O2	1.5878 (12)	C7—C8	1.382 (2)
P1—O3	1.6002 (13)	C7—C12	1.385 (3)
P1—N1	1.6158 (15)	C8—C9	1.392 (3)
O2—C1	1.408 (2)	C8—H8A	0.9500
O3—C7	1.397 (2)	C9—C10	1.380 (3)
N1—C13	1.472 (2)	C9—H9A	0.9500
N1—H1N	0.9080	C10—C11	1.386 (3)
C1—C2	1.379 (3)	C10—H10A	0.9500
C1—C6	1.383 (3)	C11—C12	1.389 (3)
C2—C3	1.387 (3)	C11—H11A	0.9500
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.384 (3)	C13—C14	1.513 (2)
C3—H3A	0.9500	C13—H13A	0.9900
C4—C5	1.380 (3)	C13—H13B	0.9900
C4—H4A	0.9500	C14—C14^i	1.522 (3)
C5—C6	1.392 (3)	C14—H14A	0.9900
C5—H5A	0.9500	C14—H14B	0.9900
O1—P1—O2	117.79 (7)	C8—C7—O3	116.27 (16)
O1—P1—O3	113.79 (7)	C12—C7—O3	122.17 (16)
O2—P1—O3	93.89 (7)	C7—C8—C9	118.67 (18)
O1—P1—N1	113.17 (8)	C7—C8—H8A	120.7
O2—P1—N1	106.00 (7)	C9—C8—H8A	120.7
O3—P1—N1	110.48 (8)	C10—C9—C8	120.83 (18)
C1—O2—P1	120.98 (11)	C10—C9—H9A	119.6
C7—O3—P1	121.77 (11)	C8—C9—H9A	119.6
C13—N1—P1	122.99 (12)	C9—C10—C11	119.51 (18)
C13—N1—H1N	114.6	C9—C10—H10A	120.2
P1—N1—H1N	118.4	C11—C10—H10A	120.2
C2—C1—C6	121.83 (17)	C10—C11—C12	120.68 (18)
C2—C1—O2	119.21 (16)	C10—C11—H11A	119.7
C6—C1—O2	118.85 (15)	C12—C11—H11A	119.7
C1—C2—C3	118.96 (18)	C7—C12—C11	118.75 (17)
C1—C2—H2A	120.5	C7—C12—H12A	120.6
C3—C2—H2A	120.5	C11—C12—H12A	120.6
C4—C3—C2	120.23 (18)	N1—C13—C14	113.10 (14)
C4—C3—H3A	119.9	N1—C13—H13A	109.0
C2—C3—H3A	119.9	C14—C13—H13A	109.0
C5—C4—C3	119.99 (19)	N1—C13—H13B	109.0
C5—C4—H4A	120.0	C14—C13—H13B	109.0
C3—C4—H4A	120.0	H13A—C13—H13B	107.8
C4—C5—C6	120.58 (19)	C13—C14—C14^i	112.07 (17)
C4—C5—H5A	119.7	C13—C14—H14A	109.2
C6—C5—H5A	119.7	C14^i—C14—H14A	109.2
C1—C6—C5	118.41 (17)	C13—C14—H14B	109.2
C1—C6—H6A	120.8	C14^i—C14—H14B	109.2
C5—C6—H6A	120.8	H14A—C14—H14B	107.9
C8—C7—C12	121.53 (17)
O1—P1—O2—C1	−65.65 (15)	C2—C1—C6—C5	−0.4 (3)
O3—P1—O2—C1	174.82 (13)	O2—C1—C6—C5	−176.34 (17)
N1—P1—O2—C1	62.22 (14)	C4—C5—C6—C1	0.1 (3)
O1—P1—O3—C7	43.33 (15)	P1—O3—C7—C8	−145.45 (14)
O2—P1—O3—C7	166.06 (13)	P1—O3—C7—C12	36.6 (2)
N1—P1—O3—C7	−85.26 (14)	C12—C7—C8—C9	−0.8 (3)
O1—P1—N1—C13	−178.63 (12)	O3—C7—C8—C9	−178.84 (16)
O2—P1—N1—C13	50.80 (14)	C7—C8—C9—C10	−0.7 (3)
O3—P1—N1—C13	−49.71 (14)	C8—C9—C10—C11	1.7 (3)
P1—O2—C1—C2	81.68 (19)	C9—C10—C11—C12	−1.2 (3)
P1—O2—C1—C6	−102.27 (17)	C8—C7—C12—C11	1.3 (3)
C6—C1—C2—C3	0.3 (3)	O3—C7—C12—C11	179.20 (16)
O2—C1—C2—C3	176.19 (17)	C10—C11—C12—C7	−0.3 (3)
C1—C2—C3—C4	0.2 (3)	P1—N1—C13—C14	112.68 (15)
C2—C3—C4—C5	−0.5 (3)	N1—C13—C14—C14^i	175.84 (18)
C3—C4—C5—C6	0.3 (3)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^ii	0.91	2.21	3.060 (2)	156

Symmetry code: (ii) −x+1, −y+2, −z+2.