Two closely related {4-[(N-substituted amino)(diethoxyphosphoryl)methyl]phenyl}boronic acids

Organic phospho­nic acids and organic phospho­nic acid esters have been of much inter­est due to their applications in the fields of medicine, agriculture and industrial chemistry. Boronic acids can act as synthetic inter­mediates and building blocks and are used in sensing, protein manipulation, therapeutics, biological labelling and separation. The additional introduction of an amino­phospho­nic acid group into a boronic acid may give new opportunities for application. To study the structure of such multifunctional compounds, we pre­pared two new derivatives which can be easily converted to the corresponding phospho­nic acids. In the title compounds, {4-[(butylamino)(diethoxy­phosphoryl)methyl]phenyl}boronic acid monohydrate, C₁₅H₂₇BNO₅P·H₂O, (I), and {4-[(diethoxyphosphoryl)(4-nitroanilino)methyl]phenyl}boronic acid, C₁₇H₂₂BN₂O₇P, (II), three different substituents are attached to a central C—H group, namely 4-boronophenyl, di­eth­oxy­phosphoryl and amine. Compound (I) crystallizes as a monohydrate and O_B—H...N hydrogen bonds link neighbouring mol­ecules into chains along the [001] direction. The solvent water mol­ecule connects two such chains running in opposite directions. Compound (II) crystallizes as an ansolvate and classical hydrogen bonds result in a layer structure in the (001) plane.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Bruker, 2010). Software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) for (1); SHELXTL (Bruker, 2010) for (2).

(1) {4-[(Butylamino)(diethoxyphosphoryl)methyl]phenyl}boronic acid monohydrate

Crystal data

C15H27BNO5P·H2O	F(000) = 776
Mr = 361.17	Dx = 1.182 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4370 (2) Å	Cell parameters from 1321 reflections
b = 23.5403 (4) Å	θ = 2.2–25.0°
c = 10.3281 (2) Å	µ = 0.16 mm^−1
β = 98.1871 (7)°	T = 295 K
V = 2030.35 (7) Å^3	Sheet, white
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.036
φ and ω scans	θmax = 25.1°, θmin = 3.0°
73764 measured reflections	h = −10→9
3569 independent reflections	k = −28→28
3198 reflections with I > 2σ(I)	l = −12→12

