Reversible CO2 fixation by N-heterocyclic imines forming water-stable zwitterionic nitrogen-base–CO2 adducts
Wilm, Lukas F. B.; Eder, Tobias; Mück-Lichtenfeld, Christian; Mehlmann, Paul; Wünsche, Marius; Buß, Florenz; Dielmann, Fabian; Green Chemistry 21 (2019) 640–; doi:10.1039/C8GC02952K

data_7232137
_publ_section_title
;
 Reversible CO2 fixation by N-heterocyclic imines forming water-stable
 zwitterionic nitrogen-base--CO2 adducts
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              640
_journal_paper_doi               10.1039/C8GC02952K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C13 H19 N3'
_chemical_formula_sum            'C13 H19 N3'
_chemical_formula_weight         217.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_audit_update_record
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9385(2)
_cell_length_b                   10.0425(2)
_cell_length_c                   24.7502(4)
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.591
_cell_measurement_theta_min      2.884
_cell_volume                     2470.25(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_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  0.0214
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            34800
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.604
_diffrn_reflns_theta_min         2.612
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1206 before and 0.0311 after correction.
The Ratio of minimum to maximum transmission is 0.9440.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         6911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.9793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6692
_reflns_number_total             6911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02952k2.cif
_cod_data_source_block           p212121_neu
_cod_depositor_comments
'Adding full bibliography for 7232134--7232146.cif.'
_cod_database_code               7232137
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24), C8(H8), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C4(H4A), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,
 H13B,H13C)
;
_shelx_res_checksum              76937