Crystal structure of di­fluorido­{2-[(4-hy­droxy­phen­yl)diazen­yl]-3,5-di­methyl­pyrrolido}boron

The asymmetric unit contains two independent mol­ecules, which are linked by an O—H...O hydrogen bond. The dimers are further assembled into one-dimensional ladder like structure through O—H...F hydrogen bonds and stabilized by π–π inter­actions. The ladders are further linked by C—H...π contacts.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.116
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C12 H12 B F2 N3 O
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.787 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C12 H12 B F2 N3 O
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        58% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Difluorido{2-[(4-hydroxyphenyl)diazenyl-κN²]-3,5-dimethylpyrrolido-\ κN}boron

Crystal data

C12H12BF2N3O	F(000) = 1088
Mr = 263.06	Dx = 1.453 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8080 (4) Å	Cell parameters from 3432 reflections
b = 24.8217 (18) Å	θ = 4.1–28.6°
c = 14.4744 (9) Å	µ = 0.12 mm^−1
β = 100.489 (6)°	T = 100 K
V = 2405.1 (3) Å^3	Block, dark green
Z = 8	0.25 × 0.22 × 0.2 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas S2 diffractometer	4228 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3277 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.043
Detector resolution: 5.2740 pixels mm^-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −29→29
Tmin = 0.680, Tmax = 1.000	l = −17→15
11903 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 1.6938P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4228 reflections	Δρmax = 0.25 e Å^−3
349 parameters	Δρmin = −0.26 e Å^−3
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
F1	1.31342 (18)	0.53429 (5)	0.89956 (9)	0.0210 (3)
F2	1.46735 (18)	0.45513 (5)	0.87853 (8)	0.0205 (3)
O1	0.5707 (2)	0.40021 (7)	0.61520 (11)	0.0272 (4)
H1	0.5225	0.3893	0.6596	0.041*
N1	1.5952 (3)	0.53806 (7)	0.81633 (12)	0.0156 (4)
N2	1.3878 (3)	0.52607 (8)	0.67448 (13)	0.0178 (4)
N3	1.2967 (3)	0.50217 (7)	0.73622 (13)	0.0162 (4)
C1	1.5603 (3)	0.54666 (9)	0.72074 (15)	0.0162 (5)
C2	1.7710 (3)	0.56211 (9)	0.85288 (16)	0.0166 (5)
