Tri­phenyl­boroxin N,N-diethyl­hydroxy­lamine adduct (di­methyl­form­amide solvate)

N,N-Diethyl­hydroxy­lamine(O–B)­tri­phenyl­boroxin N,N-di­methyl­form­amide [2-(diethyl­ammonio­oxy)-2,4,6-tri­phenyl-1,3,5-trioxa-4,6-dibora-2-borata­cyclo­hexane N,N-di­methyl­form­amide], C₂₂H₂₆B₃NO₄·C₃H₇NO, contains one mol­ecule of N,N-diethyl­hydroxy­lamine in its N-oxide form added to a boroxin heterocycle, with N,N-di­methyl­form­amide solvent linked by an O...H—N hydrogen bond to the protonated hydroxy­lamine moiety.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.081
• wR factor = 0.264
• Data-to-parameter ratio = 14.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_211  Alert A ADP of atom C22     is non-positive-definite .          ?

PLAT_360  Alert A Short  C(sp3)-C(sp3) Bond  C(21)  -   C(22)  =       1.23 Ang.

Author response: See _publ_section_comment

 Alert Level C:



RFACR_01  Alert C The value of the weighted R factor is > 0.25
          Weighted R factor given   0.264

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(19)  -   C(20)  =       1.42 Ang.


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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Computing details

Data collection: D*TREK (Molecular Structure Corporation, 1997); cell refinement: D*TREK; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(IV)

Crystal data

C22H26B3NO4·C3H7NO	Z = 2
Mr = 473.98	F(000) = 504
Triclinic, P1	Dx = 1.151 Mg m^−3
a = 13.0046 (7) Å	Mo Kα radiation, λ = 0.7107 Å
b = 14.071 (1) Å	Cell parameters from 5239 reflections
c = 7.9235 (8) Å	θ = 3.0–25.0°
α = 92.79 (2)°	µ = 0.08 mm^−1
β = 96.95 (2)°	T = 273 K
γ = 71.85 (1)°	Prism, colorless
V = 1367.5 (2) Å^3	0.50 × 0.25 × 0.10 mm

Data collection

Quantum CCD diffractometer	4675 independent reflections
Radiation source: X-ray tube	2346 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.041
CCD scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (d*TREK; Molecular Structure Corporation, 1997)	h = −15→15
Tmin = 0.96, Tmax = 0.99	k = −16→16
11054 measured reflections	l = −9→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.081	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.264	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + 0.0025(Fo^2)^2]
S = 1.40	(Δ/σ)max = 0.05
4675 reflections	Δρmax = 0.56 e Å^−3
320 parameters	Δρmin = −0.38 e Å^−3

Special details

Refinement. H30 (bonded to N1) was refined (xyzB), other H atoms were fixed.