Refinement

Refinement on F^2	15 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.172	w = 1/[σ^2(Fo^2) + (0.0593P)^2 + 2.5299P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
3569 reflections	Δρmax = 0.45 e Å^−3
235 parameters	Δρmin = −0.38 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
P1	0.05753 (10)	0.40870 (3)	0.71854 (7)	0.0481 (3)
O1	0.1336 (3)	0.46466 (10)	0.7185 (2)	0.0611 (6)
O2	−0.0129 (3)	0.38463 (11)	0.5818 (2)	0.0665 (7)
O3	−0.0862 (3)	0.40558 (11)	0.7994 (2)	0.0670 (7)
O4	0.2651 (3)	0.34135 (10)	1.42919 (19)	0.0626 (7)
H4	0.277 (5)	0.3502 (18)	1.507 (2)	0.094*
O5	0.4082 (4)	0.42696 (12)	1.4122 (2)	0.0715 (7)
H5	0.410 (6)	0.438 (2)	1.485 (2)	0.107*
B1	0.3262 (4)	0.38153 (15)	1.3577 (3)	0.0459 (8)
N1	0.3284 (3)	0.35052 (10)	0.7090 (2)	0.0436 (6)
H1A	0.383 (3)	0.3827 (10)	0.725 (3)	0.052*
C1	0.1922 (3)	0.35215 (12)	0.7835 (2)	0.0419 (6)
H1	0.134086	0.316227	0.767298	0.050*
C2	0.2342 (3)	0.35877 (12)	0.9314 (2)	0.0406 (6)
C5	0.2975 (3)	0.37367 (12)	1.2048 (2)	0.0418 (6)
C3	0.3349 (4)	0.40162 (13)	0.9851 (3)	0.0486 (7)
H3	0.382282	0.425729	0.930449	0.058*
C4	0.3660 (4)	0.40905 (13)	1.1197 (3)	0.0492 (7)
H4A	0.433818	0.438198	1.153717	0.059*
C6	0.1986 (4)	0.33071 (13)	1.1486 (3)	0.0510 (7)
H6	0.151848	0.306181	1.202778	0.061*
C7	0.1671 (4)	0.32304 (13)	1.0147 (3)	0.0497 (7)
H7	0.100297	0.293629	0.980550	0.060*
C8	0.4360 (5)	0.30250 (15)	0.7458 (3)	0.0662 (9)
H8A	0.376131	0.267351	0.730837	0.079*
H8B	0.476126	0.304861	0.838410	0.079*
C9	0.5732 (6)	0.3013 (2)	0.6707 (4)	0.0936 (15)
H9A	0.635529	0.335676	0.689549	0.112*
H9B	0.532184	0.301411	0.578058	0.112*
C10	0.6810 (9)	0.2514 (3)	0.6992 (6)	0.151 (3)
H10A	0.746084	0.258244	0.783024	0.181*
H10B	0.614097	0.218779	0.710277	0.181*
C11	0.7818 (11)	0.2363 (3)	0.6134 (7)	0.182 (4)
H11A	0.720401	0.223469	0.533343	0.273*
H11B	0.850853	0.206307	0.650418	0.273*
H11C	0.845195	0.268535	0.595891	0.273*
C12	−0.1070 (7)	0.4194 (2)	0.4847 (4)	0.1016 (17)
H12A	−0.198092	0.434697	0.520682	0.122*
H12B	−0.042565	0.451007	0.461969	0.122*
C13	−0.1621 (7)	0.3875 (2)	0.3701 (4)	0.1058 (17)
H13A	−0.072158	0.371401	0.335712	0.159*
H13B	−0.220208	0.411959	0.305696	0.159*
H13C	−0.231169	0.357533	0.391441	0.159*
