#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202187.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2202187
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o739
_journal_page_last  o741
_publ_section_title
;
Ethyl N-(2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)carbamate
;
loop_
_publ_author_name
  'Shi, Da-Xin'
  'Feng, Ya-Qing'
  'Li, Xiao-Fang'
_chemical_formula_moiety  'C15 H18 N2 O4'
_chemical_formula_sum  'C15 H18 N2 O4'
_chemical_formula_iupac  'C15 H18 N2 O4'
_chemical_formula_weight  290.31
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  6.933(2)
_cell_length_b  14.210(4)
_cell_length_c  15.913(5)
_cell_angle_alpha  99.657(6)
_cell_angle_beta  101.373(6)
_cell_angle_gamma  91.120(6)
_cell_volume  1512.8(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.275
_exptl_crystal_density_meas  NONE
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.2078(4) 0.74190(18) 0.65282(16) 0.0753(8) Uani d . 1 . . O
  O2 0.2449(4) 1.05357(18) 0.61838(18) 0.0852(9) Uani d . 1 . . O
  O3 0.2613(5) 0.7533(2) 0.19331(17) 0.0892(10) Uani d . 1 . . O
  O4 0.2792(4) 0.59472(19) 0.18682(15) 0.0713(8) Uani d D 1 . . O
  O5 0.3010(4) 0.18798(17) 0.36444(16) 0.0729(8) Uani d . 1 . . O
  O6 0.2679(4) 0.51277(17) 0.40089(17) 0.0765(8) Uani d . 1 . . O
  O7 0.2139(4) 0.3674(2) 0.82189(17) 0.0822(9) Uani d . 1 . . O
  O8 0.2318(4) 0.2111(2) 0.83008(16) 0.0833(9) Uani d D 1 . . O
  N1 0.2251(5) 0.9050(2) 0.65709(19) 0.0633(9) Uani d . 1 . . N
  N2 0.2604(4) 0.6823(2) 0.31219(18) 0.0569(8) Uani d . 1 . . N
  H2C 0.2591 0.6266 0.3266 0.068 Uiso calc R 1 B . H
  N3 0.2910(4) 0.3499(2) 0.36153(18) 0.0564(8) Uani d . 1 . . N
  N4 0.2387(4) 0.2537(2) 0.70447(18) 0.0594(8) Uani d . 1 . . N
  H4C 0.2457 0.1929 0.6904 0.071 Uiso calc R 1 A 2 H
  C1 0.7594(9) 0.9999(4) 0.8653(4) 0.141(2) Uani d U 1 . . C
  H1A 0.8555 1.0434 0.8544 0.211 Uiso calc R 1 . . H
  H1B 0.8082 0.9368 0.8609 0.211 Uiso calc R 1 . . H
  H1C 0.7348 1.0202 0.9227 0.211 Uiso calc R 1 . . H
  C2 0.5683(8) 0.9986(3) 0.7983(3) 0.0958(15) Uani d . 1 . . C
  H2A 0.5217 1.0628 0.8023 0.115 Uiso calc R 1 . . H
  H2B 0.5951 0.9796 0.7405 0.115 Uiso calc R 1 . . H
  C3 0.4107(8) 0.9328(3) 0.8102(3) 0.0899(15) Uani d . 1 . . C
  H3A 0.3917 0.9489 0.8696 0.108 Uiso calc R 1 . . H
  H3B 0.4545 0.8680 0.8022 0.108 Uiso calc R 1 . . H
  C4 0.2146(7) 0.9352(3) 0.7488(3) 0.0796(13) Uani d . 1 . . C
