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

The cation of the title hydrated salt, C₁₇H₁₇BN₃⁺·I⁻·H₂O, is a di­aza­borinane featuring substitution at the 1, 2, and 3 positions in the nitro­gen–boron six-membered heterocycle. The cation is approximately planar with a dihedral angle between the pyridyl ring and the di­aza­borinane ring system of 5.40 (5)°. In the crystal, the cations stack along [100] in an alternating head-to-tail manner, while the iodide ion and water mol­ecule form one-dimensional hydrogen-bonded chains beside the cation stack. The cation stacks and I⁻–water chains are crosslinked by N—H...I and N—H...O hydrogen bonds.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.056
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.32 Report
PLAT756_ALERT_4_C H...A   Calc     3.14000, Rep   3.1403(8) ......  Senseless s.u.
              H2       -I1              1_555   1_555 ........     #    5 Check
PLAT756_ALERT_4_C H...A   Calc     2.98000, Rep   2.9846(8) ......  Senseless s.u.
              H14      -I1              1_555   1_554 ........     #    6 Check
PLAT756_ALERT_4_C H...A   Calc     3.15000, Rep   3.1541(9) ......  Senseless s.u.
              H13      -I1              1_555   4_575 ........     #    7 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.468 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         18 Report
                2  0  0,   0  4  0,   2  5  0,   0  6  0,  -2  1  1,   0  4  1,
                1  4  1,   7  9  1,  -7 10  1,  -1  0  2,   0  0  2,   0  2  2,
               -7 10  2,   0  2  3,  -1  4  5,   0  4  5,   6  9  6,  -4 12  6,
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note
                2  0  0,   0  6  0,  -2  1  1,   1  4  1,   0  0  2,

Alert level G
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2       ..I1       .       3.14 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13      ..I1       .       3.15 Ang.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              H2 O
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
                1  0  0,   0  2  0,   0  1  1,   0  2  1,
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.5 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.21 Note
              Predicted wR2: Based on SigI   2  2.51 or SHELX Weight  5.48       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 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
   8 ALERT level G = General information/check it is not something unexpected

   1 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
   5 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 monohydrate

Crystal data

C17H17BN3^+·I^−·H2O	F(000) = 832
Mr = 419.06	Dx = 1.652 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 6.746 (2) Å	Cell parameters from 6255 reflections
b = 23.041 (7) Å	θ = 1.8–30.9°
c = 10.939 (3) Å	µ = 1.91 mm^−1
β = 97.616 (5)°	T = 93 K
V = 1685.4 (9) Å^3	Block, pale yellow
Z = 4	0.18 × 0.18 × 0.10 mm

Data collection

Saturn724+ diffractometer	3463 reflections with I > 2σ(I)
Detector resolution: 28.445 pixels mm^-1	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −6→8
Tmin = 0.879, Tmax = 0.900	k = −22→29
13511 measured reflections	l = −14→14
3846 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0201P)^2 + 1.9341P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
3846 reflections	Δρmax = 0.92 e Å^−3
224 parameters	Δρmin = −0.40 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. The positions of the N-bound and 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(carrier) or 1.5U_eq(methyl carrier).

