#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/09/7200955.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_7200955
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
'Threlfall, Terence L.'
_publ_section_title
;
 Co-crystallisation of organic α,ω-dicarboxylic acids with the cyclic
 amides 2-pyrrolidinone and 2-imidazolidinone
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1609
_journal_paper_doi               10.1039/b901453e
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C8 H14 N2 O5'
_chemical_formula_weight         218.21
_chemical_name_systematic
;
7
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 94.012(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3007(4)
_cell_length_b                   19.374(2)
_cell_length_c                   10.0780(9)
_cell_measurement_reflns_used    20712
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1032.43(16)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8779
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1186
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0421
_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)+(0.0651P)²+0.3364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1005
_reflns_number_total             1186
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b901453e.txt
_cod_data_source_block           07skc0005cc
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7200955
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4059(6) 0.40824(15) 1.0002(3) 0.0252(7) Uani 1 1 d . . .
C2 C -0.3910(6) 0.44225(16) 0.8670(3) 0.0240(6) Uani 1 1 d . . .
H2A H -0.3661 0.4925 0.8798 0.029 Uiso 1 1 calc R . .
H2B H -0.5526 0.4352 0.8133 0.029 Uiso 1 1 calc R . .
C3 C -0.1740(6) 0.41304(17) 0.7918(3) 0.0264(6) Uani 1 1 d . . .
H3A H -0.0135 0.4190 0.8470 0.032 Uiso 1 1 calc R . .
H3B H -0.2013 0.3629 0.7780 0.032 Uiso 1 1 calc R . .
C4 C -0.1502(6) 0.44747(16) 0.6578(3) 0.0256(6) Uani 1 1 d . . .
H4A H -0.3158 0.4459 0.6060 0.031 Uiso 1 1 calc R . .
H4B H -0.1035 0.4965 0.6719 0.031 Uiso 1 1 calc R . .
C5 C 0.0457(5) 0.41278(15) 0.5797(3) 0.0226(6) Uani 1 1 d . . .
O1A O -0.2623(4) 0.36267(13) 1.0400(2) 0.0368(6) Uani 1 1 d . . .
O1B O -0.5930(4) 0.43159(12) 1.0691(2) 0.0291(5) Uani 1 1 d . . .
H1 H -0.5933 0.4102 1.1416 0.044 Uiso 1 1 calc R . .
O5A O 0.1942(4) 0.36998(13) 0.6275(2) 0.0337(6) Uani 1 1 d . . .
O5B O 0.0410(4) 0.43294(12) 0.4536(2) 0.0290(5) Uani 1 1 d . . .
H5 H 0.1670 0.4167 0.4182 0.044 Uiso 1 1 calc R . .
C22 C -0.4488(5) 0.33005(15) 0.3590(3) 0.0248(6) Uani 1 1 d . . .
C24 C -0.1278(6) 0.24876(17) 0.3686(3) 0.0275(7) Uani 1 1 d . . .
H24A H 0.0448 0.2680 0.3835 0.033 Uiso 1 1 calc R . .
H24B H -0.1177 0.2023 0.3282 0.033 Uiso 1 1 calc R . .
C25 C -0.2635(6) 0.24629(16) 0.4988(3) 0.0285(7) Uani 1 1 d . . .
H25A H -0.3640 0.2035 0.5049 0.034 Uiso 1 1 calc R . .
H25B H -0.1418 0.2498 0.5776 0.034 Uiso 1 1 calc R . .
N21 N -0.4268(5) 0.30739(14) 0.4856(3) 0.0303(6) Uani 1 1 d . . .
H21 H -0.5007 0.3267 0.5518 0.036 Uiso 1 1 calc R . .
N23 N -0.2917(5) 0.29463(14) 0.2855(3) 0.0299(6) Uani 1 1 d . . .
H23 H -0.2877 0.2985 0.1986 0.036 Uiso 1 1 calc R . .
O22 O -0.5974(4) 0.37721(11) 0.3150(2) 0.0287(5) Uani 1 1 d . . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A C1 O1B 123.2(3) . . ?
O1A C1 C2 122.9(3) . . ?
O1B C1 C2 113.9(3) . . ?
C1 C2 C3 111.6(2) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 113.0(3) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.9(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O5A C5 O5B 123.1(3) . . ?
O5A C5 C4 123.2(3) . . ?
O5B C5 C4 113.7(2) . . ?
C1 O1B H1 109.5 . . ?
C5 O5B H5 109.5 . . ?
O22 C22 N23 124.8(3) . . ?
O22 C22 N21 125.3(3) . . ?
N23 C22 N21 109.9(3) . . ?
N23 C24 C25 102.3(2) . . ?
N23 C24 H24A 111.3 . . ?
C25 C24 H24A 111.3 . . ?
N23 C24 H24B 111.3 . . ?
C25 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C24 101.9(2) . . ?
N21 C25 H25A 111.4 . . ?
C24 C25 H25A 111.4 . . ?
N21 C25 H25B 111.4 . . ?
C24 C25 H25B 111.4 . . ?
H25A C25 H25B 109.3 . . ?
C22 N21 C25 111.1(3) . . ?
C22 N21 H21 124.4 . . ?
C25 N21 H21 124.4 . . ?
C22 N23 C24 111.1(3) . . ?
C22 N23 H23 124.4 . . ?
C24 N23 H23 124.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1A 1.216(4) . ?
C1 O1B 1.330(4) . ?
C1 C2 1.502(4) . ?
C2 C3 1.529(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.505(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5A 1.219(4) . ?
C5 O5B 1.328(4) . ?
O1B H1 0.8400 . ?
O5B H5 0.8400 . ?
C22 O22 1.266(4) . ?
C22 N23 1.342(4) . ?
C22 N21 1.346(4) . ?
C24 N23 1.464(4) . ?
C24 C25 1.541(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.467(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O22 0.84 1.86 2.694(3) 170.5 1_556
O5B H5 O22 0.84 1.85 2.676(3) 169.6 1_655
N21 H21 O5A 0.88 2.02 2.820(3) 150.9 1_455
N23 H23 O1A 0.88 2.04 2.817(3) 147.1 1_554
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653586
