#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:27:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180340 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/09/7200952.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_7200952
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            'C10 H18 N4 O6'
_chemical_formula_weight         290.28
_chemical_name_systematic
;
4
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.839(3)
_cell_angle_beta                 91.938(3)
_cell_angle_gamma                95.093(3)
_cell_formula_units_Z            2
_cell_length_a                   5.5097(15)
_cell_length_b                   9.529(2)
_cell_length_c                   13.030(3)
_cell_measurement_reflns_used    913
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.25
_cell_measurement_theta_min      3.61
_cell_volume                     657.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6905
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5694
_diffrn_reflns_theta_full        26.64
_diffrn_reflns_theta_max         26.64
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0507
_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)+(0.0846P)²+0.3023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                2337
_reflns_number_total             2909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901453e.txt
_cod_data_source_block           ssf1338
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.0960(3) 0.32238(17) 0.90949(13) 0.0175(3) Uani 1 1 d . . .
C2 C -0.0540(3) 0.42133(17) 0.98461(13) 0.0184(4) Uani 1 1 d . . .
H2A H -0.0702 0.3868 1.0498 0.022 Uiso 1 1 calc R . .
H2B H -0.2197 0.4153 0.9510 0.022 Uiso 1 1 calc R . .
O1A O 0.0212(2) 0.18438(13) 0.89571(10) 0.0232(3) Uani 1 1 d . . .
H1 H 0.1091 0.1331 0.8529 0.035 Uiso 1 1 calc R . .
O1B O 0.2693(2) 0.36534(13) 0.86537(10) 0.0252(3) Uani 1 1 d . . .
C22 C 0.5970(3) -0.01663(18) 0.29276(13) 0.0190(3) Uani 1 1 d . . .
C24 C 0.2806(3) 0.04334(19) 0.40366(14) 0.0214(4) Uani 1 1 d . . .
H24A H 0.1433 0.0823 0.3727 0.026 Uiso 1 1 calc R . .
H24B H 0.2789 0.0735 0.4822 0.026 Uiso 1 1 calc R . .
C25 C 0.2681(3) -0.12373(19) 0.36197(14) 0.0225(4) Uani 1 1 d . . .
H25A H 0.3026 -0.1700 0.4201 0.027 Uiso 1 1 calc R . .
H25B H 0.1063 -0.1653 0.3266 0.027 Uiso 1 1 calc R . .
N21 N 0.4589(3) -0.14198(17) 0.28625(13) 0.0280(4) Uani 1 1 d . . .
H21 H 0.4809 -0.2256 0.2415 0.034 Uiso 1 1 calc R . .
N23 N 0.5132(3) 0.09167(16) 0.36767(12) 0.0225(3) Uani 1 1 d . . .
H23 H 0.5894 0.1799 0.3916 0.027 Uiso 1 1 calc R . .
O22 O 0.7753(2) 0.00200(13) 0.23943(10) 0.0236(3) Uani 1 1 d . . .
C31 C 0.2363(3) 0.50094(17) 0.59371(13) 0.0178(3) Uani 1 1 d . . .
C32 C 0.4099(3) 0.44165(17) 0.51072(13) 0.0185(3) Uani 1 1 d . . .
H32A H 0.3150 0.3904 0.4437 0.022 Uiso 1 1 calc R . .
H32B H 0.5009 0.3693 0.5343 0.022 Uiso 1 1 calc R . .
O31A O 0.0674(3) 0.40081(14) 0.60433(11) 0.0299(3) Uani 1 1 d . . .
H31 H -0.0205 0.4369 0.6538 0.045 Uiso 1 1 calc R . .
O31B O 0.2497(2) 0.62819(13) 0.64550(10) 0.0238(3) Uani 1 1 d . . .
C42 C -0.7204(3) 0.39826(18) 1.20842(13) 0.0182(3) Uani 1 1 d . . .
C44 C -0.5363(3) 0.21210(19) 1.09930(14) 0.0210(4) Uani 1 1 d . . .
H44A H -0.3892 0.1899 1.1355 0.025 Uiso 1 1 calc R . .
H44B H -0.5274 0.1751 1.0214 0.025 Uiso 1 1 calc R . .
C45 C -0.7712(3) 0.14809(18) 1.13788(13) 0.0212(4) Uani 1 1 d . . .
H45A H -0.9016 0.1175 1.0802 0.025 Uiso 1 1 calc R . .
H45B H -0.7416 0.0640 1.1665 0.025 Uiso 1 1 calc R . .
