2,2-Di­fluoro-3-(4-fluoro­phen­yl)-2H-benzo[e][1,3,2]oxaza­borinin-3-ium-2-uide

There is one independent mol­ecule in the asymmetric unit of the title compound, C₁₃H₉BF₃NO, which crystallizes in the non-centrosymmetric space group Cc. In the mol­ecular structure, the BF₂-carrying ring is distorted from planarity and its mean plane makes a dihedral angle of 42.3 (1)° with the 4-fluorophenyl ring. F atoms are involved in all of the short inter­molecular contacts of the crystal structure, which link molecules to form chains along [001] and [010].

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.027
• wR factor = 0.068
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    0.200
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.34 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         84 %

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  Cc              Ia Note
PLAT395_ALERT_2_G Deviating  X-O-Y  Angle from 120 Deg for  O1          122.1 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.13 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Note

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

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

2,2-Difluoro-3-(4-fluorophenyl)-2H-benzo[e][1,3,2]oxazaborinin-3-ium-2-uide

Crystal data

C13H9BF3NO	F(000) = 536
Mr = 263.02	Dx = 1.567 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 16.4374 (9) Å	Cell parameters from 3617 reflections
b = 6.2657 (2) Å	θ = 3.6–26.0°
c = 12.5689 (6) Å	µ = 0.13 mm^−1
β = 120.523 (7)°	T = 100 K
V = 1115.11 (11) Å^3	Irregular, colourless
Z = 4	0.30 × 0.27 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	1893 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θmax = 26.0°, θmin = 3.6°
ω scan	h = −20→20
3617 measured reflections	k = −7→6
2009 independent reflections	l = −15→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0483P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.068	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.32 e Å^−3
2009 reflections	Δρmin = −0.16 e Å^−3
172 parameters	Absolute structure: Flack x determined using 822 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.4 (2)

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. All H atoms were found in a difference map but set to idealized positions and treated as riding with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

