#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/80/2228024.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_2228024
loop_
_publ_author_name
'Bhatti, Moazzam H.'
'Yunus, Uzma'
Imtiaz-ud-Din
'Shams-ul-Islam, S.'
'Wong, Wai-Yeung'
_publ_section_title
;
 2-[2-(1,3-Dioxoisoindolin-2-yl)acetamido]acetic acid
;
_journal_coeditor_code           SU2220
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2969
_journal_paper_doi               10.1107/S1600536810043047
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 N2 O5'
_chemical_formula_moiety         'C12 H10 N2 O5'
_chemical_formula_sum            'C12 H10 N2 O5'
_chemical_formula_weight         262.22
_chemical_name_systematic
;
2-[2-(1,3-Dioxoisoindolin-2-yl)acetamido]acetic acid
;
_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                 90.170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8195(5)
_cell_length_b                   10.3415(11)
_cell_length_c                   22.629(2)
_cell_measurement_reflns_used    6788
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.67
_cell_volume                     1127.84(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω and φ 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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6788
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0373
_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)+(0.0370P)²+0.5790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2533
_reflns_number_total             2731
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2220.cif
_cod_data_source_block           I
_cod_original_cell_volume        1127.9(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228024
_cod_database_fobs_code          2228024
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 1.42937(19) 0.17860(9) 0.07903(4) 0.0274(3) Uani . . 1.000
O O2 0.7194(2) 0.46000(10) 0.04263(4) 0.0338(3) Uani . . 1.000
O O3 1.11056(19) 0.36795(9) 0.23395(4) 0.0250(3) Uani . . 1.000
O O4 0.8527(2) 0.07998(11) 0.31666(4) 0.0333(3) Uani . . 1.000
O O5 1.05382(19) 0.04425(9) 0.22876(4) 0.0264(3) Uani . . 1.000
N N1 1.0744(2) 0.32888(10) 0.07534(4) 0.0205(3) Uani . . 1.000
N N2 0.8077(2) 0.25359(10) 0.18003(4) 0.0214(3) Uani . . 1.000
C C1 1.1901(3) 0.10108(14) -0.04587(6) 0.0285(4) Uani . . 1.000
C C2 1.0418(3) 0.09730(15) -0.09889(6) 0.0336(4) Uani . . 1.000
C C3 0.8300(3) 0.18476(15) -0.11078(6) 0.0329(4) Uani . . 1.000
C C4 0.7551(3) 0.27995(14) -0.06977(6) 0.0279(4) Uani . . 1.000
C C5 0.9028(2) 0.28280(12) -0.01754(5) 0.0223(3) Uani . . 1.000
C C6 1.1163(2) 0.19590(12) -0.00576(5) 0.0219(3) Uani . . 1.000
C C7 1.2343(2) 0.22725(12) 0.05335(5) 0.0208(3) Uani . . 1.000
C C8 0.8738(2) 0.37080(12) 0.03419(5) 0.0223(3) Uani . . 1.000
C C9 1.1328(2) 0.39863(11) 0.12934(5) 0.0206(3) Uani . . 1.000
C C10 1.0158(2) 0.33726(11) 0.18492(5) 0.0190(3) Uani . . 1.000
C C11 0.6866(2) 0.19718(13) 0.23289(6) 0.0245(3) Uani . . 1.000
C C12 0.8745(2) 0.10203(12) 0.26443(5) 0.0218(3) Uani . . 1.000
H H1A 1.33480 0.04130 -0.03780 0.0340 Uiso calc R 1.000
H H2 0.743(4) 0.2331(18) 0.1435(8) 0.037(5) Uiso . . 1.000
H H2A 1.08690 0.03340 -0.12750 0.0400 Uiso calc R 1.000
H H3A 0.73430 0.17980 -0.14740 0.0390 Uiso calc R 1.000
H H4A 0.60970 0.33960 -0.07750 0.0340 Uiso calc R 1.000
H H5 1.159(4) -0.018(2) 0.2480(8) 0.043(5) Uiso . . 1.000
H H9A 1.05660 0.48720 0.12570 0.0250 Uiso calc R 1.000
H H9B 1.33640 0.40630 0.13380 0.0250 Uiso calc R 1.000
H H11A 0.51250 0.15240 0.22190 0.0290 Uiso calc R 1.000
H H11B 0.63790 0.26770 0.26060 0.0290 Uiso calc R 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O5 H5 . . . 112.5(11) no
C7 N1 C9 . . . 124.79(9) no
C8 N1 C9 . . . 122.45(10) no