  H4A 0.1183 0.8938 0.7635 0.096 Uiso calc R 1 . . H
  H4B 0.1699 0.9998 0.7567 0.096 Uiso calc R 1 . . H
  C5 0.2223(5) 0.8104(3) 0.6169(2) 0.0568(10) Uani d . 1 . . C
  C6 0.2372(5) 0.8119(2) 0.5262(2) 0.0479(9) Uani d . 1 B . C
  C7 0.2408(5) 0.7379(2) 0.4594(2) 0.0505(9) Uani d . 1 . . C
  H7A 0.2338 0.6748 0.4676 0.061 Uiso calc R 1 B . H
  C8 0.2551(5) 0.7598(2) 0.3785(2) 0.0494(9) Uani d . 1 B . C
  C9 0.2647(5) 0.8548(3) 0.3670(2) 0.0625(11) Uani d . 1 . . C
  H9A 0.2731 0.8686 0.3127 0.075 Uiso calc R 1 B . H
  C10 0.2618(6) 0.9289(3) 0.4355(2) 0.0652(11) Uani d . 1 B . C
  H10A 0.2688 0.9922 0.4277 0.078 Uiso calc R 1 . . H
  C11 0.2482(5) 0.9068(2) 0.5154(2) 0.0541(9) Uani d . 1 . . C
  C12 0.2405(6) 0.9670(3) 0.5997(3) 0.0627(10) Uani d . 1 B . C
  C13 0.2672(6) 0.6844(3) 0.2283(2) 0.0631(10) Uani d D 1 B . C
  C14 0.336(5) 0.5752(16) 0.1028(12) 0.089(10) Uani d PDU 0.23(2) B 1 C
  H14A 0.4720 0.5575 0.1093 0.107 Uiso calc PR 0.23(2) B 1 H
  H14B 0.3214 0.6308 0.0745 0.107 Uiso calc PR 0.23(2) B 1 H
  C15 0.196(5) 0.492(3) 0.050(2) 0.102(10) Uani d PDU 0.23(2) B 1 C
  H15A 0.2039 0.4849 -0.0105 0.153 Uiso calc PR 0.23(2) B 1 H
  H15B 0.0634 0.5044 0.0558 0.153 Uiso calc PR 0.23(2) B 1 H
  H15C 0.2329 0.4338 0.0708 0.153 Uiso calc PR 0.23(2) B 1 H
  C14' 0.2600(18) 0.5866(4) 0.0916(3) 0.072(2) Uani d PDU 0.77(2) B 2 C
  H14C 0.3558 0.6298 0.0786 0.087 Uiso calc PR 0.77(2) B 2 H
  H14D 0.1291 0.6022 0.0649 0.087 Uiso calc PR 0.77(2) B 2 H
  C15' 0.297(2) 0.4850(5) 0.0585(6) 0.091(3) Uani d PDU 0.77(2) B 2 C
  H15D 0.2866 0.4759 -0.0034 0.137 Uiso calc PR 0.77(2) B 2 H
  H15E 0.2006 0.4433 0.0718 0.137 Uiso calc PR 0.77(2) B 2 H
  H15F 0.4262 0.4706 0.0859 0.137 Uiso calc PR 0.77(2) B 2 H
  C16 -0.2171(9) 0.3378(5) 0.1388(4) 0.144(2) Uani d U 1 C 2 C
  H16A -0.3198 0.3817 0.1427 0.216 Uiso calc R 1 C 2 H
  H16B -0.2603 0.2768 0.1489 0.216 Uiso calc R 1 C 2 H
  H16C -0.1868 0.3306 0.0818 0.216 Uiso calc R 1 C 2 H
  C17 -0.0326(7) 0.3764(3) 0.2074(3) 0.0890(14) Uani d . 1 C 2 C
  H17A 0.0078 0.4389 0.1978 0.107 Uiso calc R 1 C 2 H
  H17B -0.0648 0.3844 0.2647 0.107 Uiso calc R 1 C 2 H
  C18 0.1357(7) 0.3124(3) 0.2052(3) 0.0805(13) Uani d . 1 C 2 C
  H18A 0.1677 0.3050 0.1479 0.097 Uiso calc R 1 C 2 H
  H18B 0.0938 0.2498 0.2139 0.097 Uiso calc R 1 C 2 H
  C19 0.3203(6) 0.3477(3) 0.2728(2) 0.0711(12) Uani d . 1 C 2 C
  H19A 0.4260 0.3062 0.2627 0.085 Uiso calc R 1 C 2 H
