#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:49:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180450 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/19/7211932.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_7211932
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
'Threlfall, Terence L.'
_publ_section_title
;
 A systematic study of the crystallisation products of a series of
 dicarboxylic acids with imidazole derivatives
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              898
_journal_paper_doi               10.1039/b917191f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C10 H18 N2 O5'
_chemical_formula_weight         246.26
_chemical_name_common            'Adipic Acid and 2-Methylimidazole'
_chemical_name_systematic
;
Adipic Acid and 2-Methylimidazole
;
_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                96.9510(10)
_cell_angle_beta                 94.4750(10)
_cell_angle_gamma                107.3840(10)
_cell_formula_units_Z            2
_cell_length_a                   4.8629(3)
_cell_length_b                   7.9978(5)
_cell_length_c                   16.5263(11)
_cell_measurement_reflns_used    3399
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      2.96
_cell_volume                     604.44(7)
_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 0.957
_diffrn_measured_fraction_theta_max 0.957
_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     0.67100
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5294
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0940P)²+0.1815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1518
_reflns_number_gt                2332
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b917191f.txt
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7211932
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
C1 C 0.7807(3) 0.40570(18) 0.33759(8) 0.0162(3) Uani 1 1 d .
C2 C 0.6430(3) 0.51297(18) 0.39390(8) 0.0183(3) Uani 1 1 d .
H2A H 0.4646 0.5201 0.3633 0.022 Uiso 1 1 calc R
H2B H 0.7785 0.6351 0.4084 0.022 Uiso 1 1 calc R
C3 C 0.5643(3) 0.44048(18) 0.47293(8) 0.0170(3) Uani 1 1 d .
H3A H 0.7404 0.4306 0.5037 0.020 Uiso 1 1 calc R
H3B H 0.4220 0.3202 0.4593 0.020 Uiso 1 1 calc R
O1A O 0.8633(2) 0.28434(13) 0.36149(6) 0.0204(3) Uani 1 1 d .
O1B O 0.8110(2) 0.44532(14) 0.26536(6) 0.0234(3) Uani 1 1 d .
C22 C 0.7542(3) 0.98177(18) -0.23857(9) 0.0189(3) Uani 1 1 d .
C24 C 0.8726(3) 0.7967(2) -0.16393(9) 0.0224(3) Uani 1 1 d .
H24 H 0.9490 0.7077 -0.1480 0.027 Uiso 1 1 calc R
C25 C 0.7328(3) 0.88781(19) -0.11764(9) 0.0209(3) Uani 1 1 d .
H25 H 0.6923 0.8757 -0.0630 0.025 Uiso 1 1 calc R
C26 C 0.7221(4) 1.0795(2) -0.30718(9) 0.0263(4) Uani 1 1 d .
H26A H 0.8643 1.0704 -0.3450 0.039 Uiso 1 1 calc R
H26B H 0.7551 1.2044 -0.2856 0.039 Uiso 1 1 calc R
H26C H 0.5257 1.0284 -0.3365 0.039 Uiso 1 1 calc R
N21 N 0.6602(3) 1.00225(16) -0.16545(7) 0.0189(3) Uani 1 1 d .
H21 H 0.5664 1.0770 -0.1500 0.023 Uiso 1 1 calc R
N23 N 0.8838(3) 0.85711(16) -0.23859(8) 0.0204(3) Uani 1 1 d .
H23 H 0.9642 0.8190 -0.2799 0.024 Uiso 1 1 calc R
C31 C 0.6964(3) 0.68074(17) 0.13570(8) 0.0152(3) Uani 1 1 d .
C32 C 0.8589(3) 0.55855(17) 0.10181(8) 0.0151(3) Uani 1 1 d .
H32A H 0.7407 0.4349 0.1037 0.018 Uiso 1 1 calc R
H32B H 1.0417 0.5832 0.1386 0.018 Uiso 1 1 calc R
C33 C 0.9332(3) 0.57173(17) 0.01498(8) 0.0152(3) Uani 1 1 d .
H33A H 1.0721 0.6901 0.0133 0.018 Uiso 1 1 calc R
H33B H 0.7551 0.5582 -0.0220 0.018 Uiso 1 1 calc R
O31A O 0.6259(2) 0.66800(14) 0.20946(6) 0.0216(3) Uani 1 1 d .