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

	x	y	z	Uiso*/Ueq
O1	0.3832 (2)	0.3713 (1)	0.4080 (2)	0.0628 (6)
O2	0.2525 (2)	0.3109 (1)	0.2394 (2)	0.0594 (6)
O3	0.3847 (1)	0.2002 (1)	0.4311 (2)	0.0611 (6)
O4	0.4895 (2)	0.2712 (1)	0.6457 (2)	0.0676 (6)
O5	0.1918 (3)	0.3016 (4)	0.6712 (6)	0.159 (2)
N1	0.4061 (3)	0.2907 (2)	0.7530 (3)	0.077 (1)
N2	0.0479 (4)	0.2484 (6)	0.5607 (7)	0.156 (2)
C1	0.5582 (2)	0.2322 (2)	0.3648 (3)	0.0637 (9)
C2	0.5975 (3)	0.1353 (3)	0.2994 (5)	0.080 (1)
C3	0.6889 (4)	0.1036 (3)	0.2158 (6)	0.101 (1)
C4	0.7470 (4)	0.1677 (4)	0.1975 (6)	0.116 (2)
C5	0.7118 (4)	0.2632 (5)	0.2571 (7)	0.122 (2)
C6	0.6177 (3)	0.2953 (3)	0.3388 (5)	0.094 (1)
C7	0.2345 (2)	0.4956 (2)	0.2257 (4)	0.0592 (8)
C8	0.2800 (3)	0.5724 (2)	0.2653 (4)	0.070 (1)
C9	0.2305 (3)	0.6677 (2)	0.1980 (5)	0.089 (1)
C10	0.1355 (3)	0.6872 (3)	0.0952 (6)	0.098 (1)
C11	0.0882 (3)	0.6142 (3)	0.0561 (6)	0.107 (1)
C12	0.1380 (3)	0.5187 (2)	0.1185 (5)	0.083 (1)
C13	0.2425 (2)	0.1349 (2)	0.2660 (3)	0.0538 (8)
C14	0.1576 (3)	0.1468 (2)	0.1367 (4)	0.075 (1)
C15	0.1112 (3)	0.0713 (3)	0.0964 (6)	0.099 (1)
C16	0.1477 (3)	−0.0165 (3)	0.1836 (6)	0.096 (1)
C17	0.2316 (3)	−0.0308 (2)	0.3096 (5)	0.094 (1)
C18	0.2788 (3)	0.0435 (2)	0.3493 (4)	0.075 (1)
C19	0.4386 (4)	0.2206 (4)	0.8928 (5)	0.119 (2)
C20	0.4464 (5)	0.1221 (4)	0.8347 (7)	0.146 (2)
C21	0.3676 (7)	0.4062 (7)	0.8125 (9)	0.186 (3)
C22	0.440 (1)	0.4309 (7)	0.901 (2)	0.252 (6)
C23	0.1440 (6)	0.2393 (7)	0.6496 (9)	0.179 (3)
C24	0.0018 (8)	0.167 (1)	0.536 (1)	0.269 (6)
C25	−0.0020 (8)	0.3382 (9)	0.485 (1)	0.219 (4)
B1	0.4506 (3)	0.2692 (3)	0.4587 (4)	0.0580 (9)
B2	0.2930 (3)	0.3881 (2)	0.2964 (4)	0.0531 (9)
B3	0.2965 (2)	0.2179 (2)	0.3158 (4)	0.0518 (9)
H2	0.5580	0.0879	0.3136	0.097*
H3	0.7127	0.0356	0.1696	0.121*
H4	0.8137	0.1453	0.1415	0.139*
H5	0.7527	0.3096	0.2430	0.147*
H6	0.5930	0.3648	0.3796	0.113*
H8	0.3478	0.5593	0.3418	0.085*
H9	0.2646	0.7205	0.2250	0.106*
H10	0.1004	0.7543	0.0488	0.118*
H11	0.0186	0.6292	−0.0163	0.129*
H12	0.1041	0.4663	0.0864	0.100*
H14	0.1303	0.2094	0.0732	0.090*
H15	0.0516	0.0811	0.0039	0.119*
H16	0.1131	−0.0688	0.1554	0.116*
H17	0.2586	−0.0939	0.3714	0.113*
H18	0.3399	0.0319	0.4391	0.090*
H19B	0.3845	0.2411	0.9743	0.143*
H19A	0.5097	0.2214	0.9493	0.143*
H20C	0.5102	0.0958	0.7725	0.176*
H20A	0.3805	0.1229	0.7592	0.176*
H20B	0.4535	0.0793	0.9322	0.176*
H21B	0.3039	0.4187	0.8759	0.222*
H21A	0.3446	0.4490	0.7096	0.222*
H22A	0.4621	0.3905	1.0060	0.310*
H22B	0.4154	0.5019	0.9338	0.310*
H22C	0.5046	0.4183	0.8394	0.310*
H23	0.1800	0.1744	0.7040	0.216*
