Bio-based 1,3-diisobutyl imidazolium hydrogen oxalate [iBu2IM](HC2O4) as CO2 shuttle
de Robillard, G.; Fournier, A. H.; Cattey, H.; Devillers, C. H.; Andrieu, J.; Green Chem.  (2017) –; doi:10.1039/C7GC02167D

data_7229225
_publ_section_title
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 Bio-based 1,3-diisobutyl imidazolium hydrogen oxalate [iBu2IM](HC2O4) as
 CO2 shuttle
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_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC02167D
_journal_year                    2017
_chemical_formula_moiety         'C11 H21 N2, C2 H O4'
_chemical_formula_sum            'C13 H22 N2 O4'
_chemical_formula_weight         270.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.5633(11)
_cell_length_b                   10.2111(5)
_cell_length_c                   13.1867(5)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      3.10
_cell_volume                     3038.2(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55853
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         3.090
_diffrn_source                   'X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0636 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9163.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6599
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0377P)^2^+0.4587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                5365
_reflns_number_total             6599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc02167d2.cif
_cod_data_source_block           Bu2IMHC2O4
_cod_depositor_comments
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2018-02-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
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_cod_original_formula_moiety     '2(C11 H21 N2), C4 H2 O8'
_cod_original_formula_sum        'C26 H44 N4 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     540.65
_cod_database_code               7229225
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C20(H20), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C19(H19A,H19B), C4(H4A,H4B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C1(H1), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,
 H11C)
;
_shelx_res_checksum              28014