#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230328.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230328
loop_
_publ_author_name
'Talipov, Samat'
'Yuldashev, Abdurasul'
'Karimov, Zakirjon'
'Turgunov, Kambarali'
'Ibragimov, Bakhtiyar'
_publ_section_title
;
 2-{2-[2-(1,3-Dioxoisoindol-2-yl)ethoxy]ethyl}isoindole-1,3-dione
;
_journal_coeditor_code           GW2102
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1487
_journal_paper_doi               10.1107/S1600536811018496
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H16 N2 O5'
_chemical_formula_moiety         'C20 H16 N2 O5'
_chemical_formula_sum            'C20 H16 N2 O5'
_chemical_formula_weight         364.35
_chemical_name_common            '2-(Phthalimido)ethyl ether'
_chemical_name_systematic
;
2-{2-[2-(1,3-Dioxoisoindol-2-yl)ethoxy]ethyl}isoindole-1,3-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.6330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.89280(10)
_cell_length_b                   11.96560(10)
_cell_length_c                   14.3572(2)
_cell_measurement_reflns_used    9302
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.5044
_cell_measurement_theta_min      3.3082
_cell_volume                     1739.50(3)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2576
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14673
_diffrn_reflns_theta_full        75.64
_diffrn_reflns_theta_max         75.64
_diffrn_reflns_theta_min         4.40
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlisPro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.0094(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0682P)²+0.1804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                3075
_reflns_number_total             3575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gw2102.cif
_cod_data_source_block           I
_cod_original_cell_volume        1739.49(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230328
_cod_database_fobs_code          2230328
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.20673(10) 0.08438(9) 0.31107(8) 0.0482(3) Uani d . 1 1 . .
N N2 0.37536(10) -0.01311(9) 0.06449(8) 0.0456(3) Uani d . 1 1 . .
O O1 0.14477(11) 0.03279(11) 0.44214(8) 0.0705(3) Uani d . 1 1 . .
O O2 0.32443(10) 0.15162(9) 0.21829(7) 0.0564(3) Uani d . 1 1 . .
O O3 0.19329(8) -0.09719(7) 0.16698(6) 0.0470(2) Uani d . 1 1 . .
O O4 0.26607(11) 0.11689(10) -0.05545(9) 0.0714(3) Uani d . 1 1 . .
O O5 0.52801(11) -0.10263(11) 0.19907(8) 0.0726(3) Uani d . 1 1 . .
C C1 0.22559(13) 0.07069(11) 0.41171(10) 0.0491(3) Uani d . 1 1 . .
C C2 0.36170(13) 0.11145(10) 0.46882(9) 0.0445(3) Uani d . 1 1 . .
C C3 0.41737(12) 0.14479(10) 0.40088(9) 0.0423(3) Uani d . 1 1 . .
C C4 0.31715(12) 0.12978(10) 0.29806(9) 0.0444(3) Uani d . 1 1 . .
C C5 0.43090(15) 0.11709(11) 0.57083(10) 0.0524(3) Uani d . 1 1 . .
H H5A 0.3929 0.0948 0.6162 0.063 Uiso calc R 1 1 . .
C C6 0.55940(14) 0.15730(12) 0.60309(10) 0.0554(3) Uani d . 1 1 . .
H H6A 0.6084 0.1625 0.6714 0.067 Uiso calc R 1 1 . .
C C7 0.61590(14) 0.18991(11) 0.53518(11) 0.0541(3) Uani d . 1 1 . .
H H7A 0.7024 0.2161 0.5588 0.065 Uiso calc R 1 1 . .
C C8 0.54558(13) 0.18413(10) 0.43237(10) 0.0485(3) Uani d . 1 1 . .
H H8A 0.5833 0.2059 0.3867 0.058 Uiso calc R 1 1 . .
C C9 0.08711(13) 0.05067(13) 0.22883(11) 0.0547(3) Uani d . 1 1 . .
H H9A 0.0767 0.0963 0.1706 0.066 Uiso calc R 1 1 . .
H H9B 0.0114 0.0638 0.2476 0.066 Uiso calc R 1 1 . .
C C10 0.09011(13) -0.07152(12) 0.20170(10) 0.0514(3) Uani d . 1 1 . .
H H10A 0.1008 -0.1169 0.2601 0.062 Uiso calc R 1 1 . .
H H10B 0.0061 -0.0910 0.1500 0.062 Uiso calc R 1 1 . .
C C11 0.15869(12) -0.07463(12) 0.06348(9) 0.0483(3) Uani d . 1 1 . .
H H11A 0.1335 0.0032 0.0500 0.058 Uiso calc R 1 1 . .
H H11B 0.0839 -0.1204 0.0246 0.058 Uiso calc R 1 1 . .
C C12 0.27467(14) -0.09957(12) 0.03325(10) 0.0521(3) Uani d . 1 1 . .
H H12A 0.3137 -0.1702 0.0627 0.062 Uiso calc R 1 1 . .
H H12B 0.2435 -0.1074 -0.0390 0.062 Uiso calc R 1 1 . .
C C13 0.35959(14) 0.09081(11) 0.01785(10) 0.0511(3) Uani d . 1 1 . .
C C14 0.47835(15) 0.15636(13) 0.07673(12) 0.0603(4) Uani d . 1 1 . .
C C15 0.55826(14) 0.08926(15) 0.15356(11) 0.0613(4) Uani d . 1 1 . .
C C16 0.49218(13) -0.02092(13) 0.14666(10) 0.0514(3) Uani d . 1 1 . .
C C17 0.5109(2) 0.26603(16) 0.06645(19) 0.0904(7) Uani d . 1 1 . .
