Ethyl N-[2-(hydroxy­acetyl)­phenyl]­carbamate, ethyl N-[2-(hydroxy­acetyl)-4-iodo­phenyl]­carbamate and ethyl N-[2-(hydroxy­acetyl)-4-methyl­phenyl]­carbamate

Garden, S.J.; Corrêa, M.B.; Pinto, A.C.; Wardell, J.L.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270107008682

Ethyl N-[2-(hydroxyacetyl)phenyl]carbamate, ethyl N-[2-(hydroxyacetyl)-4-iodophenyl]carbamate and ethyl N-[2-(hydroxyacetyl)-4-methylphenyl]carbamate

S. J. Garden, M. B. Corrêa, A. C. Pinto, J. L. Wardell, J. N. Low and C. Glidewell

In ethyl N-[2-(hydroxyacetyl)phenyl]carbamate, C₁₁H₁₃NO₄, all of the non-H atoms lie on a mirror plane in the space group Pnma; the molecules are linked into simple chains by a single C-H

O hydrogen bond. The molecules of ethyl N-[2-(hydroxyacetyl)-4-iodophenyl]carbamate, C₁₁H₁₂INO₄, are linked into sheets by a combination of O-H

I and C-H

O hydrogen bonds and a dipolar I

O contact. Ethyl N-[2-(hydroxyacetyl)-4-methylphenyl]carbamate, C₁₂H₁₅NO₄, crystallizes with Z' = 2 in the space group P $\overline{1}$ ; pairs of molecules are weakly linked by an O-H

O hydrogen bond and these aggregates are linked into chains by two independent aromatic [pi]

stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107008682/sk3102sup1.cif Contains datablocks global, I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270107008682/sk3102Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270107008682/sk3102IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270107008682/sk3102IIIsup4.hkl Contains datablock III

CCDC references: 645576; 645577; 645578

Computing details top

Data collection: COLLECT (Nonius, 1999) for (I), (II); APEX2 (Bruker, 2003) for (III). Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT for (I), (II); SAINT (Bruker, 2001) for (III). Data reduction: DENZO and COLLECT for (I), (II); SAINT for (III). For all compounds, program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

(I) Ethyl N-[2-(hydroxyacetyl)phenyl]carbamate top

Crystal data top

C₁₁H₁₃NO₄	F(000) = 472
M_r = 223.22	D_x = 1.394 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 6615 reflections
a = 8.2526 (6) Å	θ = 2.9–27.5°
b = 6.5210 (2) Å	µ = 0.11 mm⁻¹
c = 19.7707 (2) Å	T = 120 K
V = 1063.96 (8) Å³	Block, colourless
Z = 4	0.22 × 0.15 × 0.07 mm

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	1327 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1105 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −8→8
T_min = 0.969, T_max = 0.993	l = −24→25
10184 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0534P)² + 0.4154P] where P = (F_o² + 2F_c²)/3
1327 reflections	(Δ/σ)_max < 0.001
98 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O11	0.55153 (15)	0.7500	0.35591 (6)	0.0231 (3)
O12	0.81203 (14)	0.7500	0.39178 (6)	0.0189 (3)
O21	0.74913 (15)	0.7500	0.59367 (6)	0.0233 (3)
O22	0.74354 (16)	0.7500	0.72455 (7)	0.0294 (4)
N1	0.61998 (17)	0.7500	0.46941 (7)	0.0159 (3)
C1	0.4690 (2)	0.7500	0.50134 (9)	0.0159 (4)
C2	0.46311 (19)	0.7500	0.57333 (8)	0.0154 (4)
C3	0.3110 (2)	0.7500	0.60528 (9)	0.0189 (4)
C4	0.1685 (2)	0.7500	0.56890 (9)	0.0218 (4)
C5	0.1762 (2)	0.7500	0.49842 (9)	0.0228 (4)
C6	0.3232 (2)	0.7500	0.46504 (9)	0.0187 (4)
C11	0.6504 (2)	0.7500	0.40150 (8)	0.0170 (4)
C12	0.8622 (2)	0.7500	0.32124 (8)	0.0220 (4)
C13	1.0447 (2)	0.7500	0.32077 (10)	0.0301 (5)
C21	0.6094 (2)	0.7500	0.61591 (8)	0.0167 (4)
C22	0.5904 (2)	0.7500	0.69238 (9)	0.0223 (4)
H1	0.7053	0.7500	0.4961	0.019*
H3	0.3062	0.7500	0.6533	0.023*
H4	0.0668	0.7500	0.5914	0.026*
H5	0.0786	0.7500	0.4729	0.027*
H6	0.3255	0.7500	0.4170	0.022*
H12A	0.8202	0.8733	0.2979	0.026*	0.50
H12B	0.8202	0.6267	0.2979	0.026*	0.50
H13A	1.0836	0.7500	0.2739	0.045*
H13B	1.0846	0.6273	0.3440	0.045*	0.50
H13C	1.0846	0.8727	0.3440	0.045*	0.50
H22A	0.5286	0.8729	0.7065	0.027*	0.50
H22B	0.5286	0.6271	0.7065	0.027*	0.50
H22	0.8168	0.7624	0.6953	0.044*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0164 (8)	0.0149 (8)	0.0163 (8)	0.000	0.0005 (6)	0.000
N1	0.0131 (7)	0.0226 (8)	0.0118 (7)	0.000	−0.0008 (5)	0.000
C11	0.0182 (8)	0.0172 (8)	0.0155 (8)	0.000	0.0009 (7)	0.000
O11	0.0208 (7)	0.0353 (7)	0.0132 (6)	0.000	−0.0017 (5)	0.000
O12	0.0168 (6)	0.0279 (7)	0.0120 (6)	0.000	0.0016 (5)	0.000
C12	0.0216 (9)	0.0328 (10)	0.0116 (8)	0.000	0.0034 (7)	0.000
C13	0.0216 (10)	0.0505 (13)	0.0181 (9)	0.000	0.0046 (7)	0.000
C2	0.0156 (8)	0.0166 (8)	0.0141 (8)	0.000	−0.0008 (6)	0.000
C21	0.0183 (8)	0.0160 (8)	0.0158 (8)	0.000	0.0002 (7)	0.000
O21	0.0158 (6)	0.0371 (8)	0.0170 (6)	0.000	−0.0007 (5)	0.000
C22	0.0191 (9)	0.0328 (10)	0.0151 (8)	0.000	−0.0012 (7)	0.000
O22	0.0219 (7)	0.0504 (9)	0.0160 (6)	0.000	−0.0055 (5)	0.000
C3	0.0202 (9)	0.0210 (8)	0.0156 (8)	0.000	0.0024 (7)	0.000
C4	0.0150 (8)	0.0267 (9)	0.0238 (10)	0.000	0.0023 (7)	0.000
C5	0.0162 (8)	0.0275 (10)	0.0248 (10)	0.000	−0.0036 (7)	0.000
C6	0.0177 (9)	0.0227 (9)	0.0157 (8)	0.000	−0.0018 (7)	0.000

