Exploring the synthesis of aminal guanidine-based molecules: synthesis of cernumidine and analogues, and survey of its anti-inflammatory activity
Rippel, Rafael; Leitão, Flávia; Georgieva, Miglena K.; Mamede, Rafael; Gomes, Clara S. B.; Roma-Rodrigues, Catarina; Fernandes, Alexandra R.; Lourenço, Ana; Ferreira, Luísa M.; Branco, Paula S.; New Journal of Chemistry 48 (2024) 5247–5257; doi:10.1039/D3NJ05406C

data_7063058
_publ_section_title
;
 Exploring the synthesis of aminal guanidine-based molecules: synthesis of
 cernumidine and analogues, and survey of its anti-inflammatory activity
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5247
_journal_page_last               5257
_journal_paper_doi               10.1039/D3NJ05406C
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-11-09 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.499(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0552(3)
_cell_length_b                   9.2248(5)
_cell_length_c                   25.6961(13)
_cell_measurement_reflns_used    8210
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.23
_cell_measurement_theta_min      3.44
_cell_volume                     1198.25(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX and enCIFer'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1277
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22687
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.317
_diffrn_reflns_theta_min         3.440
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1373 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0083(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0704
_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^)+(0.0884P)^2^+1.6448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3708
_reflns_number_total             4429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05406c2.cif
_cod_data_source_block           19
_cod_depositor_comments
'Adding full bibliography for 7063057--7063058.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7063058
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.878
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              11356
_shelx_hkl_checksum              74811