A second polymorph of bis-(triphenyl-λ(5)-phosphanyl-idene)ammonium chloride-boric acid adduct.

The title crystal structure is a new triclinic polymorph of [(Ph3P)2N]Cl·(B(OH)3) or C36H30NP2 (+)·Cl(-)·BH3O3. The crystal structure of the ortho-rhom-bic polymorph was reported by [Andrews et al. (1983 ▶). Acta Cryst. C39, 880-882]. In the crystal, the [(Ph3P)2N](+) cations have no significant contacts to the chloride ions nor to the boric acid mol-ecules. This is indicated by the P-N-P angle of 137.28 (8)°, which is in the expected range for a free [(Ph3P)2N](+) cation. The boric acid mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds, and each boric acid mol-ecule forms two additional O-H⋯Cl hydrogen bonds to one chloride anion. These entities fill channels, created by the [(Ph3P)2N](+) cations, along the c-axis direction.

Related literature

For the ortho­rhom­bic polymorph of the title compound, see: Andrews et al. (1983 ▶). Other bis­(tri­phenyl­phosphine)iminium halide structures include [(Ph3P)2N]Cl (Knapp & Uzun, 2010a ▶), [(Ph3P)2N]Br·CH3CN (Knapp & Uzun, 2010b ▶), [(Ph3P)2N]I (Beckett et al., 2010 ▶) and [(Ph3P)2N][ClHCl] (Gellhaar & Knapp, 2011 ▶). For a discussion of the [(Ph3P)2N]+ cation, see: Lewis & Dance (2000 ▶). For a theoretical study on boric acid dimers, see: Larkin et al. (2006 ▶). For an overview of the different polymorphs of boric acid, see: Shuvalov & Burns (2003 ▶).

Experimental

Crystal data

C36H30NP2 +·Cl−·BH3O3

M = 635.83

Triclinic,

a = 10.7720 (2) Å

b = 11.4243 (3) Å

c = 14.3507 (4) Å

α = 107.244 (2)°

β = 105.648 (2)°

γ = 93.2742 (19)°

V = 1605.99 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 150 K

0.18 × 0.14 × 0.10 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.256, T max = 1.000

14941 measured reflections

8731 independent reflections

6913 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.098

S = 1.04

8731 reflections

409 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg et al., 2012 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813020886/su2629sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020886/su2629Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020886/su2629Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C36H30NP2+·Cl−·BH3O3	Z = 2
Mr = 635.83	F(000) = 664
Triclinic, P1	Dx = 1.315 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7720 (2) Å	Cell parameters from 6049 reflections
b = 11.4243 (3) Å	θ = 30.0–1.9°
c = 14.3507 (4) Å	µ = 0.26 mm−1
α = 107.244 (2)°	T = 150 K
β = 105.648 (2)°	Block, colourless
γ = 93.2742 (19)°	0.18 × 0.14 × 0.10 mm
V = 1605.99 (7) Å3

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	8731 independent reflections
Radiation source: fine-focus sealed tube	6913 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.2705 pixels mm-1	θmax = 30.9°, θmin = 1.9°
ω scans	h = −14→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −14→15
Tmin = 0.256, Tmax = 1.000	l = −20→20
14941 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.4455P] where P = (Fo2 + 2Fc2)/3
8731 reflections	(Δ/σ)max = 0.001
409 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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 > 2σ(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. All hydrogen atoms attached to the aromatic rings were placed in calculated positions (C—H = 0.93 Å) and refined as riding atoms, with Uiso(H) = 1.2 Ueq(C). The oxygen-bonded hydrogen atoms were taken from the Fourier map and were refined isotropically.