H24	−0.0682	0.1898	0.4646	0.332*
H25	0.0519	0.1117	0.4781	0.332*
H26	−0.0085	0.1458	0.6455	0.332*
H27	−0.0132	0.3923	0.5717	0.262*
H28	0.0429	0.3507	0.4028	0.262*
H29	−0.0732	0.3392	0.4260	0.262*
H30	0.345 (3)	0.283 (2)	0.696 (4)	0.071 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.072 (1)	0.062 (1)	0.057 (1)	−0.031 (1)	−0.015 (1)	0.0090 (9)
O2	0.067 (1)	0.057 (1)	0.054 (1)	−0.0244 (9)	−0.0144 (9)	0.0083 (9)
O3	0.067 (1)	0.065 (1)	0.055 (1)	−0.029 (1)	−0.0153 (9)	0.0166 (9)
O4	0.074 (1)	0.084 (1)	0.047 (1)	−0.034 (1)	−0.015 (1)	0.009 (1)
O5	0.100 (3)	0.213 (4)	0.168 (4)	−0.062 (3)	0.012 (3)	−0.047 (3)
N1	0.096 (2)	0.092 (2)	0.050 (2)	−0.040 (2)	−0.001 (2)	0.004 (1)
N2	0.081 (3)	0.262 (7)	0.118 (4)	−0.042 (4)	0.029 (2)	−0.051 (4)
C1	0.063 (2)	0.082 (2)	0.047 (2)	−0.030 (2)	−0.014 (1)	0.013 (1)
C2	0.077 (2)	0.076 (2)	0.085 (2)	−0.017 (2)	0.002 (2)	0.021 (2)
C3	0.093 (3)	0.094 (3)	0.109 (3)	−0.015 (2)	0.022 (2)	0.011 (2)
C4	0.084 (3)	0.149 (4)	0.116 (4)	−0.032 (3)	0.028 (3)	−0.007 (3)
C5	0.104 (3)	0.156 (4)	0.141 (4)	−0.084 (3)	0.037 (3)	−0.030 (4)
C6	0.093 (3)	0.109 (3)	0.099 (3)	−0.061 (2)	0.020 (2)	−0.024 (2)
C7	0.064 (2)	0.057 (2)	0.058 (2)	−0.020 (1)	0.005 (1)	0.005 (1)
C8	0.072 (2)	0.066 (2)	0.075 (2)	−0.025 (2)	0.006 (2)	0.000 (2)
C9	0.096 (3)	0.053 (2)	0.121 (3)	−0.028 (2)	0.013 (2)	0.007 (2)
C10	0.092 (3)	0.059 (2)	0.136 (4)	−0.015 (2)	−0.002 (3)	0.025 (2)
C11	0.082 (3)	0.081 (2)	0.148 (4)	−0.021 (2)	−0.032 (3)	0.043 (3)
C12	0.077 (2)	0.067 (2)	0.106 (3)	−0.031 (2)	−0.022 (2)	0.022 (2)
C13	0.054 (2)	0.055 (2)	0.051 (1)	−0.018 (1)	−0.002 (1)	−0.002 (1)
C14	0.070 (2)	0.059 (2)	0.087 (2)	−0.020 (2)	−0.024 (2)	0.001 (2)
C15	0.080 (2)	0.088 (3)	0.121 (3)	−0.033 (2)	−0.040 (2)	−0.008 (2)
C16	0.100 (3)	0.067 (2)	0.124 (3)	−0.041 (2)	−0.020 (3)	−0.008 (2)
C17	0.113 (3)	0.063 (2)	0.109 (3)	−0.044 (2)	−0.025 (2)	0.010 (2)
C18	0.084 (2)	0.065 (2)	0.074 (2)	−0.031 (2)	−0.020 (2)	0.010 (2)
C19	0.158 (4)	0.143 (4)	0.063 (2)	−0.060 (3)	−0.006 (2)	0.029 (3)
C20	0.212 (6)	0.091 (3)	0.123 (4)	−0.045 (3)	−0.037 (4)	0.036 (3)
C21	0.180 (6)	0.274 (9)	0.138 (5)	−0.126 (6)	0.048 (4)	−0.131 (6)
C22	0.31 (1)	0.189 (7)	0.29 (1)	−0.074 (8)	16 (1)	−0.023 (8)
C23	0.111 (5)	0.29 (1)	0.117 (5)	−0.031 (5)	0.019 (4)	−0.043 (5)
C24	0.173 (8)	0.43 (2)	0.25 (1)	−0.16 (1)	0.089 (7)	−0.14 (1)
C25	0.192 (8)	0.27 (1)	0.165 (7)	−0.002 (7)	0.078 (6)	0.016 (7)
B1	0.063 (2)	0.068 (2)	0.045 (2)	−0.028 (2)	−0.012 (1)	0.012 (1)
B2	0.058 (2)	0.059 (2)	0.044 (2)	−0.021 (2)	0.000 (1)	0.004 (1)
B3	0.054 (2)	0.059 (2)	0.043 (2)	−0.020 (1)	0.001 (1)	0.003 (1)

