Phenyl­boronate of an N-hydroxy-N-(2-hydroxy­alkyl)­pyridox­amine

The title compound, 4-{[3-hydroxy-5-(hydroxy­methyl)-2-methyl-4-pyridyl]­phenyl­methyl}-6,6-penta­methyl­ene-2-phenyl-1,3-dioxa-4-aza-2-bora­cyclo­hexane, C₂₇H₃₁BN₂O₄, is formed by thermally induced rearrangement of the di­phenyl­boron chelate of a pyridoxal nitro­ne derivative and contains a six-membered BONCCO heterocycle in which all atoms except for one carbon are approximately coplanar. The B—O bonds are short, consistent with a degree of O—B pπ back donation. An intramolecular hydrogen bond is formed between the phenolic OH of the pyridoxyl residue and the nitro­gen of the BONCCO ring. Three intermolecular hydrogen bonds (one O—H...N and two C—H...O), all involving the hydroxy­methyl O atom, link the mol­ecules into chains parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 133 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.122
• Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

4-{[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridyl]phenylmethyl}-6,6- pentamethylene-2-phenyl-1,3-dioxa-4-aza-2-boracyclohexane

Crystal data

C27H31BN2O4	F(000) = 976
Mr = 458.35	Dx = 1.257 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3840 (12) Å	Cell parameters from 5414 reflections
b = 21.504 (2) Å	θ = 2.3–30.5°
c = 10.1728 (11) Å	µ = 0.08 mm^−1
β = 103.437 (3)°	T = 133 K
V = 2422.2 (4) Å^3	Tablet, colourless
Z = 4	0.50 × 0.28 × 0.11 mm

Data collection

Bruker SMART 1000 CCD diffractometer	5325 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 30.0°, θmin = 1.8°
Detector resolution: 8.192 pixels mm^-1	h = −15→16
ω–scan	k = −29→30
33115 measured reflections	l = −14→14
7074 independent reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.071P)^2] where P = (Fo^2 + 2Fc^2)/3
7074 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.26 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.1165 (0.0042) x + 11.8791 (0.0095) y + 7.6004 (0.0031) z = 12.8738 (0.0038)

* -0.0079 (0.0007) B * -0.0556 (0.0006) O17 * 0.0677 (0.0007) O19 * 0.0583 (0.0005) N16 * -0.0625 (0.0005) C20 - 0.7101 (0.0013) C21

Rms deviation of fitted atoms = 0.0548

=============================================================================

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.3021 (0.0056) x + 9.8933 (0.0092) y + 8.9822 (0.0025) z = 11.5560 (0.0035)

* -0.0003 (0.0008) C27 * -0.0031 (0.0008) C28 * 0.0043 (0.0008) C29 * -0.0022 (0.0009) C30 * -0.0012 (0.0009) C31 * 0.0025 (0.0008) C32

Rms deviation of fitted atoms = 0.0026

1.6975 (0.0054) x + 11.1321 (0.0099) y + 7.9834 (0.0033) z = 12.5897 (0.0036)

Angle to previous plane (with approximate e.s.d.) = 15.66 (0.06)

* -0.0009 (0.0003) C27 * 0.0030 (0.0010) B * -0.0010 (0.0003) O17 * -0.0011 (0.0003) O19

Rms deviation of fitted atoms = 0.0017

=============================================================================

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

1.5644 (0.0063) x + 16.5574 (0.0075) y + 5.8405 (0.0046) z = 13.9838 (0.0023)

