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_7232142
_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 H23 N3 O2'
_chemical_formula_sum            'C13 H23 N3 O2'
_chemical_formula_weight         253.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.6046(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.37650(10)
_cell_length_b                   13.1188(2)
_cell_length_c                   11.2806(2)
_cell_measurement_reflns_used    6238
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      2.659
_cell_volume                     1396.17(4)
_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, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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  0.0151
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9420
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.555
_diffrn_reflns_theta_min         2.659
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1005 before and 0.0292 after correction.
The Ratio of minimum to maximum transmission is 0.9350.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0655P)^2^+0.7830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3728
_reflns_number_total             3803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02952k2.cif
_cod_data_source_block           c2c
_cod_depositor_comments
'Adding full bibliography for 7232134--7232146.cif.'
_cod_original_cell_volume        1396.16(4)
_cod_database_code               7232142
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5A(0.036) H5B(0.036) H5C(0.036) H6A(0.041) H6B(0.041) H6C(0.041)
 H8(0.02) H10A(0.036) H10B(0.036) H10C(0.036) H9A(0.036) H9B(0.036) H9C(0.036)
 H11(0.025) H12A(0.039) H12B(0.039) H12C(0.039) H13A(0.054) H13B(0.054)
 H13C(0.054) H7A(0.039) H7B(0.039) H7C(0.039)
 Fixed X: H5A(-0.36) H5B(-0.2637) H5C(-0.3956) H6A(-0.0159) H6B(-0.0471)
 H6C(0.0886) H8(-0.3753) H10A(-0.5195) H10B(-0.6003) H10C(-0.5444) H9A(-0.3927)
 H9B(-0.4423) H9C(-0.2773) H11(0.0589) H12A(0.189) H12B(0.2824) H12C(0.2279)
 H13A(0.1) H13B(0.1453) H13C(-0.0188) H7A(-0.2106) H7B(-0.3107) H7C(-0.1559)
 Fixed Y: H5A(-0.6381) H5B(-0.7158) H5C(-0.6608) H6A(-0.674) H6B(-0.7215) H6C(-
 0.6504) H8(-0.3413) H10A(-0.444) H10B(-0.4051) H10C(-0.5201) H9A(-0.506) H9B(-
 0.3911) H9C(-0.4169) H11(-0.3541) H12A(-0.4286) H12B(-0.4092) H12C(-0.5217)
 H13A(-0.5381) H13B(-0.4263) H13C(-0.4561) H7A(-0.1801) H7B(-0.2767) H7C(-
 0.2729)
 Fixed Z: H5A(-0.5107) H5B(-0.5478) H5C(-0.6605) H6A(-0.6646) H6B(-0.5485)
 H6C(-0.5163) H8(-0.5742) H10A(-0.7566) H10B(-0.6714) H10C(-0.6572) H9A(-
 0.4169) H9B(-0.4125) H9C(-0.3631) H11(-0.6078) H12A(-0.402) H12B(-0.4825)
 H12C(-0.4729) H13A(-0.7179) H13B(-0.7426) H13C(-0.7972) H7A(-0.7085) H7B(-
 0.7691) H7C(-0.7674)
;
_shelx_res_checksum              21296
_olex2_submission_special_instructions 'No special instructions were received'