4-(1H-2,3-Dihydro­naphtho­[1,8-de][1,3,2]di­aza­borinin-2-yl)-1-ethylpyridin-1-ium iodide

The title compound, C₁₇H₁₇BN₃I, is a type of di­aza­borinane featuring substitution at the 1, 2, and 3 positions of the nitro­gen–boron six-membered heterocycle. The organic mol­ecule has a planar structure, the dihedral angle between the pyridyl ring and the fused ring system being 3.46 (4)°. In the crystal, mol­ecules are stacked in a head-to-tail manner. The iodide ion makes close contacts with three organic mol­ecules and supports the alternating stack.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.020
• wR factor = 0.052
• Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
              Calc: C17 H17 B N3, I
              Rep.: I, C17 H17 B N3
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.71 Report
PLAT756_ALERT_4_C H...A   Calc     3.16000, Rep   3.1572(2) ......  Senseless s.u.
              H2       -I1              1_555   1_555 ........     #    2 Check
PLAT756_ALERT_4_C H...A   Calc     3.07000, Rep   3.0728(2) ......  Senseless s.u.
              H14      -I1              1_555   1_545 ........     #    4 Check
PLAT758_ALERT_4_C D-H..A  Calc      161.00, Rep   161.17(8) ......  Senseless s.u.
              C2      -H2      -I1         1_555  1_555  1_555     #    2 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
                1  0  0,  -1  1  0,   0  1  0,   1  1  0,   0 -1  1,   0  0  1,
                1  0  1,   0  1  1,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         23 Report
               -2  2  0,  -1  2  0,  -2  3  0,  -1  3  0,  -2  4  0,  -3  5  0,
               -2  5  0,  -3  6  0,   1 -1  1,  -2  1  1,  -3  2  1,  -2  2  1,
               -4  3  1,  -3  3  1,  -5  4  1,  -4  4  1,  -6  5  1,  -5  5  1,
               -6  8  1,  -5  4  2,  -7  5  2,  -6  5  2,  -7  6  2,

Alert level G
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)     0.0003 Ang.
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2       ..I1       .       3.16 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H14      ..I1       .       3.07 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        998 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.8 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.78 Note
              Predicted wR2: Based on SigI   2  1.88 or SHELX Weight  4.98       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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

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Computing details

4-(1H-2,3-Dihydronaphtho[1,8-de][1,3,2]diazaborinin-2-yl)-1-ethylpyridin-1-ium iodide

Crystal data

C17H17BN3^+·I^−	Z = 2
Mr = 401.04	F(000) = 396
Triclinic, P1	Dx = 1.626 Mg m^−3
a = 7.0800 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6304 (3) Å	Cell parameters from 7826 reflections
c = 11.0650 (3) Å	θ = 3.8–31.4°
α = 89.715 (2)°	µ = 1.95 mm^−1
β = 79.711 (3)°	T = 293 K
γ = 89.598 (2)°	Plate, clear red
V = 819.37 (5) Å^3	0.1 × 0.05 × 0.03 mm

Data collection

XtaLAB AFC10 (RCD3): fixed-χ single diffractometer	4404 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Mo) X-ray Source	4088 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 10.0000 pixels mm^-1	θmax = 31.6°, θmin = 3.7°
ω scans	h = −7→10
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −14→14
Tmin = 0.942, Tmax = 1.000	l = −15→15
12190 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.052	w = 1/[σ^2(Fo^2) + (0.0288P)^2 + 0.2552P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.004
4404 reflections	Δρmax = 0.78 e Å^−3
208 parameters	Δρmin = −0.29 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.

Refinement. The positions of the N-bound and the O-bound H atoms were obtained from difference Fourier maps and were refined isotropically. The C-bound H atoms were placed at ideal positions and were refined as riding on their parent C atoms. U_iso(H) values of the H atoms were set at 1.2U_eq(parent atom for C_sp2) and 1.5U_eq(parent atom for C_sp3).