* 0.0000 (0.0000) O17 * 0.0000 (0.0000) C21 * 0.0000 (0.0000) C9 0.5217 (0.0010) N16 2.1971 (0.0166) H05

Rms deviation of fitted atoms = 0.0000

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
B	0.35304 (10)	0.54695 (6)	0.73963 (12)	0.0219 (2)
N1	−0.02575 (8)	0.58873 (4)	1.06874 (9)	0.0245 (2)
C2	−0.09055 (10)	0.55762 (5)	0.96153 (11)	0.0243 (2)
H2	−0.1548	0.5320	0.9748	0.029*
C3	−0.06947 (9)	0.56056 (5)	0.83276 (10)	0.0205 (2)
C4	0.02387 (8)	0.59905 (4)	0.81134 (10)	0.01791 (19)
O5	0.17939 (7)	0.67342 (4)	0.91390 (8)	0.02447 (17)
H05	0.1975 (15)	0.6631 (8)	0.8376 (17)	0.052 (5)*
C5	0.08917 (9)	0.63303 (4)	0.92205 (10)	0.0192 (2)
C6	0.06323 (9)	0.62586 (5)	1.04986 (10)	0.0216 (2)
C7	0.13719 (11)	0.65955 (5)	1.17037 (11)	0.0285 (2)
H7A	0.0947	0.6589	1.2438	0.034*
H7B	0.1494	0.7027	1.1456	0.034*
H7C	0.2157	0.6390	1.2002	0.034*
O8	−0.06913 (8)	0.47331 (4)	0.67982 (8)	0.02763 (18)
H08	−0.0321 (15)	0.4524 (8)	0.7455 (17)	0.050 (5)*
C8	−0.14157 (10)	0.51985 (5)	0.72199 (11)	0.0253 (2)
H8A	−0.2074	0.4995	0.7547	0.030*
H8B	−0.1789	0.5461	0.6435	0.030*
C9	0.05015 (8)	0.60310 (5)	0.67111 (10)	0.01782 (19)
H9	0.0325	0.5616	0.6264	0.021*
C10	−0.02763 (8)	0.65133 (5)	0.58269 (10)	0.0186 (2)
C11	−0.08512 (10)	0.63583 (5)	0.45018 (11)	0.0262 (2)
H11	−0.0760	0.5952	0.4170	0.031*
C12	−0.15552 (11)	0.67936 (6)	0.36648 (12)	0.0332 (3)
H12	−0.1950	0.6683	0.2767	0.040*
C13	−0.16842 (10)	0.73869 (6)	0.41297 (12)	0.0307 (3)
H13	−0.2147	0.7687	0.3546	0.037*
C14	−0.11341 (9)	0.75426 (5)	0.54536 (12)	0.0269 (2)
H14	−0.1232	0.7948	0.5781	0.032*
C15	−0.04401 (9)	0.71067 (5)	0.63019 (11)	0.0223 (2)
H15	−0.0075	0.7214	0.7211	0.027*
N16	0.18159 (7)	0.61639 (4)	0.68753 (8)	0.01881 (18)
O17	0.23601 (6)	0.55840 (3)	0.74805 (8)	0.02368 (17)
O19	0.41518 (6)	0.58464 (4)	0.67336 (8)	0.02649 (18)
C20	0.35653 (9)	0.63616 (5)	0.59205 (10)	0.0204 (2)
C21	0.22008 (9)	0.62597 (5)	0.56077 (10)	0.0202 (2)
H21A	0.1782	0.6626	0.5126	0.024*
H21B	0.1985	0.5892	0.5017	0.024*
C22	0.40228 (10)	0.63512 (6)	0.46206 (11)	0.0267 (2)
H22A	0.3809	0.5948	0.4156	0.032*
H22B	0.3618	0.6685	0.4010	0.032*
C23	0.53895 (10)	0.64430 (6)	0.49020 (12)	0.0325 (3)
H23A	0.5800	0.6087	0.5434	0.039*
H23B	0.5644	0.6456	0.4036	0.039*
C24	0.57637 (11)	0.70449 (7)	0.56801 (13)	0.0369 (3)
H24A	0.6655	0.7078	0.5907	0.044*
H24B	0.5434	0.7404	0.5101	0.044*
C25	0.53100 (11)	0.70688 (6)	0.69754 (13)	0.0340 (3)
H25A	0.5511	0.7478	0.7415	0.041*
H25B	0.5724	0.6744	0.7606	0.041*
C26	0.39458 (10)	0.69669 (5)	0.66917 (11)	0.0258 (2)
H26A	0.3529	0.7321	0.6156	0.031*
H26B	0.3692	0.6956	0.7559	0.031*
C27	0.41325 (9)	0.48675 (5)	0.81029 (11)	0.0232 (2)
C28	0.53875 (10)	0.47961 (5)	0.83605 (12)	0.0272 (2)
H28	0.5861	0.5110	0.8076	0.033*
C29	0.59517 (11)	0.42735 (6)	0.90260 (12)	0.0316 (3)
