Crystal structure of cis-1-phenyl-8-(pyridin-2-ylmeth­yl)dibenzo[1,2-c:2,1-h]-2,14-dioxa-8-aza-1-borabi­cyclo­[4.4.0]deca-3,8-diene

The present work describes the synthesis and crystal structure of the new B-phenyl­oxaza­borocine, C₂₆H₂₃BN₂O₂. The title compound adopts a zwitterionic form with a significant intra­molecular N→B dative bond and inter­molecular C—H...O inter­actions connecting mol­ecules parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.115
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     18.130 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.353 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             120.8 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O2             121.4 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

cis-1-Phenyl-8-(pyridin-2-ylmethyl)dibenzo[1,2-c:2,1-h]-2,14-dioxa-8-aza-1-borabicyclo[4.4.0]deca-3,8-diene

Crystal data

C26H23BN2O2	Z = 2
Mr = 406.27	F(000) = 428
Triclinic, P1	Dx = 1.324 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8803 (7) Å	Cell parameters from 5951 reflections
b = 10.0871 (8) Å	θ = 2.4–28.2°
c = 11.7586 (10) Å	µ = 0.08 mm^−1
α = 97.298 (2)°	T = 100 K
β = 98.464 (2)°	Prism, colourless
γ = 98.234 (2)°	0.22 × 0.16 × 0.12 mm
V = 1019.21 (14) Å^3

Data collection

Bruker APEXII CCD diffractometer	2161 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: gaussian (XPREP and SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.780, Tmax = 0.875	k = −12→10
8344 measured reflections	l = −14→14
4004 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0336P)^2] where P = (Fo^2 + 2Fc^2)/3
4004 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.31 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.