	x	y	z	Uiso*/Ueq
P2	0.64033 (4)	0.84597 (3)	0.28032 (3)	0.01673 (9)
P1	0.49238 (4)	0.60975 (3)	0.26011 (3)	0.01533 (8)
N1	0.61330 (12)	0.70542 (11)	0.27330 (10)	0.0187 (3)
C7	0.34257 (14)	0.61496 (13)	0.16954 (11)	0.0171 (3)
C19	0.73612 (14)	0.85848 (13)	0.19766 (11)	0.0177 (3)
C25	0.73552 (15)	0.94085 (14)	0.40702 (11)	0.0206 (3)
C1	0.53257 (14)	0.45674 (13)	0.21385 (11)	0.0173 (3)
C13	0.45827 (14)	0.62377 (13)	0.37872 (11)	0.0178 (3)
C6	0.43562 (16)	0.35398 (14)	0.17729 (12)	0.0229 (3)
H6	0.3478	0.3649	0.1734	0.027*
C21	0.86818 (16)	0.98473 (16)	0.14146 (13)	0.0263 (3)
H21	0.9109	1.0634	0.1486	0.032*
C10	0.11519 (16)	0.62679 (15)	0.02598 (12)	0.0253 (3)
H10	0.0378	0.6313	−0.0230	0.030*
C8	0.32793 (15)	0.56684 (14)	0.06508 (12)	0.0217 (3)
H8	0.3962	0.5303	0.0427	0.026*
C24	0.74587 (15)	0.75343 (14)	0.12204 (12)	0.0225 (3)
H24	0.7052	0.6743	0.1157	0.027*
C20	0.79778 (15)	0.97397 (14)	0.20726 (12)	0.0219 (3)
H20	0.7916	1.0457	0.2592	0.026*
C26	0.82218 (15)	0.88565 (15)	0.46632 (12)	0.0237 (3)
H26	0.8255	0.7994	0.4412	0.028*
C12	0.24218 (15)	0.66948 (15)	0.20093 (12)	0.0225 (3)
H12	0.2513	0.7033	0.2718	0.027*
C3	0.69251 (16)	0.32136 (15)	0.18846 (13)	0.0265 (3)
H3	0.7801	0.3098	0.1918	0.032*
C14	0.35051 (15)	0.55110 (15)	0.38051 (12)	0.0242 (3)
H14	0.2924	0.4959	0.3186	0.029*
C4	0.59580 (17)	0.21979 (14)	0.15264 (13)	0.0275 (4)
H4	0.6174	0.1385	0.1320	0.033*
C32	0.43908 (15)	0.89028 (15)	0.13559 (13)	0.0252 (3)
H32	0.4843	0.8532	0.0887	0.030*
C2	0.66115 (15)	0.44051 (14)	0.21962 (12)	0.0212 (3)
H2	0.7273	0.5105	0.2447	0.025*
C18	0.54362 (17)	0.70184 (14)	0.46993 (12)	0.0261 (3)
H18	0.6175	0.7508	0.4693	0.031*
C16	0.41352 (17)	0.63913 (15)	0.56316 (13)	0.0271 (3)
H16	0.3973	0.6457	0.6262	0.033*