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

	x	y	z	Uiso*/Ueq
I1	0.89530 (2)	0.83028 (2)	0.76189 (2)	0.01877 (6)
O1	0.6094 (4)	1.10388 (9)	0.20283 (18)	0.0265 (4)
N1	0.7490 (3)	0.86217 (8)	0.19278 (17)	0.0134 (4)
N2	0.7739 (3)	0.97508 (8)	0.61095 (18)	0.0129 (4)
N3	0.7269 (3)	1.05026 (8)	0.45657 (18)	0.0134 (4)
C9	0.7933 (3)	1.09991 (10)	0.8927 (2)	0.0151 (5)
H8	0.8004	1.1279	0.9569	0.018*
C3	0.7379 (3)	0.94374 (10)	0.3791 (2)	0.0126 (4)
C14	0.7397 (3)	1.09351 (10)	0.5472 (2)	0.0125 (4)
C12	0.7480 (3)	1.19358 (10)	0.6120 (2)	0.0164 (5)
H10	0.7463	1.2336	0.5911	0.020*
C5	0.7167 (3)	0.91855 (10)	0.1633 (2)	0.0150 (5)
H4	0.6979	0.9300	0.0791	0.018*
C7	0.7968 (3)	0.99955 (10)	0.8283 (2)	0.0152 (5)
H6	0.8050	0.9596	0.8500	0.018*
C11	0.7647 (3)	1.17771 (10)	0.7336 (2)	0.0165 (5)
H9	0.7718	1.2068	0.7956	0.020*
C1	0.7676 (3)	0.84457 (10)	0.3109 (2)	0.0139 (4)
H1	0.7844	0.8045	0.3298	0.017*
C13	0.7334 (3)	1.15171 (10)	0.5175 (2)	0.0159 (5)
H11	0.7192	1.1635	0.4336	0.019*
C4	0.7108 (3)	0.95958 (10)	0.2540 (2)	0.0148 (5)
H3	0.6880	0.9991	0.2318	0.018*
C8	0.8044 (3)	1.04216 (10)	0.9213 (2)	0.0163 (5)
H7	0.8174	1.0305	1.0053	0.020*
C17	0.5808 (4)	0.78797 (11)	0.0480 (2)	0.0214 (5)
H16	0.6051	0.7605	−0.0168	0.026*
H15	0.5339	0.7668	0.1165	0.026*
H17	0.4789	0.8161	0.0145	0.026*
C15	0.7622 (3)	1.07573 (9)	0.6732 (2)	0.0117 (4)
C6	0.7776 (3)	1.01577 (10)	0.7059 (2)	0.0126 (4)
C10	0.7714 (3)	1.11839 (10)	0.7680 (2)	0.0133 (4)
C2	0.7624 (3)	0.88432 (10)	0.4052 (2)	0.0144 (4)
H2	0.7756	0.8713	0.4883	0.017*
C16	0.7726 (3)	0.81952 (10)	0.0940 (2)	0.0161 (5)
H13	0.8756	0.7907	0.1259	0.019*
H14	0.8206	0.8400	0.0240	0.019*
B1	0.7452 (4)	0.99074 (11)	0.4849 (2)	0.0127 (5)
H12	0.704 (4)	1.0625 (12)	0.386 (3)	0.024 (8)*
H5	0.787 (4)	0.9418 (13)	0.639 (3)	0.022 (8)*
H18	0.704 (6)	1.1246 (18)	0.201 (4)	0.058 (13)*
H19	0.517 (6)	1.1225 (17)	0.212 (3)	0.049 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02772 (10)	0.01391 (8)	0.01487 (8)	0.00169 (6)	0.00351 (6)	0.00146 (6)
O1	0.0302 (12)	0.0232 (10)	0.0257 (10)	−0.0001 (9)	0.0025 (9)	0.0040 (8)
N1	0.0122 (10)	0.0158 (10)	0.0123 (9)	−0.0011 (7)	0.0020 (7)	−0.0026 (7)
N2	0.0141 (10)	0.0104 (9)	0.0141 (9)	0.0002 (7)	0.0011 (7)	0.0004 (7)
N3	0.0157 (10)	0.0151 (10)	0.0089 (9)	0.0000 (7)	−0.0007 (7)	0.0008 (7)
C9	0.0120 (11)	0.0190 (12)	0.0146 (11)	−0.0001 (9)	0.0022 (8)	−0.0020 (9)
C3	0.0063 (10)	0.0146 (11)	0.0167 (11)	−0.0008 (8)	0.0008 (8)	−0.0002 (8)
C14	0.0087 (11)	0.0153 (11)	0.0132 (10)	0.0012 (8)	−0.0001 (8)	−0.0010 (8)
C12	0.0140 (12)	0.0128 (11)	0.0215 (12)	0.0020 (9)	−0.0010 (9)	0.0015 (9)
C5	0.0138 (11)	0.0187 (12)	0.0120 (10)	−0.0018 (9)	−0.0006 (8)	0.0016 (9)
C7	0.0152 (12)	0.0143 (11)	0.0157 (11)	−0.0001 (9)	0.0002 (8)	0.0011 (8)
C11	0.0122 (11)	0.0154 (11)	0.0216 (12)	0.0012 (9)	0.0006 (9)	−0.0033 (9)
C1	0.0117 (11)	0.0144 (11)	0.0157 (11)	−0.0014 (8)	0.0017 (8)	−0.0002 (8)
C13	0.0161 (12)	0.0156 (11)	0.0157 (11)	0.0006 (9)	0.0002 (9)	0.0028 (9)
C4	0.0131 (12)	0.0154 (11)	0.0153 (11)	−0.0007 (9)	0.0000 (8)	0.0013 (8)
C8	0.0157 (12)	0.0197 (12)	0.0133 (11)	0.0010 (9)	0.0010 (9)	0.0005 (9)
C17	0.0164 (13)	0.0222 (13)	0.0250 (13)	−0.0001 (10)	0.0008 (10)	−0.0090 (10)
C15	0.0061 (10)	0.0141 (11)	0.0146 (10)	0.0015 (8)	0.0007 (8)	−0.0004 (8)
C6	0.0091 (11)	0.0144 (11)	0.0143 (10)	−0.0007 (8)	0.0016 (8)	0.0001 (8)
C10	0.0082 (11)	0.0151 (11)	0.0163 (11)	0.0019 (8)	−0.0002 (8)	−0.0013 (9)
C2	0.0140 (11)	0.0171 (11)	0.0122 (10)	0.0003 (9)	0.0019 (8)	0.0012 (8)
C16	0.0161 (12)	0.0172 (12)	0.0155 (11)	−0.0001 (9)	0.0038 (9)	−0.0045 (9)
B1	0.0062 (11)	0.0173 (12)	0.0142 (12)	0.0012 (9)	−0.0006 (9)	0.0004 (10)