Geometric parameters (Å, º) top

C1—N1	1.397 (2)	C2—C21	1.472 (2)
C1—C6	1.401 (2)	C21—O21	1.234 (2)
C1—C2	1.424 (2)	C21—C22	1.520 (2)
N1—C11	1.366 (2)	C22—O22	1.415 (2)
N1—H1	0.88	C22—H22A	0.99
C11—O11	1.216 (2)	C22—H22B	0.99
C11—O12	1.348 (2)	O22—H22	0.84
O12—C12	1.455 (2)	C3—C4	1.379 (2)
C12—C13	1.506 (3)	C3—H3	0.95
C12—H12A	0.99	C4—C5	1.395 (3)
C12—H12B	0.99	C4—H4	0.95
C13—H13A	0.98	C5—C6	1.381 (2)
C13—H13B	0.98	C5—H5	0.95
C13—H13C	0.98	C6—H6	0.95
C2—C3	1.405 (2)

N1—C1—C6	122.32 (15)	C1—C2—C21	122.94 (15)
N1—C1—C2	118.80 (14)	O21—C21—C2	124.24 (16)
C6—C1—C2	118.88 (15)	O21—C21—C22	116.79 (15)
C11—N1—C1	127.45 (14)	C2—C21—C22	118.97 (15)
C11—N1—H1	116.3	O22—C22—C21	110.80 (14)
C1—N1—H1	116.3	O22—C22—H22A	109.5
O11—C11—O12	123.96 (16)	C21—C22—H22A	109.5
O11—C11—N1	127.25 (16)	O22—C22—H22B	109.5
O12—C11—N1	108.79 (14)	C21—C22—H22B	109.5
C11—O12—C12	114.74 (13)	H22A—C22—H22B	108.1
O12—C12—C13	106.90 (14)	C22—O22—H22	109.5
O12—C12—H12A	110.3	C4—C3—C2	121.84 (15)
C13—C12—H12A	110.3	C4—C3—H3	119.1
O12—C12—H12B	110.3	C2—C3—H3	119.1
C13—C12—H12B	110.3	C3—C4—C5	118.82 (16)
H12A—C12—H12B	108.6	C3—C4—H4	120.6
C12—C13—H13A	109.5	C5—C4—H4	120.6
C12—C13—H13B	109.5	C6—C5—C4	121.18 (17)
H13A—C13—H13B	109.5	C6—C5—H5	119.4
C12—C13—H13C	109.5	C4—C5—H5	119.4
H13A—C13—H13C	109.5	C5—C6—C1	120.62 (16)
H13B—C13—H13C	109.5	C5—C6—H6	119.7
C3—C2—C1	118.66 (15)	C1—C6—H6	119.7
C3—C2—C21	118.40 (15)

C6—C1—N1—C11	0.000	C1—C2—C21—O21	0.0
C2—C1—N1—C11	180.0	C3—C2—C21—C22	0.0
C1—N1—C11—O11	0.000	C1—C2—C21—C22	180.0
C1—N1—C11—O12	180.0	O21—C21—C22—O22	0.0
O11—C11—O12—C12	0.0	C2—C21—C22—O22	180.0
N1—C11—O12—C12	180.0	C1—C2—C3—C4	0.0
C11—O12—C12—C13	180.0	C21—C2—C3—C4	180.0
N1—C1—C2—C3	180.0	C2—C3—C4—C5	0.0
C6—C1—C2—C3	0.0	C3—C4—C5—C6	0.000
N1—C1—C2—C21	0.0	C4—C5—C6—C1	0.000
C6—C1—C2—C21	180.0	N1—C1—C6—C5	180.0
C3—C2—C21—O21	180.0	C2—C1—C6—C5	0.000

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.88	1.96	2.6780 (18)	137
O22—H22···O21	0.84	2.09	2.5880 (18)	118
C3—H3···O22ⁱ	0.95	2.47	3.410 (2)	170

Symmetry code: (i) x−1/2, −y+3/2, −z+3/2.