Geometric parameters (Å, º)

O1—B1	1.477 (4)	C10—H10	0.98
O1—B2	1.346 (4)	C11—C12	1.383 (4)
O2—B2	1.384 (4)	C11—H11	0.98
O2—B3	1.390 (3)	C12—H12	0.98
O3—B1	1.475 (4)	C13—C14	1.388 (4)
O3—B3	1.343 (3)	C13—C18	1.393 (4)
O4—N1	1.411 (4)	C13—B3	1.554 (4)
O4—B1	1.508 (3)	C14—C15	1.384 (4)
O5—C23	1.22 (1)	C14—H14	0.98
N1—C19	1.454 (4)	C15—C16	1.367 (5)
N1—C21	1.610 (8)	C15—H15	0.98
N1—H30	0.90 (3)	C16—C17	1.360 (5)
N2—C23	1.330 (8)	C16—H16	0.98
N2—C24	1.44 (1)	C17—C18	1.374 (4)
N2—C25	1.36 (1)	C17—H17	0.98
C1—C2	1.396 (5)	C18—H18	0.98
C1—C6	1.383 (4)	C19—C20	1.416 (7)
C1—B1	1.595 (5)	C19—H19B	0.98
C2—C3	1.371 (5)	C19—H19A	0.98
C2—H2	0.98	C20—H20C	0.98
C3—C4	1.368 (6)	C20—H20A	0.98
C3—H3	0.98	C20—H20B	0.98
C4—C5	1.358 (7)	C21—C22	1.24 (1)
C4—H4	0.98	C21—H21B	0.99
C5—C6	1.393 (6)	C21—H21A	1.00
C5—H5	0.98	C22—H22A	0.99
C6—H6	0.98	C22—H22B	0.98
C7—C8	1.392 (4)	C22—H22C	0.98
C7—C12	1.385 (4)	C23—H23	0.98
C7—B2	1.563 (4)	C24—H24	0.98
C8—C9	1.396 (4)	C24—H25	0.98
C8—H8	0.98	C24—H26	0.97
C9—C10	1.354 (5)	C25—H27	0.99
C9—H9	0.98	C25—H28	0.98
C10—C11	1.359 (5)	C25—H29	0.98
O3···O5	3.257 (5)	N2···C13	3.600 (5)
O5···N1	2.741 (5)	C13···C23	3.517 (7)
O5···C21	3.157 (8)	C22···C22^i	3.10 (3)
O5···B3	3.283 (6)	C23···B3	3.441 (8)
O5···C19	3.353 (6)
B1—O1—B2	121.9 (2)	C15—C16—H16	119.9
B2—O2—B3	119.2 (2)	C17—C16—H16	120.2
B1—O3—B3	122.2 (2)	C16—C17—C18	119.8 (3)
N1—O4—B1	114.3 (2)	C16—C17—H17	120.1
O4—N1—C19	110.2 (3)	C18—C17—H17	120.1
O4—N1—C21	111.6 (4)	C13—C18—C17	122.2 (3)
O4—N1—H30	111 (2)	C13—C18—H18	118.8
C19—N1—C21	113.9 (4)	C17—C18—H18	119.0
C19—N1—H30	107 (2)	N1—C19—C20	111.3 (4)
C21—N1—H30	103 (2)	N1—C19—H19B	109.0
C23—N2—C24	122.9 (9)	N1—C19—H19A	109.1
C23—N2—C25	115.5 (9)	C20—C19—H19B	109.0
C24—N2—C25	121.4 (7)	C20—C19—H19A	109.0
C2—C1—C6	115.3 (3)	H19B—C19—H19A	109.4
C2—C1—B1	122.7 (3)	C19—C20—H20C	109.5
C6—C1—B1	121.9 (3)	C19—C20—H20A	109.5
C1—C2—C3	123.0 (4)	C19—C20—H20B	109.5
C1—C2—H2	118.5	H20C—C20—H20A	109.5
C3—C2—H2	118.5	H20C—C20—H20B	109.5
C2—C3—C4	119.6 (4)	H20A—C20—H20B	109.4
C2—C3—H3	120.4	N1—C21—C22	112.8 (9)
C4—C3—H3	119.9	N1—C21—H21B	109.3
C3—C4—C5	119.8 (4)	N1—C21—H21A	108.8
C3—C4—H4	120.5	C22—C21—H21B	109.6
C5—C4—H4	119.8	C22—C21—H21A	108.6
C4—C5—C6	120.1 (4)	H21B—C21—H21A	107.7
C4—C5—H5	120.0	C21—C22—H22A	109.3
C6—C5—H5	119.9	C21—C22—H22B	111.2
C1—C6—C5	122.1 (4)	C21—C22—H22C	110.3
C1—C6—H6	119.0	H22A—C22—H22B	108.6
C5—C6—H6	118.9	H22A—C22—H22C	108.3
C8—C7—C12	116.9 (3)	H22B—C22—H22C	109.1