Geometric parameters (Å, º)

O1—H18	0.80 (4)	C5—H4	0.9500
O1—H19	0.77 (4)	C5—C4	1.375 (3)
N1—C5	1.349 (3)	C7—H6	0.9500
N1—C1	1.344 (3)	C7—C8	1.410 (3)
N1—C16	1.485 (3)	C7—C6	1.380 (3)
N2—C6	1.397 (3)	C11—H9	0.9500
N2—B1	1.413 (3)	C11—C10	1.417 (3)
N2—H5	0.83 (3)	C1—H1	0.9500
N3—C14	1.400 (3)	C1—C2	1.383 (3)
N3—B1	1.408 (3)	C13—H11	0.9500
N3—H12	0.81 (3)	C4—H3	0.9500
C9—H8	0.9500	C8—H7	0.9500
C9—C8	1.367 (3)	C17—H16	0.9800
C9—C10	1.418 (3)	C17—H15	0.9800
C3—C4	1.404 (3)	C17—H17	0.9800
C3—C2	1.404 (3)	C17—C16	1.511 (3)
C3—B1	1.581 (3)	C15—C6	1.427 (3)
C14—C13	1.379 (3)	C15—C10	1.424 (3)
C14—C15	1.426 (3)	C2—H2	0.9500
C12—H10	0.9500	C16—H13	0.9900
C12—C11	1.370 (3)	C16—H14	0.9900
C12—C13	1.408 (3)
H18—O1—H19	109 (4)	C14—C13—H11	120.1
C5—N1—C16	119.52 (19)	C12—C13—H11	120.1
C1—N1—C5	120.79 (19)	C3—C4—H3	119.6
C1—N1—C16	119.64 (19)	C5—C4—C3	120.8 (2)
C6—N2—B1	122.7 (2)	C5—C4—H3	119.6
C6—N2—H5	111 (2)	C9—C8—C7	121.1 (2)
B1—N2—H5	127 (2)	C9—C8—H7	119.4
C14—N3—B1	122.82 (19)	C7—C8—H7	119.4
C14—N3—H12	114 (2)	H16—C17—H15	109.5
B1—N3—H12	123 (2)	H16—C17—H17	109.5
C8—C9—H8	119.7	H15—C17—H17	109.5
C8—C9—C10	120.5 (2)	C16—C17—H16	109.5
C10—C9—H8	119.7	C16—C17—H15	109.5
C4—C3—B1	121.5 (2)	C16—C17—H17	109.5
C2—C3—C4	116.6 (2)	C14—C15—C6	121.0 (2)
C2—C3—B1	121.8 (2)	C10—C15—C14	119.6 (2)
N3—C14—C15	117.9 (2)	C10—C15—C6	119.4 (2)
C13—C14—N3	121.9 (2)	N2—C6—C15	117.99 (19)
C13—C14—C15	120.2 (2)	C7—C6—N2	122.0 (2)
C11—C12—H10	119.4	C7—C6—C15	120.0 (2)
C11—C12—C13	121.3 (2)	C9—C10—C15	118.8 (2)
C13—C12—H10	119.4	C11—C10—C9	122.7 (2)
N1—C5—H4	119.7	C11—C10—C15	118.4 (2)
N1—C5—C4	120.6 (2)	C3—C2—H2	119.7
C4—C5—H4	119.7	C1—C2—C3	120.5 (2)
C8—C7—H6	120.0	C1—C2—H2	119.7
C6—C7—H6	120.0	N1—C16—C17	113.04 (19)
C6—C7—C8	120.1 (2)	N1—C16—H13	109.0
