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The title compound, C10H12N2O4, crystallizes in the monoclinic non-centrosymmetric space group Pn with Z = 2. The two methyl carbamate groups, —N(H)—C(=O)—OCH3, are twisted away from the aromatic ring mean plane, but form a semiflexible eight-membered cavity involving the atoms of the MeO—C(=O)—N(H)—CH2—CH2—N(H)—C(=O)—OMe group. The NH groups act as hydrogen-bond donors and the C=O groups as acceptors to form intermolecular N—H...O hydrogen bonding with an R21(7) motif, generating extended ribbons along the b direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018690/lh6247sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018690/lh6247Isup2.hkl
Contains datablock I

CCDC reference: 251643

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.081
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.51 From the CIF: _reflns_number_total 1203 Count of symmetry unique reflns 1210 Completeness (_total/calc) 99.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX2003 (Farrugia, 1999).

Dimethyl N,N'-(1,2-phenylene)dicarbamate top
Crystal data top
C10H12N2O4F(000) = 236
Mr = 224.22Dx = 1.418 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 600 reflections
a = 9.3056 (19) Åθ = 20–25°
b = 4.840 (1) ŵ = 0.11 mm1
c = 11.843 (2) ÅT = 293 K
β = 100.181 (3)°Block, colourless
V = 525.00 (19) Å30.52 × 0.42 × 0.36 mm
Z = 2
Data collection top
Bruker SMART Area-detector
diffractometer
1168 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
φ and ω scansh = 1112
4221 measured reflectionsk = 66
1203 independent reflectionsl = 1514
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0358P]
where P = (Fo2 + 2Fc2)/3
1203 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.25 e Å3
2 restraintsΔρmin = 0.24 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O80.19061 (14)0.1083 (3)0.10711 (12)0.0208 (4)
O90.35873 (14)0.4484 (3)0.09391 (12)0.0209 (4)
O120.27835 (16)0.8008 (3)0.01981 (13)0.0264 (4)
O130.09521 (15)1.1075 (3)0.06882 (12)0.0247 (4)
N70.12992 (17)0.5497 (3)0.16398 (13)0.0185 (4)
N110.08810 (17)0.8377 (3)0.07911 (14)0.0205 (4)
C10.0202 (2)0.4979 (4)0.20952 (15)0.0180 (5)
C20.1292 (2)0.6385 (4)0.16561 (16)0.0191 (5)
C30.2751 (2)0.5854 (4)0.21131 (19)0.0265 (6)
C40.3108 (2)0.3919 (5)0.2986 (2)0.0302 (6)
C50.2023 (3)0.2534 (5)0.34212 (18)0.0274 (6)
C60.0572 (2)0.3093 (4)0.29873 (16)0.0220 (5)
C80.22298 (19)0.3497 (4)0.12072 (14)0.0171 (5)
C100.4680 (2)0.2582 (4)0.03770 (18)0.0251 (6)
C120.1666 (2)0.9051 (4)0.00369 (15)0.0189 (5)
C140.1645 (2)1.1978 (5)0.16184 (17)0.0269 (6)
H30.348610.679440.183420.0318*