C11	0.12891 (16)	0.67475 (16)	0.12927 (13)	0.0274 (3)
H11	0.0604	0.7115	0.1512	0.033*
C15	0.32914 (16)	0.56022 (16)	0.47325 (13)	0.0275 (3)
H15	0.2556	0.5115	0.4747	0.033*
C23	0.81557 (15)	0.76481 (16)	0.05559 (12)	0.0261 (3)
H23	0.8217	0.6933	0.0034	0.031*
C31	0.49389 (15)	0.90944 (13)	0.23950 (12)	0.0211 (3)
C36	0.42608 (17)	0.96328 (15)	0.30771 (14)	0.0295 (4)
H36	0.4609	0.9743	0.3785	0.035*
C9	0.21448 (16)	0.57221 (15)	−0.00586 (12)	0.0255 (3)
H9	0.2046	0.5382	−0.0769	0.031*
C22	0.87572 (15)	0.87948 (16)	0.06513 (13)	0.0266 (3)
H22	0.9226	0.8865	0.0192	0.032*
C29	0.81699 (19)	1.13927 (16)	0.53898 (14)	0.0339 (4)
H29	0.8165	1.2261	0.5637	0.041*
C28	0.90074 (18)	1.08346 (18)	0.59779 (14)	0.0364 (4)
H28	0.9569	1.1320	0.6633	0.044*
C5	0.46804 (17)	0.23583 (14)	0.14666 (13)	0.0277 (4)
H5	0.4022	0.1656	0.1214	0.033*
C27	0.90334 (17)	0.95721 (18)	0.56189 (13)	0.0320 (4)
H27	0.9610	0.9195	0.6030	0.038*
C30	0.73351 (17)	1.06866 (14)	0.44378 (13)	0.0267 (3)
H30	0.6752	1.1069	0.4036	0.032*
C17	0.52151 (19)	0.70874 (15)	0.56217 (13)	0.0310 (4)
H17	0.5809	0.7615	0.6246	0.037*
C35	0.30674 (18)	1.00078 (16)	0.27085 (18)	0.0386 (5)
H35	0.2615	1.0397	0.3173	0.046*
C34	0.25385 (17)	0.98210 (16)	0.16809 (17)	0.0383 (5)
H34	0.1727	1.0084	0.1439	0.046*
C33	0.31852 (17)	0.92524 (17)	0.10030 (16)	0.0337 (4)
H33	0.2805	0.9099	0.0291	0.040*
Cl1	0.08761 (5)	0.28422 (4)	0.19113 (3)	0.03497 (11)
O2	0.01672 (13)	0.41861 (12)	0.38407 (10)	0.0308 (3)
O3	−0.04705 (13)	0.61727 (12)	0.42973 (11)	0.0362 (3)
O1	−0.00992 (14)	0.54155 (15)	0.27226 (11)	0.0380 (3)
B1	−0.01301 (18)	0.52440 (19)	0.36165 (15)	0.0277 (4)
H2O	0.036 (2)	0.370 (2)	0.340 (2)	0.063 (8)*
H1O	0.009 (3)	0.481 (3)	0.243 (2)	0.065 (9)*
H3O	−0.038 (2)	0.606 (2)	0.487 (2)	0.066 (8)*