  H19B 0.3599 0.4115 0.2662 0.085 Uiso calc R 1 C 2 H
  C20 0.2861(5) 0.2690(3) 0.3999(2) 0.0550(9) Uani d . 1 C 2 C
  C21 0.2629(5) 0.3043(2) 0.4906(2) 0.0468(9) Uani d . 1 C 2 C
  C22 0.2584(5) 0.2547(2) 0.5569(2) 0.0500(9) Uani d . 1 C 2 C
  H22A 0.2670 0.1886 0.5486 0.060 Uiso calc R 1 C 2 H
  C23 0.2406(5) 0.3068(2) 0.6378(2) 0.0492(9) Uani d . 1 C 2 C
  C24 0.2264(5) 0.4055(2) 0.6486(2) 0.0571(10) Uani d . 1 C 2 C
  H24A 0.2129 0.4393 0.7023 0.069 Uiso calc R 1 C 2 H
  C25 0.2320(5) 0.4540(2) 0.5804(2) 0.0585(10) Uani d . 1 C 2 C
  H25A 0.2235 0.5201 0.5879 0.070 Uiso calc R 1 C 2 H
  C26 0.2503(5) 0.4026(2) 0.5012(2) 0.0512(9) Uani d . 1 C 2 C
  C27 0.2696(5) 0.4326(3) 0.4189(2) 0.0567(10) Uani d . 1 C 2 C
  C28 0.2273(6) 0.2862(3) 0.7881(2) 0.0635(10) Uani d D 1 C 2 C
  C29 0.1836(18) 0.2220(11) 0.9163(6) 0.085(5) Uani d PDU 0.528(18) C 1 C
  H29A 0.0765 0.1777 0.9176 0.102 Uiso calc PR 0.528(18) C 1 H
  H29B 0.1504 0.2868 0.9363 0.102 Uiso calc PR 0.528(18) C 1 H
  C30 0.381(2) 0.1972(14) 0.9700(8) 0.123(5) Uani d PDU 0.528(18) C 1 C
  H30A 0.3736 0.2049 1.0303 0.185 Uiso calc PR 0.528(18) C 1 H
  H30B 0.4855 0.2390 0.9633 0.185 Uiso calc PR 0.528(18) C 1 H
  H30C 0.4076 0.1321 0.9496 0.185 Uiso calc PR 0.528(18) C 1 H
  C29' 0.254(3) 0.2426(8) 0.9266(5) 0.072(4) Uani d PDU 0.472(18) C 2 C
  H29C 0.1383 0.2749 0.9395 0.087 Uiso calc PR 0.472(18) C 2 H
  H29D 0.3687 0.2861 0.9495 0.087 Uiso calc PR 0.472(18) C 2 H
  C30' 0.276(3) 0.1531(8) 0.9663(8) 0.099(5) Uani d PDU 0.472(18) C 2 C
  H30D 0.2793 0.1691 1.0276 0.148 Uiso calc PR 0.472(18) C 2 H
  H30E 0.3968 0.1249 0.9572 0.148 Uiso calc PR 0.472(18) C 2 H
  H30F 0.1670 0.1085 0.9393 0.148 Uiso calc PR 0.472(18) C 2 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1 0.112(2) 0.0555(16) 0.0669(18) -0.0036(15) 0.0308(16) 0.0200(14)
  O2 0.129(3) 0.0428(16) 0.087(2) 0.0120(16) 0.0293(18) 0.0103(14)
  O3 0.140(3) 0.0706(19) 0.0563(17) -0.0100(18) 0.0121(17) 0.0207(15)
  O4 0.093(2) 0.0732(19) 0.0501(16) 0.0037(15) 0.0216(14) 0.0082(14)
  O5 0.109(2) 0.0485(16) 0.0622(17) 0.0231(14) 0.0222(15) 0.0050(13)
  O6 0.107(2) 0.0474(16) 0.0833(19) 0.0077(14) 0.0313(16) 0.0212(14)
  O7 0.114(2) 0.0688(19) 0.0608(18) 0.0134(16) 0.0187(16) -0.0005(15)
  O8 0.127(3) 0.0767(19) 0.0534(17) 0.0236(17) 0.0289(17) 0.0169(15)
  N1 0.087(2) 0.0477(19) 0.061(2) 0.0043(16) 0.0295(18) 0.0095(16)