C14	−0.1265 (9)	0.4492 (2)	0.8822 (7)	0.139 (3)
H14A	−0.028179	0.466011	0.925846	0.167*
H14B	−0.183683	0.478541	0.828409	0.167*
C15	−0.2186 (9)	0.4332 (3)	0.9763 (6)	0.140 (3)
H15A	−0.312922	0.413941	0.935302	0.210*
H15B	−0.249024	0.466268	1.021131	0.210*
H15C	−0.157815	0.408122	1.037812	0.210*
O6	0.4407 (3)	0.47579 (13)	0.6604 (3)	0.0710 (7)
H6A	0.348 (3)	0.479 (2)	0.675 (5)	0.106*
H6B	0.475 (6)	0.5065 (12)	0.644 (5)	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0524 (5)	0.0569 (5)	0.0339 (4)	−0.0004 (4)	0.0020 (3)	0.0014 (3)
O1	0.0670 (14)	0.0561 (13)	0.0593 (14)	−0.0023 (11)	0.0060 (11)	0.0070 (10)
O2	0.0814 (16)	0.0733 (15)	0.0381 (11)	0.0075 (13)	−0.0150 (11)	0.0008 (10)
O3	0.0584 (14)	0.0775 (16)	0.0677 (15)	−0.0042 (12)	0.0177 (12)	−0.0089 (12)
O4	0.0901 (17)	0.0735 (15)	0.0245 (10)	−0.0178 (13)	0.0091 (11)	0.0012 (10)
O5	0.0982 (19)	0.0794 (17)	0.0393 (12)	−0.0287 (14)	0.0180 (13)	−0.0160 (11)
B1	0.0512 (19)	0.059 (2)	0.0276 (15)	0.0022 (15)	0.0075 (13)	0.0005 (14)
N1	0.0575 (15)	0.0476 (13)	0.0259 (11)	0.0006 (11)	0.0069 (10)	−0.0005 (9)
C1	0.0546 (16)	0.0478 (15)	0.0229 (12)	−0.0047 (12)	0.0035 (11)	−0.0003 (11)
C2	0.0498 (15)	0.0467 (15)	0.0249 (12)	−0.0004 (12)	0.0042 (11)	0.0007 (11)
C5	0.0490 (15)	0.0507 (16)	0.0259 (13)	0.0035 (12)	0.0060 (11)	0.0011 (11)
C3	0.0625 (18)	0.0567 (17)	0.0274 (13)	−0.0145 (14)	0.0087 (12)	0.0027 (12)
C4	0.0615 (18)	0.0577 (18)	0.0281 (13)	−0.0118 (14)	0.0053 (12)	−0.0026 (12)
C6	0.0667 (19)	0.0574 (18)	0.0299 (14)	−0.0109 (15)	0.0102 (13)	0.0075 (12)
C7	0.0641 (19)	0.0531 (17)	0.0312 (14)	−0.0148 (14)	0.0043 (13)	0.0014 (12)
C8	0.086 (3)	0.060 (2)	0.0538 (19)	0.0168 (18)	0.0159 (18)	0.0056 (16)
C9	0.101 (3)	0.110 (3)	0.074 (3)	0.047 (3)	0.026 (2)	0.011 (2)
C10	0.160 (6)	0.180 (6)	0.122 (5)	0.114 (5)	0.054 (4)	0.041 (4)
C11	0.232 (9)	0.186 (7)	0.137 (6)	0.130 (7)	0.060 (6)	0.014 (5)
C12	0.140 (4)	0.093 (3)	0.057 (2)	0.027 (3)	−0.040 (3)	0.003 (2)
C13	0.127 (4)	0.115 (4)	0.062 (2)	0.021 (3)	−0.037 (3)	−0.011 (2)
C14	0.181 (6)	0.100 (4)	0.163 (6)	−0.010 (4)	0.115 (5)	−0.041 (4)
C15	0.189 (7)	0.114 (4)	0.140 (5)	−0.003 (4)	0.106 (5)	−0.013 (4)
O6	0.0797 (18)	0.0816 (18)	0.0535 (14)	−0.0191 (15)	0.0156 (13)	0.0030 (13)