C8—C7—B2	120.5 (3)	O5—C23—N2	127.8 (9)
C12—C7—B2	122.5 (3)	O5—C23—H23	116.8
C7—C8—C9	121.1 (3)	N2—C23—H23	115.5
C7—C8—H8	119.5	N2—C24—H24	109.3
C9—C8—H8	119.4	N2—C24—H25	108.8
C8—C9—C10	119.9 (3)	N2—C24—H26	109.2
C8—C9—H9	120.0	H24—C24—H25	109.4
C10—C9—H9	120.1	H24—C24—H26	110.1
C9—C10—C11	120.4 (3)	H25—C24—H26	110.0
C9—C10—H10	119.9	N2—C25—H27	110.1
C11—C10—H10	119.7	N2—C25—H28	110.4
C10—C11—C12	120.2 (3)	N2—C25—H29	110.0
C10—C11—H11	119.9	H27—C25—H28	108.6
C12—C11—H11	119.9	H27—C25—H29	108.7
C7—C12—C11	121.5 (3)	H28—C25—H29	109.0
C7—C12—H12	119.2	O1—B1—O3	109.9 (2)
C11—C12—H12	119.3	O1—B1—O4	108.3 (2)
C14—C13—C18	116.7 (3)	O1—B1—C1	111.8 (2)
C14—C13—B3	122.4 (2)	O3—B1—O4	108.5 (2)
C18—C13—B3	120.9 (2)	O3—B1—C1	112.4 (3)
C13—C14—C15	120.7 (3)	O4—B1—C1	105.6 (2)
C13—C14—H14	119.6	O1—B2—O2	120.9 (2)
C15—C14—H14	119.7	O1—B2—C7	119.9 (3)
C14—C15—C16	120.7 (3)	O2—B2—C7	119.2 (2)
C14—C15—H15	119.4	O2—B3—O3	120.4 (3)
C16—C15—H15	119.8	O2—B3—C13	119.2 (2)
C15—C16—C17	119.8 (3)	O3—B3—C13	120.4 (2)
O1—B1—O3—B3	25.3 (4)	C1—B1—O3—B3	−99.9 (3)
O1—B1—O4—N1	67.3 (3)	C2—C1—C6—C5	−1.7 (5)
O1—B1—C1—C2	−138.4 (3)	C2—C3—C4—C5	−2.2 (7)
O1—B1—C1—C6	40.0 (4)	C3—C2—C1—C6	0.4 (5)
O1—B2—O2—B3	9.0 (4)	C3—C2—C1—B1	178.8 (3)
O1—B2—C7—C8	5.7 (5)	C3—C4—C5—C6	0.9 (8)
O1—B2—C7—C12	−176.1 (3)	C5—C6—C1—B1	179.9 (4)
O2—B2—O1—B1	7.6 (4)	C7—C8—C9—C10	1.4 (6)
O2—B2—C7—C8	−172.6 (3)	C7—C12—C11—C10	2.1 (7)
O2—B2—C7—C12	5.6 (5)	C7—B2—O1—B1	−170.7 (3)
O2—B3—O3—B1	−11.7 (4)	C7—B2—O2—B3	−172.8 (2)
O2—B3—C13—C14	5.9 (4)	C8—C7—C12—C11	−1.1 (6)
O2—B3—C13—C18	−174.9 (3)	C8—C9—C10—C11	−0.4 (7)
O3—B1—O1—B2	−23.2 (4)	C9—C8—C7—C12	−0.6 (5)
O3—B1—O4—N1	−52.1 (3)	C9—C8—C7—B2	177.7 (3)
O3—B1—C1—C2	−14.2 (4)	C9—C10—C11—C12	−1.3 (7)
O3—B1—C1—C6	164.2 (3)	C11—C12—C7—B2	−179.4 (4)
O3—B3—O2—B2	−6.9 (4)	C13—C14—C15—C16	0.3 (6)
O3—B3—C13—C14	−174.0 (3)	C13—C18—C17—C16	1.0 (7)
O3—B3—C13—C18	5.2 (4)	C13—B3—O2—B2	173.1 (2)
O4—N1—C19—C20	−67.7 (5)	C13—B3—O3—B1	168.3 (3)
O4—N1—C21—C22	−64.3 (9)	C14—C13—C18—C17	−1.7 (5)
O4—B1—O1—B2	−141.7 (3)	C14—C15—C16—C17	−1.0 (7)
O4—B1—O3—B3	143.7 (3)	C15—C14—C13—C18	1.0 (5)
O4—B1—C1—C2	104.0 (3)	C15—C14—C13—B3	−179.7 (3)
O4—B1—C1—C6	−77.7 (3)	C15—C16—C17—C18	0.4 (7)
O5—C23—N2—C24	176.3 (7)	C17—C18—C13—B3	179.0 (3)
O5—C23—N2—C25	0 (1)	C19—N1—O4—B1	133.5 (3)
N1—O4—B1—C1	−172.8 (2)	C19—N1—C21—C22	61 (1)
C1—C2—C3—C4	1.6 (6)	C20—C19—N1—C21	166.0 (5)
C1—C6—C5—C4	1.1 (7)	C21—N1—O4—B1	−98.9 (4)
C1—B1—O1—B2	102.4 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.