H29	0.6805	0.4235	0.9203	0.038*
C30	0.52713 (12)	0.38109 (5)	0.94297 (12)	0.0328 (3)
H30	0.5656	0.3452	0.9876	0.039*
C31	0.40262 (11)	0.38701 (6)	0.91850 (13)	0.0325 (3)
H31	0.3558	0.3552	0.9465	0.039*
C32	0.34638 (10)	0.43953 (5)	0.85291 (11)	0.0275 (2)
H32	0.2611	0.4434	0.8368	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B	0.0193 (5)	0.0247 (6)	0.0214 (6)	0.0009 (4)	0.0041 (4)	−0.0013 (4)
N1	0.0310 (5)	0.0222 (4)	0.0219 (4)	0.0024 (4)	0.0095 (4)	0.0001 (3)
C2	0.0260 (5)	0.0220 (5)	0.0274 (5)	−0.0012 (4)	0.0116 (4)	0.0008 (4)
C3	0.0188 (5)	0.0202 (5)	0.0226 (5)	0.0009 (4)	0.0053 (4)	0.0004 (4)
C4	0.0165 (4)	0.0182 (4)	0.0192 (5)	0.0032 (3)	0.0044 (4)	0.0011 (4)
O5	0.0213 (4)	0.0280 (4)	0.0237 (4)	−0.0056 (3)	0.0046 (3)	−0.0037 (3)
C5	0.0164 (4)	0.0184 (5)	0.0221 (5)	0.0021 (3)	0.0031 (4)	0.0004 (4)
C6	0.0235 (5)	0.0203 (5)	0.0204 (5)	0.0049 (4)	0.0036 (4)	−0.0002 (4)
C7	0.0314 (6)	0.0303 (6)	0.0218 (5)	0.0035 (5)	0.0021 (4)	−0.0036 (4)
O8	0.0381 (5)	0.0234 (4)	0.0218 (4)	−0.0041 (3)	0.0077 (3)	−0.0026 (3)
C8	0.0225 (5)	0.0274 (5)	0.0263 (5)	−0.0058 (4)	0.0064 (4)	−0.0010 (4)
C9	0.0153 (4)	0.0192 (4)	0.0188 (5)	−0.0011 (3)	0.0036 (3)	−0.0002 (4)
C10	0.0147 (4)	0.0215 (5)	0.0199 (5)	−0.0017 (4)	0.0043 (4)	0.0020 (4)
C11	0.0252 (5)	0.0314 (6)	0.0210 (5)	−0.0005 (4)	0.0031 (4)	−0.0017 (4)
C12	0.0301 (6)	0.0448 (7)	0.0211 (5)	−0.0005 (5)	−0.0015 (4)	0.0043 (5)
C13	0.0202 (5)	0.0367 (6)	0.0338 (6)	0.0026 (4)	0.0037 (4)	0.0146 (5)
C14	0.0217 (5)	0.0229 (5)	0.0366 (6)	0.0006 (4)	0.0076 (4)	0.0053 (4)
C15	0.0197 (5)	0.0230 (5)	0.0236 (5)	−0.0013 (4)	0.0035 (4)	0.0011 (4)
N16	0.0150 (4)	0.0203 (4)	0.0212 (4)	0.0022 (3)	0.0043 (3)	0.0041 (3)
O17	0.0197 (3)	0.0243 (4)	0.0280 (4)	0.0058 (3)	0.0076 (3)	0.0077 (3)
O19	0.0183 (4)	0.0301 (4)	0.0315 (4)	0.0029 (3)	0.0066 (3)	0.0080 (3)
C20	0.0163 (4)	0.0249 (5)	0.0201 (5)	−0.0004 (4)	0.0044 (4)	0.0022 (4)
C21	0.0178 (5)	0.0245 (5)	0.0184 (5)	−0.0024 (4)	0.0044 (4)	0.0000 (4)
C22	0.0241 (5)	0.0360 (6)	0.0215 (5)	−0.0034 (4)	0.0083 (4)	−0.0020 (4)
C23	0.0245 (6)	0.0453 (7)	0.0315 (6)	−0.0027 (5)	0.0141 (5)	0.0012 (5)
C24	0.0270 (6)	0.0512 (8)	0.0347 (7)	−0.0149 (5)	0.0118 (5)	0.0000 (6)
C25	0.0257 (6)	0.0449 (7)	0.0308 (6)	−0.0150 (5)	0.0053 (5)	−0.0044 (5)
C26	0.0243 (5)	0.0300 (6)	0.0243 (5)	−0.0068 (4)	0.0078 (4)	−0.0030 (4)
C27	0.0221 (5)	0.0260 (5)	0.0213 (5)	0.0034 (4)	0.0045 (4)	−0.0015 (4)
C28	0.0228 (5)	0.0301 (6)	0.0292 (6)	0.0040 (4)	0.0070 (4)	−0.0003 (4)
C29	0.0249 (5)	0.0350 (6)	0.0329 (6)	0.0096 (5)	0.0027 (5)	−0.0014 (5)
C30	0.0378 (7)	0.0262 (6)	0.0297 (6)	0.0089 (5)	−0.0020 (5)	−0.0001 (5)
C31	0.0353 (6)	0.0264 (6)	0.0331 (6)	−0.0016 (5)	0.0023 (5)	0.0032 (5)
C32	0.0245 (5)	0.0275 (6)	0.0295 (6)	0.0009 (4)	0.0041 (4)	−0.0001 (4)

