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_7157916
_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         'C7 H11 N3 O, 2(Cl)'
_chemical_formula_sum            'C7 H11 Cl2 N3 O'
_chemical_formula_weight         224.09
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 93.014(6)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   4.4199(3)
_cell_length_b                   11.7058(6)
_cell_length_c                   20.2357(15)
_cell_measurement_reflns_used    1621
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31.1540
_cell_measurement_theta_min      4.6040
_cell_volume                     1045.52(12)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2017)'
_computing_structure_solution    'SIR-2014 (Burla et al., 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1892
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         4.394
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0499P)^2^+0.0144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1596
_reflns_number_total             1892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           8g_295K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_cell_volume        1045.51(12)
_cod_database_code               7157916
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8831(15)
 0.1169(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              23613
_olex2_submission_special_instructions 'No special instructions were received'