Abstract
 
Computing details
Data collection: Smart (Bruker AXS); cell refinement: Saint (Bruker AXS); data reduction: Saint (Bruker AXS); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2013); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: ORTEP-3.2 for Windows; software used to prepare material for publication: publCIF (IUCR).
References
NOT FOUND
('selenium dicyanide 18-crown-6 adduct')
Crystal data
C_13.33H_24F_0N_1.33O_6Se_0.67 | F(000) = 1104
M_r = 351.64 | D_x = 1.404 Mg m^-3
Monoclinic, P2_1/n | Mo Ka radiation, l = 0.71073 Å
a = 14.766 (4) Å | q = 4.7–50.0°
b = 9.834 (3) Å | m = 1.55 mm^-1
c = 18.608 (5) Å | T = 133 K
b = 112.511 (5)° | Prism, colourless
V = 2496.2 (11)  Å^3 | 0.33 × 0.27 × 0.18 mm
Z = 6 |

Data collection

Bruker AXS Smart CCD 
diffractometer

3817 reflections with I > 2s(I)

Radiation source: sealed tube | R_int = 0.063
w scan | q_max = 25.1°, q_min = 2.2°

Absorption correction: multi-scan 
SADABS2008/1 (Bruker-AXS)

h = -12®17

T_min = 0.500, T_max = 0.745 | k = -11®11
25644 measured reflections | l = -22®22
4444 independent reflections |

Refinement
Refinement on F^2 | 0 restraints
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2s(F^2)] = 0.045 | H-atom parameters constrained