C3	1.8484 (3)	0.58566 (9)	0.77884 (16)	0.0182 (5)
H3	1.9686	0.6043	0.7852	0.022*
C4	1.7176 (3)	0.57669 (9)	0.69470 (16)	0.0180 (5)
C5	1.8540 (3)	0.56219 (10)	0.95504 (15)	0.0211 (5)
H5A	1.8228	0.5958	0.9820	0.032*
H5B	1.9964	0.5578	0.9645	0.032*
H5C	1.7965	0.5331	0.9848	0.032*
C6	1.7354 (4)	0.59469 (11)	0.59812 (16)	0.0257 (6)
H6A	1.6381	0.5762	0.5528	0.038*
H6B	1.8669	0.5866	0.5869	0.038*
H6C	1.7125	0.6328	0.5926	0.038*
C7	1.1152 (3)	0.47520 (9)	0.70490 (15)	0.0163 (5)
C8	1.0407 (3)	0.46718 (9)	0.60966 (16)	0.0198 (5)
H8	1.1142	0.4786	0.5650	0.024*
C9	0.8590 (3)	0.44247 (10)	0.58158 (16)	0.0223 (5)
H9	0.8086	0.4380	0.5179	0.027*
C10	0.7495 (3)	0.42404 (9)	0.64779 (16)	0.0190 (5)
C11	0.8254 (3)	0.43105 (9)	0.74289 (16)	0.0179 (5)
H11	0.7541	0.4185	0.7876	0.021*
C12	1.0063 (3)	0.45662 (9)	0.77097 (15)	0.0170 (5)
H12	1.0560	0.4615	0.8346	0.020*
B1	1.4183 (4)	0.50677 (11)	0.84252 (18)	0.0174 (6)
F3	−0.50768 (19)	0.27493 (6)	0.54470 (9)	0.0247 (3)
F4	−0.33107 (18)	0.19699 (6)	0.55925 (9)	0.0237 (3)
O2	0.3980 (2)	0.36293 (7)	0.76431 (11)	0.0226 (4)
H2	0.4090	0.3820	0.8112	0.034*
N4	−0.6118 (3)	0.20404 (8)	0.64279 (13)	0.0172 (4)
N5	−0.4053 (3)	0.23598 (8)	0.77401 (13)	0.0176 (4)
N6	−0.3216 (3)	0.25089 (8)	0.70328 (12)	0.0167 (4)
C13	−0.5729 (3)	0.20907 (9)	0.73934 (15)	0.0168 (5)
C14	−0.7850 (3)	0.17649 (9)	0.61832 (16)	0.0188 (5)
C15	−0.8566 (3)	0.16381 (9)	0.70106 (16)	0.0198 (5)
H15	−0.9737	0.1451	0.7036	0.024*
C16	−0.7251 (3)	0.18365 (9)	0.77825 (16)	0.0193 (5)
C17	−0.8717 (3)	0.16370 (11)	0.51897 (17)	0.0261 (6)
H17A	−0.9208	0.1961	0.4867	0.039*
H17B	−0.9797	0.1386	0.5171	0.039*
H17C	−0.7707	0.1481	0.4889	0.039*
C18	−0.7344 (4)	0.17973 (10)	0.88049 (16)	0.0254 (6)
H18A	−0.6142	0.1943	0.9169	0.038*
H18B	−0.7476	0.1426	0.8971	0.038*
H18C	−0.8474	0.1997	0.8931	0.038*
C19	−0.1401 (3)	0.28017 (9)	0.72225 (15)	0.0155 (5)
C20	−0.0500 (3)	0.29409 (9)	0.64649 (16)	0.0186 (5)
H20	−0.1105	0.2848	0.5857	0.022*
C21	0.1291 (3)	0.32173 (9)	0.66166 (16)	0.0182 (5)
H21	0.1898	0.3308	0.6112	0.022*
C22	0.2179 (3)	0.33579 (9)	0.75205 (16)	0.0170 (5)
C23	0.1294 (3)	0.32146 (9)	0.82758 (16)	0.0183 (5)
H23	0.1907	0.3306	0.8883	0.022*
C24	−0.0496 (3)	0.29372 (9)	0.81286 (15)	0.0180 (5)
