Amidino substituted 2-aminophenols: biologically important building blocks for the amidino-functionalization of 2-substituted benzoxazoles.
Ptiček, Lucija; Hok, Lucija; Grbčić, Petra; Topić, Filip; Cetina, Mario; Rissanen, Kari; Pavelić, Sandra Kraljević; Vianello, Robert; Racané, Livio; Organic & biomolecular chemistry 19 (2021) 2784–2793; doi:10.1039/d1ob00235j

data_7157921
_publ_section_title
;
 Amidino substituted 2-aminophenols: biologically important building
 blocks for the amidino-functionalization of 2-substituted benzoxazoles.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2784
_journal_page_last               2793
_journal_paper_doi               10.1039/d1ob00235j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C9 H11 N3 O, 4.335(H2 O), 0.400(O)'
_chemical_formula_sum            'C9 H19.669 N3 O5.735'
_chemical_formula_weight         261.70
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.269(4)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.7267(7)
_cell_length_b                   36.3350(18)
_cell_length_c                   7.3619(4)
_cell_measurement_reflns_used    5404
_cell_measurement_temperature    123.0(1)
_cell_measurement_theta_max      73.0990
_cell_measurement_theta_min      3.8540
_cell_volume                     3939.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23933
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         74.349
_diffrn_reflns_theta_min         3.864
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1686.6
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     942
_refine_ls_number_reflns         7808
_refine_ls_number_restraints     2744
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0889
_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^)+(0.0876P)^2^+10.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2339
_refine_ls_wR_factor_ref         0.2503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5659
_reflns_number_total             7808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           8b'_123K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157921
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.761
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              80050