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

	x	y	z	Uiso*/Ueq
I1	0.41685 (2)	0.80629 (2)	0.76854 (2)	0.03537 (5)
N1	0.38277 (16)	0.22734 (11)	0.80569 (10)	0.0189 (2)
N2	0.22902 (17)	0.60900 (11)	0.53955 (11)	0.0206 (2)
N3	0.24819 (18)	0.43530 (12)	0.39835 (11)	0.0220 (2)
C6	0.19028 (19)	0.69330 (13)	0.45019 (12)	0.0202 (2)
C4	0.3287 (2)	0.25792 (13)	0.60271 (13)	0.0221 (3)
H3	0.3186	0.2239	0.5269	0.026*
C3	0.30663 (18)	0.38741 (12)	0.62082 (12)	0.0181 (2)
C2	0.3276 (2)	0.43318 (13)	0.73619 (13)	0.0217 (3)
H2	0.3151	0.5189	0.7522	0.026*
C1	0.3666 (2)	0.35186 (13)	0.82613 (13)	0.0219 (3)
H1	0.3820	0.3835	0.9019	0.026*
C5	0.3656 (2)	0.17955 (13)	0.69587 (13)	0.0222 (3)
H4	0.3785	0.0934	0.6826	0.027*
C16	0.4153 (2)	0.14270 (14)	0.90731 (13)	0.0233 (3)
H13	0.4977	0.1841	0.9559	0.028*
H14	0.4801	0.0667	0.8733	0.028*
C15	0.18123 (18)	0.64498 (13)	0.33129 (12)	0.0197 (2)
C14	0.2089 (2)	0.51456 (14)	0.30483 (13)	0.0218 (3)
C7	0.1655 (2)	0.82045 (14)	0.47347 (14)	0.0267 (3)
H6	0.1693	0.8515	0.5514	0.032*
C10	0.14939 (19)	0.73002 (14)	0.23651 (13)	0.0232 (3)
C11	0.1474 (2)	0.68118 (17)	0.11772 (14)	0.0292 (3)
H9	0.1297	0.7353	0.0543	0.035*
C9	0.1257 (2)	0.85948 (15)	0.26407 (14)	0.0275 (3)
H8	0.1040	0.9157	0.2033	0.033*
C8	0.1343 (2)	0.90312 (15)	0.37892 (16)	0.0299 (3)
H7	0.1193	0.9888	0.3949	0.036*
C13	0.2006 (2)	0.47006 (16)	0.18876 (14)	0.0296 (3)
H11	0.2143	0.3845	0.1721	0.035*
C12	0.1712 (2)	0.55533 (18)	0.09582 (14)	0.0327 (3)
H10	0.1680	0.5250	0.0175	0.039*
C17	0.2286 (2)	0.10846 (19)	0.98868 (17)	0.0362 (4)
H17	0.1531	0.0588	0.9431	0.054*
H15	0.1592	0.1838	1.0168	0.054*
H16	0.2543	0.0610	1.0580	0.054*
B1	0.2602 (2)	0.47939 (14)	0.51714 (14)	0.0189 (3)
H5	0.246 (3)	0.639 (2)	0.604 (2)	0.035 (6)*
H12	0.280 (3)	0.365 (2)	0.373 (2)	0.035 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.06050 (9)	0.01998 (6)	0.02905 (6)	0.00500 (4)	−0.01733 (5)	−0.00322 (4)
N1	0.0171 (5)	0.0176 (5)	0.0217 (5)	0.0001 (4)	−0.0027 (4)	0.0065 (4)
N2	0.0239 (6)	0.0190 (5)	0.0187 (5)	0.0031 (4)	−0.0037 (4)	0.0041 (4)
N3	0.0252 (6)	0.0176 (5)	0.0238 (6)	0.0014 (4)	−0.0063 (4)	0.0032 (4)
C6	0.0177 (6)	0.0196 (6)	0.0224 (6)	0.0025 (5)	−0.0016 (5)	0.0066 (5)
C4	0.0259 (7)	0.0191 (6)	0.0216 (6)	−0.0010 (5)	−0.0053 (5)	0.0034 (5)
C3	0.0148 (6)	0.0175 (6)	0.0210 (6)	−0.0001 (4)	−0.0007 (4)	0.0056 (4)
C2	0.0251 (7)	0.0160 (6)	0.0232 (6)	0.0015 (5)	−0.0028 (5)	0.0037 (5)
C1	0.0261 (7)	0.0186 (6)	0.0210 (6)	0.0018 (5)	−0.0041 (5)	0.0019 (5)
C5	0.0256 (7)	0.0148 (6)	0.0264 (6)	0.0002 (5)	−0.0049 (5)	0.0035 (5)
C16	0.0238 (7)	0.0212 (6)	0.0259 (7)	0.0008 (5)	−0.0076 (5)	0.0099 (5)
C15	0.0146 (6)	0.0225 (6)	0.0210 (6)	0.0010 (5)	−0.0008 (4)	0.0067 (5)
C14	0.0187 (6)	0.0241 (7)	0.0225 (6)	0.0007 (5)	−0.0041 (5)	0.0047 (5)
C7	0.0313 (8)	0.0207 (6)	0.0281 (7)	0.0047 (5)	−0.0056 (6)	0.0039 (5)
C10	0.0152 (6)	0.0293 (7)	0.0242 (6)	0.0017 (5)	−0.0012 (5)	0.0107 (5)
C11	0.0222 (7)	0.0418 (9)	0.0233 (7)	0.0048 (6)	−0.0037 (5)	0.0107 (6)
C9	0.0224 (7)	0.0278 (7)	0.0309 (7)	0.0028 (6)	−0.0012 (5)	0.0154 (6)
C8	0.0304 (8)	0.0211 (7)	0.0372 (8)	0.0047 (6)	−0.0041 (6)	0.0097 (6)
C13	0.0326 (8)	0.0308 (8)	0.0270 (7)	0.0049 (6)	−0.0100 (6)	−0.0013 (6)
C12	0.0317 (8)	0.0459 (10)	0.0218 (7)	0.0072 (7)	−0.0084 (6)	0.0005 (6)
C17	0.0270 (8)	0.0448 (10)	0.0364 (8)	−0.0022 (7)	−0.0053 (6)	0.0246 (7)
B1	0.0158 (6)	0.0184 (6)	0.0221 (7)	−0.0008 (5)	−0.0026 (5)	0.0060 (5)