Geometric parameters (Å, º)

B—O19	1.3540 (14)	C29—C30	1.3806 (18)
B—O17	1.3769 (13)	C30—C31	1.3868 (18)
B—C27	1.5600 (16)	C31—C32	1.3900 (16)
N1—C6	1.3382 (14)	C2—H2	0.9500
N1—C2	1.3444 (14)	O5—H05	0.876 (17)
C2—C3	1.3869 (15)	C7—H7A	0.9800
C3—C4	1.4034 (14)	C7—H7B	0.9800
C3—C8	1.5100 (14)	C7—H7C	0.9800
C4—C5	1.4021 (14)	O8—H08	0.834 (17)
C4—C9	1.5266 (14)	C8—H8A	0.9900
O5—C5	1.3623 (12)	C8—H8B	0.9900
C5—C6	1.4071 (15)	C9—H9	1.0000
C6—C7	1.5023 (15)	C11—H11	0.9500
O8—C8	1.4247 (13)	C12—H12	0.9500
C9—N16	1.4941 (12)	C13—H13	0.9500
C9—C10	1.5162 (13)	C14—H14	0.9500
C10—C15	1.3922 (15)	C15—H15	0.9500
C10—C11	1.3952 (14)	C21—H21A	0.9900
C11—C12	1.3879 (16)	C21—H21B	0.9900
C12—C13	1.3804 (18)	C22—H22A	0.9900
C13—C14	1.3879 (17)	C22—H22B	0.9900
C14—C15	1.3894 (15)	C23—H23A	0.9900
N16—O17	1.4632 (10)	C23—H23B	0.9900
N16—C21	1.4697 (13)	C24—H24A	0.9900
O19—C20	1.4493 (12)	C24—H24B	0.9900
C20—C21	1.5272 (14)	C25—H25A	0.9900
C20—C26	1.5297 (15)	C25—H25B	0.9900
C20—C22	1.5299 (14)	C26—H26A	0.9900
C22—C23	1.5278 (16)	C26—H26B	0.9900
C23—C24	1.5252 (18)	C28—H28	0.9500
C24—C25	1.5239 (17)	C29—H29	0.9500
C25—C26	1.5280 (15)	C30—H30	0.9500
C27—C32	1.3971 (16)	C31—H31	0.9500
C27—C28	1.3998 (15)	C32—H32	0.9500
C28—C29	1.3898 (16)
O19—B—O17	123.29 (10)	H7A—C7—H7C	109.5
O19—B—C27	120.11 (9)	H7B—C7—H7C	109.5
O17—B—C27	116.59 (9)	C8—O8—H08	110.9 (11)
C6—N1—C2	118.13 (9)	O8—C8—H8A	109.1
N1—C2—C3	124.11 (10)	C3—C8—H8A	109.1
C2—C3—C4	118.49 (9)	O8—C8—H8B	109.1
C2—C3—C8	119.68 (9)	C3—C8—H8B	109.1
C4—C3—C8	121.73 (9)	H8A—C8—H8B	107.9
C5—C4—C3	117.51 (9)	N16—C9—H9	108.2
C5—C4—C9	122.58 (9)	C10—C9—H9	108.2
C3—C4—C9	119.91 (9)	C4—C9—H9	108.2
O5—C5—C4	123.36 (9)	C12—C11—H11	119.8
O5—C5—C6	116.69 (9)	C10—C11—H11	119.8
C4—C5—C6	119.95 (9)	C13—C12—H12	119.8
N1—C6—C5	121.76 (9)	C11—C12—H12	119.8
N1—C6—C7	118.03 (9)	C12—C13—H13	120.1
C5—C6—C7	120.20 (10)	C14—C13—H13	120.1
O8—C8—C3	112.31 (8)	C13—C14—H14	119.9
N16—C9—C10	111.54 (8)	C15—C14—H14	119.9