wR(F^2) = 0.121

w = 1/[s^2(F_o^2) + (0.0605P)^2 + 5.2754P]   
where P = (F_o^2 + 2F_c^2)/3

S = 1.04 | (D/s)_max = 0.001
4444 reflections | Dρ_max = 2.47 e Å^-3
289 parameters | Dρ_min = -0.66 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2)
| x | y | z | U_iso*/U_eq
Se1 | 0.00011 (2) | 0.36871 (3) | 0.77989 (2) | 0.02259 (13)
O3 | 0.91843 (16) | 0.1788 (2) | 0.64092 (12) | 0.0203 (5)
O5 | 0.78553 (17) | 0.5262 (2) | 0.75618 (13) | 0.0238 (5)
O8 | 0.11409 (19) | 0.5325 (3) | 0.62796 (16) | 0.0346 (6)
N1 | 0.0202 (3) | 0.6715 (3) | 0.7901 (2) | 0.0383 (8)
O2 | 1.02373 (17) | 0.0792 (2) | 0.79813 (12) | 0.0214 (5)
O7 | 0.20220 (19) | 0.3234 (3) | 0.57732 (15) | 0.0326 (6)
O4 | 0.84145 (17) | 0.4471 (2) | 0.63324 (12) | 0.0216 (5)
O6 | 0.89631 (17) | 0.4453 (2) | 0.91330 (13) | 0.0221 (5)
O9 | -0.04267 (19) | 0.8191 (3) | 0.55205 (16) | 0.0324 (6)
O1 | 0.97265 (16) | 0.1720 (2) | 0.92547 (12) | 0.0210 (5)
C6 | 0.8312 (3) | 0.3659 (3) | 0.56666 (19) | 0.0248 (7)
H6A | 0.8245 | 0.4256 | 0.5221 | 0.030*
H6B | 0.7715 | 0.3092 | 0.5522 | 0.030*
C14 | 0.2311 (3) | 0.3571 (4) | 0.6572 (2) | 0.0321 (8)
H14A | 0.3009 | 0.3338 | 0.6859 | 0.039*
H14B | 0.1913 | 0.3055 | 0.6803 | 0.039*
C1N | 0.0121 (3) | 0.5582 (4) | 0.78609 (19) | 0.0251 (8)
C11 | 0.9118 (3) | 0.3553 (3) | 0.97680 (19) | 0.0224 (7)
H11A | 0.8529 | 0.2981 | 0.9662 | 0.027*
H11B | 0.9233 | 0.4083 | 1.0248 | 0.027*
C18 | -0.1445 (3) | 0.8459 (4) | 0.5221 (2) | 0.0337 (9)
H18A | -0.1547 | 0.9422 | 0.5325 | 0.040*
H18B | -0.1753 | 0.7889 | 0.5503 | 0.040*
C3 | 1.0006 (3) | 0.0026 (3) | 0.72803 (19) | 0.0227 (7)
H3A | 0.9347 | -0.0385 | 0.7129 | 0.027*
H3B | 1.0488 | -0.0716 | 0.7364 | 0.027*
C2N | 0.1236 (3) | 0.3554 (3) | 0.8595 (2) | 0.0259 (8)
C17 | -0.0176 (3) | 0.6786 (3) | 0.5697 (2) | 0.0271 (8)
H17A | -0.0307 | 0.6266 | 0.5212 | 0.033*
H17B | -0.0571 | 0.6390 | 0.5971 | 0.033*
C4 | 1.0028 (2) | 0.0944 (3) | 0.66511 (19) | 0.0223 (7)
H4A | 1.0627 | 0.1511 | 0.6845 | 0.027*
H4B | 1.0035 | 0.0400 | 0.6206 | 0.027*
C8 | 0.7662 (3) | 0.6088 (3) | 0.68921 (19) | 0.0243 (7)
H8A | 0.8217 | 0.6716 | 0.6975 | 0.029*
H8B | 0.7063 | 0.6636 | 0.6791 | 0.029*
C15 | 0.2158 (3) | 0.5065 (4) | 0.6628 (2) | 0.0333 (9)
H15A | 0.2416 | 0.5352 | 0.7180 | 0.040*
H15B | 0.2508 | 0.5579 | 0.6356 | 0.040*
C10 | 0.8029 (3) | 0.5089 (4) | 0.8876 (2) | 0.0236 (7)
H10A | 0.7959 | 0.5595 | 0.9312 | 0.028*
H10B | 0.7508 | 0.4389 | 0.8698 | 0.028*
N2 | 0.1994 (3) | 0.3468 (3) | 0.9080 (2) | 0.0386 (8)
C9 | 0.7920 (3) | 0.6041 (3) | 0.8224 (2) | 0.0241 (7)
H9A | 0.7322 | 0.6598 | 0.8102 | 0.029*
H9B | 0.8492 | 0.6659 | 0.8374 | 0.029*
C7 | 0.7524 (3) | 0.5174 (4) | 0.62135 (19) | 0.0252 (7)
H7A | 0.6996 | 0.4510 | 0.6154 | 0.030*
H7B | 0.7327 | 0.5721 | 0.5731 | 0.030*
C2 | 1.0215 (3) | -0.0033 (3) | 0.86022 (19) | 0.0225 (7)
H2A | 1.0676 | -0.0803 | 0.8687 | 0.027*
H2B | 0.9548 | -0.0408 | 0.8468 | 0.027*
C12 | 0.9985 (3) | 0.2670 (3) | 0.98788 (18) | 0.0223 (7)
H12A | 1.0543 | 0.3235 | 0.9886 | 0.027*
H12B | 1.0184 | 0.2182 | 1.0381 | 0.027*
C5 | 0.9191 (3) | 0.2770 (3) | 0.58489 (19) | 0.0250 (7)
H5A | 0.9174 | 0.2309 | 0.5371 | 0.030*
H5B | 0.9797 | 0.3323 | 0.6059 | 0.030*
C1 | 1.0497 (2) | 0.0798 (3) | 0.93258 (18) | 0.0215 (7)
H1A | 1.0620 | 0.0196 | 0.9780 | 0.026*
H1B | 1.1107 | 0.1308 | 0.9408 | 0.026*
C13 | 0.1956 (3) | 0.1803 (4) | 0.5638 (2) | 0.0348 (9)
H13A | 0.1584 | 0.1375 | 0.5922 | 0.042*
H13B | 0.2621 | 0.1400 | 0.5830 | 0.042*
C16 | 0.0894 (3) | 0.6723 (4) | 0.6206 (2) | 0.0271 (8)
H16A | 0.1286 | 0.7223 | 0.5964 | 0.033*
H16B | 0.1015 | 0.7128 | 0.6722 | 0.033*