	U11	U22	U33	U12	U13	U23
P2	0.01776 (18)	0.01352 (17)	0.02030 (19)	0.00226 (13)	0.00854 (15)	0.00497 (14)
P1	0.01602 (18)	0.01386 (16)	0.01754 (18)	0.00255 (13)	0.00670 (14)	0.00562 (13)
N1	0.0181 (6)	0.0151 (6)	0.0242 (6)	0.0017 (5)	0.0081 (5)	0.0069 (5)
C7	0.0170 (7)	0.0149 (6)	0.0208 (7)	0.0015 (5)	0.0064 (6)	0.0076 (5)
C19	0.0159 (7)	0.0189 (7)	0.0203 (7)	0.0039 (5)	0.0065 (6)	0.0080 (6)
C25	0.0227 (8)	0.0183 (7)	0.0215 (7)	−0.0009 (6)	0.0119 (6)	0.0033 (6)
C1	0.0201 (7)	0.0158 (6)	0.0176 (7)	0.0029 (5)	0.0069 (6)	0.0065 (5)
C13	0.0197 (7)	0.0173 (7)	0.0198 (7)	0.0060 (5)	0.0081 (6)	0.0086 (6)
C6	0.0221 (8)	0.0191 (7)	0.0272 (8)	0.0013 (6)	0.0073 (6)	0.0075 (6)
C21	0.0246 (8)	0.0280 (8)	0.0301 (9)	0.0000 (6)	0.0090 (7)	0.0149 (7)
C10	0.0215 (8)	0.0283 (8)	0.0256 (8)	0.0030 (6)	0.0031 (7)	0.0118 (7)
C8	0.0243 (8)	0.0222 (7)	0.0212 (7)	0.0064 (6)	0.0105 (6)	0.0071 (6)
C24	0.0208 (7)	0.0211 (7)	0.0250 (8)	0.0024 (6)	0.0095 (6)	0.0044 (6)
C20	0.0231 (8)	0.0198 (7)	0.0243 (8)	0.0021 (6)	0.0081 (6)	0.0086 (6)
C26	0.0226 (8)	0.0237 (8)	0.0248 (8)	0.0003 (6)	0.0108 (6)	0.0051 (6)
C12	0.0221 (8)	0.0272 (8)	0.0206 (7)	0.0071 (6)	0.0089 (6)	0.0084 (6)
C3	0.0264 (8)	0.0263 (8)	0.0317 (9)	0.0113 (7)	0.0141 (7)	0.0104 (7)
C14	0.0195 (7)	0.0304 (8)	0.0240 (8)	0.0008 (6)	0.0067 (6)	0.0109 (7)
C4	0.0391 (10)	0.0159 (7)	0.0297 (9)	0.0104 (7)	0.0134 (8)	0.0066 (6)
C32	0.0217 (8)	0.0224 (7)	0.0354 (9)	0.0054 (6)	0.0098 (7)	0.0138 (7)
C2	0.0205 (7)	0.0198 (7)	0.0247 (8)	0.0032 (6)	0.0088 (6)	0.0073 (6)
C18	0.0329 (9)	0.0198 (7)	0.0246 (8)	−0.0035 (6)	0.0090 (7)	0.0067 (6)
C16	0.0387 (10)	0.0288 (8)	0.0242 (8)	0.0148 (7)	0.0174 (7)	0.0146 (7)
C11	0.0217 (8)	0.0353 (9)	0.0290 (9)	0.0107 (7)	0.0097 (7)	0.0126 (7)
C15	0.0235 (8)	0.0371 (9)	0.0307 (9)	0.0070 (7)	0.0129 (7)	0.0190 (7)
C23	0.0217 (8)	0.0320 (8)	0.0251 (8)	0.0071 (7)	0.0111 (7)	0.0058 (7)
C31	0.0203 (7)	0.0145 (6)	0.0319 (8)	0.0035 (5)	0.0122 (7)	0.0080 (6)
C36	0.0273 (9)	0.0231 (8)	0.0404 (10)	0.0021 (7)	0.0186 (8)	0.0064 (7)
C9	0.0313 (9)	0.0259 (8)	0.0196 (8)	0.0051 (7)	0.0074 (7)	0.0077 (6)
C22	0.0201 (8)	0.0396 (9)	0.0264 (8)	0.0059 (7)	0.0109 (7)	0.0160 (7)
C29	0.0424 (11)	0.0232 (8)	0.0322 (9)	−0.0050 (7)	0.0223 (8)	−0.0050 (7)
C28	0.0334 (10)	0.0421 (10)	0.0231 (9)	−0.0109 (8)	0.0128 (8)	−0.0055 (8)
C5	0.0313 (9)	0.0164 (7)	0.0326 (9)	−0.0011 (6)	0.0086 (7)	0.0058 (6)
C27	0.0265 (9)	0.0433 (10)	0.0245 (8)	−0.0006 (7)	0.0084 (7)	0.0088 (7)
C30	0.0313 (9)	0.0202 (7)	0.0301 (9)	0.0017 (6)	0.0165 (7)	0.0042 (6)
C17	0.0456 (11)	0.0235 (8)	0.0199 (8)	−0.0004 (7)	0.0083 (8)	0.0040 (6)
C35	0.0281 (9)	0.0234 (8)	0.0701 (14)	0.0062 (7)	0.0302 (10)	0.0091 (9)
C34	0.0204 (8)	0.0271 (9)	0.0725 (15)	0.0071 (7)	0.0147 (9)	0.0223 (9)
C33	0.0240 (8)	0.0301 (9)	0.0498 (11)	0.0045 (7)	0.0061 (8)	0.0213 (8)
Cl1	0.0384 (2)	0.0343 (2)	0.0308 (2)	0.00153 (18)	0.01415 (19)	0.00595 (18)
O2	0.0378 (7)	0.0278 (6)	0.0289 (7)	0.0064 (5)	0.0132 (6)	0.0089 (5)
O3	0.0450 (8)	0.0345 (7)	0.0383 (8)	0.0161 (6)	0.0178 (6)	0.0185 (6)
O1	0.0394 (8)	0.0480 (9)	0.0370 (8)	0.0125 (7)	0.0168 (6)	0.0230 (7)
B1	0.0202 (9)	0.0330 (10)	0.0306 (10)	0.0019 (7)	0.0061 (8)	0.0132 (8)