(II) Ethyl N-[2-(hydroxyacetyl)-4-iodophenyl]carbamate top

Crystal data top

C₁₁H₁₂INO₄	F(000) = 680
M_r = 349.12	D_x = 1.946 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2770 reflections
a = 4.7535 (2) Å	θ = 2.9–27.5°
b = 15.7179 (4) Å	µ = 2.69 mm⁻¹
c = 16.0700 (5) Å	T = 120 K
β = 97.123 (2)°	Lath, colourless
V = 1191.40 (7) Å³	0.12 × 0.05 × 0.01 mm
Z = 4

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	2721 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.6°
φ and ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −20→20
T_min = 0.738, T_max = 0.974	l = −20→20
14451 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²)P)² + 4.7303P] where P = (F_o² + 2F_c²)/3
2721 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I4	0.10231 (6)	0.045792 (18)	0.639545 (18)	0.02036 (10)
O11	0.8879 (7)	0.3011 (2)	0.37346 (19)	0.0247 (7)
O12	1.2042 (7)	0.3917 (2)	0.44328 (19)	0.0232 (7)
O21	1.0130 (7)	0.3681 (2)	0.67550 (19)	0.0235 (7)
O22	0.8062 (7)	0.4056 (2)	0.8138 (2)	0.0276 (8)
N1	0.9391 (8)	0.3151 (2)	0.5174 (2)	0.0187 (8)
C1	0.7438 (9)	0.2572 (3)	0.5418 (3)	0.0166 (9)
C2	0.6837 (9)	0.2599 (3)	0.6267 (3)	0.0186 (9)
C3	0.4910 (9)	0.1996 (3)	0.6528 (3)	0.0174 (9)
C4	0.3688 (9)	0.1396 (3)	0.5981 (3)	0.0188 (9)
C5	0.4244 (9)	0.1379 (3)	0.5151 (3)	0.0209 (9)
C6	0.6094 (10)	0.1966 (3)	0.4878 (3)	0.0209 (9)
C11	1.0001 (9)	0.3320 (3)	0.4381 (3)	0.0187 (9)
C12	1.2883 (10)	0.4218 (3)	0.3647 (3)	0.0241 (10)
C13	1.5012 (10)	0.4911 (3)	0.3860 (3)	0.0246 (10)
C21	0.8122 (9)	0.3226 (3)	0.6876 (3)	0.0185 (9)
C22	0.6929 (10)	0.3340 (3)	0.7701 (3)	0.0227 (10)
H1	1.0352	0.3445	0.5580	0.022*
H3	0.4461	0.2009	0.7088	0.021*
H5	0.3356	0.0966	0.4773	0.025*
H6	0.6454	0.1955	0.4309	0.025*
H12A	1.1218	0.4440	0.3280	0.029*
H12B	1.3730	0.3749	0.3350	0.029*
H13A	1.4151	0.5368	0.4157	0.037*
H13B	1.5625	0.5137	0.3343	0.037*
H13C	1.6653	0.4681	0.4219	0.037*
H22A	0.4842	0.3398	0.7590	0.027*
H22B	0.7356	0.2827	0.8052	0.027*
H22	0.9555	0.4206	0.7948	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.019 (2)	0.016 (2)	0.015 (2)	0.0022 (16)	0.0028 (17)	0.0040 (16)
N1	0.023 (2)	0.0184 (19)	0.0151 (18)	−0.0048 (15)	0.0033 (15)	−0.0018 (14)
C11	0.018 (2)	0.021 (2)	0.017 (2)	0.0070 (17)	0.0053 (17)	0.0033 (17)
O11	0.0297 (18)	0.0254 (18)	0.0199 (17)	0.0001 (14)	0.0069 (14)	−0.0004 (13)
O12	0.0267 (18)	0.0267 (18)	0.0168 (16)	−0.0076 (13)	0.0044 (13)	0.0018 (13)
C12	0.027 (2)	0.031 (3)	0.017 (2)	−0.002 (2)	0.0112 (19)	0.0042 (19)
C13	0.029 (3)	0.025 (3)	0.022 (2)	0.001 (2)	0.0109 (19)	0.0018 (19)
C2	0.017 (2)	0.017 (2)	0.021 (2)	0.0008 (17)	0.0012 (17)	0.0037 (17)
C21	0.016 (2)	0.020 (2)	0.020 (2)	0.0036 (17)	0.0012 (17)	0.0026 (17)
O21	0.0240 (17)	0.0266 (18)	0.0201 (16)	−0.0068 (14)	0.0035 (13)	−0.0027 (13)
C22	0.030 (3)	0.022 (2)	0.017 (2)	−0.0069 (19)	0.0050 (19)	−0.0001 (18)
O22	0.0283 (19)	0.0312 (19)	0.0240 (18)	−0.0061 (15)	0.0067 (14)	−0.0088 (14)
C3	0.017 (2)	0.018 (2)	0.018 (2)	0.0037 (17)	0.0019 (17)	0.0024 (17)
C4	0.015 (2)	0.016 (2)	0.026 (2)	−0.0005 (16)	0.0040 (17)	0.0051 (18)
I4	0.02063 (16)	0.01792 (16)	0.02260 (16)	−0.00127 (12)	0.00294 (11)	0.00290 (12)
C5	0.024 (2)	0.020 (2)	0.019 (2)	−0.0023 (18)	−0.0001 (18)	0.0008 (18)
C6	0.027 (2)	0.020 (2)	0.016 (2)	0.0043 (18)	0.0010 (18)	0.0002 (17)