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 > 2sigma(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
O2	0.33571 (19)	0.80339 (16)	0.66654 (14)	0.0162 (4)
C7	0.2240 (3)	0.5768 (2)	0.7698 (2)	0.0154 (6)
H7A	0.186984	0.481569	0.777707	0.018*
H7B	0.15142	0.602455	0.707238	0.018*
O1	0.45343 (19)	0.81457 (16)	0.86313 (14)	0.0155 (4)
N1	0.3811 (2)	0.58730 (19)	0.73635 (17)	0.0142 (5)
N2	0.3294 (3)	0.3306 (2)	0.87553 (18)	0.0228 (6)
C1	0.3311 (3)	0.7832 (2)	0.9193 (2)	0.0141 (6)
C15	0.6210 (3)	0.7798 (2)	0.7133 (2)	0.0145 (6)
C6	0.2247 (3)	0.6666 (2)	0.8822 (2)	0.0143 (6)
C8	0.2760 (3)	0.7354 (2)	0.5582 (2)	0.0149 (6)
C22	0.4325 (3)	0.3686 (2)	0.8075 (2)	0.0164 (6)
C20	0.6479 (3)	0.8046 (2)	0.6034 (2)	0.0168 (6)
H20	0.562356	0.799166	0.543102	0.02*
C14	0.3653 (3)	0.5215 (2)	0.6124 (2)	0.0159 (6)
H14A	0.469245	0.515167	0.593371	0.019*
H14B	0.307445	0.428216	0.603349	0.019*
C13	0.2833 (3)	0.5988 (2)	0.5288 (2)	0.0154 (6)
C2	0.3191 (3)	0.8716 (3)	1.0178 (2)	0.0184 (6)
H2	0.391788	0.952737	1.042134	0.022*
C19	0.7968 (3)	0.8371 (3)	0.5794 (2)	0.0218 (7)
H19	0.811445	0.851654	0.503233	0.026*
C3	0.2016 (3)	0.8410 (3)	1.0797 (2)	0.0209 (7)
H3	0.192493	0.901899	1.145982	0.025*
C26	0.4860 (3)	0.2759 (2)	0.7329 (2)	0.0183 (6)
H26	0.56079	0.305733	0.687579	0.022*
C5	0.1087 (3)	0.6353 (3)	0.9472 (2)	0.0195 (6)
H5	0.036794	0.553633	0.923746	0.023*
C9	0.2030 (3)	0.8050 (3)	0.4773 (2)	0.0190 (7)
H9	0.198548	0.898346	0.497886	0.023*
C16	0.7521 (3)	0.7913 (2)	0.7980 (2)	0.0197 (7)
H16	0.738836	0.77471	0.873908	0.024*
C12	0.2147 (3)	0.5337 (3)	0.4180 (2)	0.0183 (6)
H12	0.216587	0.439785	0.397566	0.022*
C4	0.0970 (3)	0.7221 (3)	1.0458 (2)	0.0226 (7)
H4	0.017669	0.699995	1.089651	0.027*
C25	0.4296 (3)	0.1387 (3)	0.7247 (2)	0.0222 (7)
H25	0.464256	0.073442	0.673508	0.027*
C17	0.9002 (3)	0.8257 (3)	0.7761 (2)	0.0217 (7)
H17	0.986288	0.834068	0.836496	0.026*
C10	0.1376 (3)	0.7395 (3)	0.3682 (2)	0.0223 (7)
H10	0.087663	0.787534	0.313513	0.027*
C21	0.4862 (3)	0.5193 (2)	0.8156 (2)	0.0168 (6)
H21A	0.591196	0.534146	0.795601	0.02*
H21B	0.492924	0.562668	0.896988	0.02*
C24	0.3225 (3)	0.0994 (3)	0.7923 (2)	0.0204 (7)
H24	0.2805	0.006461	0.788101	0.024*
C11	0.1438 (3)	0.6029 (3)	0.3371 (2)	0.0224 (7)
H11	0.099895	0.557761	0.260997	0.027*
C18	0.9221 (3)	0.8480 (2)	0.6656 (2)	0.0226 (7)
H18	1.023545	0.870859	0.649451	0.027*
C23	0.2776 (3)	0.1973 (3)	0.8658 (2)	0.0239 (7)
H23	0.204908	0.168795	0.913098	0.029*