P1—N1	1.5839 (12)	C4—C5	1.382 (2)
P2—N1	1.5836 (12)	C32—H32	0.9500
P2—C19	1.7990 (15)	C32—C31	1.392 (2)
P2—C25	1.7976 (16)	C32—C33	1.388 (2)
P2—C31	1.8004 (16)	C2—H2	0.9500
P1—C7	1.7951 (15)	C18—H18	0.9500
P1—C1	1.7993 (14)	C18—C17	1.388 (2)
P1—C13	1.8001 (14)	C16—H16	0.9500
C7—C8	1.396 (2)	C16—C15	1.374 (2)
C7—C12	1.391 (2)	C16—C17	1.377 (2)
C19—C24	1.390 (2)	C11—H11	0.9500
C19—C20	1.394 (2)	C15—H15	0.9500
C25—C26	1.396 (2)	C23—H23	0.9500
C25—C30	1.401 (2)	C23—C22	1.380 (2)
C1—C6	1.394 (2)	C31—C36	1.396 (2)
C1—C2	1.391 (2)	C36—H36	0.9500
C13—C14	1.399 (2)	C36—C35	1.395 (3)
C13—C18	1.385 (2)	C9—H9	0.9500
C6—H6	0.9500	C22—H22	0.9500
C6—C5	1.386 (2)	C29—H29	0.9500
C21—H21	0.9500	C29—C28	1.381 (3)
C21—C20	1.388 (2)	C29—C30	1.388 (2)
C21—C22	1.389 (2)	C28—H28	0.9500
C10—H10	0.9500	C28—C27	1.385 (3)
C10—C11	1.382 (2)	C5—H5	0.9500
C10—C9	1.383 (2)	C27—H27	0.9500
C8—H8	0.9500	C30—H30	0.9500
C8—C9	1.381 (2)	C17—H17	0.9500
C24—H24	0.9500	C35—H35	0.9500
C24—C23	1.392 (2)	C35—C34	1.375 (3)
C20—H20	0.9500	C34—H34	0.9500
C26—H26	0.9500	C34—C33	1.377 (3)
C26—C27	1.386 (2)	C33—H33	0.9500
C12—H12	0.9500	Cl1—H2O	2.30 (3)
C12—C11	1.385 (2)	Cl1—H1O	2.42 (3)
C3—H3	0.9500	O1—B1	1.362 (2)
C3—C4	1.384 (2)	O2—B1	1.373 (2)
C3—C2	1.393 (2)	O2—H2O	0.79 (3)
C14—H14	0.9500	O3—B1	1.356 (2)
C14—C15	1.386 (2)	O3—H3O	0.86 (3)
C4—H4	0.9500	O1—H1O	0.77 (3)
N1—P2—C19	109.24 (7)	C1—C2—C3	119.79 (14)
N1—P2—C25	111.46 (7)	C1—C2—H2	120.1
N1—P2—C31	113.23 (7)	C3—C2—H2	120.1
C19—P2—C31	106.52 (7)	C13—C18—H18	119.9
C25—P2—C19	105.98 (7)	C13—C18—C17	120.21 (15)
C25—P2—C31	110.02 (7)	C17—C18—H18	119.9
N1—P1—C7	115.63 (7)	C15—C16—H16	119.9
N1—P1—C1	107.25 (7)	C15—C16—C17	120.25 (15)
N1—P1—C13	112.91 (7)	C17—C16—H16	119.9
C7—P1—C1	106.21 (7)	C10—C11—C12	120.26 (15)
C7—P1—C13	107.10 (7)	C10—C11—H11	119.9
C1—P1—C13	107.25 (6)	C12—C11—H11	119.9
P1—N1—P2	137.28 (8)	C14—C15—H15	119.7
C8—C7—P1	119.31 (11)	C16—C15—C14	120.51 (15)
C12—C7—P1	121.57 (11)	C16—C15—H15	119.7
C12—C7—C8	119.08 (14)	C24—C23—H23	119.9
C24—C19—P2	120.08 (11)	C22—C23—C24	120.30 (15)
C24—C19—C20	119.75 (13)	C22—C23—H23	119.9
C20—C19—P2	120.15 (11)	C32—C31—P2	118.76 (12)
C26—C25—P2	117.86 (11)	C32—C31—C36	119.40 (15)