Geometric parameters (Å, º) top

C1—C6	1.389 (6)	C2—C21	1.467 (6)
C1—N1	1.390 (5)	C21—O21	1.227 (5)
C1—C2	1.430 (6)	C21—C22	1.516 (6)
N1—C11	1.368 (5)	C22—O22	1.399 (5)
N1—H1	0.88	C22—H22A	0.99
C11—O11	1.210 (5)	C22—H22B	0.99
C11—O12	1.344 (5)	O22—H22	0.84
O12—C12	1.451 (5)	C3—C4	1.369 (6)
C12—C13	1.496 (7)	C3—H3	0.95
C12—H12A	0.99	C4—C5	1.393 (6)
C12—H12B	0.99	C4—I4	2.104 (4)
C13—H13A	0.98	C5—C6	1.383 (6)
C13—H13B	0.98	C5—H5	0.95
C13—H13C	0.98	C6—H6	0.95
C2—C3	1.417 (6)

C6—C1—N1	123.0 (4)	C1—C2—C21	122.7 (4)
C6—C1—C2	119.1 (4)	O21—C21—C2	123.6 (4)
N1—C1—C2	118.0 (4)	O21—C21—C22	116.9 (4)
C11—N1—C1	128.0 (4)	C2—C21—C22	119.5 (4)
C11—N1—H1	116.0	O22—C22—C21	111.8 (4)
C1—N1—H1	116.0	O22—C22—H22A	109.3
O11—C11—O12	124.8 (4)	C21—C22—H22A	109.3
O11—C11—N1	126.9 (4)	O22—C22—H22B	109.3
O12—C11—N1	108.3 (4)	C21—C22—H22B	109.3
C11—O12—C12	116.7 (3)	H22A—C22—H22B	107.9
O12—C12—C13	106.8 (4)	C22—O22—H22	109.5
O12—C12—H12A	110.4	C4—C3—C2	120.6 (4)
C13—C12—H12A	110.4	C4—C3—H3	119.7
O12—C12—H12B	110.4	C2—C3—H3	119.7
C13—C12—H12B	110.4	C3—C4—C5	120.8 (4)
H12A—C12—H12B	108.6	C3—C4—I4	120.3 (3)
C12—C13—H13A	109.5	C5—C4—I4	118.9 (3)
C12—C13—H13B	109.5	C6—C5—C4	119.7 (4)
H13A—C13—H13B	109.5	C6—C5—H5	120.2
C12—C13—H13C	109.5	C4—C5—H5	120.2
H13A—C13—H13C	109.5	C5—C6—C1	121.4 (4)
H13B—C13—H13C	109.5	C5—C6—H6	119.3
C3—C2—C1	118.4 (4)	C1—C6—H6	119.3
C3—C2—C21	118.9 (4)

C6—C1—N1—C11	10.8 (7)	C3—C2—C21—C22	−12.8 (6)
C2—C1—N1—C11	−170.2 (4)	C1—C2—C21—C22	166.9 (4)
C1—N1—C11—O11	2.4 (7)	O21—C21—C22—O22	9.7 (6)
C1—N1—C11—O12	−179.3 (4)	C2—C21—C22—O22	−169.6 (4)
O11—C11—O12—C12	1.6 (6)	C1—C2—C3—C4	0.9 (6)
N1—C11—O12—C12	−176.8 (4)	C21—C2—C3—C4	−179.4 (4)
C11—O12—C12—C13	176.3 (4)	C2—C3—C4—C5	−1.9 (6)
C6—C1—C2—C3	0.8 (6)	C2—C3—C4—I4	176.3 (3)
N1—C1—C2—C3	−178.3 (4)	C3—C4—C5—C6	1.2 (7)
C6—C1—C2—C21	−178.9 (4)	I4—C4—C5—C6	−177.0 (3)
N1—C1—C2—C21	2.0 (6)	C4—C5—C6—C1	0.5 (7)
C3—C2—C21—O21	167.9 (4)	N1—C1—C6—C5	177.5 (4)
C1—C2—C21—O21	−12.4 (7)	C2—C1—C6—C5	−1.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.88	1.94	2.655 (4)	137
O22—H22···O21	0.84	2.14	2.607 (4)	115
O22—H22···I4ⁱ	0.84	2.98	3.578 (3)	130
C22—H22A···O21ⁱⁱ	0.99	2.50	3.439 (6)	157