H31 H 0.6996 0.5979 0.2300 0.032 Uiso 1 1 calc R
O31B O 0.6303(2) 0.78561(13) 0.09505(6) 0.0187(3) Uani 1 1 d .
O1W O 0.7897(3) 0.0793(2) 0.49132(9) 0.0400(4) Uani 1 1 d D
H1W H 0.827(11) -0.009(4) 0.473(3) 0.19(2) Uiso 1 1 d D
H2W H 0.808(5) 0.151(3) 0.4576(13) 0.050(7) Uiso 1 1 d 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
O1A C1 O1B 121.59(12) . .
O1A C1 C2 120.88(11) . .
O1B C1 C2 117.53(12) . .
C1 C2 C3 115.18(11) . .
C1 C2 H2A 108.5 . .
C3 C2 H2A 108.5 . .
C1 C2 H2B 108.5 . .
C3 C2 H2B 108.5 . .
H2A C2 H2B 107.5 . .
C2 C3 C3 111.67(13) . 2_666
C2 C3 H3A 109.3 . .
C3 C3 H3A 109.3 2_666 .
C2 C3 H3B 109.3 . .
C3 C3 H3B 109.3 2_666 .
H3A C3 H3B 107.9 . .
N23 C22 N21 107.48(13) . .
N23 C22 C26 125.92(13) . .
N21 C22 C26 126.60(13) . .
C25 C24 N23 107.13(13) . .
C25 C24 H24 126.4 . .
N23 C24 H24 126.4 . .
C24 C25 N21 106.49(12) . .
C24 C25 H25 126.8 . .
N21 C25 H25 126.8 . .
C22 C26 H26A 109.5 . .
C22 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C22 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C22 N21 C25 109.45(12) . .
C22 N21 H21 125.3 . .
C25 N21 H21 125.3 . .
C22 N23 C24 109.45(12) . .
C22 N23 H23 125.3 . .
C24 N23 H23 125.3 . .
O31B C31 O31A 121.51(12) . .
O31B C31 C32 121.81(12) . .
O31A C31 C32 116.67(11) . .
C31 C32 C33 116.09(11) . .
C31 C32 H32A 108.3 . .
C33 C32 H32A 108.3 . .
C31 C32 H32B 108.3 . .
C33 C32 H32B 108.3 . .
H32A C32 H32B 107.4 . .
C32 C33 C33 110.75(13) . 2_765
C32 C33 H33A 109.5 . .
C33 C33 H33A 109.5 2_765 .
C32 C33 H33B 109.5 . .
C33 C33 H33B 109.5 2_765 .
H33A C33 H33B 108.1 . .
C31 O31A H31 109.5 . .
H1W O1W H2W 112(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.2493(17) .
C1 O1B 1.2799(16) .
C1 C2 1.5160(18) .
C2 C3 1.5221(18) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C3 1.528(2) 2_666
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C22 N23 1.3292(18) .
C22 N21 1.3338(18) .
C22 C26 1.476(2) .
C24 C25 1.349(2) .
C24 N23 1.3775(19) .
C24 H24 0.9500 .
C25 N21 1.3826(18) .
C25 H25 0.9500 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
N21 H21 0.8800 .
N23 H23 0.8800 .
C31 O31B 1.2336(16) .
C31 O31A 1.2992(16) .
C31 C32 1.5138(17) .
C32 C33 1.5151(17) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C33 1.530(2) 2_765
C33 H33A 0.9900 .
C33 H33B 0.9900 .
O31A H31 0.8400 .
O1W H1W 0.813(19) .
O1W H2W 0.840(16) .
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
O31A H31 O1B 0.84 1.63 2.4619(14) 173.9 .
O1W H2W O1A 0.840(16) 2.008(17) 2.8358(16) 169(2) .
N21 H21 O31B 0.88 1.86 2.7273(16) 166.9 2_675
N23 H23 O1A 0.88 1.88 2.7537(15) 173.3 2_765
O1W H1W O1W 0.813(19) 2.16(4) 2.724(3) 126(5) 2_756