B1	0.4511 (3)	0.7520 (3)	0.7450 (3)	0.0153 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0199 (11)	0.0149 (10)	0.0135 (10)	0.0035 (8)	0.0013 (8)	0.0025 (8)
C7	0.0131 (15)	0.0146 (15)	0.0167 (15)	−0.0010 (12)	0.0014 (12)	0.0005 (12)
O1	0.0169 (10)	0.0147 (10)	0.0132 (10)	−0.0016 (8)	0.0041 (8)	−0.0008 (8)
N1	0.0138 (12)	0.0135 (12)	0.0141 (12)	0.0002 (9)	0.0017 (10)	0.0012 (9)
N2	0.0325 (15)	0.0179 (14)	0.0204 (14)	0.0036 (11)	0.0096 (12)	0.0061 (11)
C1	0.0124 (15)	0.0148 (15)	0.0151 (15)	0.0013 (12)	0.0020 (12)	0.0038 (12)
C15	0.0188 (15)	0.0087 (14)	0.0155 (15)	0.0021 (11)	0.0023 (12)	0.0002 (11)
C6	0.0158 (15)	0.0140 (15)	0.0131 (14)	0.0009 (12)	0.0021 (12)	0.0043 (12)
C8	0.0127 (14)	0.0195 (15)	0.0113 (14)	−0.0002 (12)	0.0030 (12)	0.0000 (12)
C22	0.0192 (16)	0.0147 (15)	0.0143 (15)	0.0030 (12)	−0.0025 (13)	0.0046 (12)
C20	0.0165 (16)	0.0133 (15)	0.0195 (16)	−0.0007 (12)	0.0029 (13)	0.0018 (12)
C14	0.0213 (16)	0.0119 (14)	0.0131 (14)	0.0016 (12)	0.0041 (12)	−0.0036 (11)
C13	0.0164 (15)	0.0186 (15)	0.0120 (14)	0.0025 (12)	0.0037 (12)	0.0043 (12)
C2	0.0231 (17)	0.0171 (15)	0.0140 (15)	0.0029 (13)	0.0009 (13)	0.0013 (12)
C19	0.0253 (17)	0.0179 (15)	0.0210 (16)	−0.0003 (13)	0.0055 (14)	0.0015 (13)
C3	0.0284 (17)	0.0200 (16)	0.0146 (15)	0.0036 (13)	0.0080 (13)	−0.0008 (12)
C26	0.0182 (16)	0.0173 (16)	0.0209 (16)	0.0019 (12)	0.0071 (13)	0.0052 (12)
C5	0.0200 (16)	0.0170 (15)	0.0196 (16)	−0.0012 (12)	0.0022 (13)	0.0018 (12)
C9	0.0208 (16)	0.0172 (15)	0.0208 (16)	0.0049 (12)	0.0065 (13)	0.0043 (13)
C16	0.0224 (17)	0.0198 (16)	0.0170 (16)	0.0034 (13)	0.0049 (13)	0.0021 (12)
C12	0.0174 (15)	0.0202 (15)	0.0174 (16)	0.0014 (12)	0.0049 (13)	0.0029 (12)
C4	0.0281 (18)	0.0237 (17)	0.0183 (16)	0.0047 (14)	0.0095 (14)	0.0051 (13)
C25	0.0270 (17)	0.0165 (16)	0.0229 (16)	0.0074 (13)	0.0031 (14)	−0.0005 (12)
C17	0.0152 (16)	0.0222 (16)	0.0258 (17)	0.0028 (13)	0.0003 (13)	−0.0001 (13)
C10	0.0196 (16)	0.0322 (17)	0.0162 (16)	0.0085 (13)	0.0012 (13)	0.0056 (13)
C21	0.0193 (15)	0.0170 (15)	0.0137 (15)	0.0050 (12)	−0.0010 (12)	0.0028 (12)
C24	0.0257 (17)	0.0131 (15)	0.0217 (16)	0.0003 (12)	0.0027 (13)	0.0049 (12)
C11	0.0181 (16)	0.0306 (17)	0.0155 (15)	−0.0012 (13)	0.0013 (13)	0.0001 (13)
C18	0.0218 (17)	0.0160 (16)	0.0307 (18)	0.0002 (13)	0.0111 (15)	0.0019 (13)
C23	0.0266 (18)	0.0220 (17)	0.0259 (17)	0.0037 (13)	0.0094 (14)	0.0089 (13)
B1	0.0192 (18)	0.0107 (16)	0.0141 (17)	0.0007 (13)	0.0022 (14)	−0.0022 (13)