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

	x	y	z	Uiso*/Ueq
B1	0.77468 (19)	0.1468 (4)	0.5089 (2)	0.0181 (6)
N1	0.77972 (13)	0.3792 (3)	0.46252 (16)	0.0156 (4)
O1	0.74538 (11)	0.1567 (2)	0.59940 (15)	0.0198 (4)
F1	0.86187 (10)	0.0523 (2)	0.56040 (12)	0.0238 (3)
F2	0.70869 (10)	0.03147 (19)	0.40483 (13)	0.0238 (3)
F3	0.98722 (11)	0.5268 (2)	0.23374 (14)	0.0305 (4)
C1	0.68820 (15)	0.3108 (3)	0.59781 (19)	0.0154 (5)
C2	0.64062 (16)	0.2866 (4)	0.66190 (19)	0.0181 (5)
H2A	0.6467	0.1614	0.7050	0.022*
C3	0.58407 (17)	0.4510 (4)	0.6609 (2)	0.0218 (5)
H3A	0.5516	0.4334	0.7030	0.026*
C4	0.57420 (17)	0.6424 (4)	0.5989 (2)	0.0237 (5)
H4A	0.5360	0.7508	0.5999	0.028*
C5	0.62172 (16)	0.6682 (4)	0.5364 (2)	0.0200 (5)
H5A	0.6161	0.7956	0.4952	0.024*
C6	0.67883 (16)	0.5040 (3)	0.5339 (2)	0.0173 (5)
C7	0.73105 (16)	0.5331 (3)	0.4728 (2)	0.0156 (5)
H7A	0.7303	0.6659	0.4392	0.019*
C8	0.83503 (15)	0.4185 (4)	0.40454 (19)	0.0161 (5)
C9	0.88431 (16)	0.6091 (4)	0.4256 (2)	0.0190 (5)
H9A	0.8829	0.7109	0.4785	0.023*
C10	0.93566 (17)	0.6471 (4)	0.3674 (2)	0.0217 (5)
H10A	0.9683	0.7746	0.3799	0.026*
C11	0.93716 (17)	0.4909 (4)	0.2905 (2)	0.0205 (5)
C12	0.88997 (16)	0.2993 (4)	0.2704 (2)	0.0194 (5)
H12A	0.8927	0.1961	0.2192	0.023*
C13	0.83857 (17)	0.2640 (3)	0.3283 (2)	0.0174 (5)
H13A	0.8063	0.1360	0.3158	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0223 (13)	0.0108 (11)	0.0220 (14)	0.0011 (10)	0.0117 (12)	0.0001 (10)
N1	0.0181 (9)	0.0121 (8)	0.0143 (9)	−0.0008 (8)	0.0066 (8)	−0.0015 (7)
O1	0.0261 (9)	0.0143 (8)	0.0216 (8)	0.0034 (7)	0.0140 (7)	0.0039 (6)
F1	0.0296 (8)	0.0170 (7)	0.0295 (8)	0.0092 (6)	0.0185 (7)	0.0086 (6)
F2	0.0357 (8)	0.0142 (7)	0.0229 (7)	−0.0078 (6)	0.0160 (7)	−0.0047 (5)
F3	0.0319 (8)	0.0403 (9)	0.0308 (8)	−0.0023 (7)	0.0243 (8)	0.0007 (7)
C1	0.0125 (10)	0.0170 (11)	0.0128 (11)	−0.0020 (8)	0.0037 (9)	−0.0027 (8)
C2	0.0193 (11)	0.0213 (11)	0.0138 (12)	−0.0028 (9)	0.0084 (10)	0.0012 (9)
C3	0.0182 (12)	0.0304 (13)	0.0177 (12)	−0.0018 (10)	0.0098 (10)	−0.0033 (10)
C4	0.0179 (12)	0.0234 (11)	0.0255 (13)	0.0031 (10)	0.0079 (11)	−0.0037 (10)
C5	0.0181 (12)	0.0161 (11)	0.0203 (12)	−0.0002 (9)	0.0058 (10)	0.0003 (9)
C6	0.0160 (11)	0.0200 (11)	0.0138 (10)	−0.0054 (9)	0.0062 (10)	−0.0033 (8)
C7	0.0164 (11)	0.0126 (10)	0.0160 (11)	−0.0002 (8)	0.0069 (10)	−0.0004 (8)
C8	0.0160 (11)	0.0198 (11)	0.0124 (11)	0.0035 (9)	0.0071 (9)	0.0018 (9)
C9	0.0205 (12)	0.0166 (11)	0.0187 (11)	0.0030 (9)	0.0092 (10)	0.0006 (9)
C10	0.0202 (12)	0.0173 (11)	0.0226 (13)	−0.0027 (9)	0.0071 (11)	0.0010 (9)
C11	0.0178 (12)	0.0271 (13)	0.0185 (11)	0.0033 (10)	0.0106 (10)	0.0064 (10)
C12	0.0204 (11)	0.0227 (11)	0.0145 (11)	0.0033 (10)	0.0085 (10)	−0.0027 (9)
C13	0.0170 (11)	0.0159 (10)	0.0165 (11)	0.0013 (9)	0.0066 (10)	0.0016 (9)

Geometric parameters (Å, º)

