#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/49/2224939.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_2224939
loop_
_publ_author_name
'Yang, Kai'
'Guo, Qiang'
'Wang, Shi-Fan'
_publ_section_title
;
 Bis[2-(1,3-dioxoisoindolin-2-yl)ethyl] phthalate
;
_journal_coeditor_code           DN2524
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o337
_journal_paper_doi               10.1107/S160053680905524X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C28 H20 N2 O8'
_chemical_formula_moiety         'C28 H20 N2 O8'
_chemical_formula_sum            'C28 H20 N2 O8'
_chemical_formula_weight         512.46
_chemical_name_systematic
;
Bis[2-(1,3-dioxoisoindolin-2-yl)ethyl] phthalate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.125(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.021(2)
_cell_length_b                   12.3953(19)
_cell_length_c                   25.954(4)
_cell_measurement_reflns_used    19894
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.02
_cell_measurement_theta_min      2.27
_cell_volume                     4832.4(12)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18257
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0561P)²+1.0157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                3689
_reflns_number_total             4718
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2524.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4832.5(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224939
_cod_database_fobs_code          2224939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.97630(11) 1.05121(13) 0.91255(6) 0.0416(4) Uani d . 1 . .
C C2 0.97412(11) 0.96188(13) 0.87460(6) 0.0418(4) Uani d . 1 . .
C C3 1.03959(12) 0.89040(15) 0.85964(7) 0.0553(5) Uani d . 1 . .
H H3 1.0973 0.8957 0.8724 0.066 Uiso calc R 1 . .
C C4 1.01605(15) 0.81098(16) 0.82513(7) 0.0650(5) Uani d . 1 . .
H H4 1.0588 0.7616 0.8144 0.078 Uiso calc R 1 . .
C C5 0.93112(15) 0.80299(16) 0.80617(7) 0.0640(5) Uani d . 1 . .
H H5 0.9172 0.7483 0.7830 0.077 Uiso calc R 1 . .
C C6 0.86611(13) 0.87458(16) 0.82088(6) 0.0548(5) Uani d . 1 . .
H H6 0.8086 0.8695 0.8078 0.066 Uiso calc R 1 . .
C C7 0.88892(10) 0.95428(13) 0.85562(6) 0.0400(4) Uani d . 1 . .
C C8 0.83416(10) 1.03777(13) 0.88082(6) 0.0431(4) Uani d . 1 . .
C C9 0.86318(12) 1.18167(13) 0.94637(6) 0.0481(4) Uani d . 1 . .
H H9A 0.8060 1.2084 0.9345 0.058 Uiso calc R 1 . .
H H9B 0.9060 1.2399 0.9432 0.058 Uiso calc R 1 . .
C C10 0.85568(11) 1.15007(13) 1.00187(6) 0.0459(4) Uani d . 1 . .
H H10A 0.9140 1.1333 1.0159 0.055 Uiso calc R 1 . .
H H10B 0.8301 1.2085 1.0218 0.055 Uiso calc R 1 . .
C C11 0.75624(10) 1.03503(12) 1.04734(6) 0.0388(4) Uani d . 1 . .
C C12 0.70715(10) 0.93102(12) 1.04218(6) 0.0389(4) Uani d . 1 . .
C C13 0.73462(12) 0.84711(14) 1.07294(6) 0.0501(4) Uani d . 1 . .
H H13 0.7771 0.8590 1.0984 0.060 Uiso calc R 1 . .
C C14 0.69920(14) 0.74499(15) 1.06614(7) 0.0579(5) Uani d . 1 . .
H H14 0.7186 0.6882 1.0867 0.069 Uiso calc R 1 . .
C C15 0.63546(13) 0.72739(15) 1.02905(7) 0.0553(5) Uani d . 1 . .
H H15 0.6118 0.6587 1.0245 0.066 Uiso calc R 1 . .
C C16 0.60667(11) 0.81130(13) 0.99856(7) 0.0475(4) Uani d . 1 . .
H H16 0.5633 0.7991 0.9736 0.057 Uiso calc R 1 . .
C C17 0.64183(10) 0.91381(12) 1.00478(6) 0.0382(4) Uani d . 1 . .
C C18 0.60827(10) 1.00635(13) 0.97419(6) 0.0402(4) Uani d . 1 . .
C C19 0.53654(12) 1.06028(14) 0.89801(6) 0.0475(4) Uani d . 1 . .
H H19A 0.5853 1.1012 0.8833 0.057 Uiso calc R 1 . .
H H19B 0.4993 1.1091 0.9177 0.057 Uiso calc R 1 . .
C C20 0.48331(11) 1.00681(15) 0.85621(6) 0.0492(4) Uani d . 1 . .
H H20A 0.4368 0.9635 0.8718 0.059 Uiso calc R 1 . .
H H20B 0.4550 1.0618 0.8353 0.059 Uiso calc R 1 . .
C C21 0.59113(10) 0.97752(15) 0.78414(6) 0.0430(4) Uani d . 1 . .
