#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/18/2201828.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_2201828
loop_
_publ_author_name
'Simon, Monika'
'Csunderlik, Carol'
'Jones, Peter G.'
'Neda, Ion'
'Tarta-Micle, Andreea'
_publ_section_title
;
 N,N'-Carbonyldisuccinimide
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o686
_journal_page_last               o687
_journal_paper_doi               10.1107/S1600536803007815
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C9 H8 N2 O5'
_chemical_formula_moiety         'C9 H8 N2 O5'
_chemical_formula_sum            'C9 H8 N2 O5'
_chemical_formula_weight         224.17
_chemical_name_systematic
;
N,N'-Carbonyldisuccinimide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.01(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2372(11)
_cell_length_b                   13.396(2)
_cell_length_c                   9.5519(12)
_cell_measurement_reflns_used    5487
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.6
_cell_volume                     926.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10780
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0338
_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)+(0.0616P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                2463
_reflns_number_total             2707
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6268.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2201828
_cod_database_fobs_code          2201828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 0.41164(16) 0.32990(8) 0.36638(12) 0.0183(2) Uani d . 1 . . C
C2 0.54508(17) 0.29243(8) 0.25841(12) 0.0208(2) Uani d . 1 . . C
H2A 0.4927 0.2343 0.2081 0.025 Uiso calc R 1 . . H
H2B 0.6627 0.2720 0.3030 0.025 Uiso calc R 1 . . H
C3 0.57723(17) 0.37883(8) 0.15781(13) 0.0219(2) Uani d . 1 . . C
H3A 0.7103 0.3955 0.1529 0.026 Uiso calc R 1 . . H
H3B 0.5337 0.3613 0.0627 0.026 Uiso calc R 1 . . H
C4 0.46894(17) 0.46550(8) 0.21485(13) 0.0181(2) Uani d . 1 . . C
C5 0.09495(17) 0.65256(8) 0.38654(12) 0.0200(2) Uani d . 1 . . C
C6 -0.03924(17) 0.69540(8) 0.28252(13) 0.0215(2) Uani d . 1 . . C
H6A 0.0086 0.7588 0.2436 0.026 Uiso calc R 1 . . H
H6B -0.1600 0.7085 0.3276 0.026 Uiso calc R 1 . . H
C7 -0.05975(18) 0.61750(8) 0.16713(13) 0.0217(2) Uani d . 1 . . C
H7A -0.1915 0.6006 0.1525 0.026 Uiso calc R 1 . . H
H7B -0.0079 0.6426 0.0779 0.026 Uiso calc R 1 . . H
C8 0.04637(17) 0.52753(8) 0.21734(13) 0.0186(2) Uani d . 1 . . C
C9 0.25744(19) 0.49079(8) 0.41943(11) 0.0178(2) Uani d . 1 . . C
N1 0.37242(13) 0.43113(7) 0.33546(10) 0.0169(2) Uani d . 1 . . N
N2 0.14044(14) 0.55489(7) 0.34214(10) 0.01756(19) Uani d . 1 . . N
O1 0.34308(13) 0.28462(7) 0.46152(10) 0.0268(2) Uani d . 1 . . O
O2 0.46206(13) 0.54986(6) 0.17273(10) 0.0259(2) Uani d . 1 . . O
O3 0.15995(15) 0.69204(7) 0.48906(10) 0.0315(2) Uani d . 1 . . O
O4 0.05253(13) 0.44548(6) 0.16693(10) 0.0258(2) Uani d . 1 . . O
O5 0.25761(15) 0.48718(7) 0.54497(8) 0.0251(2) Uani d . 1 . . O
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
_geom_angle_publ_flag
O1 C1 N1 123.98(11) ?
O1 C1 C2 128.17(10) ?
N1 C1 C2 107.82(9) ?
C1 C2 C3 106.15(9) ?
C1 C2 H2A 110.5 ?
C3 C2 H2A 110.5 ?
C1 C2 H2B 110.5 ?
C3 C2 H2B 110.5 ?
H2A C2 H2B 108.7 ?
C4 C3 C2 106.18(10) ?
C4 C3 H3A 110.5 ?
C2 C3 H3A 110.5 ?
C4 C3 H3B 110.5 ?
C2 C3 H3B 110.5 ?
H3A C3 H3B 108.7 ?
O2 C4 N1 123.72(11) ?
O2 C4 C3 128.84(11) ?
N1 C4 C3 107.43(9) ?
O3 C5 N2 123.88(11) ?
