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_7232145
_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         'C15 H27 N3 O2, 0.75(C6 H6)'
_chemical_formula_sum            'C19.5 H31.5 N3 O2'
_chemical_formula_weight         339.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 117.1590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.6071(2)
_cell_length_b                   41.9109(7)
_cell_length_c                   14.5422(2)
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.50
_cell_volume                     7921.1(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            107880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         1.567
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1642 before and 0.0458 after correction. The Ratio of minimum to maximum transmission is 0.7945. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       block
_exptl_crystal_F_000             2968
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.548
_exptl_crystal_size_min          0.521
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     931
_refine_ls_number_reflns         16183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0449P)^2^+5.5312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13986
_reflns_number_total             16183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02952k2.cif
_cod_data_source_block           p2c_a
_cod_depositor_comments
'Adding full bibliography for 7232134--7232146.cif.'
_cod_original_formula_sum        'C19.50 H31.50 N3 O2'
_cod_database_code               7232145
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H33(0.028) H34(0.029) H35A(0.046) H35B(0.046) H35C(0.046)
 H35D(0.046) H36A(0.03) H36B(0.03) H36C(0.029) H36D(0.029) H37A(0.043)
 H37B(0.043) H37C(0.043) H37D(0.048) H37E(0.048) H37F(0.048) H39A(0.056)
 H39B(0.056) H39C(0.056) H40A(0.051) H40B(0.051) H40C(0.051) H41A(0.041)
 H41B(0.041) H41C(0.041) H43A(0.055) H43B(0.055) H43C(0.055) H44A(0.048)
 H44B(0.048) H44C(0.048) H45A(0.076) H45B(0.076) H45C(0.076) H18(0.032)
 H19(0.036) H20A(0.045) H20B(0.045) H21A(0.051) H21B(0.051) H22A(0.09)
 H22B(0.09) H22C(0.09) H24A(0.084) H24B(0.084) H24C(0.084) H25A(0.086)
 H25B(0.086) H25C(0.086) H26A(0.059) H26B(0.059) H26C(0.059) H28A(0.082)
 H28B(0.082) H28C(0.082) H29A(0.081) H29B(0.081) H29C(0.081) H30A(0.074)
 H30B(0.074) H30C(0.074) H48(0.023) H49(0.022) H50A(0.024) H50B(0.024)
 H51A(0.028) H51B(0.028) H52A(0.044) H52B(0.044) H52C(0.044) H54A(0.076)
 H54B(0.076) H54C(0.076) H55A(0.051) H55B(0.051) H55C(0.051) H56A(0.06)
 H56B(0.06) H56C(0.06) H58A(0.048) H58B(0.048) H58C(0.048) H59A(0.042)
 H59B(0.042) H59C(0.042) H60A(0.042) H60B(0.042) H60C(0.042) H3(0.032)
 H4(0.033) H5A(0.031) H5B(0.031) H6A(0.036) H6B(0.036) H7A(0.062) H7B(0.062)
 H7C(0.062) H9A(0.054) H9B(0.054) H9C(0.054) H10A(0.063) H10B(0.063)
