#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:27:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180340 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/09/7200954.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_7200954
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            'C12 H22 N6 O7'
_chemical_formula_weight         362.36
_chemical_name_systematic
;
6
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.299(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6403(10)
_cell_length_b                   14.4382(5)
_cell_length_c                   7.6872(5)
_cell_measurement_reflns_used    1896
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     1641.20(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10932
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9785
_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    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0473
_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)+(0.0707P)²+0.8687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                1411
_reflns_number_total             1868
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b901453e.txt
_cod_data_source_block           06skc0046c2c
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7200954
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_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
C2 C 0.0000 0.25717(19) 0.7500 0.0229(7) Uani 1 2 d S . .
H2A H -0.0189 0.2978 0.6340 0.028 Uiso 0.50 1 calc PR . .
H2B H 0.0189 0.2978 0.8660 0.028 Uiso 0.50 1 calc PR . .
C1 C 0.08090(14) 0.20172(14) 0.7720(3) 0.0227(5) Uani 1 1 d . . .
O1A O 0.09902(11) 0.12454(10) 0.8410(3) 0.0314(4) Uani 1 1 d . . .
O1B O 0.13161(11) 0.24960(10) 0.7127(3) 0.0286(4) Uani 1 1 d . . .
H1 H 0.1792 0.2200 0.7386 0.043 Uiso 1 1 calc R . .
C22 C 0.30067(14) 0.09879(14) 0.7980(3) 0.0237(5) Uani 1 1 d . . .
C24 C 0.27549(15) -0.05963(14) 0.8004(3) 0.0254(5) Uani 1 1 d . . .
H24A H 0.2379 -0.1009 0.6899 0.031 Uiso 1 1 calc R . .
H24B H 0.2812 -0.0868 0.9238 0.031 Uiso 1 1 calc R . .
C25 C 0.36896(15) -0.04279(14) 0.8104(3) 0.0250(5) Uani 1 1 d . . .
H25A H 0.4172 -0.0754 0.9235 0.030 Uiso 1 1 calc R . .
H25B H 0.3701 -0.0634 0.6888 0.030 Uiso 1 1 calc R . .
N21 N 0.37930(12) 0.05759(12) 0.8336(3) 0.0255(5) Uani 1 1 d . . .
H21 H 0.4304 0.0873 0.8667 0.031 Uiso 1 1 calc R . .
N23 N 0.23769(12) 0.03373(12) 0.7703(3) 0.0278(5) Uani 1 1 d . . .
H23 H 0.1808 0.0461 0.7381 0.033 Uiso 1 1 calc R . .
O22 O 0.28866(10) 0.18457(10) 0.7921(3) 0.0301(4) Uani 1 1 d . . .
C32 C 0.5000 0.2475(2) 0.7500 0.0219(6) Uani 1 2 d S . .
C35 C 0.45317(16) 0.39936(15) 0.7483(4) 0.0297(6) Uani 1 1 d . . .
H35A H 0.4532 0.4387 0.8539 0.036 Uiso 1 1 calc R . .
H35B H 0.4052 0.4209 0.6206 0.036 Uiso 1 1 calc R . .
N31 N 0.44173(13) 0.30174(12) 0.7809(3) 0.0256(5) Uani 1 1 d . . .
H31 H 0.4017 0.2808 0.8163 0.031 Uiso 1 1 calc R . .
O32 O 0.5000 0.16140(14) 0.7500 0.0256(5) Uani 1 2 d S . .
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
C1 C2 C1 115.8(2) . 2_556 ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 2_556 . ?
C1 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 2_556 . ?
H2A C2 H2B 107.4 . . ?
O1A C1 O1B 124.16(19) . . ?
O1A C1 C2 124.60(19) . . ?
O1B C1 C2 111.20(17) . . ?
C1 O1B H1 109.5 . . ?
O22 C22 N21 124.65(19) . . ?
O22 C22 N23 125.69(19) . . ?
N21 C22 N23 109.67(18) . . ?
N23 C24 C25 102.36(17) . . ?
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 102.84(16) . . ?
N21 C25 H25A 111.2 . . ?
C24 C25 H25A 111.2 . . ?
N21 C25 H25B 111.2 . . ?
C24 C25 H25B 111.2 . . ?
H25A C25 H25B 109.1 . . ?
C22 N21 C25 111.38(17) . . ?
C22 N21 H21 124.3 . . ?
C25 N21 H21 124.3 . . ?
C22 N23 C24 111.75(17) . . ?
C22 N23 H23 124.1 . . ?
C24 N23 H23 124.1 . . ?
O32 C32 N31 125.46(12) . 2_656 ?
O32 C32 N31 125.46(12) . . ?
N31 C32 N31 109.1(2) 2_656 . ?
N31 C35 C35 101.93(12) . 2_656 ?
N31 C35 H35A 111.4 . . ?
C35 C35 H35A 111.4 2_656 . ?
N31 C35 H35B 111.4 . . ?
C35 C35 H35B 111.4 2_656 . ?
H35A C35 H35B 109.2 . . ?
C32 N31 C35 111.68(18) . . ?
C32 N31 H31 124.2 . . ?
C35 N31 H31 124.2 . . ?
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
C2 C1 1.508(3) . ?
C2 C1 1.508(3) 2_556 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 O1A 1.211(3) . ?
C1 O1B 1.323(3) . ?
O1B H1 0.8400 . ?
C22 O22 1.252(3) . ?
C22 N21 1.346(3) . ?
C22 N23 1.350(3) . ?
C24 N23 1.460(3) . ?
C24 C25 1.541(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.461(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.244(3) . ?
C32 N31 1.349(2) 2_656 ?
C32 N31 1.349(2) . ?
C35 N31 1.459(3) . ?
C35 C35 1.547(5) 2_656 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31 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 1.75 2.573(2) 166.3 .
N21 H21 O32 0.88 2.06 2.807(2) 142.1 .
N23 H23 O1A 0.88 2.18 2.914(2) 140.7 .
N31 H31 O22 0.88 2.28 3.092(2) 153.9 .