C7 N1 C8 . . . 112.00(9) no
C10 N2 C11 . . . 119.81(10) no
C10 N2 H2 . . . 119.0(12) no
C11 N2 H2 . . . 121.2(12) no
C2 C1 C6 . . . 116.87(13) no
C1 C2 C3 . . . 121.49(13) no
C2 C3 C4 . . . 121.31(13) no
C3 C4 C5 . . . 116.72(13) no
C4 C5 C8 . . . 129.61(11) no
C4 C5 C6 . . . 122.03(11) no
C6 C5 C8 . . . 108.37(9) no
C1 C6 C5 . . . 121.57(11) no
C1 C6 C7 . . . 130.24(11) no
C5 C6 C7 . . . 108.18(10) no
N1 C7 C6 . . . 105.94(9) no
O1 C7 C6 . . . 129.35(11) no
O1 C7 N1 . . . 124.71(11) no
O2 C8 N1 . . . 123.76(11) no
O2 C8 C5 . . . 130.84(10) no
N1 C8 C5 . . . 105.41(9) no
N1 C9 C10 . . . 114.81(9) no
N2 C10 C9 . . . 119.02(10) no
O3 C10 N2 . . . 121.14(10) no
O3 C10 C9 . . . 119.83(10) no
N2 C11 C12 . . . 114.03(9) no
O4 C12 O5 . . . 124.66(11) no
O4 C12 C11 . . . 121.99(11) no
O5 C12 C11 . . . 113.31(10) no
C2 C1 H1A . . . 121.00 no
C6 C1 H1A . . . 122.00 no
C1 C2 H2A . . . 119.00 no
C3 C2 H2A . . . 119.00 no
C2 C3 H3A . . . 119.00 no
C4 C3 H3A . . . 119.00 no
C3 C4 H4A . . . 122.00 no
C5 C4 H4A . . . 122.00 no
N1 C9 H9A . . . 109.00 no
N1 C9 H9B . . . 108.00 no
C10 C9 H9A . . . 108.00 no
C10 C9 H9B . . . 109.00 no
H9A C9 H9B . . . 108.00 no
N2 C11 H11A . . . 109.00 no
N2 C11 H11B . . . 109.00 no
C12 C11 H11A . . . 109.00 no
C12 C11 H11B . . . 109.00 no
H11A C11 H11B . . . 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . . 1.2130(14) no
O2 C8 . . 1.2008(15) no
O3 C10 . . 1.2399(14) no
O4 C12 . . 1.2086(15) no
O5 C12 . . 1.3265(14) no
O5 H5 . . 0.93(2) no
N1 C8 . . 1.4087(14) no
N1 C9 . . 1.4459(15) no
N1 C7 . . 1.3959(15) no
N2 C10 . . 1.3290(14) no
N2 C11 . . 1.4546(16) no
N2 H2 . . 0.908(18) no
C1 C2 . . 1.395(2) no
C1 C6 . . 1.3834(18) no
C2 C3 . . 1.390(2) no
C3 C4 . . 1.401(2) no
C4 C5 . . 1.3782(18) no
C5 C8 . . 1.4896(17) no
C5 C6 . . 1.3913(16) no
C6 C7 . . 1.4877(16) no
C9 C10 . . 1.5188(16) no
C11 C12 . . 1.5146(17) no
C1 H1A . . 0.9500 no
C2 H2A . . 0.9500 no
C3 H3A . . 0.9500 no
C4 H4A . . 0.9500 no
C9 H9A . . 0.9900 no
C9 H9B . . 0.9900 no
C11 H11A . . 0.9900 no
C11 H11B . . 0.9900 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
_geom_hbond_publ_flag
N2 H2 O1 1_455 0.908(18) 2.172(19) 3.0208(13) 155.3(17) yes
O5 H5 O3 2_745 0.93(2) 1.67(2) 2.5777(13) 165.4(17) yes
C2 H2A O5 3_755 0.95 2.52 3.3142(17) 141 yes
C9 H9A O4 2_655 0.99 2.56 3.2407(15) 126 yes
C9 H9B O4 2_755 0.99 2.59 3.3378(15) 132 yes
C11 H11A O5 1_455 0.99 2.48 3.4364(14) 162 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C7 C6 . . . . -173.65(10) no
C7 N1 C8 O2 . . . . -177.27(11) no
C9 N1 C8 O2 . . . . -6.78(17) no
C7 N1 C8 C5 . . . . 2.75(12) no
C8 N1 C7 O1 . . . . 176.11(11) no
C9 N1 C7 O1 . . . . 5.88(18) no
C8 N1 C7 C6 . . . . -3.42(12) no
C8 N1 C9 C10 . . . . 104.76(12) no
C9 N1 C8 C5 . . . . 173.24(9) no
C7 N1 C9 C10 . . . . -85.99(12) no
C11 N2 C10 O3 . . . . 0.39(17) no
C11 N2 C10 C9 . . . . -177.90(10) no
C10 N2 C11 C12 . . . . -70.18(14) no
C2 C1 C6 C7 . . . . -178.78(12) no
C2 C1 C6 C5 . . . . 0.48(19) no
C6 C1 C2 C3 . . . . 0.0(2) no
C1 C2 C3 C4 . . . . -0.5(2) no
C2 C3 C4 C5 . . . . 0.4(2) no
C3 C4 C5 C8 . . . . -179.94(13) no
C3 C4 C5 C6 . . . . 0.06(19) no
C4 C5 C6 C1 . . . . -0.53(19) no
C6 C5 C8 N1 . . . . -0.90(12) no
C8 C5 C6 C7 . . . . -1.12(12) no
C4 C5 C6 C7 . . . . 178.88(11) no
C8 C5 C6 C1 . . . . 179.47(11) no
C6 C5 C8 O2 . . . . 179.13(12) no
C4 C5 C8 O2 . . . . -0.9(2) no
C4 C5 C8 N1 . . . . 179.11(12) no
C1 C6 C7 O1 . . . . 2.6(2) no
C5 C6 C7 O1 . . . . -176.76(12) no
C5 C6 C7 N1 . . . . 2.74(12) no
C1 C6 C7 N1 . . . . -177.93(12) no
N1 C9 C10 O3 . . . . 161.21(10) no
N1 C9 C10 N2 . . . . -20.48(14) no
N2 C11 C12 O4 . . . . 154.71(12) no
N2 C11 C12 O5 . . . . -27.42(14) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 69926