Geometric parameters (Å, º)

P1—O1	1.465 (2)	C8—C9	1.483 (5)
P1—O2	1.559 (2)	C8—H8A	0.9700
P1—O3	1.569 (2)	C8—H8B	0.9700
P1—C1	1.816 (3)	C9—C10	1.488 (6)
O2—C12	1.441 (4)	C9—H9A	0.9700
O3—C14	1.409 (5)	C9—H9B	0.9700
O4—B1	1.347 (4)	C10—C11	1.360 (7)
O4—H4	0.818 (19)	C10—H10A	0.9700
O5—B1	1.352 (4)	C10—H10B	0.9700
O5—H5	0.795 (19)	C11—H11A	0.9600
B1—C5	1.574 (4)	C11—H11B	0.9600
N1—C8	1.466 (4)	C11—H11C	0.9600
N1—C1	1.471 (4)	C12—C13	1.423 (5)
N1—H1A	0.890 (18)	C12—H12A	0.9700
C1—C2	1.526 (3)	C12—H12B	0.9700
C1—H1	0.9800	C13—H13A	0.9600
C2—C7	1.381 (4)	C13—H13B	0.9600
C2—C3	1.383 (4)	C13—H13C	0.9600
C5—C6	1.385 (4)	C14—C15	1.380 (7)
C5—C4	1.395 (4)	C14—H14A	0.9700
C3—C4	1.388 (4)	C14—H14B	0.9700
C3—H3	0.9300	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C6—C7	1.382 (4)	C15—H15C	0.9600
C6—H6	0.9300	O6—H6A	0.825 (19)
C7—H7	0.9300	O6—H6B	0.807 (19)
O1—P1—O2	115.92 (14)	H8A—C8—H8B	107.9
O1—P1—O3	114.45 (14)	C8—C9—C10	114.4 (4)
O2—P1—O3	103.97 (14)	C8—C9—H9A	108.7
O1—P1—C1	114.09 (14)	C10—C9—H9A	108.7
O2—P1—C1	101.88 (13)	C8—C9—H9B	108.7
O3—P1—C1	105.05 (13)	C10—C9—H9B	108.7
C12—O2—P1	121.7 (2)	H9A—C9—H9B	107.6
C14—O3—P1	124.1 (3)	C11—C10—C9	119.9 (6)
B1—O4—H4	111 (3)	C11—C10—H10A	107.4
B1—O5—H5	126 (4)	C9—C10—H10A	107.4
O4—B1—O5	122.7 (3)	C11—C10—H10B	107.4
O4—B1—C5	116.8 (3)	C9—C10—H10B	107.4
O5—B1—C5	120.5 (3)	H10A—C10—H10B	106.9
C8—N1—C1	112.7 (2)	C10—C11—H11A	109.5
C8—N1—H1A	109 (2)	C10—C11—H11B	109.5
C1—N1—H1A	108 (2)	H11A—C11—H11B	109.5
N1—C1—C2	116.0 (2)	C10—C11—H11C	109.5
N1—C1—P1	108.69 (18)	H11A—C11—H11C	109.5
C2—C1—P1	109.78 (19)	H11B—C11—H11C	109.5
N1—C1—H1	107.3	C13—C12—O2	111.2 (4)
C2—C1—H1	107.3	C13—C12—H12A	109.4
P1—C1—H1	107.3	O2—C12—H12A	109.4
C7—C2—C3	118.5 (2)	C13—C12—H12B	109.4
C7—C2—C1	120.3 (2)	O2—C12—H12B	109.4
C3—C2—C1	121.2 (2)	H12A—C12—H12B	108.0
C6—C5—C4	116.8 (2)	C12—C13—H13A	109.5
C6—C5—B1	120.2 (3)	C12—C13—H13B	109.5
C4—C5—B1	123.0 (3)	H13A—C13—H13B	109.5
C2—C3—C4	120.8 (3)	C12—C13—H13C	109.5
C2—C3—H3	119.6	H13A—C13—H13C	109.5
C4—C3—H3	119.6	H13B—C13—H13C	109.5
C3—C4—C5	121.3 (3)	C15—C14—O3	115.8 (5)
C3—C4—H4A	119.3	C15—C14—H14A	108.3
C5—C4—H4A	119.3	O3—C14—H14A	108.3
C7—C6—C5	122.2 (3)	C15—C14—H14B	108.3
C7—C6—H6	118.9	O3—C14—H14B	108.3
C5—C6—H6	118.9	H14A—C14—H14B	107.4
C2—C7—C6	120.4 (3)	C14—C15—H15A	109.5
C2—C7—H7	119.8	C14—C15—H15B	109.5
C6—C7—H7	119.8	H15A—C15—H15B	109.5
N1—C8—C9	112.4 (3)	C14—C15—H15C	109.5
N1—C8—H8A	109.1	H15A—C15—H15C	109.5
C9—C8—H8A	109.1	H15B—C15—H15C	109.5
N1—C8—H8B	109.1	H6A—O6—H6B	109 (5)
C9—C8—H8B	109.1
O1—P1—O2—C12	−44.9 (4)	O5—B1—C5—C6	−172.8 (3)
O3—P1—O2—C12	81.6 (4)	O4—B1—C5—C4	−174.0 (3)
C1—P1—O2—C12	−169.4 (4)	O5—B1—C5—C4	6.2 (5)
O1—P1—O3—C14	−9.3 (5)	C7—C2—C3—C4	−0.9 (5)
O2—P1—O3—C14	−136.8 (5)	C1—C2—C3—C4	176.8 (3)
C1—P1—O3—C14	116.6 (5)	C2—C3—C4—C5	0.2 (5)
C8—N1—C1—C2	61.4 (3)	C6—C5—C4—C3	0.5 (5)
C8—N1—C1—P1	−174.3 (2)	B1—C5—C4—C3	−178.4 (3)
O1—P1—C1—N1	−56.1 (2)	C4—C5—C6—C7	−0.5 (5)
O2—P1—C1—N1	69.6 (2)	B1—C5—C6—C7	178.5 (3)
O3—P1—C1—N1	177.75 (18)	C3—C2—C7—C6	0.9 (5)
O1—P1—C1—C2	71.8 (2)	C1—C2—C7—C6	−176.8 (3)
O2—P1—C1—C2	−162.6 (2)	C5—C6—C7—C2	−0.2 (5)
O3—P1—C1—C2	−54.4 (2)	C1—N1—C8—C9	−179.8 (3)
N1—C1—C2—C7	−130.9 (3)	N1—C8—C9—C10	−176.7 (5)
P1—C1—C2—C7	105.4 (3)	C8—C9—C10—C11	161.2 (8)
N1—C1—C2—C3	51.4 (4)	P1—O2—C12—C13	−178.0 (4)
P1—C1—C2—C3	−72.2 (3)	P1—O3—C14—C15	−159.5 (6)
O4—B1—C5—C6	7.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N1^i	0.82 (2)	2.07 (2)	2.872 (3)	165 (4)
O5—H5···O6^i	0.80 (2)	2.00 (2)	2.787 (3)	170 (5)
N1—H1A···O6	0.89 (2)	2.36 (2)	3.159 (4)	149 (3)
O6—H6A···O1	0.83 (2)	1.95 (2)	2.754 (4)	164 (5)
O6—H6B···O5^ii	0.81 (2)	1.98 (2)	2.775 (4)	168 (5)

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+2.

