C—I...N short contacts as tools for the construction of the crystal packing in the crystal structure of 3,3′-(ethane-1,2-di­yl)bis­(6-iodo-3,4-di­hydro-2H-1,3-benzoxazine)

The packing of the title compound features short C—I...N contacts.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.076
• Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.344 Check

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT431_ALERT_2_G Short Inter HL..A  Contact I1     ..  N1      ..       3.38 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         29 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

3,3'-(Ethane-1,2-diyl)bis(6-iodo-3,4-dihydro-2H-1,3-benzoxazine)

Crystal data

C18H18I2N2O2	F(000) = 1048
Mr = 548.14	Dx = 2.017 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.4200 (9) Å	Cell parameters from 39259 reflections
b = 5.9477 (2) Å	θ = 3.3–29.9°
c = 17.8414 (8) Å	µ = 3.50 mm^−1
β = 123.607 (3)°	T = 173 K
V = 1804.69 (14) Å^3	Block, colourless
Z = 4	0.29 × 0.27 × 0.27 mm

Data collection

Stoe IPDS II two-circle diffractometer	2456 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.076
ω scans	θmax = 29.7°, θmin = 3.6°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −28→28
Tmin = 0.395, Tmax = 1.000	k = −7→8
39259 measured reflections	l = −24→24
2531 independent reflections

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)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0378P)^2 + 4.0804P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max = 0.002
S = 1.22	Δρmax = 1.46 e Å^−3
2531 reflections	Δρmin = −1.35 e Å^−3
110 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0034 (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.

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

	x	y	z	Uiso*/Ueq
I1	0.60686 (2)	−0.05887 (3)	0.93105 (2)	0.02375 (9)
O1	0.68205 (12)	0.6146 (3)	0.71878 (13)	0.0231 (4)
N1	0.60465 (12)	0.4020 (4)	0.58050 (14)	0.0174 (4)
C1	0.53347 (15)	0.5410 (4)	0.54603 (16)	0.0207 (5)
H1A	0.545662	0.699539	0.541455	0.025*
H1B	0.516975	0.534394	0.588747	0.025*
C2	0.67584 (15)	0.5254 (5)	0.63881 (17)	0.0214 (5)
H2A	0.678708	0.651795	0.604633	0.026*
H2B	0.721287	0.425521	0.657944	0.026*
C3	0.66459 (15)	0.4585 (4)	0.76215 (17)	0.0187 (4)
C4	0.62686 (14)	0.2547 (4)	0.72243 (15)	0.0171 (4)
C5	0.60538 (15)	0.1994 (4)	0.62851 (16)	0.0199 (4)
H5A	0.643793	0.090235	0.632478	0.024*
H5B	0.552776	0.128136	0.594033	0.024*
C6	0.61047 (15)	0.1080 (4)	0.77133 (16)	0.0191 (4)
H6	0.585192	−0.031336	0.745502	0.023*
C7	0.63083 (15)	0.1641 (5)	0.85739 (16)	0.0208 (5)
C8	0.66757 (17)	0.3687 (5)	0.89574 (17)	0.0250 (5)
H8	0.681043	0.407706	0.954297	0.030*
C9	0.68424 (17)	0.5143 (5)	0.84831 (17)	0.0236 (5)
H9	0.709313	0.653654	0.874439	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02726 (12)	0.02815 (12)	0.01965 (12)	0.00072 (6)	0.01537 (9)	0.00344 (6)
O1	0.0281 (9)	0.0214 (8)	0.0185 (8)	−0.0058 (7)	0.0121 (7)	−0.0023 (7)
N1	0.0167 (9)	0.0205 (9)	0.0129 (8)	0.0030 (7)	0.0069 (7)	0.0024 (7)
C1	0.0207 (11)	0.0228 (11)	0.0130 (10)	0.0046 (9)	0.0060 (9)	0.0010 (8)
C2	0.0188 (10)	0.0271 (12)	0.0168 (10)	−0.0008 (9)	0.0089 (9)	0.0013 (9)
C3	0.0185 (10)	0.0207 (11)	0.0150 (10)	0.0001 (8)	0.0081 (9)	0.0021 (8)
C4	0.0166 (9)	0.0219 (10)	0.0109 (9)	0.0022 (8)	0.0064 (8)	0.0017 (8)
C5	0.0248 (11)	0.0198 (10)	0.0133 (9)	0.0014 (9)	0.0093 (9)	−0.0005 (8)
C6	0.0196 (10)	0.0197 (10)	0.0154 (10)	0.0005 (8)	0.0081 (8)	0.0009 (8)
C7	0.0235 (11)	0.0227 (11)	0.0163 (10)	0.0011 (9)	0.0110 (9)	0.0030 (9)
C8	0.0338 (13)	0.0266 (13)	0.0156 (10)	−0.0017 (11)	0.0144 (10)	−0.0019 (9)
C9	0.0311 (13)	0.0224 (11)	0.0151 (10)	−0.0037 (10)	0.0114 (10)	−0.0032 (9)