O3 C5 C6 128.32(11) ?
N2 C5 C6 107.78(9) ?
C5 C6 C7 106.22(9) ?
C5 C6 H6A 110.5 ?
C7 C6 H6A 110.5 ?
C5 C6 H6B 110.5 ?
C7 C6 H6B 110.5 ?
H6A C6 H6B 108.7 ?
C8 C7 C6 105.53(10) ?
C8 C7 H7A 110.6 ?
C6 C7 H7A 110.6 ?
C8 C7 H7B 110.6 ?
C6 C7 H7B 110.6 ?
H7A C7 H7B 108.8 ?
O4 C8 N2 123.69(11) ?
O4 C8 C7 128.55(11) ?
N2 C8 C7 107.74(9) ?
O5 C9 N1 123.16(12) y
O5 C9 N2 123.14(12) y
N1 C9 N2 113.70(9) y
C9 N1 C1 122.96(10) ?
C9 N1 C4 124.65(9) ?
C1 N1 C4 112.33(9) ?
C9 N2 C5 123.00(9) ?
C9 N2 C8 124.63(9) ?
C5 N2 C8 112.26(9) ?
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 . 1.2001(14) ?
C1 N1 . 1.4167(14) ?
C1 C2 . 1.4996(16) ?
C2 C3 . 1.5223(16) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5031(16) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 O2 . 1.2006(14) ?
C4 N1 . 1.4239(15) ?
C5 O3 . 1.2082(14) ?
C5 N2 . 1.4143(14) ?
C5 C6 . 1.5031(17) ?
C6 C7 . 1.5250(16) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.5075(16) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 O4 . 1.2007(14) ?
C8 N2 . 1.4207(15) ?
C9 O5 . 1.2001(13) y
C9 N1 . 1.4052(15) y
C9 N2 . 1.4139(15) y
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
C2 H2A O1 4_565 0.99 2.60 3.3530(15) 132
C6 H6B O1 2 0.99 3.23 3.4198(16) 93
C3 H3B O1 4_565 0.99 2.58 3.3436(15) 134
C3 H3B O2 3_665 0.99 2.54 3.3108(16) 134
C7 H7A O2 1_455 0.99 2.60 3.5779(17) 168
C2 H2B O3 3_666 0.99 2.41 3.2274(16) 139
C7 H7B O3 4_575 0.99 2.66 3.4543(15) 137
C7 H7B O4 3_565 0.99 2.64 3.3011(16) 124
C3 H3A O4 1_655 0.99 2.57 3.5548(16) 174
C6 H6A O4 2 0.99 2.68 3.3862(15) 129
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
_geom_torsion_publ_flag
O1 C1 C2 C3 176.48(12) ?
N1 C1 C2 C3 -1.80(13) ?
C1 C2 C3 C4 2.86(13) ?
C2 C3 C4 O2 175.89(13) ?
C2 C3 C4 N1 -2.91(13) ?
O3 C5 C6 C7 174.57(12) ?
N2 C5 C6 C7 -3.72(13) ?
C5 C6 C7 C8 6.42(13) ?
C6 C7 C8 O4 171.75(13) ?
C6 C7 C8 N2 -6.91(13) ?
O5 C9 N1 C1 39.17(18) y
N2 C9 N1 C1 -140.34(11) ?
O5 C9 N1 C4 -137.79(14) ?
N2 C9 N1 C4 42.70(15) y
O1 C1 N1 C9 4.30(18) ?
C2 C1 N1 C9 -177.34(10) ?
O1 C1 N1 C4 -178.40(12) ?
C2 C1 N1 C4 -0.04(13) ?
O2 C4 N1 C9 0.26(18) ?
C3 C4 N1 C9 179.14(11) ?
O2 C4 N1 C1 -176.99(12) ?
C3 C4 N1 C1 1.89(13) ?
O5 C9 N2 C5 37.12(19) ?
N1 C9 N2 C5 -143.37(10) ?
O5 C9 N2 C8 -138.71(13) ?
N1 C9 N2 C8 40.80(16) ?
O3 C5 N2 C9 4.64(18) ?
C6 C5 N2 C9 -176.98(11) ?
O3 C5 N2 C8 -179.07(11) ?
C6 C5 N2 C8 -0.69(13) ?
O4 C8 N2 C9 2.37(19) ?
C7 C8 N2 C9 -178.89(11) ?
O4 C8 N2 C5 -173.85(12) ?
C7 C8 N2 C5 4.89(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 473807
