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#$Date: 2021-04-05 18:20:26 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157920.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_7157920
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         'C14 H19 N6 O2, Cl, 2(H2 O)'
_chemical_formula_sum            'C14 H23 Cl N6 O4'
_chemical_formula_weight         374.83
_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           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                 113.446(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.3443(4)
_cell_length_b                   14.5191(9)
_cell_length_c                   15.9472(15)
_cell_measurement_reflns_used    869
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.5400
_cell_measurement_theta_min      4.4200
_cell_volume                     922.83(15)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3508
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.239
_diffrn_reflns_theta_max         25.239
_diffrn_reflns_theta_min         4.409
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.695
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0440
_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)+(0.0446P)²+0.1532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1235
_reflns_number_total             1661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           8a_I_295K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157920
_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.
;
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
N1 N 1.0529(4) 0.04506(11) 0.25212(11) 0.0419(4) Uani 1 1 d G . . . .
H1A H 1.216783 0.074993 0.299106 0.059(6) Uiso 1 1 d G . . . .
H1B H 1.123348 0.017229 0.212147 0.059(7) Uiso 1 1 d G . . . .
N2 N 0.4623(4) 0.32639(13) 0.32724(12) 0.0529(5) Uani 1 1 d . . . . .
H2A H 0.420756 0.375601 0.350904 0.058(7) Uiso 1 1 calc R . . . .
H2B H 0.565434 0.281152 0.361814 0.090(10) Uiso 1 1 calc R . . . .
N3 N 0.2112(5) 0.38935(13) 0.18593(14) 0.0638(6) Uani 1 1 d . . . . .
H3A H 0.169993 0.438472 0.209790 0.082(8) Uiso 1 1 calc R . . . .
H3B H 0.149211 0.385575 0.127673 0.104(11) Uiso 1 1 calc R . . . .
O1 O 0.6194(3) -0.00243(9) 0.08387(8) 0.0450(4) Uani 1 1 d . . . . .
H1 H 0.500000 0.000000 0.000000 0.105(13) Uiso 1 2 d S . P . .
C4 C 0.4357(5) 0.23683(13) 0.19700(13) 0.0389(5) Uani 1 1 d . . . . .
C5 C 0.2200(5) 0.21052(14) 0.10978(13) 0.0442(5) Uani 1 1 d . . . . .
H5 H 0.034511 0.246851 0.077084 0.053 Uiso 1 1 calc R U . . .
C6 C 0.2779(5) 0.13082(14) 0.07097(13) 0.0431(5) Uani 1 1 d . . . . .
H6 H 0.129858 0.113973 0.012529 0.052 Uiso 1 1 calc R U . . .
C1 C 0.5535(4) 0.07558(13) 0.11789(12) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.7772(4) 0.10292(12) 0.20588(12) 0.0346(4) Uani 1 1 d . . . . .
C3 C 0.7148(4) 0.18180(13) 0.24472(13) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.860388 0.198600 0.303435 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3681(5) 0.32032(13) 0.23829(14) 0.0422(5) Uani 1 1 d . . . . .
Cl1 Cl 0.7220(4) 0.13006(10) 0.44877(9) 0.0603(4) Uani 0.42 1 d . . P A 1
Cl2 Cl 1.000000 0.000000 0.500000 0.0615(15) Uani 0.16 2 d S . P B 2
O1W O 0.4773(8) 0.1546(3) 0.4307(2) 0.0687(9) Uani 0.55 1 d G . P C 3
H11W H 0.355299 0.128440 0.451192 0.103 Uiso 0.55 1 d G U P C 3
H12W H 0.623955 0.183023 0.471737 0.103 Uiso 0.55 1 d G U P C 3
O2W O 1.1187(11) 0.0749(3) 0.5008(3) 0.0806(12) Uani 0.45 1 d G . P D 4
H21W H 0.949169 0.046225 0.469554 0.121 Uiso 0.45 1 d G U P D 4
H22W H 1.266666 0.038735 0.530568 0.121 Uiso 0.45 1 d G U P D 4
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
C2 N1 H1A 111.7 . . ?
C2 N1 H1B 110.7 . . ?
H1A N1 H1B 114.8 . . ?
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 . . ?
C1 O1 H1 110.63 . . ?
C5 C4 C3 118.85(18) . . ?
C5 C4 C7 120.20(18) . . ?
C3 C4 C7 120.95(17) . . ?
C6 C5 C4 120.62(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.96(18) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C1 C6 123.36(16) . . ?
O1 C1 C2 117.97(16) . . ?
C6 C1 C2 118.66(17) . . ?
C3 C2 N1 122.59(17) . . ?
C3 C2 C1 120.01(17) . . ?
N1 C2 C1 117.36(16) . . ?
C2 C3 C4 120.87(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N3 C7 N2 119.79(19) . . ?
N3 C7 C4 119.60(18) . . ?
N2 C7 C4 120.61(18) . . ?
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
N1 C2 1.407(2) . ?
N1 H1A 0.9124 . ?
N1 H1B 0.9048 . ?
N2 C7 1.314(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C7 1.309(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O1 C1 1.335(2) . ?
O1 H1 1.2277 . ?
C4 C5 1.386(3) . ?
C4 C3 1.398(3) . ?
C4 C7 1.464(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.387(3) . ?
C6 H6 0.9300 . ?
C1 C2 1.409(2) . ?
C2 C3 1.379(2) . ?
C3 H3 0.9300 . ?
O1W H11W 0.8189 . ?
O1W H12W 0.8205 . ?
O2W H21W 0.8199 . ?
O2W H22W 0.8200 . ?
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
C3 C4 C5 C6 0.6(3) . . . . ?
C7 C4 C5 C6 -178.66(16) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C5 C6 C1 O1 179.42(16) . . . . ?
C5 C6 C1 C2 -0.8(3) . . . . ?
O1 C1 C2 C3 -178.39(15) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
O1 C1 C2 N1 -0.8(2) . . . . ?
C6 C1 C2 N1 179.45(15) . . . . ?
N1 C2 C3 C4 -179.14(16) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C7 C4 C3 C2 179.69(16) . . . . ?
C5 C4 C7 N3 -30.1(3) . . . . ?
C3 C4 C7 N3 150.62(19) . . . . ?
C5 C4 C7 N2 149.6(2) . . . . ?
C3 C4 C7 N2 -29.7(3) . . . . ?