N16—C9—C4	108.36 (8)	C14—C15—H15	119.8
C10—C9—C4	112.28 (8)	C10—C15—H15	119.8
C15—C10—C11	118.93 (10)	N16—C21—H21A	109.8
C15—C10—C9	121.87 (9)	C20—C21—H21A	109.8
C11—C10—C9	119.20 (9)	N16—C21—H21B	109.8
C12—C11—C10	120.40 (10)	C20—C21—H21B	109.8
C13—C12—C11	120.36 (11)	H21A—C21—H21B	108.2
C12—C13—C14	119.70 (10)	C23—C22—H22A	109.2
C13—C14—C15	120.21 (11)	C20—C22—H22A	109.2
C14—C15—C10	120.36 (10)	C23—C22—H22B	109.2
O17—N16—C21	107.77 (7)	C20—C22—H22B	109.2
O17—N16—C9	101.48 (7)	H22A—C22—H22B	107.9
C21—N16—C9	115.07 (8)	C24—C23—H23A	109.5
B—O17—N16	116.58 (8)	C22—C23—H23A	109.5
B—O19—C20	121.13 (8)	C24—C23—H23B	109.5
O19—C20—C21	108.70 (8)	C22—C23—H23B	109.5
O19—C20—C26	108.65 (8)	H23A—C23—H23B	108.1
C21—C20—C26	112.46 (9)	C25—C24—H24A	109.3
O19—C20—C22	106.14 (8)	C23—C24—H24A	109.3
C21—C20—C22	110.60 (8)	C25—C24—H24B	109.3
C26—C20—C22	110.05 (9)	C23—C24—H24B	109.3
N16—C21—C20	109.48 (8)	H24A—C24—H24B	108.0
C23—C22—C20	111.88 (9)	C24—C25—H25A	109.3
C24—C23—C22	110.87 (10)	C26—C25—H25A	109.3
C25—C24—C23	111.56 (10)	C24—C25—H25B	109.3
C24—C25—C26	111.45 (10)	C26—C25—H25B	109.3
C25—C26—C20	111.91 (9)	H25A—C25—H25B	108.0
C32—C27—C28	117.92 (10)	C25—C26—H26A	109.2
C32—C27—B	122.23 (10)	C20—C26—H26A	109.2
C28—C27—B	119.83 (10)	C25—C26—H26B	109.2
C29—C28—C27	121.06 (11)	C20—C26—H26B	109.2
C30—C29—C28	119.99 (11)	H26A—C26—H26B	107.9
C29—C30—C31	120.07 (11)	C29—C28—H28	119.5
C30—C31—C32	119.89 (11)	C27—C28—H28	119.5
C31—C32—C27	121.07 (11)	C30—C29—H29	120.0
N1—C2—H2	117.9	C28—C29—H29	120.0
C3—C2—H2	117.9	C29—C30—H30	120.0
C5—O5—H05	103.2 (11)	C31—C30—H30	120.0
C6—C7—H7A	109.5	C30—C31—H31	120.1
C6—C7—H7B	109.5	C32—C31—H31	120.1
H7A—C7—H7B	109.5	C31—C32—H32	119.5
C6—C7—H7C	109.5	C27—C32—H32	119.5
C6—N1—C2—C3	1.38 (16)	C4—C9—N16—C21	−175.99 (8)
N1—C2—C3—C4	−1.09 (16)	O19—B—O17—N16	−3.47 (15)
N1—C2—C3—C8	175.29 (10)	C27—B—O17—N16	177.09 (8)
C2—C3—C4—C5	−0.91 (14)	C21—N16—O17—B	39.61 (11)
C8—C3—C4—C5	−177.21 (9)	C9—N16—O17—B	160.88 (8)