C26—C25—C30	119.66 (15)	C36—C31—P2	121.35 (13)
C30—C25—P2	122.24 (13)	C31—C36—H36	120.3
C6—C1—P1	119.74 (11)	C35—C36—C31	119.35 (18)
C2—C1—P1	120.12 (11)	C35—C36—H36	120.3
C2—C1—C6	120.05 (14)	C10—C9—H9	119.8
C14—C13—P1	120.66 (12)	C8—C9—C10	120.32 (15)
C18—C13—P1	119.79 (11)	C8—C9—H9	119.8
C18—C13—C14	119.44 (14)	C21—C22—H22	119.8
C1—C6—H6	120.2	C23—C22—C21	120.45 (14)
C5—C6—C1	119.65 (15)	C23—C22—H22	119.8
C5—C6—H6	120.2	C28—C29—H29	120.0
C20—C21—H21	120.3	C28—C29—C30	120.07 (16)
C20—C21—C22	119.44 (15)	C30—C29—H29	120.0
C22—C21—H21	120.3	C29—C28—H28	119.8
C11—C10—H10	120.1	C29—C28—C27	120.40 (17)
C11—C10—C9	119.81 (15)	C27—C28—H28	119.8
C9—C10—H10	120.1	C6—C5—H5	119.9
C7—C8—H8	119.9	C4—C5—C6	120.27 (15)
C9—C8—C7	120.24 (14)	C4—C5—H5	119.9
C9—C8—H8	119.9	C26—C27—H27	119.9
C19—C24—H24	120.2	C28—C27—C26	120.29 (18)
C19—C24—C23	119.66 (14)	C28—C27—H27	119.9
C23—C24—H24	120.2	C25—C30—H30	120.1
C19—C20—H20	119.8	C29—C30—C25	119.83 (17)
C21—C20—C19	120.40 (14)	C29—C30—H30	120.1
C21—C20—H20	119.8	C18—C17—H17	120.0
C25—C26—H26	120.1	C16—C17—C18	120.01 (16)
C27—C26—C25	119.73 (16)	C16—C17—H17	120.0
C27—C26—H26	120.1	C36—C35—H35	119.6
C7—C12—H12	119.9	C34—C35—C36	120.74 (17)
C11—C12—C7	120.28 (14)	C34—C35—H35	119.6
C11—C12—H12	119.9	C35—C34—H34	120.0
C4—C3—H3	120.1	C35—C34—C33	119.96 (17)
C4—C3—C2	119.82 (15)	C33—C34—H34	120.0
C2—C3—H3	120.1	C32—C33—H33	119.9
C13—C14—H14	120.2	C34—C33—C32	120.27 (18)
C15—C14—C13	119.55 (15)	C34—C33—H33	119.9
C15—C14—H14	120.2	H2O—Cl1—H1O	53.1 (9)
C3—C4—H4	119.8	B1—O2—H2O	112.3 (19)
C5—C4—C3	120.42 (14)	B1—O3—H3O	113.2 (17)
C5—C4—H4	119.8	B1—O1—H1O	103 (2)
C31—C32—H32	119.9	O3—B1—O2	120.11 (16)
C33—C32—H32	119.9	O3—B1—O1	117.20 (17)
C33—C32—C31	120.22 (16)	O1—B1—O2	122.69 (17)
P2—C19—C24—C23	177.23 (12)	C1—P1—C13—C14	−65.54 (14)
P2—C19—C20—C21	−177.83 (12)	C1—P1—C13—C18	110.61 (13)
P2—C25—C26—C27	175.93 (12)	C1—C6—C5—C4	0.3 (2)
P2—C25—C30—C29	−174.63 (12)	C13—P1—N1—P2	−82.61 (13)
P2—C31—C36—C35	−174.05 (12)	C13—P1—C7—C8	−159.22 (11)
P1—C7—C8—C9	−178.67 (12)	C13—P1—C7—C12	22.92 (14)
P1—C7—C12—C11	178.46 (12)	C13—P1—C1—C6	70.30 (13)
P1—C1—C6—C5	−176.66 (12)	C13—P1—C1—C2	−106.26 (13)
P1—C1—C2—C3	176.75 (12)	C13—C14—C15—C16	−0.6 (2)