H H17A 0.4569 0.3112 0.0149 0.108 Uiso calc R 1 1 . .
C C18 0.6273(3) 0.3050(2) 0.1364(3) 0.1217(11) Uani d . 1 1 . .
H H18A 0.6528 0.3782 0.1312 0.146 Uiso calc R 1 1 . .
C C19 0.7070(3) 0.2397(3) 0.2133(2) 0.1250(12) Uani d . 1 1 . .
H H19A 0.7838 0.2700 0.2597 0.150 Uiso calc R 1 1 . .
C C20 0.67502(18) 0.1286(2) 0.22309(15) 0.0915(7) Uani d . 1 1 . .
H H20A 0.7298 0.0833 0.2741 0.110 Uiso calc R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 . . 112.37(10) ?
C1 N1 C9 . . 123.68(11) ?
C4 N1 C9 . . 123.90(11) ?
C16 N2 C13 . . 112.47(11) ?
C16 N2 C12 . . 124.58(11) ?
C13 N2 C12 . . 122.82(11) ?
C11 O3 C10 . . 112.80(10) ?
O1 C1 N1 . . 124.89(13) ?
O1 C1 C2 . . 129.50(13) ?
N1 C1 C2 . . 105.61(11) ?
C5 C2 C3 . . 121.62(12) ?
C5 C2 C1 . . 130.14(12) ?
C3 C2 C1 . . 108.24(11) ?
C8 C3 C2 . . 121.35(12) ?
C8 C3 C4 . . 130.44(12) ?
C2 C3 C4 . . 108.21(11) ?
O2 C4 N1 . . 125.04(12) ?
O2 C4 C3 . . 129.43(12) ?
N1 C4 C3 . . 105.53(10) ?
C2 C5 C6 . . 117.40(13) ?
C2 C5 H5A . . 121.3 ?
C6 C5 H5A . . 121.3 ?
C7 C6 C5 . . 121.13(12) ?
C7 C6 H6A . . 119.4 ?
C5 C6 H6A . . 119.4 ?
C6 C7 C8 . . 121.21(13) ?
C6 C7 H7A . . 119.4 ?
C8 C7 H7A . . 119.4 ?
C3 C8 C7 . . 117.29(12) ?
C3 C8 H8A . . 121.4 ?
C7 C8 H8A . . 121.4 ?
N1 C9 C10 . . 112.19(11) ?
N1 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
N1 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O3 C10 C9 . . 113.15(11) ?
O3 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
O3 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.8 ?
O3 C11 C12 . . 109.66(10) ?
O3 C11 H11A . . 109.7 ?
C12 C11 H11A . . 109.7 ?
O3 C11 H11B . . 109.7 ?
C12 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
N2 C12 C11 . . 112.77(11) ?
N2 C12 H12A . . 109.0 ?
C11 C12 H12A . . 109.0 ?
N2 C12 H12B . . 109.0 ?
C11 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
O4 C13 N2 . . 124.47(13) ?
O4 C13 C14 . . 129.80(14) ?
N2 C13 C14 . . 105.74(12) ?
C17 C14 C15 . . 121.74(18) ?
C17 C14 C13 . . 130.25(18) ?
C15 C14 C13 . . 107.95(13) ?
C20 C15 C14 . . 121.39(18) ?
C20 C15 C16 . . 130.21(18) ?
C14 C15 C16 . . 108.34(13) ?
O5 C16 N2 . . 124.80(14) ?
O5 C16 C15 . . 129.70(14) ?
N2 C16 C15 . . 105.51(12) ?
C18 C17 C14 . . 116.6(2) ?
C18 C17 H17A . . 121.7 ?
C14 C17 H17A . . 121.7 ?
C19 C18 C17 . . 122.3(2) ?
C19 C18 H18A . . 118.8 ?
C17 C18 H18A . . 118.8 ?
C18 C19 C20 . . 121.2(2) ?
C18 C19 H19A . . 119.4 ?
C20 C19 H19A . . 119.4 ?
C15 C20 C19 . . 116.8(2) ?
C15 C20 H20A . . 121.6 ?
C19 C20 H20A . . 121.6 ?
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
N1 C1 . 1.3922(16) ?
N1 C4 . 1.3937(17) ?
N1 C9 . 1.4561(16) ?
N2 C16 . 1.3830(16) ?
N2 C13 . 1.3926(17) ?
N2 C12 . 1.4531(17) ?
O1 C1 . 1.2062(16) ?
O2 C4 . 1.2055(15) ?
O3 C11 . 1.4178(15) ?
O3 C10 . 1.4209(16) ?
O4 C13 . 1.2051(17) ?
O5 C16 . 1.2075(18) ?
C1 C2 . 1.4873(18) ?
C2 C5 . 1.3798(18) ?
C2 C3 . 1.3836(17) ?
C3 C8 . 1.3823(18) ?
C3 C4 . 1.4884(17) ?
C5 C6 . 1.388(2) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.387(2) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.3917(19) ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 C10 . 1.517(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.5092(19) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.482(2) ?
C14 C17 . 1.381(2) ?
C14 C15 . 1.382(2) ?
C15 C20 . 1.378(2) ?
C15 C16 . 1.488(2) ?
C17 C18 . 1.376(4) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.369(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.395(4) ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5A O5 3_656 0.93 2.47 3.171(2) 132 y
C19 H19A O5 2_655 0.93 2.45 3.286(4) 150 y
C11 H11B Cg3 2_545 0.97 2.84 3.624(2) 139 y
C12 H12B Cg4 3_655 0.97 2.94 3.567(2) 123 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 216947
