Crystal structures of two bis­(iodo­meth­yl)benzene derivatives: similarities and differences in the crystal packing

The mol­ecular and crystal structures of two isomeric bis­(iodo­meth­yl)benzene derivatives are reported. A comparison is made of the inter­molecular contacts stabilizing the packing in the two closely related systems.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.044
• Data-to-parameter ratio = 36.2

Structure: II

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.024
• wR factor = 0.048
• Data-to-parameter ratio = 37.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  I1      ..       3.38 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H112   ..  I1      ..       3.33 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  I1      ..       3.36 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2     ..  I1      ..       4.26 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        129 Note

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

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




Datablock: _II



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B   ..  I1      ..       3.22 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  I1      ..       3.25 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31A   ..  I3      ..       3.27 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C31    ..  I3      ..       4.22 Ang.

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        264 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 and SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

(I) 1,2-Bis(iodomethyl)benzene

Crystal data

C8H8I2	F(000) = 648
Mr = 357.94	Dx = 2.573 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.5485 (5) Å	Cell parameters from 5091 reflections
b = 8.0461 (3) Å	θ = 2.6–32.9°
c = 8.0582 (3) Å	µ = 6.74 mm^−1
β = 101.637 (2)°	T = 90 K
V = 923.89 (6) Å^3	Block, colourless
Z = 4	0.31 × 0.17 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	1552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
ω scans	θmax = 33.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −21→21
Tmin = 0.534, Tmax = 1.000	k = −11→12
8422 measured reflections	l = −12→10
1667 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.018	H-atom parameters constrained
wR(F^2) = 0.044	w = 1/[σ^2(Fo^2) + (0.0175P)^2 + 1.2212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.002
1667 reflections	Δρmax = 0.52 e Å^−3
46 parameters	Δρmin = −1.23 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. One low angle reflection with F_o << Fc was omitted from the final refinement cycles.

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

	x	y	z	Uiso*/Ueq
I1	0.31503 (2)	0.11885 (2)	0.75250 (2)	0.01529 (5)
C11	0.41526 (13)	0.2215 (2)	0.6102 (3)	0.0142 (3)
H111	0.4651	0.1386	0.6070	0.017*
H112	0.3826	0.2433	0.4921	0.017*
C1	0.45886 (13)	0.3782 (2)	0.6864 (2)	0.0111 (3)
C2	0.41839 (13)	0.5301 (2)	0.6268 (3)	0.0136 (3)
H2	0.3623	0.5307	0.5427	0.016*
C3	0.45882 (14)	0.6802 (2)	0.6886 (3)	0.0156 (4)
H3	0.4304	0.7823	0.6470	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01370 (7)	0.01474 (7)	0.01747 (8)	−0.00335 (4)	0.00325 (5)	0.00078 (4)
C11	0.0139 (8)	0.0163 (8)	0.0132 (9)	−0.0016 (6)	0.0044 (7)	−0.0027 (7)
C1	0.0115 (8)	0.0123 (8)	0.0102 (8)	−0.0008 (5)	0.0039 (6)	−0.0001 (6)
C2	0.0131 (8)	0.0158 (8)	0.0122 (9)	0.0026 (6)	0.0035 (7)	0.0011 (7)
C3	0.0212 (9)	0.0122 (8)	0.0153 (9)	0.0026 (7)	0.0085 (7)	0.0031 (7)

Geometric parameters (Å, º)

I1—C11	2.1902 (19)	C1—C1^i	1.410 (4)
C11—C1	1.487 (3)	C2—C3	1.391 (3)
C11—H111	0.9900	C2—H2	0.9500
C11—H112	0.9900	C3—C3^i	1.392 (4)
C1—C2	1.399 (3)	C3—H3	0.9500
C1—C11—I1	112.15 (13)	C1^i—C1—C11	121.93 (11)
C1—C11—H111	109.2	C3—C2—C1	121.16 (18)
I1—C11—H111	109.2	C3—C2—H2	119.4
C1—C11—H112	109.2	C1—C2—H2	119.4
I1—C11—H112	109.2	C2—C3—C3^i	119.72 (12)
H111—C11—H112	107.9	C2—C3—H3	120.1
C2—C1—C1^i	119.10 (11)	C3^i—C3—H3	120.1
C2—C1—C11	118.94 (18)
I1—C11—C1—C2	−93.41 (19)	C11—C1—C2—C3	−177.12 (17)
I1—C11—C1—C1^i	88.3 (2)	C1—C2—C3—C3^i	0.2 (3)
C1^i—C1—C2—C3	1.2 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···I1^ii	0.95	3.38	4.046 (2)	129
C11—H112···I1^iii	0.99	3.33	4.179 (2)	145
C2—H2···I1^iii	0.95	3.36	4.257 (2)	158