(2) {4-[(Diethoxyphosphoryl)(4-nitroanilino)methyl]phenyl}boronic acid

Crystal data

C17H22BN2O7P	Dx = 1.315 Mg m^−3
Mr = 408.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 3802 reflections
a = 10.2590 (8) Å	θ = 3.2–25.3°
b = 14.5721 (14) Å	µ = 0.17 mm^−1
c = 27.577 (3) Å	T = 173 K
V = 4122.6 (6) Å^3	Sheet, white
Z = 8	0.20 × 0.20 × 0.10 mm
F(000) = 1712

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.056
φ and ω scans	θmax = 25.4°, θmin = 3.2°
15530 measured reflections	h = −12→11
3726 independent reflections	k = −17→16
2312 reflections with I > 2σ(I)	l = −33→33

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)] = 0.060	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 5.3769P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.197	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.61 e Å^−3
3726 reflections	Δρmin = −0.33 e Å^−3
265 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0023 (6)

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	0.29978 (9)	0.26468 (7)	0.11014 (4)	0.0374 (3)
O1	0.2977 (3)	0.2135 (2)	0.06424 (9)	0.0493 (8)
O2	0.2926 (3)	0.37114 (19)	0.10325 (10)	0.0499 (7)
O3	0.1866 (2)	0.2417 (2)	0.14604 (10)	0.0464 (7)
O4	0.9308 (3)	0.4994 (2)	0.06307 (10)	0.0504 (8)
H4A	0.980 (4)	0.528 (3)	0.0449 (16)	0.076*
O5	0.9167 (3)	0.40026 (19)	−0.00333 (10)	0.0465 (7)
H5	0.877 (4)	0.360 (3)	−0.0180 (16)	0.070*
O6	0.9018 (4)	0.0213 (3)	0.29736 (15)	0.0873 (12)
O7	0.8391 (4)	−0.1102 (3)	0.26851 (14)	0.0847 (12)
N1	0.4546 (3)	0.1441 (2)	0.15380 (11)	0.0367 (7)
H1A	0.425 (4)	0.106 (2)	0.1318 (12)	0.044*
N2	0.8307 (4)	−0.0258 (3)	0.27132 (15)	0.0630 (11)
B1	0.8743 (4)	0.4260 (3)	0.04156 (15)	0.0388 (10)
C1	0.4439 (3)	0.2426 (2)	0.14655 (13)	0.0342 (8)
H1	0.432820	0.272842	0.178838	0.041*
C2	0.5610 (3)	0.2859 (3)	0.12075 (12)	0.0335 (8)
C3	0.5982 (4)	0.3751 (3)	0.13295 (13)	0.0376 (9)
H3	0.554918	0.406402	0.158492	0.045*
C4	0.6987 (4)	0.4182 (3)	0.10778 (13)	0.0362 (8)
H4	0.723602	0.478739	0.116592	0.043*
C5	0.7636 (4)	0.3740 (2)	0.06975 (13)	0.0362 (9)
C6	0.7260 (4)	0.2845 (3)	0.05856 (14)	0.0414 (9)
H6	0.769276	0.252873	0.033096	0.050*
C7	0.6264 (4)	0.2402 (3)	0.08377 (13)	0.0387 (9)
H7	0.603298	0.178985	0.075717	0.046*
C8	0.5481 (3)	0.1044 (3)	0.18368 (13)	0.0366 (9)
C9	0.6302 (4)	0.1570 (3)	0.21332 (13)	0.0400 (9)
H9	0.623234	0.222027	0.213320	0.048*
C10	0.7215 (4)	0.1140 (3)	0.24265 (14)	0.0437 (10)
H10	0.776478	0.149409	0.263115	0.052*
C11	0.7320 (4)	0.0200 (3)	0.24194 (14)	0.0449 (10)
C12	0.6501 (4)	−0.0334 (3)	0.21345 (15)	0.0509 (11)
H12	0.657407	−0.098356	0.213849	0.061*
C13	0.5581 (4)	0.0087 (3)	0.18455 (14)	0.0434 (10)
