#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:20:26 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157919.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_7157919
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_absolute_configuration unk
_chemical_formula_moiety         'C7 H9 N3 O, 2(H2 O)'
_chemical_formula_sum            'C7 H13 N3 O3'
_chemical_formula_weight         187.20
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.890(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1400(8)
_cell_length_b                   4.0229(4)
_cell_length_c                   10.8744(12)
_cell_measurement_reflns_used    1002
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_volume                     438.26(7)
_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-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.963
_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  0.0551
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2959
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.025
_diffrn_reflns_theta_min         1.895
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1918
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0630
_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)+(0.0841P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                1340
_reflns_number_total             1918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           8a'_170K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157919
_shelx_shelxl_version_number     2017/1
_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   0.962
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 C 0.6324(4) 0.5904(11) 0.2432(4) 0.0269(9) Uani 1 1 d . . . . .
C2 C 0.5898(4) 0.4020(11) 0.3408(4) 0.0282(10) Uani 1 1 d . . . . .
C3 C 0.4571(3) 0.3239(13) 0.3373(4) 0.0285(9) Uani 1 1 d . . . . .
H3 H 0.430686 0.197957 0.403313 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3600(4) 0.4265(11) 0.2384(4) 0.0272(10) Uani 1 1 d . . . . .
C5 C 0.4007(4) 0.6196(13) 0.1443(4) 0.0290(9) Uani 1 1 d . . . . .
H5 H 0.336393 0.698066 0.077781 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5348(4) 0.6975(12) 0.1474(4) 0.0316(11) Uani 1 1 d . . . . .
H6 H 0.560367 0.827767 0.082102 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2207(4) 0.3196(12) 0.2309(4) 0.0277(9) Uani 1 1 d . . . . .
N1 N 0.6877(3) 0.3039(11) 0.4416(4) 0.0335(9) Uani 1 1 d G . . . .
H1A H 0.664883 0.113710 0.478383 0.050 Uiso 1 1 d G U . . .
H1B H 0.762277 0.267485 0.406498 0.050 Uiso 1 1 d G U . . .
N2 N 0.1823(3) 0.1534(12) 0.3244(3) 0.0363(9) Uani 1 1 d . . . . .
H2A H 0.098781 0.088354 0.319720 0.044 Uiso 1 1 calc R U . . .
H2B H 0.240238 0.108019 0.391193 0.044 Uiso 1 1 calc R U . . .
N3 N 0.1321(3) 0.3840(11) 0.1322(4) 0.0361(10) Uani 1 1 d . . . . .
H3A H 0.049001 0.316986 0.129163 0.043 Uiso 1 1 calc R U . . .
H3B H 0.155773 0.494062 0.069189 0.043 Uiso 1 1 calc R U . . .
O1 O 0.7612(2) 0.6472(9) 0.2438(3) 0.0322(8) Uani 1 1 d . . . . .
O1W O 0.8591(3) 0.1487(10) 0.1162(3) 0.0344(8) Uani 1 1 d G . . . .
H11W H 0.830374 -0.023636 0.152399 0.052 Uiso 1 1 d G U . . .
H12W H 0.834338 0.329157 0.150310 0.052 Uiso 1 1 d G U . . .
O2W O 0.9613(3) 0.8407(10) 0.4136(3) 0.0390(8) Uani 1 1 d G . . . .
H21W H 0.989869 0.659591 0.452548 0.058 Uiso 1 1 d G U . . .
H22W H 0.892694 0.795021 0.357714 0.058 Uiso 1 1 d G 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
O1 C1 C6 122.5(4) . . ?
O1 C1 C2 120.0(4) . . ?
C6 C1 C2 117.4(3) . . ?
C3 C2 N1 121.5(4) . . ?
C3 C2 C1 120.6(4) . . ?
N1 C2 C1 117.9(3) . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 120.9(4) . . ?
C3 C4 C7 120.8(4) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.9(4) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N3 C7 N2 118.7(4) . . ?
N3 C7 C4 121.3(4) . . ?
N2 C7 C4 120.0(4) . . ?
C2 N1 H1A 112.3 . . ?
C2 N1 H1B 104.4 . . ?
H1A N1 H1B 109.5 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
H11W O1W H12W 109.5 . . ?
H21W O2W H22W 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
C1 O1 1.325(4) . ?
C1 C6 1.391(6) . ?
C1 C2 1.424(6) . ?
C2 C3 1.377(5) . ?
C2 N1 1.417(5) . ?
C3 C4 1.403(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(6) . ?
C4 C7 1.466(5) . ?
C5 C6 1.390(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N3 1.315(5) . ?
C7 N2 1.325(6) . ?
N1 H1A 0.9096 . ?
N1 H1B 0.9100 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
O1W H11W 0.8696 . ?
O1W H12W 0.8697 . ?
O2W H21W 0.8696 . ?
O2W H22W 0.8697 . ?
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
O1 C1 C2 C3 -176.0(4) . . . . ?
C6 C1 C2 C3 1.6(6) . . . . ?
O1 C1 C2 N1 5.1(6) . . . . ?
C6 C1 C2 N1 -177.3(4) . . . . ?
N1 C2 C3 C4 178.8(4) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C2 C3 C4 C7 175.1(4) . . . . ?
C3 C4 C5 C6 2.0(6) . . . . ?
C7 C4 C5 C6 -174.9(4) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
O1 C1 C6 C5 176.2(4) . . . . ?
C2 C1 C6 C5 -1.3(7) . . . . ?
C5 C4 C7 N3 4.3(7) . . . . ?
C3 C4 C7 N3 -172.5(4) . . . . ?
C5 C4 C7 N2 -176.0(4) . . . . ?
C3 C4 C7 N2 7.1(7) . . . . ?