Geometric parameters (Å, º)

N1—C1	1.3446 (18)	C16—H14	0.9700
N1—C5	1.3452 (19)	C16—C17	1.506 (2)
N1—C16	1.4855 (16)	C15—C14	1.423 (2)
N2—C6	1.3930 (16)	C15—C10	1.4283 (18)
N2—B1	1.4100 (19)	C14—C13	1.382 (2)
N2—H5	0.81 (2)	C7—H6	0.9300
N3—C14	1.3961 (17)	C7—C8	1.409 (2)
N3—B1	1.415 (2)	C10—C11	1.418 (2)
N3—H12	0.81 (2)	C10—C9	1.413 (2)
C6—C15	1.427 (2)	C11—H9	0.9300
C6—C7	1.381 (2)	C11—C12	1.365 (3)
C4—H3	0.9300	C9—H8	0.9300
C4—C3	1.3957 (19)	C9—C8	1.367 (2)
C4—C5	1.3816 (18)	C8—H7	0.9300
C3—C2	1.4012 (19)	C13—H11	0.9300
C3—B1	1.5808 (19)	C13—C12	1.410 (2)
C2—H2	0.9300	C12—H10	0.9300
C2—C1	1.3786 (18)	C17—H17	0.9600
C1—H1	0.9300	C17—H15	0.9600
C5—H4	0.9300	C17—H16	0.9600
C16—H13	0.9700
C1—N1—C5	120.68 (11)	C14—C15—C10	119.66 (13)
C1—N1—C16	118.97 (12)	N3—C14—C15	117.96 (13)
C5—N1—C16	120.33 (12)	C13—C14—N3	121.88 (14)
C6—N2—B1	122.92 (12)	C13—C14—C15	120.15 (13)
C6—N2—H5	116.8 (16)	C6—C7—H6	120.0
B1—N2—H5	119.9 (16)	C6—C7—C8	119.91 (15)
C14—N3—B1	122.71 (13)	C8—C7—H6	120.0
C14—N3—H12	112.2 (16)	C11—C10—C15	118.47 (14)
B1—N3—H12	124.4 (16)	C9—C10—C15	118.79 (14)
N2—C6—C15	117.93 (12)	C9—C10—C11	122.73 (13)
C7—C6—N2	121.80 (13)	C10—C11—H9	119.8
C7—C6—C15	120.25 (12)	C12—C11—C10	120.44 (14)
C3—C4—H3	119.5	C12—C11—H9	119.8
C5—C4—H3	119.5	C10—C9—H8	119.6
C5—C4—C3	120.92 (13)	C8—C9—C10	120.85 (13)
C4—C3—C2	116.81 (12)	C8—C9—H8	119.6
C4—C3—B1	122.23 (12)	C7—C8—H7	119.5
C2—C3—B1	120.96 (12)	C9—C8—C7	121.07 (15)
C3—C2—H2	119.8	C9—C8—H7	119.5
C1—C2—C3	120.39 (13)	C14—C13—H11	120.2
C1—C2—H2	119.8	C14—C13—C12	119.51 (15)
N1—C1—C2	120.87 (13)	C12—C13—H11	120.2
N1—C1—H1	119.6	C11—C12—C13	121.73 (15)
C2—C1—H1	119.6	C11—C12—H10	119.1
N1—C5—C4	120.31 (13)	C13—C12—H10	119.1
N1—C5—H4	119.8	C16—C17—H17	109.5
C4—C5—H4	119.8	C16—C17—H15	109.5