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

(III) Ethyl N-[2-(hydroxyacetyl)-4-methylphenyl]carbamate top

Crystal data top

C₁₂H₁₅NO₄	Z = 4
M_r = 237.25	F(000) = 504
Triclinic, P1	D_x = 1.350 Mg m⁻³
Hall symbol: -P 1	Synchrotron (Clegg, 2000) radiation, λ = 0.7848 Å
a = 7.085 (7) Å	Cell parameters from 3115 reflections
b = 10.711 (11) Å	θ = 4.9–25.9°
c = 15.587 (16) Å	µ = 0.10 mm⁻¹
α = 87.916 (11)°	T = 120 K
β = 80.861 (13)°	Needle, colourless
γ = 89.664 (11)°	0.20 × 0.01 × 0.01 mm
V = 1167 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2117 reflections with I > 2σ(I)
Radiation source: Daresbury SRS Station 16.2smx (Clegg, 2000)	R_int = 0.039
Silicon 111 monochromator	θ_max = 25.5°, θ_min = 4.9°
fine–slice ω scans	h = −7→7
5906 measured reflections	k = −11→11
3115 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.245	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1762P)²] where P = (F_o² + 2F_c²)/3
3115 reflections	(Δ/σ)_max < 0.001
314 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O111	0.5781 (7)	0.7984 (4)	0.1820 (2)	0.0680 (13)
O112	0.5297 (4)	0.6568 (3)	0.08578 (19)	0.0362 (8)
O121	0.7641 (5)	0.8424 (3)	−0.1363 (2)	0.0413 (9)
O122	0.9040 (6)	0.9349 (4)	−0.2879 (2)	0.0587 (11)
O211	0.5168 (6)	0.6625 (3)	0.6814 (2)	0.0534 (11)
O212	0.5182 (4)	0.8301 (3)	0.58795 (19)	0.0333 (8)
O221	0.7679 (4)	0.6823 (3)	0.3659 (2)	0.0371 (8)
O222	0.9253 (5)	0.6166 (3)	0.2135 (2)	0.0503 (10)
N11	0.6480 (5)	0.8411 (3)	0.0346 (2)	0.0309 (9)
N21	0.6420 (5)	0.6541 (3)	0.5351 (2)	0.0317 (10)
C11	0.7102 (6)	0.9653 (4)	0.0298 (3)	0.0299 (11)
C12	0.7942 (6)	1.0204 (4)	−0.0512 (3)	0.0299 (11)
C13	0.8572 (6)	1.1445 (4)	−0.0546 (3)	0.0335 (12)
C14	0.8441 (6)	1.2165 (4)	0.0189 (3)	0.0342 (12)
C15	0.7557 (6)	1.1594 (4)	0.0969 (3)	0.0351 (12)
C16	0.6917 (6)	1.0373 (4)	0.1035 (3)	0.0330 (11)
C21	0.7062 (6)	0.5314 (4)	0.5286 (3)	0.0305 (11)
C22	0.7995 (6)	0.4899 (4)	0.4468 (3)	0.0297 (11)
C23	0.8672 (6)	0.3661 (4)	0.4413 (3)	0.0318 (11)
C24	0.8525 (6)	0.2841 (4)	0.5115 (3)	0.0336 (12)
C25	0.7564 (6)	0.3255 (4)	0.5908 (3)	0.0345 (12)
C26	0.6868 (6)	0.4455 (4)	0.5995 (3)	0.0336 (11)
C111	0.5839 (7)	0.7690 (5)	0.1078 (3)	0.0363 (12)
C112	0.4562 (9)	0.5702 (5)	0.1576 (3)	0.0494 (14)
C113	0.3917 (7)	0.4557 (5)	0.1244 (3)	0.0437 (13)
C121	0.8120 (6)	0.9528 (5)	−0.1332 (3)	0.0335 (11)
C122	0.8920 (8)	1.0191 (5)	−0.2189 (3)	0.0447 (13)
C141	0.9233 (7)	1.3460 (4)	0.0149 (3)	0.0410 (13)
C211	0.5554 (7)	0.7112 (5)	0.6079 (3)	0.0356 (12)
C212	0.4237 (7)	0.9022 (4)	0.6594 (3)	0.0397 (13)
C213	0.4147 (8)	1.0353 (5)	0.6290 (4)	0.0489 (14)
C221	0.8193 (6)	0.5735 (4)	0.3665 (3)	0.0307 (11)
C222	0.9111 (7)	0.5218 (5)	0.2801 (3)	0.0393 (12)
C241	0.9321 (7)	0.1528 (5)	0.5049 (3)	0.0399 (12)
H11	0.6498	0.8024	−0.0227	0.037*
H11A	0.5579	0.5508	0.1928	0.059*
H11B	0.3485	0.6095	0.1955	0.059*
H11C	0.2846	0.4743	0.0932	0.066*
H11D	0.3501	0.3963	0.1729	0.066*
H11E	0.4969	0.4192	0.0846	0.066*
H12A	0.8083	1.0902	−0.2301	0.054*
H12B	1.0207	1.0524	−0.2158	0.054*
H122	0.8679	0.8636	−0.2678	0.088*
H13	0.9112	1.1812	−0.1093	0.040*