H24	−0.1090	0.2842	0.8635	0.022*
B2	−0.4440 (4)	0.23212 (11)	0.60191 (18)	0.0192 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0209 (7)	0.0223 (8)	0.0214 (7)	−0.0015 (6)	0.0079 (5)	−0.0030 (6)
F2	0.0227 (7)	0.0171 (7)	0.0211 (7)	−0.0029 (6)	0.0027 (5)	0.0025 (6)
O1	0.0236 (9)	0.0309 (11)	0.0260 (9)	−0.0135 (8)	0.0014 (7)	0.0018 (8)
N1	0.0156 (9)	0.0132 (10)	0.0185 (10)	0.0009 (8)	0.0048 (7)	−0.0001 (8)
N2	0.0182 (10)	0.0144 (10)	0.0221 (10)	−0.0002 (8)	0.0070 (8)	0.0008 (8)
N3	0.0148 (9)	0.0148 (10)	0.0195 (10)	−0.0007 (8)	0.0047 (8)	0.0007 (8)
C1	0.0174 (11)	0.0136 (12)	0.0176 (12)	0.0017 (10)	0.0031 (9)	0.0001 (10)
C2	0.0141 (11)	0.0117 (12)	0.0243 (12)	0.0026 (9)	0.0040 (9)	−0.0012 (10)
C3	0.0148 (11)	0.0128 (12)	0.0277 (13)	−0.0022 (9)	0.0058 (9)	−0.0003 (10)
C4	0.0182 (12)	0.0129 (12)	0.0248 (12)	0.0002 (10)	0.0087 (9)	0.0005 (10)
C5	0.0204 (12)	0.0209 (13)	0.0218 (12)	−0.0014 (10)	0.0037 (9)	0.0011 (10)
C6	0.0244 (13)	0.0275 (15)	0.0262 (13)	−0.0037 (11)	0.0073 (10)	0.0049 (11)
C7	0.0163 (11)	0.0117 (12)	0.0207 (12)	−0.0006 (9)	0.0033 (9)	0.0013 (10)
C8	0.0220 (12)	0.0185 (13)	0.0198 (12)	−0.0030 (10)	0.0061 (9)	0.0021 (10)
C9	0.0265 (13)	0.0220 (14)	0.0169 (12)	−0.0048 (11)	0.0002 (9)	−0.0001 (10)
C10	0.0146 (11)	0.0152 (13)	0.0263 (13)	−0.0016 (10)	0.0009 (9)	0.0007 (10)
C11	0.0161 (11)	0.0167 (12)	0.0219 (12)	0.0019 (10)	0.0066 (9)	0.0032 (10)
C12	0.0187 (12)	0.0155 (12)	0.0168 (11)	−0.0004 (10)	0.0032 (9)	−0.0006 (10)
B1	0.0169 (13)	0.0168 (14)	0.0185 (13)	−0.0009 (11)	0.0031 (10)	0.0016 (11)
F3	0.0265 (7)	0.0242 (8)	0.0230 (7)	−0.0026 (6)	0.0035 (6)	0.0065 (6)
F4	0.0227 (7)	0.0267 (8)	0.0234 (7)	−0.0033 (6)	0.0089 (6)	−0.0067 (6)
O2	0.0197 (8)	0.0208 (10)	0.0278 (9)	−0.0056 (7)	0.0056 (7)	−0.0043 (8)
N4	0.0170 (10)	0.0160 (11)	0.0190 (10)	−0.0010 (8)	0.0049 (8)	0.0002 (8)
N5	0.0191 (10)	0.0141 (10)	0.0211 (10)	0.0006 (8)	0.0073 (8)	−0.0002 (8)
N6	0.0181 (10)	0.0139 (10)	0.0193 (10)	−0.0016 (8)	0.0064 (8)	0.0009 (8)
C13	0.0171 (12)	0.0132 (12)	0.0210 (12)	0.0021 (10)	0.0063 (9)	0.0006 (10)
C14	0.0159 (11)	0.0142 (12)	0.0266 (13)	0.0009 (10)	0.0047 (9)	0.0010 (10)
C15	0.0143 (11)	0.0153 (12)	0.0309 (13)	−0.0009 (10)	0.0065 (10)	0.0020 (11)