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

(II) 1,3-Bis(iodomethyl)benzene

Crystal data

C8H8I2	F(000) = 648
Mr = 357.94	Dx = 2.483 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5323 (3) Å	θ = 2.6–33.0°
b = 4.5464 (1) Å	µ = 6.50 mm^−1
c = 15.6269 (4) Å	T = 90 K
β = 95.203 (1)°	Needle, colourless
V = 957.46 (4) Å^3	0.45 × 0.06 × 0.05 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	2826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
ω scans	θmax = 33.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −20→20
Tmin = 0.569, Tmax = 1.000	k = −6→5
16804 measured reflections	l = −23→24
3435 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.048	w = 1/[σ^2(Fo^2) + (0.0109P)^2 + 1.4343P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
3435 reflections	Δρmax = 1.24 e Å^−3
91 parameters	Δρmin = −0.77 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
I1	0.35561 (2)	0.36401 (4)	0.46514 (2)	0.01445 (4)
C11	0.4498 (2)	0.1469 (6)	0.37746 (17)	0.0197 (5)
H11A	0.5193	0.1461	0.4034	0.024*
H11B	0.4282	−0.0599	0.3690	0.024*
C1	0.44471 (19)	0.2984 (6)	0.29275 (16)	0.0152 (5)
C2	0.51858 (18)	0.4993 (5)	0.27547 (16)	0.0138 (5)
H2	0.5707	0.5419	0.3185	0.017*
C3	0.51650 (18)	0.6379 (5)	0.19574 (16)	0.0128 (4)
C31	0.59593 (19)	0.8514 (6)	0.17788 (17)	0.0175 (5)
H31A	0.6261	0.9352	0.2326	0.021*
H31B	0.5667	1.0148	0.1421	0.021*
I3	0.71036 (2)	0.63230 (4)	0.11079 (2)	0.01692 (5)
C4	0.43920 (19)	0.5755 (6)	0.13244 (16)	0.0171 (5)
H4	0.4369	0.6696	0.0780	0.021*
C5	0.36591 (19)	0.3753 (6)	0.14961 (17)	0.0179 (5)
H5	0.3138	0.3322	0.1066	0.022*
C6	0.36832 (19)	0.2379 (6)	0.22919 (18)	0.0178 (5)
H6	0.3177	0.1021	0.2404	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01484 (7)	0.01475 (9)	0.01451 (8)	0.00033 (6)	0.00534 (5)	0.00083 (6)
C11	0.0223 (12)	0.0167 (13)	0.0216 (12)	0.0064 (11)	0.0091 (10)	0.0020 (11)
C1	0.0174 (11)	0.0125 (12)	0.0167 (11)	0.0032 (10)	0.0065 (9)	0.0003 (9)
C2	0.0149 (11)	0.0112 (12)	0.0155 (11)	0.0011 (9)	0.0035 (9)	−0.0025 (9)
C3	0.0139 (10)	0.0097 (11)	0.0153 (10)	0.0010 (9)	0.0044 (8)	−0.0013 (9)
C31	0.0191 (12)	0.0131 (13)	0.0215 (12)	−0.0020 (10)	0.0083 (10)	−0.0037 (10)
I3	0.01582 (8)	0.01765 (9)	0.01833 (8)	−0.00134 (6)	0.00728 (6)	−0.00027 (6)
C4	0.0184 (11)	0.0182 (13)	0.0148 (11)	0.0024 (10)	0.0016 (9)	0.0005 (10)
C5	0.0152 (11)	0.0191 (13)	0.0190 (12)	0.0004 (10)	−0.0012 (9)	−0.0044 (10)
C6	0.0153 (11)	0.0147 (13)	0.0243 (13)	−0.0029 (10)	0.0057 (10)	−0.0010 (11)

Geometric parameters (Å, º)

I1—C11	2.189 (3)	C3—C31	1.493 (3)
I1—I3^i	3.8662 (2)	C31—I3	2.187 (2)
C11—C1	1.488 (4)	C31—H31A	0.9900
C11—H11A	0.9900	C31—H31B	0.9900
C11—H11B	0.9900	C4—C5	1.390 (4)
C1—C6	1.394 (4)	C4—H4	0.9500
C1—C2	1.399 (3)	C5—C6	1.390 (4)
C2—C3	1.394 (3)	C5—H5	0.9500
C2—H2	0.9500	C6—H6	0.9500
C3—C4	1.402 (3)
C11—I1—I3^i	117.47 (7)	C3—C31—I3	110.27 (16)
C1—C11—I1	111.45 (17)	C3—C31—H31A	109.6
C1—C11—H11A	109.3	I3—C31—H31A	109.6
I1—C11—H11A	109.3	C3—C31—H31B	109.6
C1—C11—H11B	109.3	I3—C31—H31B	109.6
I1—C11—H11B	109.3	H31A—C31—H31B	108.1
H11A—C11—H11B	108.0	C5—C4—C3	119.7 (2)
C6—C1—C2	119.2 (2)	C5—C4—H4	120.1
C6—C1—C11	120.9 (2)	C3—C4—H4	120.1
C2—C1—C11	119.9 (2)	C6—C5—C4	120.5 (2)
C3—C2—C1	120.7 (2)	C6—C5—H5	119.7
C3—C2—H2	119.6	C4—C5—H5	119.7
C1—C2—H2	119.6	C5—C6—C1	120.3 (2)
C2—C3—C4	119.5 (2)	C5—C6—H6	119.9
C2—C3—C31	120.3 (2)	C1—C6—H6	119.9
C4—C3—C31	120.2 (2)
I1—C11—C1—C6	−83.6 (3)	C4—C3—C31—I3	−83.7 (3)
I1—C11—C1—C2	97.9 (2)	C2—C3—C4—C5	−0.3 (4)
C6—C1—C2—C3	−0.1 (4)	C31—C3—C4—C5	179.7 (2)
C11—C1—C2—C3	178.4 (2)	C3—C4—C5—C6	0.4 (4)
C1—C2—C3—C4	0.2 (4)	C4—C5—C6—C1	−0.3 (4)
C1—C2—C3—C31	−179.8 (2)	C2—C1—C6—C5	0.2 (4)
C2—C3—C31—I3	96.4 (2)	C11—C1—C6—C5	−178.4 (2)

Symmetry code: (i) x−1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···I1^ii	0.99	3.22	4.060 (3)	144
C5—H5···I1^iii	0.95	3.25	4.078 (3)	147
C31—H31A···I3^iv	0.99	3.27	4.224 (3)	162
C31—H31A···Cg^v	0.99	2.84	3.453 (3)	121

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