N1—C16—H13	109.4	C16—C17—H16	109.5
N1—C16—H14	109.4	H17—C17—H15	109.5
N1—C16—C17	111.19 (12)	H17—C17—H16	109.5
H13—C16—H14	108.0	H15—C17—H16	109.5
C17—C16—H13	109.4	N2—B1—N3	117.28 (12)
C17—C16—H14	109.4	N2—B1—C3	121.20 (12)
C6—C15—C10	119.13 (13)	N3—B1—C3	121.51 (12)
C14—C15—C6	121.19 (12)
N2—C6—C15—C14	0.62 (19)	C16—N1—C1—C2	−176.98 (12)
N2—C6—C15—C10	−177.51 (12)	C16—N1—C5—C4	177.77 (13)
N2—C6—C7—C8	177.40 (14)	C15—C6—C7—C8	−1.1 (2)
N3—C14—C13—C12	−176.41 (14)	C15—C14—C13—C12	2.2 (2)
C6—N2—B1—N3	−0.9 (2)	C15—C10—C11—C12	1.4 (2)
C6—N2—B1—C3	179.14 (12)	C15—C10—C9—C8	0.5 (2)
C6—C15—C14—N3	−0.94 (19)	C14—N3—B1—N2	0.5 (2)
C6—C15—C14—C13	−179.61 (13)	C14—N3—B1—C3	−179.49 (12)
C6—C15—C10—C11	177.85 (12)	C14—C15—C10—C11	−0.31 (19)
C6—C15—C10—C9	−0.70 (19)	C14—C15—C10—C9	−178.86 (13)
C6—C7—C8—C9	0.8 (2)	C14—C13—C12—C11	−1.1 (3)
C4—C3—C2—C1	−0.5 (2)	C7—C6—C15—C14	179.15 (13)
C4—C3—B1—N2	176.79 (13)	C7—C6—C15—C10	1.0 (2)
C4—C3—B1—N3	−3.2 (2)	C10—C15—C14—N3	177.18 (12)
C3—C4—C5—N1	−0.7 (2)	C10—C15—C14—C13	−1.5 (2)
C3—C2—C1—N1	−0.9 (2)	C10—C11—C12—C13	−0.7 (2)
C2—C3—B1—N2	−3.24 (19)	C10—C9—C8—C7	−0.5 (2)
C2—C3—B1—N3	176.80 (13)	C11—C10—C9—C8	−178.03 (15)
C1—N1—C5—C4	−0.7 (2)	C9—C10—C11—C12	179.89 (15)
C1—N1—C16—C17	84.82 (17)	B1—N2—C6—C15	0.33 (19)
C5—N1—C1—C2	1.6 (2)	B1—N2—C6—C7	−178.18 (13)
C5—N1—C16—C17	−93.72 (17)	B1—N3—C14—C15	0.3 (2)
C5—C4—C3—C2	1.3 (2)	B1—N3—C14—C13	178.99 (14)
C5—C4—C3—B1	−178.72 (13)	B1—C3—C2—C1	179.52 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···I1	0.81 (2)	2.96 (2)	3.7260 (13)	157.2 (18)
C2—H2···I1	0.93	3.16 (1)	4.0483 (14)	161 (1)
N3—H12···I1^i	0.82 (2)	3.02 (2)	3.7453 (12)	148.7 (18)
C16—H14···I1^ii	0.97	3.07 (1)	3.8981 (15)	144 (1)

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