Geometric parameters (Å, º)

I1—C7	2.107 (3)	C3—C4	1.400 (3)
O1—C3	1.376 (3)	C4—C6	1.399 (3)
O1—C2	1.460 (3)	C4—C5	1.515 (3)
N1—C2	1.435 (3)	C5—H5A	0.9900
N1—C5	1.474 (3)	C5—H5B	0.9900
N1—C1	1.478 (3)	C6—C7	1.391 (3)
C1—C1^i	1.523 (5)	C6—H6	0.9500
C1—H1A	0.9900	C7—C8	1.394 (4)
C1—H1B	0.9900	C8—C9	1.378 (4)
C2—H2A	0.9900	C8—H8	0.9500
C2—H2B	0.9900	C9—H9	0.9500
C3—C9	1.397 (4)
I1···N1^ii	3.378 (2)
C3—O1—C2	113.3 (2)	C6—C4—C5	122.1 (2)
C2—N1—C5	108.45 (19)	C3—C4—C5	119.3 (2)
C2—N1—C1	112.6 (2)	N1—C5—C4	111.6 (2)
C5—N1—C1	113.0 (2)	N1—C5—H5A	109.3
N1—C1—C1^i	111.0 (3)	C4—C5—H5A	109.3
N1—C1—H1A	109.4	N1—C5—H5B	109.3
C1^i—C1—H1A	109.4	C4—C5—H5B	109.3
N1—C1—H1B	109.4	H5A—C5—H5B	108.0
C1^i—C1—H1B	109.4	C7—C6—C4	120.7 (2)
H1A—C1—H1B	108.0	C7—C6—H6	119.7
N1—C2—O1	113.5 (2)	C4—C6—H6	119.7
N1—C2—H2A	108.9	C6—C7—C8	120.1 (2)
O1—C2—H2A	108.9	C6—C7—I1	120.46 (19)
N1—C2—H2B	108.9	C8—C7—I1	119.41 (18)
O1—C2—H2B	108.9	C9—C8—C7	119.7 (2)
H2A—C2—H2B	107.7	C9—C8—H8	120.2
O1—C3—C9	116.9 (2)	C7—C8—H8	120.2
O1—C3—C4	122.7 (2)	C8—C9—C3	120.5 (3)
C9—C3—C4	120.3 (2)	C8—C9—H9	119.7
C6—C4—C3	118.6 (2)	C3—C9—H9	119.7
C2—N1—C1—C1^i	150.8 (3)	C1—N1—C5—C4	−77.2 (2)
C5—N1—C1—C1^i	−85.9 (3)	C6—C4—C5—N1	161.7 (2)
C5—N1—C2—O1	−65.2 (3)	C3—C4—C5—N1	−18.6 (3)
C1—N1—C2—O1	60.5 (3)	C3—C4—C6—C7	0.4 (4)
C3—O1—C2—N1	47.5 (3)	C5—C4—C6—C7	−179.9 (2)
C2—O1—C3—C9	167.3 (2)	C4—C6—C7—C8	0.3 (4)
C2—O1—C3—C4	−14.5 (3)	C4—C6—C7—I1	−179.47 (18)
O1—C3—C4—C6	−179.0 (2)	C6—C7—C8—C9	−0.6 (4)
C9—C3—C4—C6	−0.9 (4)	I1—C7—C8—C9	179.2 (2)
O1—C3—C4—C5	1.2 (4)	C7—C8—C9—C3	0.1 (4)
C9—C3—C4—C5	179.3 (2)	O1—C3—C9—C8	178.9 (3)
C2—N1—C5—C4	48.3 (3)	C4—C3—C9—C8	0.7 (4)

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