Geometric parameters (Å, º)

O2—C8	1.360 (3)	C2—H2	0.95
O2—B1	1.471 (3)	C19—C18	1.372 (4)
C7—N1	1.497 (3)	C19—H19	0.95
C7—C6	1.504 (3)	C3—C4	1.382 (4)
C7—H7A	0.99	C3—H3	0.95
C7—H7B	0.99	C26—C25	1.389 (4)
O1—C1	1.372 (3)	C26—H26	0.95
O1—B1	1.446 (3)	C5—C4	1.387 (3)
N1—C14	1.501 (3)	C5—H5	0.95
N1—C21	1.517 (3)	C9—C10	1.370 (4)
N1—B1	1.674 (4)	C9—H9	0.95
N2—C23	1.343 (3)	C16—C17	1.381 (4)
N2—C22	1.348 (3)	C16—H16	0.95
C1—C6	1.378 (3)	C12—C11	1.381 (3)
C1—C2	1.396 (3)	C12—H12	0.95
C15—C20	1.396 (3)	C4—H4	0.95
C15—C16	1.396 (3)	C25—C24	1.374 (3)
C15—B1	1.602 (4)	C25—H25	0.95
C6—C5	1.395 (3)	C17—C18	1.383 (3)
C8—C13	1.391 (3)	C17—H17	0.95
C8—C9	1.391 (3)	C10—C11	1.391 (4)
C22—C26	1.383 (3)	C10—H10	0.95
C22—C21	1.513 (3)	C21—H21A	0.99
C20—C19	1.394 (4)	C21—H21B	0.99
C20—H20	0.95	C24—C23	1.371 (3)
C14—C13	1.501 (3)	C24—H24	0.95
C14—H14A	0.99	C11—H11	0.95
C14—H14B	0.99	C18—H18	0.95
C13—C12	1.391 (3)	C23—H23	0.95
C2—C3	1.380 (3)
C8—O2—B1	121.39 (18)	C22—C26—C25	119.4 (2)
N1—C7—C6	111.9 (2)	C22—C26—H26	120.3
N1—C7—H7A	109.2	C25—C26—H26	120.3
C6—C7—H7A	109.2	C4—C5—C6	120.8 (3)
N1—C7—H7B	109.2	C4—C5—H5	119.6
C6—C7—H7B	109.2	C6—C5—H5	119.6
H7A—C7—H7B	107.9	C10—C9—C8	120.3 (2)
C1—O1—B1	120.8 (2)	C10—C9—H9	119.9
C7—N1—C14	108.67 (19)	C8—C9—H9	119.9
C7—N1—C21	110.68 (18)	C17—C16—C15	122.9 (2)
C14—N1—C21	110.23 (16)	C17—C16—H16	118.6
C7—N1—B1	107.64 (16)	C15—C16—H16	118.6
C14—N1—B1	108.46 (18)	C11—C12—C13	121.2 (2)
C21—N1—B1	111.07 (19)	C11—C12—H12	119.4
C23—N2—C22	116.7 (2)	C13—C12—H12	119.4
O1—C1—C6	121.5 (2)	C3—C4—C5	119.5 (3)
O1—C1—C2	118.0 (2)	C3—C4—H4	120.3
C6—C1—C2	120.5 (2)	C5—C4—H4	120.3
C20—C15—C16	115.9 (2)	C24—C25—C26	118.6 (2)
C20—C15—B1	122.7 (2)	C24—C25—H25	120.7
C16—C15—B1	121.2 (2)	C26—C25—H25	120.7
C1—C6—C5	119.0 (2)	C16—C17—C18	119.5 (3)
C1—C6—C7	121.8 (2)	C16—C17—H17	120.3
C5—C6—C7	119.1 (2)	C18—C17—H17	120.3
O2—C8—C13	121.4 (2)	C9—C10—C11	120.4 (2)
O2—C8—C9	118.4 (2)	C9—C10—H10	119.8
C13—C8—C9	120.3 (2)	C11—C10—H10	119.8
N2—C22—C26	122.3 (2)	C22—C21—N1	113.5 (2)
N2—C22—C21	116.5 (2)	C22—C21—H21A	108.9
C26—C22—C21	121.2 (2)	N1—C21—H21A	108.9
C19—C20—C15	121.9 (3)	C22—C21—H21B	108.9
C19—C20—H20	119	N1—C21—H21B	108.9
C15—C20—H20	119	H21A—C21—H21B	107.7
C13—C14—N1	112.13 (17)	C23—C24—C25	118.5 (3)
C13—C14—H14A	109.2	C23—C24—H24	120.8
N1—C14—H14A	109.2	C25—C24—H24	120.8
C13—C14—H14B	109.2	C12—C11—C10	119.2 (3)
N1—C14—H14B	109.2	C12—C11—H11	120.4
H14A—C14—H14B	107.9	C10—C11—H11	120.4
C8—C13—C12	118.6 (2)	C19—C18—C17	119.7 (3)
C8—C13—C14	121.8 (2)	C19—C18—H18	120.1
C12—C13—C14	119.6 (2)	C17—C18—H18	120.1
C3—C2—C1	119.9 (3)	N2—C23—C24	124.5 (3)
C3—C2—H2	120.1	N2—C23—H23	117.8
C1—C2—H2	120.1	C24—C23—H23	117.8
C18—C19—C20	120.1 (3)	O1—B1—O2	108.95 (17)
C18—C19—H19	120	O1—B1—C15	109.5 (2)
C20—C19—H19	120	O2—B1—C15	113.0 (2)
C2—C3—C4	120.3 (2)	O1—B1—N1	107.1 (2)
C2—C3—H3	119.8	O2—B1—N1	104.5 (2)
C4—C3—H3	119.8	C15—B1—N1	113.46 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.95	2.57	3.503 (3)	168
C24—H24···O2^ii	0.95	2.50	3.185 (3)	129

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