Atomic displacement parameters (Å^2)
| U^11 | U^22 | U^33 | U^12 | U^13 | U^23
Se1 | 0.0257 (2) | 0.0175 (2) | 0.02066 (19) | -0.00168 (13) | 0.00448 (14) | 0.00052 (13)
O3 | 0.0252 (13) | 0.0187 (11) | 0.0167 (11) | 0.0004 (9) | 0.0078 (10) | 0.0016 (9)
O5 | 0.0302 (14) | 0.0200 (12) | 0.0171 (11) | 0.0029 (10) | 0.0042 (10) | 0.0006 (9)
O8 | 0.0264 (14) | 0.0234 (13) | 0.0473 (16) | -0.0018 (10) | 0.0067 (12) | -0.0021 (12)
N1 | 0.042 (2) | 0.0230 (18) | 0.042 (2) | 0.0000 (14) | 0.0062 (16) | 0.0004 (14)
O2 | 0.0324 (13) | 0.0138 (11) | 0.0154 (11) | -0.0031 (10) | 0.0064 (10) | 0.0002 (9)
O7 | 0.0345 (15) | 0.0244 (13) | 0.0335 (14) | 0.0006 (11) | 0.0070 (12) | -0.0003 (11)
O4 | 0.0251 (13) | 0.0201 (12) | 0.0141 (11) | 0.0021 (9) | 0.0012 (9) | 0.0002 (9)
O6 | 0.0257 (13) | 0.0217 (12) | 0.0191 (11) | 0.0013 (10) | 0.0088 (10) | 0.0016 (9)
O9 | 0.0310 (14) | 0.0227 (13) | 0.0446 (16) | 0.0001 (11) | 0.0157 (12) | -0.0041 (12)
O1 | 0.0229 (12) | 0.0185 (11) | 0.0156 (11) | -0.0001 (9) | 0.0007 (9) | -0.0038 (9)
C6 | 0.034 (2) | 0.0226 (17) | 0.0117 (15) | -0.0028 (14) | 0.0025 (14) | 0.0004 (13)
C14 | 0.027 (2) | 0.032 (2) | 0.032 (2) | -0.0009 (15) | 0.0047 (16) | 0.0003 (16)
C1N | 0.0277 (19) | 0.0177 (19) | 0.0244 (18) | -0.0016 (14) | 0.0037 (15) | 0.0023 (14)
C11 | 0.0309 (19) | 0.0187 (16) | 0.0189 (16) | -0.0047 (14) | 0.0113 (15) | -0.0027 (13)
C18 | 0.030 (2) | 0.0268 (19) | 0.048 (2) | 0.0034 (15) | 0.0194 (18) | -0.0075 (17)
C3 | 0.0280 (19) | 0.0141 (15) | 0.0224 (17) | 0.0023 (13) | 0.0058 (14) | -0.0040 (13)
C2N | 0.025 (2) | 0.0213 (17) | 0.0246 (18) | -0.0019 (14) | 0.0024 (16) | 0.0036 (14)
C17 | 0.033 (2) | 0.0201 (17) | 0.0309 (19) | -0.0019 (15) | 0.0149 (16) | -0.0048 (15)
C4 | 0.0226 (18) | 0.0243 (17) | 0.0190 (16) | -0.0002 (14) | 0.0068 (14) | -0.0054 (14)
C8 | 0.0267 (19) | 0.0211 (17) | 0.0191 (16) | 0.0047 (14) | 0.0020 (14) | 0.0052 (13)
C15 | 0.026 (2) | 0.032 (2) | 0.034 (2) | -0.0031 (16) | 0.0030 (16) | -0.0059 (16)
C10 | 0.0227 (18) | 0.0250 (17) | 0.0238 (17) | 0.0003 (14) | 0.0095 (14) | -0.0055 (14)
N2 | 0.038 (2) | 0.0284 (17) | 0.0390 (19) | -0.0014 (14) | 0.0026 (17) | 0.0039 (14)
C9 | 0.0254 (19) | 0.0211 (17) | 0.0245 (17) | 0.0039 (14) | 0.0083 (15) | -0.0037 (14)
C7 | 0.0253 (19) | 0.0249 (18) | 0.0191 (16) | 0.0036 (14) | 0.0014 (14) | 0.0048 (14)
C2 | 0.0292 (19) | 0.0137 (15) | 0.0242 (17) | 0.0026 (13) | 0.0099 (15) | 0.0051 (13)
C12 | 0.0307 (19) | 0.0185 (16) | 0.0140 (15) | -0.0063 (14) | 0.0043 (14) | -0.0024 (12)
C5 | 0.036 (2) | 0.0233 (17) | 0.0163 (16) | -0.0044 (15) | 0.0109 (15) | 0.0003 (13)
C1 | 0.0229 (18) | 0.0202 (16) | 0.0183 (16) | 0.0027 (13) | 0.0044 (14) | 0.0066 (13)
C13 | 0.034 (2) | 0.0243 (19) | 0.046 (2) | 0.0044 (16) | 0.0153 (18) | -0.0001 (17)
C16 | 0.035 (2) | 0.0242 (18) | 0.0246 (18) | -0.0031 (15) | 0.0140 (16) | -0.0045 (14)