H14A	0.9850	1.3672	−0.0446	0.061*
H14B	1.0174	1.3506	0.0545	0.061*
H14C	0.8193	1.4052	0.0323	0.061*
H15	0.7387	1.2068	0.1479	0.042*
H16	0.6351	1.0022	0.1584	0.040*
H21	0.6440	0.6870	0.4787	0.038*
H21A	0.4958	0.8954	0.7089	0.048*
H21B	0.2930	0.8696	0.6793	0.048*
H21C	0.5437	1.0648	0.6051	0.073*
H21D	0.3613	1.0862	0.6780	0.073*
H21E	0.3331	1.0423	0.5838	0.073*
H22A	1.0402	0.4894	0.2852	0.047*
H22B	0.8333	0.4518	0.2651	0.047*
H222	0.8587	0.6783	0.2315	0.075*
H23	0.9259	0.3382	0.3862	0.038*
H24A	1.0154	0.1449	0.4488	0.060*
H24B	0.8266	0.0929	0.5095	0.060*
H24C	1.0059	0.1356	0.5521	0.060*
H25	0.7388	0.2694	0.6401	0.041*
H26	0.6243	0.4706	0.6547	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.018 (2)	0.032 (3)	0.040 (3)	0.0035 (19)	−0.0055 (19)	−0.002 (2)
N11	0.024 (2)	0.039 (2)	0.030 (2)	0.0037 (17)	−0.0017 (16)	−0.0053 (17)
C111	0.035 (3)	0.042 (3)	0.030 (3)	−0.004 (2)	0.000 (2)	0.000 (2)
O111	0.116 (4)	0.052 (2)	0.036 (2)	−0.031 (2)	−0.011 (2)	0.0015 (18)
O112	0.0346 (19)	0.0348 (19)	0.0370 (19)	−0.0031 (15)	0.0012 (14)	−0.0015 (14)
C112	0.062 (4)	0.042 (3)	0.041 (3)	−0.010 (3)	−0.001 (3)	0.004 (2)
C113	0.037 (3)	0.046 (3)	0.046 (3)	−0.009 (2)	−0.001 (2)	0.004 (2)
C12	0.020 (2)	0.033 (3)	0.037 (3)	0.005 (2)	−0.006 (2)	−0.001 (2)
C121	0.017 (2)	0.045 (3)	0.038 (3)	0.000 (2)	−0.0022 (19)	−0.001 (2)
O121	0.037 (2)	0.048 (2)	0.038 (2)	−0.0020 (17)	−0.0009 (15)	−0.0079 (16)
C122	0.041 (3)	0.053 (3)	0.038 (3)	−0.004 (2)	0.000 (2)	−0.003 (2)
O122	0.056 (3)	0.077 (3)	0.041 (2)	−0.010 (2)	0.0003 (18)	−0.009 (2)
C13	0.015 (2)	0.048 (3)	0.038 (3)	0.006 (2)	−0.0047 (19)	0.003 (2)
C14	0.022 (2)	0.039 (3)	0.042 (3)	0.002 (2)	−0.010 (2)	0.000 (2)
C141	0.032 (3)	0.040 (3)	0.049 (3)	0.001 (2)	−0.001 (2)	0.001 (2)
C15	0.025 (3)	0.040 (3)	0.039 (3)	0.006 (2)	−0.001 (2)	−0.005 (2)
C16	0.027 (3)	0.033 (3)	0.039 (3)	0.000 (2)	−0.004 (2)	−0.003 (2)
C21	0.019 (2)	0.030 (3)	0.043 (3)	0.0013 (19)	−0.005 (2)	−0.002 (2)
N21	0.025 (2)	0.038 (2)	0.031 (2)	0.0058 (17)	0.0000 (16)	−0.0037 (17)
C211	0.030 (3)	0.040 (3)	0.035 (3)	0.007 (2)	0.000 (2)	0.000 (2)
O211	0.065 (3)	0.049 (2)	0.043 (2)	0.0199 (19)	0.0016 (18)	−0.0032 (18)
O212	0.0302 (18)	0.0325 (19)	0.0353 (18)	0.0056 (14)	0.0010 (13)	−0.0047 (14)
C212	0.036 (3)	0.041 (3)	0.038 (3)	0.009 (2)	0.008 (2)	−0.004 (2)
C213	0.052 (3)	0.042 (3)	0.051 (3)	0.001 (3)	−0.002 (3)	−0.008 (2)
C22	0.016 (2)	0.037 (3)	0.036 (3)	−0.001 (2)	−0.0007 (19)	−0.004 (2)
C221	0.021 (2)	0.035 (3)	0.035 (3)	−0.001 (2)	−0.0026 (19)	−0.006 (2)
O221	0.0314 (19)	0.039 (2)	0.039 (2)	0.0045 (15)	−0.0016 (14)	−0.0005 (15)
C222	0.030 (3)	0.043 (3)	0.043 (3)	0.003 (2)	0.003 (2)	−0.003 (2)
O222	0.052 (2)	0.057 (2)	0.037 (2)	0.0062 (18)	0.0057 (16)	0.0031 (17)
C23	0.019 (2)	0.041 (3)	0.035 (3)	0.004 (2)	−0.0028 (19)	−0.008 (2)
C24	0.021 (2)	0.037 (3)	0.043 (3)	0.001 (2)	−0.006 (2)	−0.007 (2)
C241	0.028 (3)	0.043 (3)	0.048 (3)	0.001 (2)	−0.003 (2)	−0.002 (2)
C25	0.026 (3)	0.037 (3)	0.041 (3)	−0.002 (2)	−0.007 (2)	0.002 (2)
C26	0.021 (2)	0.039 (3)	0.040 (3)	0.005 (2)	−0.001 (2)	−0.005 (2)