C C22 0.63316(11) 0.88163(14) 0.76059(6) 0.0462(4) Uani d . 1 . .
C C23 0.68986(12) 0.87307(18) 0.71912(7) 0.0602(5) Uani d . 1 . .
H H23 0.7077 0.9336 0.7006 0.072 Uiso calc R 1 . .
C C24 0.71909(14) 0.7715(2) 0.70614(8) 0.0773(7) Uani d . 1 . .
H H24 0.7570 0.7632 0.6781 0.093 Uiso calc R 1 . .
C C25 0.69367(17) 0.6827(2) 0.73348(9) 0.0850(7) Uani d . 1 . .
H H25 0.7161 0.6154 0.7244 0.102 Uiso calc R 1 . .
C C26 0.63520(16) 0.69062(17) 0.77446(8) 0.0742(6) Uani d . 1 . .
H H26 0.6169 0.6299 0.7926 0.089 Uiso calc R 1 . .
C C27 0.60526(12) 0.79191(15) 0.78731(7) 0.0518(4) Uani d . 1 . .
C C28 0.54202(12) 0.82721(15) 0.82772(6) 0.0509(4) Uani d . 1 . .
N N1 0.89058(8) 1.09290(10) 0.91377(5) 0.0400(3) Uani d . 1 . .
N N2 0.53736(9) 0.93881(11) 0.82350(5) 0.0434(3) Uani d . 1 . .
O O1 1.03739(8) 1.08221(10) 0.93858(5) 0.0612(4) Uani d . 1 . .
O O2 0.75574(8) 1.05580(11) 0.87512(5) 0.0634(4) Uani d . 1 . .
O O3 0.79903(7) 1.05658(8) 1.00380(4) 0.0446(3) Uani d . 1 . .
O O4 0.76146(8) 1.08763(10) 1.08580(4) 0.0541(3) Uani d . 1 . .
O O5 0.61305(9) 1.09848(9) 0.98776(5) 0.0592(3) Uani d . 1 . .
O O6 0.57008(8) 0.97564(9) 0.93053(4) 0.0485(3) Uani d . 1 . .
O O7 0.59873(9) 1.07155(10) 0.77251(5) 0.0588(3) Uani d . 1 . .
O O8 0.50082(10) 0.77394(12) 0.85785(5) 0.0771(4) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O1 C1 N1 . . 125.14(15) no
O1 C1 C2 . . 128.94(16) no
N1 C1 C2 . . 105.91(13) no
C7 C2 C3 . . 121.28(15) no
C7 C2 C1 . . 107.98(14) no
C3 C2 C1 . . 130.67(16) no
C4 C3 C2 . . 117.38(18) no
C4 C3 H3 . . 121.3 no
C2 C3 H3 . . 121.3 no
C5 C4 C3 . . 121.54(18) no
C5 C4 H4 . . 119.2 no
C3 C4 H4 . . 119.2 no
C4 C5 C6 . . 121.02(17) no
C4 C5 H5 . . 119.5 no
C6 C5 H5 . . 119.5 no
C5 C6 C7 . . 117.91(17) no
C5 C6 H6 . . 121.0 no
C7 C6 H6 . . 121.0 no
C2 C7 C6 . . 120.87(16) no
C2 C7 C8 . . 108.23(13) no
C6 C7 C8 . . 130.82(15) no
O2 C8 N1 . . 125.48(16) no
O2 C8 C7 . . 128.31(16) no
N1 C8 C7 . . 106.20(13) no
N1 C9 C10 . . 112.68(13) no
N1 C9 H9A . . 109.1 no
C10 C9 H9A . . 109.1 no
N1 C9 H9B . . 109.1 no
C10 C9 H9B . . 109.1 no
H9A C9 H9B . . 107.8 no
O3 C10 C9 . . 106.85(13) no
O3 C10 H10A . . 110.4 no
C9 C10 H10A . . 110.4 no
O3 C10 H10B . . 110.4 no
C9 C10 H10B . . 110.4 no
H10A C10 H10B . . 108.6 no
O4 C11 O3 . . 124.75(15) no
O4 C11 C12 . . 125.33(15) no
O3 C11 C12 . . 109.74(12) no
C13 C12 C17 . . 119.89(15) no
C13 C12 C11 . . 117.04(15) no
C17 C12 C11 . . 122.78(14) no
C12 C13 C14 . . 120.22(17) no
C12 C13 H13 . . 119.9 no
C14 C13 H13 . . 119.9 no
C15 C14 C13 . . 120.12(17) no
C15 C14 H14 . . 119.9 no
C13 C14 H14 . . 119.9 no
C14 C15 C16 . . 120.04(16) no
C14 C15 H15 . . 120.0 no
C16 C15 H15 . . 120.0 no
C15 C16 C17 . . 120.47(17) no
C15 C16 H16 . . 119.8 no
C17 C16 H16 . . 119.8 no
C16 C17 C12 . . 119.25(15) no
C16 C17 C18 . . 121.21(15) no
C12 C17 C18 . . 119.48(14) no
O5 C18 O6 . . 123.45(15) no
O5 C18 C17 . . 124.08(14) no
