#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:20:26 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157911.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157911
loop_
_publ_author_name
'Ptiček, Lucija'
'Hok, Lucija'
'Grbčić, Petra'
'Topić, Filip'
'Cetina, Mario'
'Rissanen, Kari'
'Pavelić, Sandra Kraljević'
'Vianello, Robert'
'Racané, Livio'
_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 & 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 H6 N2 O'
_chemical_formula_sum            'C7 H6 N2 O'
_chemical_formula_weight         134.14
_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                 99.5201(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.79610(10)
_cell_length_b                   7.4931(3)
_cell_length_c                   22.9246(9)
_cell_measurement_reflns_used    1452
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.333
_cell_measurement_theta_min      2.864
_cell_volume                     643.10(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_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_temperature      170.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEXII detector'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            1431
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.333
_diffrn_reflns_theta_min         2.864
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             280
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.028(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0574
_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/[σ²(Fo²)+(0.0607P)²+0.3895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1196
_reflns_number_total             1431
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           3c_170K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157911
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.2418(5) 0.9064(2) 0.39011(9) 0.0352(5) Uani 1 1 d . . . . .
C2A C 0.4128(5) 0.7434(2) 0.40845(9) 0.0357(5) Uani 1 1 d . . . . .
C3A C 0.4748(5) 0.6258(2) 0.36390(9) 0.0344(5) Uani 1 1 d . . . . .
C4A C 0.3704(5) 0.6651(3) 0.30389(9) 0.0382(5) Uani 1 1 d . . . . .
H4A H 0.413839 0.582135 0.274550 0.046 Uiso 1 1 calc R U . . .
C5A C 0.2043(6) 0.8248(3) 0.28774(9) 0.0399(5) Uani 1 1 d . . . . .
H5A H 0.131195 0.852919 0.247135 0.048 Uiso 1 1 calc R U . . .
C6A C 0.1440(5) 0.9450(3) 0.33130(9) 0.0377(5) Uani 1 1 d . . . . .
H6A H 0.032731 1.056137 0.319986 0.045 Uiso 1 1 calc R U . . .
C7A C 0.6479(6) 0.4590(3) 0.38066(10) 0.0411(5) Uani 1 1 d . . . . .
N1A N 0.4949(6) 0.7047(3) 0.46744(8) 0.0551(6) Uani 1 1 d G . . . .
H1A1 H 0.683396 0.635540 0.479537 0.083 Uiso 1 1 d G U . . .
H1A2 H 0.491140 0.794101 0.492911 0.083 Uiso 1 1 d G U . . .
N2A N 0.7884(6) 0.3272(2) 0.39462(10) 0.0580(6) Uani 1 1 d . . . . .
O1A O 0.1827(4) 1.01648(19) 0.43489(7) 0.0486(5) Uani 1 1 d . . . . .
H1A H 0.059239 1.104134 0.420765 0.073 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A C1A C6A 124.20(17) . . ?
O1A C1A C2A 115.02(17) . . ?
C6A C1A C2A 120.78(18) . . ?
N1A C2A C3A 123.40(18) . . ?
N1A C2A C1A 119.69(18) . . ?
C3A C2A C1A 116.85(18) . . ?
C2A C3A C4A 122.10(17) . . ?
C2A C3A C7A 118.59(18) . . ?
C4A C3A C7A 119.30(18) . . ?
C5A C4A C3A 119.39(18) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C4A C5A C6A 119.54(19) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C1A C6A C5A 121.33(18) . . ?
C1A C6A H6A 119.3 . . ?
C5A C6A H6A 119.3 . . ?
N2A C7A C3A 179.1(3) . . ?
C2A N1A H1A1 118.1 . . ?
C2A N1A H1A2 117.6 . . ?
H1A1 N1A H1A2 109.5 . . ?
C1A O1A H1A 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A O1A 1.364(2) . ?
C1A C6A 1.369(3) . ?
C1A C2A 1.414(3) . ?
C2A N1A 1.368(3) . ?
C2A C3A 1.398(3) . ?
C3A C4A 1.399(3) . ?
C3A C7A 1.435(3) . ?
C4A C5A 1.375(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.392(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A N2A 1.143(3) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8901 . ?
O1A H1A 0.8400 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A N1A 2.0(3) . . . . ?
C6A C1A C2A N1A -177.3(2) . . . . ?
O1A C1A C2A C3A 179.29(18) . . . . ?
C6A C1A C2A C3A -0.1(3) . . . . ?
N1A C2A C3A C4A 176.5(2) . . . . ?
C1A C2A C3A C4A -0.7(3) . . . . ?
N1A C2A C3A C7A -2.9(3) . . . . ?
C1A C2A C3A C7A 179.96(18) . . . . ?
C2A C3A C4A C5A 0.6(3) . . . . ?
C7A C3A C4A C5A 179.97(19) . . . . ?
C3A C4A C5A C6A 0.2(3) . . . . ?
O1A C1A C6A C5A -178.4(2) . . . . ?
C2A C1A C6A C5A 0.9(3) . . . . ?
C4A C5A C6A C1A -1.0(3) . . . . ?