Geometric parameters (Å, º) top

C11—C16	1.395 (6)	C21—N21	1.390 (6)
C11—N11	1.400 (6)	C21—C26	1.402 (7)
C11—C12	1.417 (6)	C21—C22	1.425 (6)
N11—C111	1.371 (6)	N21—C211	1.365 (6)
N11—H11	1.00	N21—H21	0.93
C111—O111	1.204 (6)	C211—O211	1.231 (6)
C111—O112	1.337 (6)	C211—O212	1.335 (6)
O112—C112	1.459 (6)	O212—C212	1.451 (5)
C112—C113	1.453 (7)	C212—C213	1.490 (7)
C112—H11A	0.99	C212—H21A	0.99
C112—H11B	0.99	C212—H21B	0.99
C113—H11C	0.98	C213—H21C	0.98
C113—H11D	0.98	C213—H21D	0.98
C113—H11E	0.98	C213—H21E	0.98
C12—C13	1.401 (6)	C22—C23	1.408 (6)
C12—C121	1.479 (6)	C22—C221	1.501 (6)
C121—O121	1.236 (6)	C221—O221	1.219 (5)
C121—C122	1.519 (7)	C221—C222	1.521 (6)
C122—O122	1.420 (6)	C222—O222	1.418 (6)
C122—H12A	0.99	C222—H22A	0.99
C122—H12B	0.99	C222—H22B	0.99
O122—H122	0.84	O222—H222	0.84
C13—C14	1.395 (6)	C23—C24	1.370 (7)
C13—H13	0.95	C23—H23	0.95
C14—C15	1.397 (7)	C24—C25	1.400 (6)
C14—C141	1.495 (7)	C24—C241	1.512 (7)
C141—H14A	0.98	C241—H24A	0.98
C141—H14B	0.98	C241—H24B	0.98
C141—H14C	0.98	C241—H24C	0.98
C15—C16	1.381 (7)	C25—C26	1.377 (7)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95

C16—C11—N11	121.5 (4)	N21—C21—C26	123.1 (4)
C16—C11—C12	118.7 (4)	N21—C21—C22	119.3 (4)
N11—C11—C12	119.9 (4)	C26—C21—C22	117.6 (4)
C111—N11—C11	127.7 (4)	C211—N21—C21	127.6 (4)
C111—N11—H11	117.5	C211—N21—H21	123.8
C11—N11—H11	114.8	C21—N21—H21	107.5
O111—C111—O112	123.2 (4)	O211—C211—O212	124.3 (4)
O111—C111—N11	126.7 (4)	O211—C211—N21	126.2 (4)
O112—C111—N11	110.1 (4)	O212—C211—N21	109.6 (4)
C111—O112—C112	116.1 (4)	C211—O212—C212	115.5 (4)
C113—C112—O112	110.2 (4)	O212—C212—C213	108.7 (4)
C113—C112—H11A	109.6	O212—C212—H21A	110.0
O112—C112—H11A	109.6	C213—C212—H21A	110.0
C113—C112—H11B	109.6	O212—C212—H21B	110.0
O112—C112—H11B	109.6	C213—C212—H21B	110.0
H11A—C112—H11B	108.1	H21A—C212—H21B	108.3
C112—C113—H11C	109.5	C212—C213—H21C	109.5
C112—C113—H11D	109.5	C212—C213—H21D	109.5
H11C—C113—H11D	109.5	H21C—C213—H21D	109.5
C112—C113—H11E	109.5	C212—C213—H21E	109.5
H11C—C113—H11E	109.5	H21C—C213—H21E	109.5
H11D—C113—H11E	109.5	H21D—C213—H21E	109.5
C13—C12—C11	119.1 (4)	C23—C22—C21	118.8 (4)
C13—C12—C121	118.6 (4)	C23—C22—C221	119.8 (4)
C11—C12—C121	122.3 (4)	C21—C22—C221	121.4 (4)
O121—C121—C12	123.1 (4)	O221—C221—C22	123.9 (4)
O121—C121—C122	116.9 (4)	O221—C221—C222	117.1 (4)
C12—C121—C122	120.0 (4)	C22—C221—C222	119.0 (4)
O122—C122—C121	110.2 (4)	O222—C222—C221	110.3 (4)
O122—C122—H12A	109.6	O222—C222—H22A	109.6
C121—C122—H12A	109.6	C221—C222—H22A	109.6
O122—C122—H12B	109.6	O222—C222—H22B	109.6
C121—C122—H12B	109.6	C221—C222—H22B	109.6
H12A—C122—H12B	108.1	H22A—C222—H22B	108.1
C122—O122—H122	109.5	C222—O222—H222	109.5
C14—C13—C12	122.9 (4)	C24—C23—C22	123.1 (4)
C14—C13—H13	118.5	C24—C23—H23	118.4
C12—C13—H13	118.5	C22—C23—H23	118.4
C13—C14—C15	115.9 (4)	C23—C24—C25	117.2 (4)
C13—C14—C141	122.1 (4)	C23—C24—C241	122.4 (4)
C15—C14—C141	122.0 (4)	C25—C24—C241	120.4 (4)
C14—C141—H14A	109.5	C24—C241—H24A	109.5
C14—C141—H14B	109.5	C24—C241—H24B	109.5
H14A—C141—H14B	109.5	H24A—C241—H24B	109.5
C14—C141—H14C	109.5	C24—C241—H24C	109.5
H14A—C141—H14C	109.5	H24A—C241—H24C	109.5
H14B—C141—H14C	109.5	H24B—C241—H24C	109.5
C16—C15—C14	123.3 (4)	C26—C25—C24	121.8 (4)
C16—C15—H15	118.4	C26—C25—H25	119.1
C14—C15—H15	118.4	C24—C25—H25	119.1
C15—C16—C11	120.1 (4)	C25—C26—C21	121.4 (4)
C15—C16—H16	119.9	C25—C26—H26	119.3
C11—C16—H16	119.9	C21—C26—H26	119.3