  N2 0.071(2) 0.0537(18) 0.0481(19) -0.0008(15) 0.0146(16) 0.0138(15)
  N3 0.069(2) 0.0499(18) 0.0546(19) 0.0116(15) 0.0197(16) 0.0126(15)
  N4 0.080(2) 0.0517(18) 0.0458(19) 0.0110(16) 0.0107(16) 0.0067(15)
  C1 0.128(5) 0.140(5) 0.147(5) 0.012(4) 0.013(4) 0.021(4)
  C2 0.122(4) 0.081(3) 0.090(3) -0.007(3) 0.037(3) 0.013(3)
  C3 0.141(5) 0.071(3) 0.062(3) -0.001(3) 0.033(3) 0.010(2)
  C4 0.119(4) 0.062(3) 0.069(3) 0.010(2) 0.048(3) 0.010(2)
  C5 0.063(3) 0.050(2) 0.062(2) 0.0004(18) 0.019(2) 0.015(2)
  C6 0.050(2) 0.041(2) 0.054(2) 0.0016(16) 0.0102(17) 0.0116(17)
  C7 0.049(2) 0.043(2) 0.061(2) 0.0022(16) 0.0084(18) 0.0152(18)
  C8 0.048(2) 0.051(2) 0.048(2) 0.0013(16) 0.0046(17) 0.0128(18)
  C9 0.077(3) 0.059(2) 0.054(2) -0.005(2) 0.010(2) 0.020(2)
  C10 0.083(3) 0.049(2) 0.065(3) 0.0005(19) 0.009(2) 0.022(2)
  C11 0.060(3) 0.045(2) 0.057(2) 0.0045(17) 0.0098(19) 0.0112(18)
  C12 0.071(3) 0.050(2) 0.070(3) 0.006(2) 0.018(2) 0.014(2)
  C13 0.068(3) 0.063(3) 0.056(3) -0.006(2) 0.003(2) 0.012(2)
  C14 0.092(13) 0.096(12) 0.078(12) -0.001(9) 0.007(8) 0.025(8)
  C15 0.106(14) 0.105(13) 0.092(12) 0.010(9) 0.018(9) 0.014(9)
  C14' 0.082(5) 0.084(4) 0.050(4) 0.001(4) 0.010(3) 0.011(3)
  C15' 0.109(7) 0.097(5) 0.071(4) 0.019(5) 0.036(5) 0.004(3)
  C16 0.130(5) 0.183(5) 0.121(4) -0.010(4) -0.010(4) 0.074(4)
  C17 0.102(4) 0.095(3) 0.080(3) 0.009(3) 0.023(3) 0.039(3)
  C18 0.123(4) 0.067(3) 0.059(3) 0.011(3) 0.029(3) 0.019(2)
  C19 0.084(3) 0.073(3) 0.066(3) 0.017(2) 0.032(2) 0.019(2)
  C20 0.057(3) 0.051(2) 0.058(2) 0.0140(18) 0.0106(19) 0.011(2)
  C21 0.046(2) 0.044(2) 0.049(2) 0.0096(16) 0.0065(17) 0.0060(17)
  C22 0.055(2) 0.0401(18) 0.051(2) 0.0089(16) 0.0022(18) 0.0044(17)
  C23 0.048(2) 0.047(2) 0.051(2) 0.0073(16) 0.0044(17) 0.0082(18)
  C24 0.065(3) 0.051(2) 0.052(2) 0.0103(18) 0.0106(19) -0.0006(18)
  C25 0.069(3) 0.0368(19) 0.067(3) 0.0105(17) 0.012(2) 0.0035(19)
  C26 0.050(2) 0.044(2) 0.060(2) 0.0067(16) 0.0114(18) 0.0081(18)
  C27 0.059(3) 0.046(2) 0.067(3) 0.0092(18) 0.015(2) 0.012(2)
  C28 0.069(3) 0.067(3) 0.055(3) 0.016(2) 0.010(2) 0.012(2)
  C29 0.094(8) 0.087(7) 0.067(6) -0.001(6) 0.013(5) -0.002(5)
  C30 0.132(9) 0.146(9) 0.089(7) 0.002(7) 0.019(6) 0.020(6)
  C29' 0.081(8) 0.088(7) 0.050(6) 0.011(6) 0.014(5) 0.017(5)
  C30' 0.134(10) 0.097(7) 0.071(6) 0.000(6) 0.028(6) 0.023(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C5 . 1.220(4) y
  O2 C12 . 1.214(4) ?