C12—C11—H9	119.6	N1—C16—H14	109.0
C12—C11—C10	120.7 (2)	C17—C16—H13	109.0
C10—C11—H9	119.6	C17—C16—H14	109.0
N1—C1—H1	119.7	H13—C16—H14	107.8
N1—C1—C2	120.6 (2)	N2—B1—C3	121.8 (2)
C2—C1—H1	119.7	N3—B1—N2	117.4 (2)
C14—C13—C12	119.7 (2)	N3—B1—C3	120.8 (2)
N1—C5—C4—C3	0.0 (3)	C8—C9—C10—C11	−178.3 (2)
N1—C1—C2—C3	−0.1 (3)	C8—C9—C10—C15	−0.3 (3)
N3—C14—C13—C12	−179.6 (2)	C8—C7—C6—N2	178.6 (2)
N3—C14—C15—C6	2.0 (3)	C8—C7—C6—C15	−1.0 (3)
N3—C14—C15—C10	−178.65 (19)	C15—C14—C13—C12	−0.4 (3)
C14—N3—B1—N2	1.2 (3)	C6—N2—B1—N3	2.3 (3)
C14—N3—B1—C3	−177.6 (2)	C6—N2—B1—C3	−178.9 (2)
C14—C15—C6—N2	1.2 (3)	C6—C7—C8—C9	−0.1 (3)
C14—C15—C6—C7	−179.2 (2)	C6—C15—C10—C9	−0.7 (3)
C14—C15—C10—C9	179.9 (2)	C6—C15—C10—C11	177.3 (2)
C14—C15—C10—C11	−2.1 (3)	C10—C9—C8—C7	0.8 (4)
C12—C11—C10—C9	178.5 (2)	C10—C15—C6—N2	−178.15 (19)
C12—C11—C10—C15	0.5 (3)	C10—C15—C6—C7	1.4 (3)
C5—N1—C1—C2	−2.8 (3)	C2—C3—C4—C5	−2.6 (3)
C5—N1—C16—C17	−96.2 (2)	C2—C3—B1—N2	−0.9 (3)
C11—C12—C13—C14	−1.3 (4)	C2—C3—B1—N3	177.9 (2)
C1—N1—C5—C4	2.8 (3)	C16—N1—C5—C4	−174.6 (2)
C1—N1—C16—C17	86.3 (3)	C16—N1—C1—C2	174.7 (2)
C13—C14—C15—C6	−177.3 (2)	B1—N2—C6—C7	177.0 (2)
C13—C14—C15—C10	2.1 (3)	B1—N2—C6—C15	−3.4 (3)
C13—C12—C11—C10	1.2 (4)	B1—N3—C14—C13	176.0 (2)
C4—C3—C2—C1	2.7 (3)	B1—N3—C14—C15	−3.2 (3)
C4—C3—B1—N2	−179.5 (2)	B1—C3—C4—C5	176.1 (2)
C4—C3—B1—N3	−0.8 (3)	B1—C3—C2—C1	−176.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H18···I1^i	0.80 (4)	2.87 (4)	3.643 (3)	162 (4)
O1—H19···I1^ii	0.77 (4)	3.04 (4)	3.793 (3)	167 (4)
N2—H5···I1	0.83 (3)	2.95 (3)	3.764 (2)	171 (2)
N3—H12···O1	0.82 (3)	2.23 (3)	3.046 (3)	172 (3)
C2—H2···I1	0.95	3.14	4.081 (2)	171
C16—H14···I1^iii	0.99	2.98	3.840 (3)	145
C16—H13···I1^iv	0.99	3.15	3.946 (3)	138

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