B1—F1	1.372 (3)	C4—H4A	0.9300
B1—F2	1.403 (3)	C5—C6	1.403 (3)
B1—O1	1.445 (3)	C5—H5A	0.9300
B1—N1	1.586 (3)	C6—C7	1.425 (3)
N1—C7	1.300 (3)	C7—H7A	0.9300
N1—C8	1.446 (3)	C8—C13	1.384 (3)
O1—C1	1.340 (3)	C8—C9	1.391 (3)
F3—C11	1.354 (3)	C9—C10	1.389 (3)
C1—C2	1.387 (3)	C9—H9A	0.9300
C1—C6	1.418 (3)	C10—C11	1.385 (3)
C2—C3	1.383 (3)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.381 (3)
C3—C4	1.394 (4)	C12—C13	1.384 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.370 (3)	C13—H13A	0.9300
F1—B1—F2	110.23 (19)	C5—C6—C1	119.7 (2)
F1—B1—O1	109.4 (2)	C5—C6—C7	120.8 (2)
F2—B1—O1	110.31 (19)	C1—C6—C7	119.5 (2)
F1—B1—N1	109.44 (19)	N1—C7—C6	121.89 (19)
F2—B1—N1	106.89 (19)	N1—C7—H7A	119.1
O1—B1—N1	110.49 (17)	C6—C7—H7A	119.1
C7—N1—C8	119.98 (18)	C13—C8—C9	120.5 (2)
C7—N1—B1	119.66 (19)	C13—C8—N1	119.2 (2)
C8—N1—B1	120.32 (17)	C9—C8—N1	120.32 (19)
C1—O1—B1	122.08 (17)	C10—C9—C8	119.8 (2)
O1—C1—C2	120.73 (19)	C10—C9—H9A	120.1
O1—C1—C6	119.8 (2)	C8—C9—H9A	120.1
C2—C1—C6	119.42 (19)	C11—C10—C9	118.5 (2)
C3—C2—C1	119.2 (2)	C11—C10—H10A	120.7
C3—C2—H2A	120.4	C9—C10—H10A	120.7
C1—C2—H2A	120.4	F3—C11—C12	118.9 (2)
C2—C3—C4	122.1 (2)	F3—C11—C10	118.8 (2)
C2—C3—H3A	118.9	C12—C11—C10	122.3 (2)
C4—C3—H3A	118.9	C11—C12—C13	118.6 (2)
C5—C4—C3	119.0 (2)	C11—C12—H12A	120.7
C5—C4—H4A	120.5	C13—C12—H12A	120.7
C3—C4—H4A	120.5	C12—C13—C8	120.2 (2)
C4—C5—C6	120.6 (2)	C12—C13—H13A	119.9
C4—C5—H5A	119.7	C8—C13—H13A	119.9
C6—C5—H5A	119.7
F1—B1—N1—C7	−143.2 (2)	O1—C1—C6—C7	−0.5 (3)
F2—B1—N1—C7	97.4 (2)	C2—C1—C6—C7	177.1 (2)
O1—B1—N1—C7	−22.6 (3)	C8—N1—C7—C6	−177.25 (19)
F1—B1—N1—C8	39.3 (3)	B1—N1—C7—C6	5.3 (3)
F2—B1—N1—C8	−80.1 (2)	C5—C6—C7—N1	−175.6 (2)
O1—B1—N1—C8	159.87 (18)	C1—C6—C7—N1	7.4 (3)
F1—B1—O1—C1	150.84 (18)	C7—N1—C8—C13	−141.0 (2)
F2—B1—O1—C1	−87.7 (2)	B1—N1—C8—C13	36.5 (3)
N1—B1—O1—C1	30.3 (3)	C7—N1—C8—C9	39.2 (3)
B1—O1—C1—C2	162.2 (2)	B1—N1—C8—C9	−143.3 (2)
B1—O1—C1—C6	−20.3 (3)	C13—C8—C9—C10	1.5 (3)
O1—C1—C2—C3	178.3 (2)	N1—C8—C9—C10	−178.7 (2)
C6—C1—C2—C3	0.7 (3)	C8—C9—C10—C11	−0.8 (3)
C1—C2—C3—C4	−0.9 (3)	C9—C10—C11—F3	−179.9 (2)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	−0.4 (3)
C3—C4—C5—C6	0.5 (3)	F3—C11—C12—C13	−179.7 (2)
C4—C5—C6—C1	−0.7 (3)	C10—C11—C12—C13	0.8 (3)
C4—C5—C6—C7	−177.7 (2)	C11—C12—C13—C8	−0.1 (3)
O1—C1—C6—C5	−177.57 (19)	C9—C8—C13—C12	−1.1 (3)
C2—C1—C6—C5	0.1 (3)	N1—C8—C13—C12	179.11 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2^i	0.93	2.49	3.328 (3)	150
C7—H7A···F2^ii	0.93	2.32	3.209 (2)	159
C9—H9A···F1^ii	0.93	2.47	3.369 (3)	162
C12—H12A···F1^iii	0.93	2.37	3.286 (3)	167
C13—H13A···F2	0.93	2.47	3.114 (3)	127

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