H13	0.501241	−0.027400	0.165172	0.052*
C14	0.3223 (8)	0.4153 (4)	0.0563 (2)	0.108 (3)
H14A	0.392259	0.380674	0.039650	0.130*
H14B	0.243855	0.414037	0.035396	0.130*
C15	0.3628 (8)	0.5076 (5)	0.0632 (3)	0.134 (3)
H15A	0.435422	0.509329	0.086279	0.201*
H15B	0.289839	0.543691	0.076042	0.201*
H15C	0.390894	0.533576	0.032157	0.201*
C16	0.0515 (4)	0.2502 (4)	0.12892 (19)	0.0640 (14)
H16A	0.034646	0.313934	0.118133	0.077*
H16B	0.036776	0.208619	0.101074	0.077*
C17	−0.0359 (5)	0.2264 (5)	0.1685 (2)	0.099 (2)
H17A	−0.015490	0.264218	0.196847	0.149*
H17B	−0.024920	0.161455	0.176680	0.149*
H17C	−0.126215	0.237538	0.158477	0.149*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0325 (5)	0.0438 (6)	0.0358 (6)	0.0042 (4)	0.0008 (4)	−0.0015 (4)
O1	0.0459 (17)	0.0640 (19)	0.0380 (15)	0.0097 (14)	−0.0052 (13)	−0.0144 (13)
O2	0.0522 (17)	0.0427 (17)	0.0547 (17)	0.0116 (13)	−0.0008 (14)	0.0035 (14)
O3	0.0302 (14)	0.0646 (19)	0.0445 (16)	0.0011 (13)	0.0044 (12)	0.0017 (14)
O4	0.063 (2)	0.0469 (17)	0.0413 (16)	−0.0219 (15)	0.0120 (14)	−0.0077 (13)
O5	0.0535 (18)	0.0457 (17)	0.0401 (16)	−0.0159 (13)	0.0113 (13)	−0.0071 (13)
O6	0.076 (3)	0.098 (3)	0.088 (3)	0.012 (2)	−0.037 (2)	0.012 (2)
O7	0.106 (3)	0.070 (3)	0.078 (3)	0.031 (2)	−0.015 (2)	0.024 (2)
N1	0.0347 (17)	0.0366 (19)	0.0387 (18)	−0.0018 (14)	−0.0031 (14)	0.0014 (14)
N2	0.062 (3)	0.072 (3)	0.055 (2)	0.019 (2)	0.000 (2)	0.024 (2)
B1	0.049 (3)	0.034 (2)	0.033 (2)	−0.002 (2)	0.005 (2)	−0.0002 (18)
C1	0.036 (2)	0.035 (2)	0.0312 (18)	0.0030 (16)	0.0026 (15)	0.0017 (15)
C2	0.0305 (19)	0.039 (2)	0.0311 (19)	0.0014 (15)	−0.0003 (15)	0.0027 (15)
C3	0.038 (2)	0.038 (2)	0.036 (2)	−0.0011 (17)	0.0034 (16)	−0.0028 (16)
C4	0.040 (2)	0.035 (2)	0.0330 (19)	−0.0021 (16)	0.0021 (16)	−0.0033 (16)
C5	0.039 (2)	0.035 (2)	0.0341 (19)	−0.0011 (16)	0.0029 (16)	0.0015 (16)
C6	0.047 (2)	0.039 (2)	0.038 (2)	−0.0028 (17)	0.0114 (18)	−0.0047 (17)
C7	0.043 (2)	0.032 (2)	0.040 (2)	−0.0046 (17)	0.0074 (17)	−0.0054 (17)
C8	0.032 (2)	0.045 (2)	0.0328 (19)	0.0022 (16)	0.0060 (16)	0.0045 (16)
C9	0.036 (2)	0.045 (2)	0.040 (2)	0.0009 (17)	0.0012 (17)	0.0050 (17)
C10	0.037 (2)	0.056 (3)	0.038 (2)	−0.0014 (18)	0.0050 (17)	0.0101 (19)
C11	0.041 (2)	0.057 (3)	0.037 (2)	0.0106 (19)	0.0039 (17)	0.0120 (19)
C12	0.064 (3)	0.044 (2)	0.046 (2)	0.010 (2)	0.010 (2)	0.0083 (19)
C13	0.052 (2)	0.042 (2)	0.037 (2)	0.0011 (19)	0.0039 (18)	0.0042 (18)
C14	0.194 (8)	0.056 (4)	0.074 (4)	−0.007 (4)	−0.028 (5)	0.020 (3)
C15	0.126 (6)	0.103 (6)	0.172 (8)	−0.006 (5)	−0.027 (6)	0.066 (6)
C16	0.030 (2)	0.089 (4)	0.073 (3)	0.005 (2)	−0.003 (2)	−0.004 (3)
C17	0.036 (3)	0.140 (6)	0.121 (5)	0.017 (3)	0.018 (3)	0.046 (5)