C16	0.0208 (12)	0.0137 (12)	0.0250 (12)	0.0029 (10)	0.0084 (10)	0.0030 (10)
C17	0.0200 (12)	0.0292 (15)	0.0280 (14)	−0.0039 (11)	0.0018 (10)	0.0011 (12)
C18	0.0283 (13)	0.0231 (14)	0.0275 (13)	0.0005 (11)	0.0123 (10)	0.0035 (11)
C19	0.0148 (11)	0.0101 (12)	0.0220 (12)	−0.0003 (9)	0.0046 (9)	0.0000 (10)
C20	0.0225 (12)	0.0171 (13)	0.0162 (11)	−0.0015 (10)	0.0039 (9)	−0.0007 (10)
C21	0.0197 (12)	0.0147 (12)	0.0223 (12)	0.0007 (10)	0.0094 (9)	0.0025 (10)
C22	0.0145 (11)	0.0130 (12)	0.0237 (12)	0.0001 (9)	0.0039 (9)	−0.0003 (10)
C23	0.0196 (12)	0.0146 (12)	0.0191 (12)	0.0001 (10)	−0.0004 (9)	−0.0028 (10)
C24	0.0194 (12)	0.0169 (13)	0.0193 (12)	0.0005 (10)	0.0079 (9)	0.0018 (10)
B2	0.0203 (13)	0.0203 (15)	0.0178 (13)	−0.0031 (12)	0.0059 (10)	0.0004 (12)

Geometric parameters (Å, º)

F1—B1	1.369 (3)	F3—B2	1.368 (3)
F2—B1	1.401 (3)	F4—B2	1.380 (3)
O1—H1	0.8200	O2—H2	0.8200
O1—C10	1.358 (3)	O2—C22	1.382 (3)
N1—C1	1.377 (3)	N4—C13	1.380 (3)
N1—C2	1.356 (3)	N4—C14	1.353 (3)
N1—B1	1.537 (3)	N4—B2	1.545 (3)
N2—N3	1.318 (3)	N5—N6	1.312 (3)
N2—C1	1.343 (3)	N5—C13	1.338 (3)
N3—C7	1.406 (3)	N6—C19	1.416 (3)
N3—B1	1.613 (3)	N6—B2	1.618 (3)
C1—C4	1.411 (3)	C13—C16	1.415 (3)
C2—C3	1.405 (3)	C14—C15	1.408 (3)
C2—C5	1.484 (3)	C14—C17	1.486 (3)
C3—H3	0.9300	C15—H15	0.9300
C3—C4	1.389 (3)	C15—C16	1.389 (3)
C4—C6	1.493 (3)	C16—C18	1.496 (3)
C5—H5A	0.9600	C17—H17A	0.9600
C5—H5B	0.9600	C17—H17B	0.9600
C5—H5C	0.9600	C17—H17C	0.9600
C6—H6A	0.9600	C18—H18A	0.9600
C6—H6B	0.9600	C18—H18B	0.9600
C6—H6C	0.9600	C18—H18C	0.9600
C7—C8	1.394 (3)	C19—C20	1.394 (3)
C7—C12	1.391 (3)	C19—C24	1.385 (3)
C8—H8	0.9300	C20—H20	0.9300
C8—C9	1.375 (3)	C20—C21	1.382 (3)
C9—H9	0.9300	C21—H21	0.9300
C9—C10	1.394 (3)	C21—C22	1.382 (3)
C10—C11	1.390 (3)	C22—C23	1.387 (3)
C11—H11	0.9300	C23—H23	0.9300
C11—C12	1.380 (3)	C23—C24	1.382 (3)
C12—H12	0.9300	C24—H24	0.9300
C10—O1—H1	109.5	C22—O2—H2	109.5
C1—N1—B1	109.05 (17)	C13—N4—B2	109.16 (18)
C2—N1—C1	107.60 (18)	C14—N4—C13	107.95 (18)
C2—N1—B1	143.30 (19)	C14—N4—B2	142.88 (19)
N3—N2—C1	108.06 (18)	N6—N5—C13	108.05 (18)
N2—N3—C7	119.34 (18)	N5—N6—C19	118.74 (18)
N2—N3—B1	113.07 (17)	N5—N6—B2	113.64 (17)
C7—N3—B1	127.56 (18)	C19—N6—B2	127.62 (18)
