#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:20:26 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157917.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_7157917
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         'C9 H12 N3 O, Cl, 2(H2 O)'
_chemical_formula_sum            'C9 H16 Cl N3 O3'
_chemical_formula_weight         249.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                108.3092(11)
_cell_angle_beta                 96.7180(11)
_cell_angle_gamma                102.1891(10)
_cell_formula_units_Z            2
_cell_length_a                   6.7656(2)
_cell_length_b                   9.4132(2)
_cell_length_c                   10.2539(2)
_cell_measurement_reflns_used    2551
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_volume                     594.05(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.978
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11385
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.377
_diffrn_reflns_theta_min         2.572
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0404
_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/[σ²(Fo²)+(0.0370P)²+0.2537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2227
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           8h_170K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_cell_volume        594.05(2)
_cod_database_code               7157917
_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   0.880
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 1.10452(7) 0.16387(5) 0.84797(4) 0.04507(15) Uani 1 1 d . . . . .
O1W O 0.7185(2) 0.17096(17) 0.64754(15) 0.0536(4) Uani 1 1 d G . . . .
H11W H 0.825762 0.163593 0.698147 0.080 Uiso 1 1 d G U . . .
H12W H 0.716148 0.123880 0.559321 0.080 Uiso 1 1 d G U . . .
O2W O 0.3549(2) -0.03969(16) 0.65441(16) 0.0556(4) Uani 1 1 d G . . . .
H2WA H 0.274529 0.011204 0.697903 0.083 Uiso 1 1 d G U . . .
H2WB H 0.472437 0.024512 0.661916 0.083 Uiso 1 1 d G U . . .
C1 C 0.8055(3) 0.7093(2) 0.67443(17) 0.0376(4) Uani 1 1 d D . . . .
C2 C 0.7705(3) 0.54737(19) 0.63446(17) 0.0360(4) Uani 1 1 d D . . . .
H2' H 0.767396 0.500683 0.704230 0.043 Uiso 0.052(3) 1 calc R U P A 2
O1 O 0.7706(2) 0.49067(16) 0.74231(13) 0.0488(4) Uani 0.948(3) 1 d D . P A 1
H1 H 0.747805 0.393691 0.709897 0.073 Uiso 0.948(3) 1 calc R U P A 1
C3 C 0.7407(3) 0.45599(19) 0.49655(17) 0.0356(4) Uani 1 1 d D . . . .
H3 H 0.717790 0.346927 0.471956 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7437(2) 0.52151(18) 0.39145(17) 0.0341(3) Uani 1 1 d D . . . .
C5 C 0.7757(3) 0.6814(2) 0.42976(18) 0.0412(4) Uani 1 1 d D . . . .
H5 H 0.776017 0.727539 0.359618 0.049 Uiso 1 1 calc R U . . .
C6 C 0.8070(3) 0.7730(2) 0.56834(19) 0.0446(4) Uani 1 1 d D . . . .
H6 H 0.830047 0.882072 0.592516 0.053 Uiso 0.948(3) 1 calc R U P A 1
O1' O 0.855(4) 0.9304(10) 0.6019(19) 0.0488(4) Uani 0.052(3) 1 d D . P A 2
H1' H 0.953914 0.972271 0.670751 0.073 Uiso 0.052(3) 1 calc DR U P A 2
C7 C 0.7148(2) 0.42521(19) 0.24567(17) 0.0345(3) Uani 1 1 d . . . . .
C8 C 0.6443(3) 0.2088(2) 0.04589(19) 0.0474(4) Uani 1 1 d . . . . .
H8A H 0.497511 0.153276 0.005236 0.057 Uiso 1 1 calc R U . . .
H8B H 0.731214 0.137396 0.013635 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7070(3) 0.3545(2) 0.00822(19) 0.0497(5) Uani 1 1 d . . . . .
H9A H 0.841740 0.363676 -0.021515 0.060 Uiso 1 1 calc R U . . .
H9B H 0.601751 0.355055 -0.067186 0.060 Uiso 1 1 calc R U . . .
N1 N 0.8313(3) 0.79922(19) 0.81175(16) 0.0507(4) Uani 1 1 d G . . . .
H1A H 0.893992 0.902702 0.844682 0.076 Uiso 1 1 d DG U . . .
H1B H 0.845004 0.761075 0.882642 0.076 Uiso 1 1 d DG U . . .
