Light-swing CO2 capture: photoirradiation-based chemical CO2 release based on photoisomerization of azobenzene-amine/guanidine derivatives
Murakami, Ryo; Shiota, Keitaro; Uchida, Ayaka; Inagaki, Fuyuhiko; Green Chemistry 26 (2024) 7406–7413; doi:10.1039/D4GC00736K

data_7248756
_publ_section_title
;
 Light-swing CO2 capture: photoirradiation-based chemical CO2 release
 based on photoisomerization of azobenzene-amine/guanidine derivatives
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              7406
_journal_page_last               7413
_journal_paper_doi               10.1039/D4GC00736K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C3 H5 O3, C15 H19 N6'
_chemical_formula_sum            'C18 H24 N6 O3'
_chemical_formula_weight         372.43
_chemical_name_common            GAB
_chemical_name_systematic
'(E)-amino((4-(4-(dimethylamino)styryl)phenyl)amino)methaniminium ethyl carbonate'
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-12-05 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.736(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6781(4)
_cell_length_b                   27.9980(13)
_cell_length_c                   9.1512(3)
_cell_measurement_reflns_used    7975
_cell_measurement_theta_max      23.2070
_cell_measurement_theta_min      2.3240
_cell_volume                     1963.07(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -74.00 110.00   0.50   23.83    --   20.00  54.00-150.00  368
  2  \w    -74.00 110.00   0.50   23.83    --   20.00  54.00 150.00  368
  3  \w    -74.00 110.00   0.50   23.83    --   20.00  54.00  90.00  368
  4  \w    -74.00 110.00   0.50   23.83    --   20.00  54.00 120.00  368
  5  \w    -74.00 110.00   0.50   23.83    --   20.00  54.00   0.00  368
  6  \w    -74.00 101.00   0.50   23.83    --   20.00  54.00 -90.00  350
  7  \w    -74.00 110.00   0.50   23.83    --   20.00  54.00 -60.00  368
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454567000
_diffrn_orient_matrix_UB_12      0.0215780000
_diffrn_orient_matrix_UB_13      0.0116352000
_diffrn_orient_matrix_UB_21      0.0587906000
_diffrn_orient_matrix_UB_22      0.0125052000
_diffrn_orient_matrix_UB_23      -0.0428788000
_diffrn_orient_matrix_UB_31      -0.0553201000
_diffrn_orient_matrix_UB_32      -0.0044553000
_diffrn_orient_matrix_UB_33      -0.0636425000
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.670
_diffrn_reflns_theta_min         2.346
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_preparation
'After dissolving in ethanol, it was left standing in air.'
_exptl_crystal_recrystallization_method 'Vapor diffusion method (EtOH)'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1458
_refine_ls_R_factor_gt           0.0747
_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^)+(0.0647P)^2^+0.8318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2921
_reflns_number_total             5917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00736k2.cif
_cod_data_source_block           ks105entry3
_cod_depositor_comments          'Adding full bibliography for 7248756.cif.'
_cod_database_code               7248756
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
018015ea8f3fde7e82fe93c442e773062a000254a5d
;
_diffrn_oxdiff_digest_hkl
;
01fd0302f65dbb3f6687176f36f9f2f0df7791
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00H,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C00D(H00D), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00P)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C00O(H00Q,H00R,H00S), C00Q(H00A,H00B,H00C), C00R(H00E,H00F,H00G)
;
_shelx_res_checksum              70576
_shelx_hkl_checksum              40112
_olex2_exptl_crystal_mounting_method 'MiTeGen Dual-Thickness MicroLoops'
_olex2_submission_original_sample_id KS105
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.889