Crystal structure of N-(2,2,2-tri­chloro-1-hy­droxy­eth­yl)formamide

Mariyatra, M.B.; Stoeckli-Evans, H.

doi:10.1107/S2056989015020459

Crystal structure of N-(2,2,2-trichloro-1-hydroxyethyl)formamide

The title compound, crystallized with two conformationally similar molecules (A and B) in the asymmetric unit. In the crystal, individual molecules are linked by pairs of O—H

O hydrogen bonds, forming A–A and B–B inversion dimers with $R_{2}^{2}$ (12) ring motifs.

Keywords: crystal structure; trichlorohydroxyethyl; formamide; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015020459/hg5462sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015020459/hg5462Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015020459/hg5462Isup3.cml Supplementary material

CCDC reference: 1009715

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.030
wR factor = 0.078
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  CL4     ..       2.91 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.244 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C5      (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note

   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

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

N-(2,2,2-Trichloro-1-hydroxyethyl)formamide top

Crystal data top

C₃H₄Cl₃NO₂	F(000) = 768
M_r = 192.42	D_x = 1.830 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.7964 (8) Å	Cell parameters from 22309 reflections
b = 9.0798 (7) Å	θ = 1.6–26.2°
c = 12.2453 (7) Å	µ = 1.24 mm⁻¹
β = 114.413 (4)°	T = 173 K
V = 1396.80 (16) Å³	Block, colourless
Z = 8	0.45 × 0.43 × 0.40 mm

Data collection top

Stoe IPDS 2 diffractometer	2645 independent reflections
Radiation source: fine-focus sealed tube	2468 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.056
φ + ω scans	θ_max = 25.7°, θ_min = 1.6°
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	h = −15→16
T_min = 0.579, T_max = 1.000	k = −11→11
16347 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0333P)² + 1.2964P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.078	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.82 e Å⁻³
2645 reflections	Δρ_min = −0.55 e Å⁻³
196 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0089 (9)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.13449 (5)	0.04880 (6)	0.08600 (5)	0.03428 (17)
Cl2	0.22308 (4)	0.28605 (6)	−0.00018 (5)	0.03123 (16)
Cl3	0.28102 (5)	0.25302 (8)	0.25345 (5)	0.04298 (19)
O1	−0.00275 (12)	0.31695 (18)	−0.01499 (14)	0.0284 (4)
H1O	0.005 (3)	0.366 (4)	−0.069 (3)	0.058 (10)*
O2	0.00144 (13)	0.53996 (16)	0.21058 (14)	0.0295 (4)
N1	0.04737 (14)	0.30393 (19)	0.18967 (16)	0.0213 (4)
H1N	0.0392 (18)	0.215 (3)	0.207 (2)	0.020 (6)*
C1	0.17653 (17)	0.2341 (2)	0.10963 (19)	0.0234 (4)
C2	0.08245 (16)	0.3364 (2)	0.09670 (18)	0.0217 (4)
H2	0.1107 (18)	0.434 (3)	0.1068 (19)	0.020 (6)*
C3	0.00885 (17)	0.4079 (2)	0.23751 (18)	0.0237 (4)
H3	−0.0156 (18)	0.374 (3)	0.299 (2)	0.026 (6)*
Cl4	0.64204 (5)	0.45558 (5)	0.52480 (5)	0.03177 (16)
Cl5	0.78172 (4)	0.22393 (6)	0.51229 (5)	0.02994 (15)
Cl6	0.71719 (4)	0.23240 (7)	0.70803 (5)	0.03280 (16)
O3	0.49315 (12)	0.20023 (18)	0.51142 (15)	0.0274 (3)
H3O	0.497 (2)	0.153 (3)	0.564 (3)	0.036 (8)*
O4	0.50422 (13)	−0.04575 (15)	0.29695 (13)	0.0281 (3)
N2	0.54593 (14)	0.19299 (19)	0.35510 (15)	0.0208 (4)
H2N	0.5415 (19)	0.274 (3)	0.332 (2)	0.023 (6)*
C4	0.67565 (16)	0.2671 (2)	0.55274 (18)	0.0216 (4)
C5	0.57819 (16)	0.1686 (2)	0.48142 (18)	0.0206 (4)
H5	0.6025 (16)	0.066 (2)	0.5015 (18)	0.012 (5)*
C6	0.51071 (16)	0.0854 (2)	0.27421 (18)	0.0230 (4)
H6	0.4911 (19)	0.119 (3)	0.190 (2)	0.028 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0493 (4)	0.0157 (3)	0.0449 (3)	0.0062 (2)	0.0265 (3)	0.0024 (2)
Cl2	0.0363 (3)	0.0317 (3)	0.0356 (3)	0.0029 (2)	0.0248 (2)	0.0016 (2)
Cl3	0.0250 (3)	0.0729 (5)	0.0282 (3)	0.0012 (3)	0.0081 (2)	−0.0095 (3)
O1	0.0292 (8)	0.0315 (9)	0.0259 (8)	0.0064 (6)	0.0127 (7)	0.0100 (7)
O2	0.0478 (10)	0.0170 (7)	0.0307 (8)	0.0078 (6)	0.0232 (7)	0.0031 (6)
N1	0.0268 (9)	0.0138 (8)	0.0279 (9)	0.0012 (7)	0.0159 (7)	0.0025 (7)
C1	0.0259 (10)	0.0227 (10)	0.0236 (10)	0.0014 (8)	0.0121 (9)	−0.0014 (8)
C2	0.0272 (10)	0.0144 (10)	0.0275 (10)	0.0016 (8)	0.0154 (8)	0.0010 (8)
C3	0.0288 (11)	0.0221 (10)	0.0229 (10)	0.0034 (8)	0.0133 (9)	0.0013 (8)
Cl4	0.0415 (3)	0.0152 (2)	0.0346 (3)	−0.0028 (2)	0.0117 (2)	−0.0021 (2)
Cl5	0.0247 (3)	0.0366 (3)	0.0304 (3)	0.0009 (2)	0.0133 (2)	0.0020 (2)
Cl6	0.0336 (3)	0.0425 (3)	0.0191 (3)	−0.0029 (2)	0.0077 (2)	0.0028 (2)
O3	0.0287 (8)	0.0303 (8)	0.0265 (8)	−0.0020 (6)	0.0150 (7)	0.0051 (7)
O4	0.0426 (9)	0.0170 (7)	0.0273 (8)	−0.0055 (6)	0.0171 (7)	−0.0019 (6)
N2	0.0271 (9)	0.0132 (8)	0.0202 (9)	−0.0017 (7)	0.0080 (7)	0.0025 (7)
C4	0.0253 (10)	0.0199 (10)	0.0199 (10)	−0.0008 (8)	0.0096 (8)	0.0008 (7)
C5	0.0253 (10)	0.0147 (10)	0.0216 (10)	−0.0018 (8)	0.0095 (8)	0.0016 (7)
C6	0.0270 (10)	0.0211 (10)	0.0217 (10)	−0.0021 (8)	0.0111 (8)	−0.0007 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.764 (2)	Cl4—C4	1.769 (2)
Cl2—C1	1.777 (2)	Cl5—C4	1.772 (2)
Cl3—C1	1.764 (2)	Cl6—C4	1.773 (2)
O1—C2	1.398 (3)	O3—C5	1.396 (3)
O1—H1O	0.84 (3)	O3—H3O	0.76 (3)
O2—C3	1.236 (3)	O4—C6	1.235 (3)
N1—C3	1.332 (3)	N2—C6	1.332 (3)
N1—C2	1.440 (3)	N2—C5	1.439 (3)
N1—H1N	0.85 (2)	N2—H2N	0.78 (3)
C1—C2	1.550 (3)	C4—C5	1.549 (3)
C2—H2	0.96 (2)	C5—H5	0.99 (2)
C3—H3	0.99 (2)	C6—H6	1.00 (2)