N1—C1—C4	110.47 (18)	N4—C13—C16	110.09 (19)
N2—C1—N1	114.66 (19)	N5—C13—N4	114.72 (19)
N2—C1—C4	134.9 (2)	N5—C13—C16	135.2 (2)
N1—C2—C3	108.23 (19)	N4—C14—C15	108.08 (19)
N1—C2—C5	122.6 (2)	N4—C14—C17	122.4 (2)
C3—C2—C5	129.2 (2)	C15—C14—C17	129.6 (2)
C2—C3—H3	125.3	C14—C15—H15	125.3
C4—C3—C2	109.40 (19)	C16—C15—C14	109.4 (2)
C4—C3—H3	125.3	C16—C15—H15	125.3
C1—C4—C6	127.1 (2)	C13—C16—C18	126.1 (2)
C3—C4—C1	104.30 (19)	C15—C16—C13	104.4 (2)
C3—C4—C6	128.6 (2)	C15—C16—C18	129.5 (2)
C2—C5—H5A	109.5	C14—C17—H17A	109.5
C2—C5—H5B	109.5	C14—C17—H17B	109.5
C2—C5—H5C	109.5	C14—C17—H17C	109.5
H5A—C5—H5B	109.5	H17A—C17—H17B	109.5
H5A—C5—H5C	109.5	H17A—C17—H17C	109.5
H5B—C5—H5C	109.5	H17B—C17—H17C	109.5
C4—C6—H6A	109.5	C16—C18—H18A	109.5
C4—C6—H6B	109.5	C16—C18—H18B	109.5
C4—C6—H6C	109.5	C16—C18—H18C	109.5
H6A—C6—H6B	109.5	H18A—C18—H18B	109.5
H6A—C6—H6C	109.5	H18A—C18—H18C	109.5
H6B—C6—H6C	109.5	H18B—C18—H18C	109.5
C8—C7—N3	121.8 (2)	C20—C19—N6	117.90 (19)
C12—C7—N3	118.89 (19)	C24—C19—N6	122.0 (2)
C12—C7—C8	119.3 (2)	C24—C19—C20	120.1 (2)
C7—C8—H8	119.9	C19—C20—H20	120.0
C9—C8—C7	120.1 (2)	C21—C20—C19	120.0 (2)
C9—C8—H8	119.9	C21—C20—H20	120.0
C8—C9—H9	119.7	C20—C21—H21	120.1
C8—C9—C10	120.6 (2)	C20—C21—C22	119.8 (2)
C10—C9—H9	119.7	C22—C21—H21	120.1
O1—C10—C9	117.5 (2)	O2—C22—C21	118.0 (2)
O1—C10—C11	123.1 (2)	O2—C22—C23	121.8 (2)
C11—C10—C9	119.4 (2)	C21—C22—C23	120.2 (2)
C10—C11—H11	120.0	C22—C23—H23	119.9
C12—C11—C10	120.0 (2)	C24—C23—C22	120.2 (2)
C12—C11—H11	120.0	C24—C23—H23	119.9
C7—C12—H12	119.7	C19—C24—H24	120.2
C11—C12—C7	120.6 (2)	C23—C24—C19	119.7 (2)
C11—C12—H12	119.7	C23—C24—H24	120.2
F1—B1—F2	110.33 (19)	F3—B2—F4	111.15 (19)
F1—B1—N1	114.5 (2)	F3—B2—N4	114.04 (19)
F1—B1—N3	112.16 (18)	F3—B2—N6	112.3 (2)
F2—B1—N1	114.19 (18)	F4—B2—N4	113.4 (2)
F2—B1—N3	109.65 (19)	F4—B2—N6	110.52 (18)
N1—B1—N3	95.14 (17)	N4—B2—N6	94.42 (16)
O1—C10—C11—C12	−178.6 (2)	O2—C22—C23—C24	−179.2 (2)
N1—C1—C4—C3	0.1 (3)	N4—C13—C16—C15	−0.5 (3)
N1—C1—C4—C6	−179.5 (2)	N4—C13—C16—C18	179.0 (2)
N1—C2—C3—C4	0.7 (3)	N4—C14—C15—C16	−0.2 (3)
N2—N3—C7—C8	8.1 (3)	N5—N6—C19—C20	177.9 (2)
N2—N3—C7—C12	−171.1 (2)	N5—N6—C19—C24	−0.4 (3)
N2—N3—B1—F1	117.8 (2)	N5—N6—B2—F3	118.5 (2)