O6 C18 C17 . . 112.45(13) no
O6 C19 C20 . . 106.72(14) no
O6 C19 H19A . . 110.4 no
C20 C19 H19A . . 110.4 no
O6 C19 H19B . . 110.4 no
C20 C19 H19B . . 110.4 no
H19A C19 H19B . . 108.6 no
N2 C20 C19 . . 112.51(13) no
N2 C20 H20A . . 109.1 no
C19 C20 H20A . . 109.1 no
N2 C20 H20B . . 109.1 no
C19 C20 H20B . . 109.1 no
H20A C20 H20B . . 107.8 no
O7 C21 N2 . . 124.87(16) no
O7 C21 C22 . . 129.12(16) no
N2 C21 C22 . . 106.00(15) no
C27 C22 C23 . . 121.37(17) no
C27 C22 C21 . . 108.09(15) no
C23 C22 C21 . . 130.53(18) no
C24 C23 C22 . . 117.4(2) no
C24 C23 H23 . . 121.3 no
C22 C23 H23 . . 121.3 no
C25 C24 C23 . . 121.4(2) no
C25 C24 H24 . . 119.3 no
C23 C24 H24 . . 119.3 no
C24 C25 C26 . . 121.4(2) no
C24 C25 H25 . . 119.3 no
C26 C25 H25 . . 119.3 no
C27 C26 C25 . . 117.4(2) no
C27 C26 H26 . . 121.3 no
C25 C26 H26 . . 121.3 no
C26 C27 C22 . . 121.03(18) no
C26 C27 C28 . . 130.66(19) no
C22 C27 C28 . . 108.31(15) no
O8 C28 N2 . . 125.08(17) no
O8 C28 C27 . . 129.23(18) no
N2 C28 C27 . . 105.69(15) no
C8 N1 C1 . . 111.67(13) no
C8 N1 C9 . . 124.20(13) no
C1 N1 C9 . . 124.13(13) no
C21 N2 C28 . . 111.88(14) no
C21 N2 C20 . . 123.93(15) no
C28 N2 C20 . . 124.20(14) no
C11 O3 C10 . . 118.61(12) no
C18 O6 C19 . . 116.31(12) no
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
C1 O1 . 1.2014(19) no
C1 N1 . 1.388(2) no
C1 C2 . 1.482(2) no
C2 C7 . 1.374(2) no
C2 C3 . 1.380(2) no
C3 C4 . 1.377(3) no
C3 H3 . 0.9300 no
C4 C5 . 1.370(3) no
C4 H4 . 0.9300 no
C5 C6 . 1.374(3) no
C5 H5 . 0.9300 no
C6 C7 . 1.380(2) no
C6 H6 . 0.9300 no
C7 C8 . 1.476(2) no
C8 O2 . 1.2077(19) no
C8 N1 . 1.383(2) no
C9 N1 . 1.448(2) no
C9 C10 . 1.497(2) no
C9 H9A . 0.9700 no
C9 H9B . 0.9700 no
C10 O3 . 1.4387(18) no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
C11 O4 . 1.1947(18) no
C11 O3 . 1.3284(18) no
C11 C12 . 1.491(2) no
C12 C13 . 1.374(2) no
C12 C17 . 1.395(2) no
C13 C14 . 1.384(3) no
C13 H13 . 0.9300 no
C14 C15 . 1.374(3) no
C14 H14 . 0.9300 no
C15 C16 . 1.376(2) no
C15 H15 . 0.9300 no
C16 C17 . 1.385(2) no
C16 H16 . 0.9300 no
C17 C18 . 1.483(2) no
C18 O5 . 1.1972(18) no
C18 O6 . 1.3250(18) no
C19 O6 . 1.437(2) no
C19 C20 . 1.501(2) no
C19 H19A . 0.9700 no
C19 H19B . 0.9700 no
C20 N2 . 1.447(2) no
C20 H20A . 0.9700 no
C20 H20B . 0.9700 no
C21 O7 . 1.209(2) no
C21 N2 . 1.389(2) no
C21 C22 . 1.479(2) no
C22 C27 . 1.376(2) no
C22 C23 . 1.378(2) no
C23 C24 . 1.375(3) no
C23 H23 . 0.9300 no
C24 C25 . 1.365(4) no
C24 H24 . 0.9300 no
C25 C26 . 1.384(3) no
C25 H25 . 0.9300 no
C26 C27 . 1.375(3) no
C26 H26 . 0.9300 no
C27 C28 . 1.483(2) no
C28 O8 . 1.197(2) no
C28 N2 . 1.389(2) no
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
C3 H3 O4 5_777 0.93 2.39 3.315(2) 174
C10 H10B O5 7_677 0.97 2.55 3.163(2) 121
C6 H6 Cg5 1_555 0.93 2.91 3.784(2) 167
C19 H19B <i>Cg</i>4 5_677 0.97 2.93 3.817(2) 152
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744198