N41 N -0.8318(3) 0.27267(16) 1.22157(11) 0.0211(3) Uani 1 1 d . . .
H41 H -0.9275 0.2665 1.2733 0.025 Uiso 1 1 calc R . .
N43 N -0.5639(3) 0.36760(15) 1.12953(11) 0.0199(3) Uani 1 1 d . . .
H43 H -0.4897 0.4324 1.1007 0.024 Uiso 1 1 calc R . .
O42 O -0.7538(2) 0.52470(13) 1.25851(10) 0.0234(3) 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1B C1 O1A 123.33(14) . . ?
O1B C1 C2 124.02(15) . . ?
O1A C1 C2 112.65(13) . . ?
C1 C2 C2 113.23(17) . 2_567 ?
C1 C2 H2A 108.9 . . ?
C2 C2 H2A 108.9 2_567 . ?
C1 C2 H2B 108.9 . . ?
C2 C2 H2B 108.9 2_567 . ?
H2A C2 H2B 107.7 . . ?
C1 O1A H1 109.5 . . ?
O22 C22 N21 127.08(16) . . ?
O22 C22 N23 123.64(16) . . ?
N21 C22 N23 109.28(15) . . ?
N23 C24 C25 102.56(13) . . ?
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 102.31(14) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 112.17(14) . . ?
C22 N21 H21 123.9 . . ?
C25 N21 H21 123.9 . . ?
C22 N23 C24 111.24(14) . . ?
C22 N23 H23 124.4 . . ?
C24 N23 H23 124.4 . . ?
O31B C31 O31A 123.53(15) . . ?
O31B C31 C32 124.09(15) . . ?
O31A C31 C32 112.38(13) . . ?
C31 C32 C32 113.14(17) . 2_666 ?
C31 C32 H32A 109.0 . . ?
C32 C32 H32A 109.0 2_666 . ?
C31 C32 H32B 109.0 . . ?
C32 C32 H32B 109.0 2_666 . ?
H32A C32 H32B 107.8 . . ?
C31 O31A H31 109.5 . . ?
O42 C42 N41 126.84(15) . . ?
O42 C42 N43 123.71(16) . . ?
N41 C42 N43 109.44(14) . . ?
N43 C44 C45 101.78(13) . . ?
N43 C44 H44A 111.4 . . ?
C45 C44 H44A 111.4 . . ?
N43 C44 H44B 111.4 . . ?
C45 C44 H44B 111.4 . . ?
H44A C44 H44B 109.3 . . ?
N41 C45 C44 101.42(13) . . ?
N41 C45 H45A 111.5 . . ?
C44 C45 H45A 111.5 . . ?
N41 C45 H45B 111.5 . . ?
C44 C45 H45B 111.5 . . ?
H45A C45 H45B 109.3 . . ?
C42 N41 C45 110.55(14) . . ?
C42 N41 H41 124.7 . . ?
C45 N41 H41 124.7 . . ?
C42 N43 C44 110.28(14) . . ?
C42 N43 H43 124.9 . . ?
C44 N43 H43 124.9 . . ?
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 O1B 1.224(2) . ?
C1 O1A 1.307(2) . ?
C1 C2 1.500(2) . ?
C2 C2 1.510(3) 2_567 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O1A H1 0.8400 . ?
C22 O22 1.248(2) . ?
C22 N21 1.340(2) . ?
C22 N23 1.353(2) . ?
C24 N23 1.456(2) . ?
C24 C25 1.539(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C31 O31B 1.2218(19) . ?
C31 O31A 1.309(2) . ?
C31 C32 1.502(2) . ?
C32 C32 1.511(3) 2_666 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
O31A H31 0.8400 . ?
C42 O42 1.248(2) . ?
C42 N41 1.349(2) . ?
C42 N43 1.355(2) . ?
C44 N43 1.456(2) . ?
C44 C45 1.536(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N41 1.463(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
N41 H41 0.8800 . ?
N43 H43 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
O1A H1 O22 0.84 1.71 2.5293(17) 165.6 2_656
N21 H21 O1B 0.88 2.26 3.047(2) 148.8 2_656
O31A H31 O42 0.84 1.72 2.5418(17) 166.6 2_467
N41 H41 O31B 0.88 2.28 3.0023(19) 139.9 2_467
N23 H23 O31B 0.88 2.13 2.914(2) 147.3 2_666
N43 H43 O1B 0.88 2.12 2.879(2) 144.0 2_567