 H10C(0.063) H11A(0.05) H11B(0.05) H11C(0.05) H13A(0.046) H13B(0.046)
 H13C(0.046) H14A(0.046) H14B(0.046) H14C(0.046) H15A(0.048) H15B(0.048)
 H15C(0.048) H61(0.047) H62(0.047) H63(0.048) H64(0.05) H65(0.044) H66(0.041)
 H73(0.055) H74(0.06) H75(0.064) H76(0.066) H77(0.061) H78(0.054) H67(0.04)
 H68(0.041) H69(0.041) H70(0.041) H71(0.043) H72(0.042)
 Fixed X: H33(0.6263) H34(0.6911) H35A(1.0772) H35B(1.0828) H35C(1.1021)
 H35D(1.0362) H36A(0.957) H36B(0.9534) H36C(1.0616) H36D(0.9773) H37A(1.1325)
 H37B(1.0615) H37C(1.1281) H37D(1.1408) H37E(1.099) H37F(1.189) H39A(0.6461)
 H39B(0.7577) H39C(0.6931) H40A(0.712) H40B(0.6175) H40C(0.6706) H41A(0.9052)
 H41B(0.8851) H41C(0.8386) H43A(0.7811) H43B(0.7859) H43C(0.8677) H44A(0.9361)
 H44B(1.0285) H44C(1.0025) H45A(1.0029) H45B(0.9048) H45C(0.9932) H18(0.4842)
 H19(0.6493) H20A(0.7072) H20B(0.6165) H21A(0.4931) H21B(0.5816) H22A(0.5568)
 H22B(0.5198) H22C(0.6398) H24A(0.3408) H24B(0.285) H24C(0.3433) H25A(0.5029)
 H25B(0.3799) H25C(0.446) H26A(0.4556) H26B(0.3982) H26C(0.5207) H28A(0.8319)
 H28B(0.9102) H28C(0.8025) H29A(0.826) H29B(0.9232) H29C(0.8422) H30A(0.7385)
 H30B(0.851) H30C(0.7516) H48(0.1247) H49(0.0208) H50A(0.3095) H50B(0.3918)
 H51A(0.5195) H51B(0.4364) H52A(0.5099) H52B(0.5389) H52C(0.4237) H54A(0.272)
 H54B(0.3569) H54C(0.3916) H55A(0.4645) H55B(0.4369) H55C(0.4905) H56A(0.2905)
 H56B(0.2392) H56C(0.357) H58A(0.2165) H58B(0.2595) H58C(0.1659) H59A(-0.0316)
 H59B(0.0334) H59C(-0.002) H60A(0.1655) H60B(0.0558) H60C(0.0661) H3(0.8813)
 H4(0.9182) H5A(0.6902) H5B(0.6519) H6A(0.6012) H6B(0.6491) H7A(0.4809)
 H7B(0.4666) H7C(0.5253) H9A(0.8848) H9B(0.7744) H9C(0.7873) H10A(0.8207)
 H10B(0.9183) H10C(0.8301) H11A(0.637) H11B(0.6558) H11C(0.648) H13A(0.8802)
 H13B(0.7691) H13C(0.8592) H14A(1.0138) H14B(1.0293) H14C(1.0069) H15A(0.7436)
 H15B(0.8418) H15C(0.8281) H61(0.2664) H62(0.3678) H63(0.4321) H64(0.3945)
 H65(0.2915) H66(0.2273) H73(0.9398) H74(1.0359) H75(1.2054) H76(1.2791)
 H77(1.183) H78(1.0148) H67(0.5388) H68(0.6234) H69(0.7524) H70(0.8001)
 H71(0.7159) H72(0.5835)
 Fixed Y: H33(0.8493) H34(0.8535) H35A(0.8494) H35B(0.8488) H35C(0.8577)
 H35D(0.8369) H36A(0.8098) H36B(0.8103) H36C(0.8286) H36D(0.8099) H37A(0.7934)
 H37B(0.7682) H37C(0.7935) H37D(0.782) H37E(0.7816) H37F(0.8057) H39A(0.8261)
 H39B(0.812) H39C(0.8296) H40A(0.9084) H40B(0.884) H40C(0.8911) H41A(0.8499)
 H41B(0.8876) H41C(0.8669) H43A(0.8618) H43B(0.8983) H43C(0.885) H44A(0.9159)
 H44B(0.891) H44C(0.9051) H45A(0.8342) H45B(0.8226) H45C(0.8429) H18(0.7862)
 H19(0.779) H20A(0.6676) H20B(0.6628) H21A(0.6737) H21B(0.6817) H22A(0.6201)
 H22B(0.6283) H22C(0.6284) H24A(0.732) H24B(0.7506) H24C(0.7701) H25A(0.721)
 H25B(0.7202) H25C(0.7008) H26A(0.7982) H26B(0.7808) H26C(0.7784) H28A(0.781)
 H28B(0.7579) H28C(0.7671) H29A(0.7049) H29B(0.7233) H29C(0.742) H30A(0.7116)