H40.408340.355260.327950.0362*
H50.226830.123530.400200.0329*
H60.015930.220640.329280.0264*
H70.161900.716320.164370.0222*
H10A0.561150.348990.022570.0377*
H10B0.473300.101440.086460.0377*
H10C0.442210.197760.033300.0377*
H110.007030.923410.078570.0246*
H14A0.107431.342200.203540.0404*
H14B0.171741.045170.212300.0404*
H14C0.260421.266190.131720.0404*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O80.0206 (7)0.0162 (6)0.0251 (7)0.0026 (5)0.0026 (5)0.0001 (5)
O90.0185 (7)0.0199 (6)0.0235 (7)0.0020 (5)0.0018 (5)0.0030 (5)
O120.0221 (7)0.0304 (7)0.0280 (7)0.0063 (6)0.0083 (5)0.0053 (6)
O130.0240 (7)0.0294 (8)0.0215 (7)0.0052 (6)0.0065 (5)0.0090 (6)
N70.0183 (8)0.0139 (7)0.0238 (8)0.0013 (6)0.0051 (6)0.0004 (6)
N110.0162 (7)0.0247 (8)0.0213 (7)0.0028 (6)0.0053 (5)0.0057 (6)
C10.0199 (9)0.0168 (8)0.0170 (8)0.0001 (7)0.0023 (6)0.0027 (7)
C20.0199 (9)0.0195 (8)0.0178 (8)0.0004 (7)0.0027 (6)0.0006 (7)
C30.0191 (9)0.0305 (10)0.0287 (10)0.0010 (8)0.0008 (7)0.0080 (8)
C40.0232 (10)0.0339 (12)0.0297 (10)0.0012 (9)0.0055 (8)0.0080 (9)
C50.0315 (11)0.0275 (10)0.0203 (9)0.0004 (8)0.0036 (7)0.0077 (8)
C60.0245 (9)0.0201 (9)0.0212 (9)0.0041 (7)0.0035 (7)0.0010 (7)
C80.0185 (9)0.0200 (9)0.0138 (8)0.0007 (7)0.0056 (6)0.0021 (6)
C100.0174 (9)0.0247 (10)0.0313 (11)0.0013 (7)0.0009 (7)0.0043 (8)
C120.0180 (9)0.0201 (9)0.0179 (8)0.0022 (7)0.0016 (6)0.0008 (7)
C140.0273 (10)0.0337 (10)0.0204 (9)0.0010 (9)0.0062 (7)0.0061 (8)
Geometric parameters (Å, º) top
O8—C81.224 (2)C2—C31.394 (3)
O9—C81.335 (2)C3—C41.391 (3)
O9—C101.444 (2)C4—C51.385 (3)
O12—C121.201 (2)C5—C61.384 (3)
O13—C121.347 (2)C3—H30.9296
O13—C141.439 (2)C4—H40.9298
N7—C11.428 (2)C5—H50.9300
N7—C81.339 (2)C6—H60.9302
N11—C21.410 (2)C10—H10A0.9600
N11—C121.362 (2)C10—H10B0.9600
N7—H70.8599C10—H10C0.9600
N11—H110.8600C14—H14A0.9600
C1—C61.393 (3)C14—H14B0.9600
C1—C21.396 (3)C14—H14C0.9597
O8···N7i2.819 (2)C10···H14Cx2.9362
O8···N11i2.976 (2)C12···H32.7650
O8···C63.093 (2)C14···H7xii2.8625
O9···C14ii3.335 (3)H3···O122.4514
O12···C32.934 (3)H3···C122.7650
O12···C10iii3.220 (3)H3···H14Axiii2.5425
O8···H7i2.0166H4···H14Axiii2.4413
O8···H11i2.1254H5···O8xiv2.6811
O8···H5iv2.6811H5···H10Cxiv2.4394
O8···H14Bv2.7812H6···O82.8894
O8···H62.8894H6···C82.9191
O8···H10B2.5988H6···O12v2.8424
O8···H10C2.6567H7···O8viii2.0166
O9···H14Aii2.6735H7···N112.7581
O12···H32.4514H7···H112.2523
O12···H10Avi2.6457H7···C14ii2.8625
O12···H10Biii2.8309H7···H14Bii2.5811
O12···H14B2.6039H10A···O12xv2.6457
O12···H14Ci2.8985H10A···H14Cx2.2768
O12···H14C2.6038H10B···O82.5988
O12···H6vii2.8424H10B···O12x2.8309
N7···O8viii2.819 (2)H10C···O82.6567