Geometric parameters (Å, º)

P1—O1	1.469 (3)	C6—C7	1.394 (5)
P1—O3	1.563 (3)	C6—H6	0.9500
P1—O2	1.565 (3)	C7—H7	0.9500
P1—C1	1.816 (4)	C8—C13	1.397 (5)
O2—C14	1.478 (6)	C8—C9	1.402 (5)
O3—C16	1.469 (5)	C9—C10	1.387 (5)
O4—B1	1.354 (5)	C9—H9	0.9500
O4—H4A	0.825 (19)	C10—C11	1.375 (6)
O5—B1	1.365 (5)	C10—H10	0.9500
O5—H5	0.823 (19)	C11—C12	1.389 (6)
O6—N2	1.232 (5)	C12—C13	1.380 (6)
O7—N2	1.236 (5)	C12—H12	0.9500
N1—C8	1.391 (5)	C13—H13	0.9500
N1—C1	1.453 (5)	C14—C15	1.421 (9)
N1—H1A	0.880 (19)	C14—H14A	0.9900
N2—C11	1.458 (5)	C14—H14B	0.9900
B1—C5	1.571 (6)	C15—H15A	0.9800
C1—C2	1.532 (5)	C15—H15B	0.9800
C1—H1	1.0000	C15—H15C	0.9800
C2—C7	1.390 (5)	C16—C17	1.454 (7)
C2—C3	1.395 (5)	C16—H16A	0.9900
C3—C4	1.393 (5)	C16—H16B	0.9900
C3—H3	0.9500	C17—H17A	0.9800
C4—C5	1.400 (5)	C17—H17B	0.9800
C4—H4	0.9500	C17—H17C	0.9800
C5—C6	1.395 (5)
O1—P1—O3	115.22 (17)	N1—C8—C13	118.4 (3)
O1—P1—O2	113.46 (17)	N1—C8—C9	122.1 (3)
O3—P1—O2	104.75 (16)	C13—C8—C9	119.5 (3)
O1—P1—C1	113.45 (16)	C10—C9—C8	119.9 (4)
O3—P1—C1	102.52 (15)	C10—C9—H9	120.1
O2—P1—C1	106.34 (16)	C8—C9—H9	120.1
C14—O2—P1	121.9 (3)	C11—C10—C9	119.7 (4)
C16—O3—P1	118.6 (3)	C11—C10—H10	120.2
B1—O4—H4A	113 (4)	C9—C10—H10	120.2
B1—O5—H5	119 (3)	C10—C11—C12	121.3 (4)
C8—N1—C1	123.0 (3)	C10—C11—N2	120.2 (4)
C8—N1—H1A	113 (3)	C12—C11—N2	118.6 (4)
C1—N1—H1A	120 (3)	C13—C12—C11	119.5 (4)
O6—N2—O7	123.3 (4)	C13—C12—H12	120.3
O6—N2—C11	118.7 (4)	C11—C12—H12	120.3
O7—N2—C11	118.0 (5)	C12—C13—C8	120.2 (4)
O4—B1—O5	118.6 (4)	C12—C13—H13	119.9
O4—B1—C5	118.3 (3)	C8—C13—H13	119.9
O5—B1—C5	123.1 (4)	C15—C14—O2	110.8 (6)
N1—C1—C2	114.3 (3)	C15—C14—H14A	109.5
N1—C1—P1	108.2 (2)	O2—C14—H14A	109.5
C2—C1—P1	108.0 (2)	C15—C14—H14B	109.5
N1—C1—H1	108.7	O2—C14—H14B	109.5
C2—C1—H1	108.7	H14A—C14—H14B	108.1
P1—C1—H1	108.7	C14—C15—H15A	109.5
C7—C2—C3	119.4 (3)	C14—C15—H15B	109.5
C7—C2—C1	121.4 (3)	H15A—C15—H15B	109.5