N2—N3—B1—F2	−119.2 (2)	N5—N6—B2—F4	−116.8 (2)
N2—N3—B1—N1	−1.2 (2)	N5—N6—B2—N4	0.2 (2)
N2—C1—C4—C3	178.7 (3)	N5—C13—C16—C15	179.5 (2)
N2—C1—C4—C6	−0.8 (4)	N5—C13—C16—C18	−1.0 (4)
N3—N2—C1—N1	−0.3 (3)	N6—N5—C13—N4	0.2 (3)
N3—N2—C1—C4	−178.9 (2)	N6—N5—C13—C16	−179.8 (3)
N3—C7—C8—C9	−177.5 (2)	N6—C19—C20—C21	−178.7 (2)
N3—C7—C12—C11	178.5 (2)	N6—C19—C24—C23	178.8 (2)
C1—N1—C2—C3	−0.6 (2)	C13—N4—C14—C15	−0.1 (3)
C1—N1—C2—C5	178.5 (2)	C13—N4—C14—C17	−179.9 (2)
C1—N1—B1—F1	−116.2 (2)	C13—N4—B2—F3	−116.9 (2)
C1—N1—B1—F2	115.2 (2)	C13—N4—B2—F4	114.5 (2)
C1—N1—B1—N3	1.0 (2)	C13—N4—B2—N6	−0.1 (2)
C1—N2—N3—C7	−177.34 (19)	C13—N5—N6—C19	−179.84 (19)
C1—N2—N3—B1	1.0 (2)	C13—N5—N6—B2	−0.3 (2)
C2—N1—C1—N2	−178.58 (19)	C14—N4—C13—N5	−179.60 (19)
C2—N1—C1—C4	0.4 (3)	C14—N4—C13—C16	0.4 (3)
C2—N1—B1—F1	60.6 (4)	C14—N4—B2—F3	62.3 (4)
C2—N1—B1—F2	−68.0 (4)	C14—N4—B2—F4	−66.2 (4)
C2—N1—B1—N3	177.8 (3)	C14—N4—B2—N6	179.2 (3)
C2—C3—C4—C1	−0.4 (3)	C14—C15—C16—C13	0.5 (3)
C2—C3—C4—C6	179.1 (2)	C14—C15—C16—C18	−179.0 (2)
C5—C2—C3—C4	−178.4 (2)	C17—C14—C15—C16	179.6 (2)
C7—N3—B1—F1	−64.0 (3)	C19—N6—B2—F3	−62.0 (3)
C7—N3—B1—F2	59.0 (3)	C19—N6—B2—F4	62.7 (3)
C7—N3—B1—N1	176.9 (2)	C19—N6—B2—N4	179.7 (2)
C7—C8—C9—C10	−1.6 (4)	C19—C20—C21—C22	−0.4 (3)
C8—C7—C12—C11	−0.7 (3)	C20—C19—C24—C23	0.5 (3)
C8—C9—C10—O1	179.7 (2)	C20—C21—C22—O2	179.4 (2)
C8—C9—C10—C11	0.3 (4)	C20—C21—C22—C23	1.1 (3)
C9—C10—C11—C12	0.8 (3)	C21—C22—C23—C24	−1.0 (3)
C10—C11—C12—C7	−0.5 (3)	C22—C23—C24—C19	0.1 (3)
C12—C7—C8—C9	1.8 (4)	C24—C19—C20—C21	−0.4 (3)
B1—N1—C1—N2	−0.6 (3)	B2—N4—C13—N5	−0.1 (3)
B1—N1—C1—C4	178.34 (19)	B2—N4—C13—C16	179.92 (19)
B1—N1—C2—C3	−177.4 (3)	B2—N4—C14—C15	−179.3 (3)
B1—N1—C2—C5	1.7 (4)	B2—N4—C14—C17	0.9 (5)
B1—N3—C7—C8	−170.0 (2)	B2—N6—C19—C20	−1.6 (3)
B1—N3—C7—C12	10.8 (3)	B2—N6—C19—C24	−179.8 (2)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg6 are the centroids of the N4/C13–C16 and N1/C1–C4 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.98	2.797 (2)	178
O2—H2···F2^i	0.82	2.06	2.812 (2)	152
C3—H3···Cg1^ii	0.93	2.62	3.501 (2)	158
C15—H15···Cg2^iii	0.93	2.63	3.506 (2)	157

Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1/2, y−1/2, −z+3/2.