P1—C13—C14—C15	177.56 (12)	C13—C18—C17—C16	−0.9 (3)
P1—C13—C18—C17	−176.87 (13)	C6—C1—C2—C3	0.2 (2)
N1—P2—C19—C24	16.53 (15)	C8—C7—C12—C11	0.6 (2)
N1—P2—C19—C20	−165.31 (12)	C24—C19—C20—C21	0.3 (2)
N1—P2—C25—C26	29.30 (14)	C24—C23—C22—C21	0.4 (3)
N1—P2—C25—C30	−156.36 (12)	C20—C19—C24—C23	−0.9 (2)
N1—P2—C31—C32	−84.03 (13)	C20—C21—C22—C23	−1.0 (2)
N1—P2—C31—C36	87.85 (14)	C26—C25—C30—C29	−0.4 (2)
N1—P1—C7—C8	73.96 (13)	C12—C7—C8—C9	−0.8 (2)
N1—P1—C7—C12	−103.90 (13)	C3—C4—C5—C6	−0.5 (3)
N1—P1—C1—C6	−168.15 (12)	C14—C13—C18—C17	−0.7 (2)
N1—P1—C1—C2	15.29 (14)	C4—C3—C2—C1	−0.5 (2)
N1—P1—C13—C14	176.53 (12)	C32—C31—C36—C35	−2.2 (2)
N1—P1—C13—C18	−7.31 (15)	C2—C1—C6—C5	−0.1 (2)
C7—P1—N1—P2	41.23 (15)	C2—C3—C4—C5	0.6 (2)
C7—P1—C1—C6	−43.96 (13)	C18—C13—C14—C15	1.4 (2)
C7—P1—C1—C2	139.48 (12)	C11—C10—C9—C8	−0.8 (2)
C7—P1—C13—C14	48.12 (14)	C15—C16—C17—C18	1.7 (3)
C7—P1—C13—C18	−135.73 (13)	C31—P2—N1—P1	−14.74 (15)
C7—C8—C9—C10	0.9 (2)	C31—P2—C19—C24	−106.11 (13)
C7—C12—C11—C10	−0.6 (2)	C31—P2—C19—C20	72.05 (14)
C19—P2—N1—P1	−133.27 (12)	C31—P2—C25—C26	155.77 (12)
C19—P2—C25—C26	−89.45 (13)	C31—P2—C25—C30	−29.89 (15)
C19—P2—C25—C30	84.89 (14)	C31—C32—C33—C34	1.7 (2)
C19—P2—C31—C32	36.06 (14)	C31—C36—C35—C34	1.8 (3)
C19—P2—C31—C36	−152.05 (12)	C36—C35—C34—C33	0.3 (3)
C19—C24—C23—C22	0.6 (2)	C9—C10—C11—C12	0.7 (3)
C25—P2—N1—P1	109.95 (13)	C22—C21—C20—C19	0.6 (2)
C25—P2—C19—C24	136.73 (13)	C29—C28—C27—C26	0.2 (3)
C25—P2—C19—C20	−45.10 (14)	C28—C29—C30—C25	−0.7 (2)
C25—P2—C31—C32	150.50 (12)	C30—C25—C26—C27	1.4 (2)
C25—P2—C31—C36	−37.61 (14)	C30—C29—C28—C27	0.8 (3)
C25—C26—C27—C28	−1.4 (2)	C17—C16—C15—C14	−1.0 (3)
C1—P1—N1—P2	159.47 (11)	C35—C34—C33—C32	−2.1 (3)
C1—P1—C7—C8	−44.85 (13)	C33—C32—C31—P2	172.50 (12)
C1—P1—C7—C12	137.28 (12)	C33—C32—C31—C36	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.86 (3)	1.90 (3)	2.7585 (19)	180 (3)
O2—H2O···Cl1	0.79 (3)	2.30 (3)	3.0595 (14)	161 (3)
O1—H1O···Cl1	0.77 (3)	2.42 (3)	3.1757 (17)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.86 (3)	1.90 (3)	2.7585 (19)	180 (3)
O2—H2O⋯Cl1	0.79 (3)	2.30 (3)	3.0595 (14)	161 (3)
O1—H1O⋯Cl1	0.77 (3)	2.42 (3)	3.1757 (17)	166 (3)

Symmetry code: (i) .