C3—C2—C1	119.1 (3)	C14—C15—H15C	109.5
C4—C3—C2	120.2 (3)	H15A—C15—H15C	109.5
C4—C3—H3	119.9	H15B—C15—H15C	109.5
C2—C3—H3	119.9	C17—C16—O3	108.7 (4)
C3—C4—C5	121.2 (3)	C17—C16—H16A	110.0
C3—C4—H4	119.4	O3—C16—H16A	110.0
C5—C4—H4	119.4	C17—C16—H16B	110.0
C6—C5—C4	117.7 (3)	O3—C16—H16B	110.0
C6—C5—B1	122.8 (3)	H16A—C16—H16B	108.3
C4—C5—B1	119.5 (3)	C16—C17—H17A	109.5
C7—C6—C5	121.7 (3)	C16—C17—H17B	109.5
C7—C6—H6	119.2	H17A—C17—H17B	109.5
C5—C6—H6	119.2	C16—C17—H17C	109.5
C2—C7—C6	119.9 (4)	H17A—C17—H17C	109.5
C2—C7—H7	120.1	H17B—C17—H17C	109.5
C6—C7—H7	120.1
O1—P1—O2—C14	−17.9 (5)	O4—B1—C5—C4	19.6 (6)
O3—P1—O2—C14	−144.4 (4)	O5—B1—C5—C4	−160.9 (4)
C1—P1—O2—C14	107.5 (4)	C4—C5—C6—C7	0.6 (6)
O1—P1—O3—C16	−55.4 (4)	B1—C5—C6—C7	−179.2 (4)
O2—P1—O3—C16	70.0 (3)	C3—C2—C7—C6	−1.6 (6)
C1—P1—O3—C16	−179.1 (3)	C1—C2—C7—C6	175.0 (3)
C8—N1—C1—C2	65.4 (4)	C5—C6—C7—C2	0.8 (6)
C8—N1—C1—P1	−174.3 (3)	C1—N1—C8—C13	−174.0 (3)
O1—P1—C1—N1	−54.5 (3)	C1—N1—C8—C9	7.2 (5)
O3—P1—C1—N1	70.4 (3)	N1—C8—C9—C10	179.7 (3)
O2—P1—C1—N1	−179.9 (2)	C13—C8—C9—C10	0.9 (5)
O1—P1—C1—C2	69.7 (3)	C8—C9—C10—C11	0.8 (6)
O3—P1—C1—C2	−165.4 (2)	C9—C10—C11—C12	−2.0 (6)
O2—P1—C1—C2	−55.7 (3)	C9—C10—C11—N2	177.8 (3)
N1—C1—C2—C7	36.7 (5)	O6—N2—C11—C10	1.6 (6)
P1—C1—C2—C7	−83.7 (4)	O7—N2—C11—C10	−178.0 (4)
N1—C1—C2—C3	−146.7 (3)	O6—N2—C11—C12	−178.6 (4)
P1—C1—C2—C3	92.8 (3)	O7—N2—C11—C12	1.8 (6)
C7—C2—C3—C4	1.0 (6)	C10—C11—C12—C13	1.3 (6)
C1—C2—C3—C4	−175.7 (3)	N2—C11—C12—C13	−178.5 (4)
C2—C3—C4—C5	0.5 (6)	C11—C12—C13—C8	0.5 (6)
C3—C4—C5—C6	−1.3 (5)	N1—C8—C13—C12	179.6 (3)
C3—C4—C5—B1	178.6 (4)	C9—C8—C13—C12	−1.6 (6)
O4—B1—C5—C6	−160.5 (4)	P1—O2—C14—C15	−155.3 (5)
O5—B1—C5—C6	18.9 (6)	P1—O3—C16—C17	−179.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1^i	0.82 (2)	1.85 (2)	2.657 (4)	166 (5)
O4—H4A···O5^ii	0.83 (2)	1.88 (2)	2.702 (4)	176 (5)

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+2, −y+1, −z.