N2 N 0.6802(2) 0.27297(17) 0.19863(15) 0.0420(3) Uani 1 1 d . . . . .
H2A H 0.678941 0.216709 0.252888 0.050 Uiso 1 1 calc R U . . .
N3 N 0.7197(3) 0.47799(17) 0.14007(15) 0.0434(4) Uani 1 1 d . . . . .
H3A H 0.729387 0.575296 0.148471 0.052 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'
Cl Cl 0.1484 0.1585 '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
H11W O1W H12W 109.5 . . ?
H2WA O2W H2WB 109.5 . . ?
N1 C1 C6 121.66(16) . . ?
N1 C1 C2 120.70(15) . . ?
C6 C1 C2 117.62(15) . . ?
C3 C2 O1 123.62(15) . . ?
C3 C2 C1 121.05(15) . . ?
O1 C2 C1 115.33(15) . . ?
C3 C2 H2' 119.5 . . ?
C1 C2 H2' 119.5 . . ?
C2 O1 H1 109.5 . . ?
C2 C3 C4 120.73(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.66(15) . . ?
C5 C4 C7 120.54(15) . . ?
C3 C4 C7 120.80(15) . . ?
C6 C5 C4 120.52(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O1' C6 C5 118.4(8) . . ?
O1' C6 C1 120.0(8) . . ?
C5 C6 C1 121.42(16) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C6 O1' H1' 109.5 . . ?
N2 C7 N3 110.16(15) . . ?
N2 C7 C4 125.13(15) . . ?
N3 C7 C4 124.71(15) . . ?
N2 C8 C9 102.07(14) . . ?
N2 C8 H8A 111.4 . . ?
C9 C8 H8A 111.4 . . ?
N2 C8 H8B 111.4 . . ?
C9 C8 H8B 111.4 . . ?
H8A C8 H8B 109.2 . . ?
N3 C9 C8 102.30(14) . . ?
N3 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
N3 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C1 N1 H1A 122.4 . . ?
C1 N1 H1B 122.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N2 C8 112.00(14) . . ?
C7 N2 H2A 124.0 . . ?
C8 N2 H2A 124.0 . . ?
C7 N3 C9 111.53(14) . . ?
C7 N3 H3A 124.2 . . ?
C9 N3 H3A 124.2 . . ?
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
O1W H11W 0.8699 . ?
O1W H12W 0.8699 . ?
O2W H2WA 0.8699 . ?
O2W H2WB 0.8699 . ?
C1 N1 1.364(2) . ?
C1 C6 1.398(2) . ?
C1 C2 1.407(2) . ?
C2 C3 1.370(2) . ?
C2 O1 1.371(2) . ?
C2 H2' 0.9500 . ?
O1 H1 0.8400 . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 C7 1.449(2) . ?
C5 C6 1.375(2) . ?
C5 H5 0.9500 . ?
C6 O1' 1.367(8) . ?
C6 H6 0.9500 . ?
O1' H1' 0.8400 . ?
C7 N2 1.319(2) . ?
C7 N3 1.327(2) . ?
C8 N2 1.460(2) . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.460(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
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
N1 C1 C2 C3 178.83(16) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
N1 C1 C2 O1 -1.7(2) . . . . ?
C6 C1 C2 O1 179.97(16) . . . . ?
O1 C2 C3 C4 -179.60(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 179.23(15) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C7 C4 C5 C6 -178.79(17) . . . . ?
C4 C5 C6 O1' 174.6(13) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
N1 C1 C6 O1' 6.5(14) . . . . ?
C2 C1 C6 O1' -175.3(13) . . . . ?
N1 C1 C6 C5 -178.36(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C5 C4 C7 N2 -178.85(17) . . . . ?
C3 C4 C7 N2 1.4(3) . . . . ?
C5 C4 C7 N3 1.3(3) . . . . ?
C3 C4 C7 N3 -178.51(16) . . . . ?
N2 C8 C9 N3 -13.20(19) . . . . ?
N3 C7 N2 C8 -3.9(2) . . . . ?
C4 C7 N2 C8 176.23(16) . . . . ?
C9 C8 N2 C7 11.2(2) . . . . ?
N2 C7 N3 C9 -5.9(2) . . . . ?
C4 C7 N3 C9 174.00(16) . . . . ?
C8 C9 N3 C7 12.3(2) . . . . ?