C16—C11—N11—C111	−7.9 (7)	C26—C21—N21—C211	1.0 (7)
C12—C11—N11—C111	172.1 (4)	C22—C21—N21—C211	−177.9 (4)
C11—N11—C111—O111	−3.7 (8)	C21—N21—C211—O211	−0.9 (8)
C11—N11—C111—O112	177.4 (4)	C21—N21—C211—O212	178.9 (4)
O111—C111—O112—C112	1.7 (7)	O211—C211—O212—C212	−0.9 (7)
N11—C111—O112—C112	−179.4 (4)	N21—C211—O212—C212	179.4 (4)
C111—O112—C112—C113	176.4 (4)	C211—O212—C212—C213	173.1 (4)
C16—C11—C12—C13	0.6 (6)	N21—C21—C22—C23	178.8 (4)
N11—C11—C12—C13	−179.4 (4)	C26—C21—C22—C23	−0.1 (6)
C16—C11—C12—C121	−177.4 (4)	N21—C21—C22—C221	−3.8 (6)
N11—C11—C12—C121	2.6 (6)	C26—C21—C22—C221	177.3 (4)
C13—C12—C121—O121	178.4 (4)	C23—C22—C221—O221	−178.6 (4)
C11—C12—C121—O121	−3.7 (7)	C21—C22—C221—O221	4.1 (7)
C13—C12—C121—C122	−1.7 (6)	C23—C22—C221—C222	0.5 (6)
C11—C12—C121—C122	176.2 (4)	C21—C22—C221—C222	−176.9 (4)
O121—C121—C122—O122	−2.7 (6)	O221—C221—C222—O222	2.1 (6)
C12—C121—C122—O122	177.3 (4)	C22—C221—C222—O222	−177.0 (4)
C11—C12—C13—C14	1.1 (6)	C21—C22—C23—C24	−1.9 (7)
C121—C12—C13—C14	179.1 (4)	C221—C22—C23—C24	−179.3 (4)
C12—C13—C14—C15	−2.8 (6)	C22—C23—C24—C25	3.3 (7)
C12—C13—C14—C141	176.1 (4)	C22—C23—C24—C241	−177.8 (4)
C13—C14—C15—C16	2.9 (6)	C23—C24—C25—C26	−2.9 (7)
C141—C14—C15—C16	−175.9 (4)	C241—C24—C25—C26	178.2 (4)
C14—C15—C16—C11	−1.4 (7)	C24—C25—C26—C21	1.1 (7)
N11—C11—C16—C15	179.6 (4)	N21—C21—C26—C25	−178.4 (4)
C12—C11—C16—C15	−0.4 (6)	C22—C21—C26—C25	0.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O121	1.00	1.86	2.660 (5)	135
N21—H21···O221	0.93	1.84	2.653 (5)	144
O122—H122···O121	0.84	2.07	2.578 (5)	118
O222—H222···O221	0.84	2.09	2.579 (5)	116
O222—H222···O111	0.84	2.57	3.216 (7)	135

Selected torsion angles (°) for compounds (II) and (III) top

Parameter	(II)	(III)	(III)
x	nil	1	2
Cx1-Cx2-Cx21-Cx22	166.9 (4)	176.2 (4)	-176.9 (4)
Cx2-Cx21-Cx22-Ox22	-169.6 (4)	177.3 (4)	-177.0 (4)
Cx2-Cx1-Nx1-Cx11	-170.2 (4)	172.1 (4)	-177.9 (4)
Cx1-Nx1-Cx11-Ox12	-179.3 (4)	177.4 (4)	178.9 (4)
Nx1-Cx11-Ox12-Cx12	-176.8 (4)	-179.4 (4)	179.4 (4)
Cx11-Ox12-Cx12-Cx13	176.3 (4)	176.4 (4)	173.1 (4)

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Ethyl N-[2-(hydroxy­acetyl)­phenyl]­carbamate, ethyl N-[2-(hydroxy­acetyl)-4-iodo­phenyl]­carbamate and ethyl N-[2-(hydroxy­acetyl)-4-methyl­phenyl]­carbamate

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Ethyl N-[2-(hydroxyacetyl)phenyl]carbamate, ethyl N-[2-(hydroxyacetyl)-4-iodophenyl]carbamate and ethyl N-[2-(hydroxyacetyl)-4-methylphenyl]carbamate