N7···N112.791 (2)H10C···C5iv3.0749
N7···C14ii3.287 (3)H10C···H5iv2.4394
N11···O8viii2.976 (2)H11···O8viii2.1254
N11···N72.791 (2)H11···N72.5248
N7···H14Cii2.9261H11···C8viii3.0765
N7···H112.5248H11···H72.2523
N11···H72.7581H14A···O9xii2.6735
C3···O122.934 (3)H14A···C3xvi3.0985
C6···O83.093 (2)H14A···C4xvi3.0498
C6···C10ix3.561 (3)H14A···H3xvi2.5425
C10···O12x3.220 (3)H14A···H4xvi2.4413
C10···C6xi3.561 (3)H14B···O122.6039
C14···O9xii3.335 (3)H14B···O8vii2.7812
C14···N7xii3.287 (3)H14B···C8vii3.0345
C3···H14Axiii3.0985H14B···H7xii2.5811
C4···H14Axiii3.0498H14C···O122.6038
C5···H10Cxiv3.0749H14C···O12viii2.8985
C8···H62.9191H14C···C10iii2.9362
C8···H14Bv3.0345H14C···H10Aiii2.2768
C8···H11i3.0765H14C···N7xii2.9261
C8—O9—C10116.17 (15)O13—C12—N11108.27 (16)
C12—O13—C14114.63 (15)O12—C12—O13124.59 (17)
C1—N7—C8122.75 (15)C2—C3—H3119.95
C2—N11—C12125.17 (16)C4—C3—H3119.98
C1—N7—H7118.62C3—C4—H4119.69
C8—N7—H7118.62C5—C4—H4119.75
C2—N11—H11117.41C4—C5—H5120.17
C12—N11—H11117.42C6—C5—H5120.17
N7—C1—C2120.03 (16)C1—C6—H6119.85
N7—C1—C6119.72 (16)C5—C6—H6119.89
C2—C1—C6120.24 (17)O9—C10—H10A109.46
C1—C2—C3119.18 (18)O9—C10—H10B109.47
N11—C2—C1118.85 (17)O9—C10—H10C109.47
N11—C2—C3121.93 (17)H10A—C10—H10B109.47
C2—C3—C4120.07 (18)H10A—C10—H10C109.47
C3—C4—C5120.56 (19)H10B—C10—H10C109.48
C4—C5—C6119.7 (2)O13—C14—H14A109.44
C1—C6—C5120.27 (18)O13—C14—H14B109.45
O8—C8—O9123.68 (17)O13—C14—H14C109.47
O8—C8—N7125.65 (17)H14A—C14—H14B109.47
O9—C8—N7110.67 (16)H14A—C14—H14C109.49
O12—C12—N11127.11 (18)H14B—C14—H14C109.50
C10—O9—C8—O85.0 (3)C6—C1—C2—N11176.99 (17)
C10—O9—C8—N7175.17 (15)N7—C1—C2—N112.2 (3)
C14—O13—C12—O120.8 (3)N7—C1—C2—C3179.91 (17)
C14—O13—C12—N11179.04 (16)C2—C1—C6—C52.0 (3)
C1—N7—C8—O9174.24 (15)C6—C1—C2—C30.7 (3)
C8—N7—C1—C2123.6 (2)N7—C1—C6—C5178.76 (18)
C8—N7—C1—C657.2 (2)N11—C2—C3—C4178.40 (19)
C1—N7—C8—O85.6 (3)C1—C2—C3—C40.8 (3)
C12—N11—C2—C331.7 (3)C2—C3—C4—C51.0 (3)
C2—N11—C12—O123.4 (3)C3—C4—C5—C60.3 (3)
C12—N11—C2—C1150.73 (18)C4—C5—C6—C11.8 (3)
C2—N11—C12—O13178.46 (16)
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+2, z+1/2; (iii) x+1, y+1, z; (iv) x1/2, y, z1/2; (v) x1/2, y+1, z+1/2; (vi) x+1, y, z; (vii) x+1/2, y+1, z1/2; (viii) x, y+1, z; (ix) x+1/2, y+1, z+1/2; (x) x1, y1, z; (xi) x1/2, y+1, z1/2; (xii) x+1/2, y+2, z1/2; (xiii) x+1/2, y+2, z+1/2; (xiv) x+1/2, y, z+1/2; (xv) x1, y, z; (xvi) x1/2, y+2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O8viii0.862.022.819 (2)155
N11—H11···O8viii0.862.132.976 (2)170
C3—H3···O120.932.452.934 (3)112
Symmetry code: (viii) x, y+1, z.
 

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