  O3 C13 . 1.202(4) ?
  O4 C13 . 1.346(4) y
  O4 C14 . 1.453(9) ?
  O4 C14' . 1.479(5) ?
  O5 C20 . 1.211(4) y
  O6 C27 . 1.220(4) ?
  O7 C28 . 1.201(4) ?
  O8 C28 . 1.349(4) y
  O8 C29 . 1.459(7) ?
  O8 C29' . 1.502(7) ?
  N1 C5 . 1.386(4) y
  N1 C12 . 1.389(4) ?
  N1 C4 . 1.467(5) ?
  N2 C13 . 1.350(4) y
  N2 C8 . 1.398(4) ?
  N2 H2C . 0.8600 ?
  N3 C27 . 1.392(4) y
  N3 C20 . 1.392(4) ?
  N3 C19 . 1.462(4) ?
  N4 C28 . 1.352(4) y
  N4 C23 . 1.402(4) ?
  N4 H4C . 0.8600 ?
  C1 C2 . 1.526(7) ?
  C1 H1A . 0.9600 ?
  C1 H1B . 0.9600 ?
  C1 H1C . 0.9600 ?
  C2 C3 . 1.485(6) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C4 . 1.515(6) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 C6 . 1.471(5) ?
  C6 C7 . 1.368(4) ?
  C6 C11 . 1.391(4) ?
  C7 C8 . 1.396(4) ?
  C7 H7A . 0.9300 ?
  C8 C9 . 1.393(5) ?
  C9 C10 . 1.386(5) ?
  C9 H9A . 0.9300 ?
  C10 C11 . 1.381(5) ?
  C10 H10A . 0.9300 ?
  C11 C12 . 1.475(5) ?
  C14 C15 . 1.535(10) ?
  C14 H14A . 0.9700 ?
  C14 H14B . 0.9700 ?
  C15 H15A . 0.9600 ?
  C15 H15B . 0.9600 ?
  C15 H15C . 0.9600 ?
  C14' C15' . 1.497(7) ?
  C14' H14C . 0.9700 ?
  C14' H14D . 0.9700 ?
  C15' H15D . 0.9600 ?
  C15' H15E . 0.9600 ?
  C15' H15F . 0.9600 ?
  C16 C17 . 1.533(6) ?
  C16 H16A . 0.9600 ?
  C16 H16B . 0.9600 ?
  C16 H16C . 0.9600 ?
  C17 C18 . 1.496(6) ?
  C17 H17A . 0.9700 ?
  C17 H17B . 0.9700 ?
  C18 C19 . 1.515(6) ?
  C18 H18A . 0.9700 ?
  C18 H18B . 0.9700 ?
  C19 H19A . 0.9700 ?
  C19 H19B . 0.9700 ?
  C20 C21 . 1.488(5) ?
  C21 C22 . 1.368(4) ?
  C21 C26 . 1.385(4) ?
  C22 C23 . 1.403(4) ?
  C22 H22A . 0.9300 ?
  C23 C24 . 1.392(4) ?
  C24 C25 . 1.388(5) ?
  C24 H24A . 0.9300 ?
  C25 C26 . 1.376(5) ?
  C25 H25A . 0.9300 ?
  C26 C27 . 1.473(5) ?
  C29 C30 . 1.546(9) ?
  C29 H29A . 0.9700 ?
  C29 H29B . 0.9700 ?
  C30 H30A . 0.9600 ?
  C30 H30B . 0.9600 ?
  C30 H30C . 0.9600 ?
  C29' C30' . 1.509(9) ?
  C29' H29C . 0.9700 ?
  C29' H29D . 0.9700 ?
  C30' H30D . 0.9600 ?
  C30' H30E . 0.9600 ?
  C30' H30F . 0.9600 ?