Formation of Ionic Co-Crystals of Amphoteric Azoles Directed by the Ionic Liquid Co-Former 1-Ethyl-3-Methylimidazolium Acetate
Titi, Hatem M.; Kelley, Steven Paul; Easton, Max; Emerson, Stephen D.; Rogers, Robin D.; Chem. Commun.  (2017) –; doi:10.1039/C7CC04429A

data_7120419
_publ_section_title
;
 Formation of Ionic Co-Crystals of Amphoteric Azoles Directed by the Ionic
 Liquid Co-Former 1-Ethyl-3-Methylimidazolium Acetate
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04429A
_journal_year                    2017
_chemical_formula_sum            'C18 H25 N11 O6'
_chemical_formula_weight         491.49
_chemical_name_systematic
'1-ethyl-3-methylimdazolium 2-methyl-4(5)-nitroimidazolate.2(2-methyl-4(5)-nitroimidazole)'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     interative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-01 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                116.269(2)
_cell_angle_beta                 98.816(3)
_cell_angle_gamma                93.667(2)
_cell_formula_units_Z            1
_cell_length_a                   7.8397(5)
_cell_length_b                   8.9624(6)
_cell_length_c                   9.2212(7)
_cell_measurement_reflns_used    6918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.238
_cell_measurement_theta_min      2.515
_cell_volume                     567.74(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.693
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.693
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20561
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.238
_diffrn_reflns_theta_min         2.515
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6949
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6133
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.0811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.514
_reflns_number_gt                5627
_reflns_number_total             6133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04429a2.cif
_cod_data_source_block           ti9
_cod_database_code               7120419
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              96828