 H30B(0.7004) H30C(0.6871) H48(0.8899) H49(0.8834) H50A(0.9173) H50B(0.8964)
 H51A(0.9114) H51B(0.934) H52A(0.9423) H52B(0.9649) H52C(0.9645) H54A(0.9231)
 H54B(0.932) H54C(0.9189) H55A(0.8879) H55B(0.8516) H55C(0.8735) H56A(0.8391)
 H56B(0.8678) H56C(0.8585) H58A(0.8286) H58B(0.8594) H58C(0.8395) H59A(0.863)
 H59B(0.8309) H59C(0.8413) H60A(0.9102) H60B(0.9127) H60C(0.8946) H3(0.4528)
 H4(0.4526) H5A(0.5734) H5B(0.5687) H6A(0.5162) H6B(0.5183) H7A(0.5573)
 H7B(0.526) H7C(0.5564) H9A(0.4758) H9B(0.4608) H9C(0.4851) H10A(0.5559)
 H10B(0.5345) H10C(0.5409) H11A(0.4944) H11B(0.5319) H11C(0.5171) H13A(0.5553)
 H13B(0.5419) H13C(0.5431) H14A(0.481) H14B(0.5182) H14C(0.5064) H15A(0.4828)
 H15B(0.4598) H15C(0.4849) H61(0.662) H62(0.6769) H63(0.6381) H64(0.5846)
 H65(0.5696) H66(0.6083) H73(0.7701) H74(0.8112) H75(0.802) H76(0.7518)
 H77(0.711) H78(0.7206) H67(0.5242) H68(0.5713) H69(0.571) H70(0.5232)
 H71(0.4759) H72(0.4766)
 Fixed Z: H33(0.6494) H34(0.8376) H35A(0.7733) H35B(0.8854) H35C(0.8352)
 H35D(0.8734) H36A(0.7186) H36B(0.8271) H36C(0.7025) H36D(0.7224) H37A(0.8046)
 H37B(0.8251) H37C(0.9126) H37D(0.7723) H37E(0.8566) H37F(0.8692) H39A(0.5232)
 H39B(0.552) H39C(0.4435) H40A(0.5534) H40B(0.5164) H40C(0.4436) H41A(0.5906)
 H41B(0.5855) H41C(0.4815) H43A(0.9974) H43B(0.9675) H43C(1.0778) H44A(0.9309)
 H44B(0.9609) H44C(1.0486) H45A(0.9823) H45B(0.9949) H45C(1.0847) H18(0.6117)
 H19(0.7669) H20A(0.6129) H20B(0.4986) H21A(0.5545) H21B(0.6684) H22A(0.574)
 H22B(0.6593) H22C(0.6898) H24A(0.4877) H24B(0.3801) H24C(0.4858) H25A(0.3615)
 H25B(0.3094) H25C(0.4139) H26A(0.4255) H26B(0.3157) H26C(0.3812) H28A(0.7829)
 H28B(0.8718) H28C(0.8686) H29A(0.6651) H29B(0.7515) H29C(0.6515) H30A(0.856)
 H30B(0.8767) H30C(0.7785) H48(0.6664) H49(0.4782) H50A(0.4589) H50B(0.4417)
 H51A(0.6106) H51B(0.621) H52A(0.4707) H52B(0.5689) H52C(0.4772) H54A(0.7845)
 H54B(0.7479) H54C(0.8625) H55A(0.7286) H55B(0.7386) H55C(0.8396) H56A(0.779)
 H56B(0.8117) H56C(0.8833) H58A(0.3898) H58B(0.3569) H58C(0.2713) H59A(0.3289)
 H59B(0.3731) H59C(0.2558) H60A(0.3185) H60B(0.3178) H60C(0.226) H3(0.9246)
 H4(0.7759) H5A(0.6585) H5B(0.7444) H6A(0.6899) H6B(0.6104) H7A(0.5931)
 H7B(0.525) H7C(0.5109) H9A(1.0661) H9B(0.993) H9C(1.083) H10A(0.9689)
 H10B(1.0401) H10C(1.0741) H11A(0.8626) H11B(0.8581) H11C(0.9557) H13A(0.6663)
 H13B(0.5877) H13C(0.5541) H14A(0.7175) H14B(0.7455) H14C(0.6325) H15A(0.552)
 H15B(0.5992) H15C(0.511) H61(0.5223) H62(0.6941) H63(0.8236) H64(0.7803)
 H65(0.6089) H66(0.4796) H73(0.5638) H74(0.5428) H75(0.5751) H76(0.6314)
 H77(0.655) H78(0.6232) H67(0.3379) H68(0.3382) H69(0.2865) H70(0.2385)
 H71(0.2388) H72(0.2869)
;
_shelx_res_checksum              68222
_olex2_date_sample_data_collection 2018-01-02
_olex2_date_sample_submission    2018-01-02
_olex2_submission_original_sample_id lw180102
_olex2_submission_special_instructions 'No special instructions were received'