Geometric parameters (Å, º)
Se1—C2N | 1.863 (4) | O6—C11 | 1.423 (4)
Se1—C1N | 1.871 (4) | O9—C18 | 1.414 (5)
O3—C4 | 1.418 (4) | O9—C17 | 1.435 (4)
O3—C5 | 1.424 (4) | O1—C1 | 1.421 (4)
O5—C8 | 1.422 (4) | O1—C12 | 1.424 (4)
O5—C9 | 1.423 (4) | C6—C5 | 1.493 (5)
O8—C15 | 1.412 (5) | C14—C15 | 1.496 (5)
O8—C16 | 1.416 (4) | C11—C12 | 1.494 (5)
N1—C1N | 1.121 (5) | C18—C13^i | 1.504 (6)
O2—C2 | 1.422 (4) | C3—C4 | 1.489 (5)
O2—C3 | 1.430 (4) | C2N—N2 | 1.140 (5)
O7—C14 | 1.421 (5) | C17—C16 | 1.500 (5)
O7—C13 | 1.426 (5) | C8—C7 | 1.499 (5)
O4—C7 | 1.426 (4) | C10—C9 | 1.492 (5)
O4—C6 | 1.432 (4) | C2—C1 | 1.492 (5)
O6—C10 | 1.420 (4) | C13—C18^i | 1.504 (6)
C2N—Se1—C1N | 88.88 (15) | O2—C3—C4 | 109.2 (3)
C4—O3—C5 | 112.2 (3) | N2—C2N—Se1 | 179.6 (4)
C8—O5—C9 | 112.1 (2) | O9—C17—C16 | 107.5 (3)
C15—O8—C16 | 114.2 (3) | O3—C4—C3 | 108.9 (3)
C2—O2—C3 | 111.6 (2) | O5—C8—C7 | 108.2 (3)
C14—O7—C13 | 112.9 (3) | O8—C15—C14 | 108.0 (3)
C7—O4—C6 | 110.5 (2) | O6—C10—C9 | 109.8 (3)
C10—O6—C11 | 112.3 (2) | O5—C9—C10 | 108.5 (3)
C18—O9—C17 | 114.4 (3) | O4—C7—C8 | 109.9 (3)
C1—O1—C12 | 112.8 (2) | O2—C2—C1 | 109.6 (3)
O4—C6—C5 | 109.6 (3) | O1—C12—C11 | 108.7 (3)
O7—C14—C15 | 108.0 (3) | O3—C5—C6 | 108.3 (3)
N1—C1N—Se1 | 179.3 (4) | O1—C1—C2 | 109.2 (3)
O6—C11—C12 | 109.4 (3) | O7—C13—C18^i | 109.2 (3)
O9—C18—C13^i | 114.3 (3) | O8—C16—C17 | 105.7 (3)

Symmetry code:  (i) -x, -y+1, -z+1.