C2—O1—H1O	112 (2)	C5—O3—H3O	110 (2)
C3—N1—C2	121.88 (17)	C6—N2—C5	122.84 (17)
C3—N1—H1N	116.3 (16)	C6—N2—H2N	118.0 (18)
C2—N1—H1N	120.8 (16)	C5—N2—H2N	118.7 (18)
C2—C1—Cl3	110.37 (14)	C5—C4—Cl4	110.64 (14)
C2—C1—Cl1	110.49 (14)	C5—C4—Cl5	109.84 (14)
Cl3—C1—Cl1	109.52 (11)	Cl4—C4—Cl5	109.91 (11)
C2—C1—Cl2	108.24 (14)	C5—C4—Cl6	108.82 (14)
Cl3—C1—Cl2	109.15 (11)	Cl4—C4—Cl6	108.79 (11)
Cl1—C1—Cl2	109.04 (11)	Cl5—C4—Cl6	108.80 (11)
O1—C2—N1	109.04 (17)	O3—C5—N2	109.32 (16)
O1—C2—C1	110.74 (16)	O3—C5—C4	111.15 (16)
N1—C2—C1	109.73 (16)	N2—C5—C4	109.14 (16)
O1—C2—H2	112.1 (13)	O3—C5—H5	111.4 (12)
N1—C2—H2	109.8 (14)	N2—C5—H5	109.6 (12)
C1—C2—H2	105.3 (14)	C4—C5—H5	106.2 (12)
O2—C3—N1	125.03 (19)	O4—C6—N2	125.30 (19)
O2—C3—H3	119.1 (14)	O4—C6—H6	120.9 (14)
N1—C3—H3	115.9 (14)	N2—C6—H6	113.7 (14)

C3—N1—C2—O1	−91.5 (2)	C6—N2—C5—O3	−95.7 (2)
C3—N1—C2—C1	147.08 (19)	C6—N2—C5—C4	142.52 (19)
Cl3—C1—C2—O1	−177.16 (14)	Cl4—C4—C5—O3	−58.44 (19)
Cl1—C1—C2—O1	−55.9 (2)	Cl5—C4—C5—O3	−179.96 (13)
Cl2—C1—C2—O1	63.45 (19)	Cl6—C4—C5—O3	61.03 (19)
Cl3—C1—C2—N1	−56.7 (2)	Cl4—C4—C5—N2	62.20 (19)
Cl1—C1—C2—N1	64.54 (19)	Cl5—C4—C5—N2	−59.31 (19)
Cl2—C1—C2—N1	−176.13 (14)	Cl6—C4—C5—N2	−178.33 (14)
C2—N1—C3—O2	−1.8 (3)	C5—N2—C6—O4	−2.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.84 (3)	1.90 (4)	2.731 (2)	169 (3)
N1—H1N···O2ⁱⁱ	0.85 (2)	2.08 (3)	2.893 (2)	159 (2)
O3—H3O···O4ⁱⁱⁱ	0.76 (3)	1.97 (3)	2.721 (2)	174 (3)
N2—H2N···O4^iv	0.78 (3)	2.17 (3)	2.917 (2)	158 (2)
C6—H6···Cl4^v	1.00 (2)	2.91 (2)	3.586 (2)	125 (2)

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

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Crystal structure of N-(2,2,2-tri­chloro-1-hy­droxy­eth­yl)formamide

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of N-(2,2,2-trichloro-1-hydroxyethyl)formamide