C2—C3—C4—C9	179.61 (9)	O17—B—O19—C20	−7.70 (16)
C8—C3—C4—C9	3.31 (14)	C27—B—O19—C20	171.72 (9)
C3—C4—C5—O5	−177.96 (9)	B—O19—C20—C21	−17.88 (13)
C9—C4—C5—O5	1.50 (14)	B—O19—C20—C26	104.80 (11)
C3—C4—C5—C6	2.53 (14)	B—O19—C20—C22	−136.88 (10)
C9—C4—C5—C6	−178.00 (9)	O17—N16—C21—C20	−65.11 (10)
C2—N1—C6—C5	0.36 (15)	C9—N16—C21—C20	−177.49 (8)
C2—N1—C6—C7	−178.76 (9)	O19—C20—C21—N16	54.15 (10)
O5—C5—C6—N1	178.13 (9)	C26—C20—C21—N16	−66.20 (11)
C4—C5—C6—N1	−2.33 (15)	C22—C20—C21—N16	170.30 (8)
O5—C5—C6—C7	−2.78 (14)	O19—C20—C22—C23	−61.47 (12)
C4—C5—C6—C7	176.76 (9)	C21—C20—C22—C23	−179.20 (9)
C2—C3—C8—O8	−112.21 (11)	C26—C20—C22—C23	55.92 (12)
C4—C3—C8—O8	64.05 (13)	C20—C22—C23—C24	−56.11 (13)
C5—C4—C9—N16	30.45 (12)	C22—C23—C24—C25	54.91 (14)
C3—C4—C9—N16	−150.10 (9)	C23—C24—C25—C26	−54.47 (15)
C5—C4—C9—C10	−93.19 (11)	C24—C25—C26—C20	54.93 (14)
C3—C4—C9—C10	86.26 (11)	O19—C20—C26—C25	60.65 (11)
N16—C9—C10—C15	−75.59 (11)	C21—C20—C26—C25	−178.97 (9)
C4—C9—C10—C15	46.26 (12)	C22—C20—C26—C25	−55.17 (12)
N16—C9—C10—C11	104.80 (10)	O19—B—C27—C32	−165.17 (10)
C4—C9—C10—C11	−133.35 (10)	O17—B—C27—C32	14.30 (15)
C15—C10—C11—C12	1.25 (16)	O19—B—C27—C28	16.58 (16)
C9—C10—C11—C12	−179.12 (10)	O17—B—C27—C28	−163.95 (10)
C10—C11—C12—C13	0.69 (18)	C32—C27—C28—C29	−0.35 (17)
C11—C12—C13—C14	−1.85 (18)	B—C27—C28—C29	177.98 (10)
C12—C13—C14—C15	1.06 (17)	C27—C28—C29—C30	0.80 (18)
C13—C14—C15—C10	0.90 (16)	C28—C29—C30—C31	−0.71 (18)
C11—C10—C15—C14	−2.04 (15)	C29—C30—C31—C32	0.18 (19)
C9—C10—C15—C14	178.35 (9)	C30—C31—C32—C27	0.27 (18)
C10—C9—N16—O17	−167.94 (7)	C28—C27—C32—C31	−0.19 (16)
C4—C9—N16—O17	67.98 (9)	B—C27—C32—C31	−178.47 (11)
C10—C9—N16—C21	−51.91 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H05···N16	0.876 (17)	1.802 (17)	2.6142 (12)	153.3 (16)
O8—H08···N1^i	0.834 (17)	2.052 (17)	2.8646 (13)	164.8 (16)
C11—H11···O8^ii	0.95	2.58	3.3794 (14)	143
C21—H21B···O8^ii	0.99	2.47	3.3979 (13)	155

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