#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:20:26 +0200 (Mon 05 de Apr de 2021) $
#$Revision: 263857 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/79/7157912.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_7157912
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         'C10 H16 N3 O 1+, Cl 1-, C2 H6 O'
_chemical_formula_sum            'C12 H22 Cl N3 O2'
_chemical_formula_weight         275.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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                 106.4436(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.96920(10)
_cell_length_b                   18.2082(2)
_cell_length_c                   9.20580(10)
_cell_measurement_reflns_used    3540
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_cell_volume                     1441.93(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    'SHELXS-97 (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  0.0579
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27245
_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         28.037
_diffrn_reflns_theta_min         2.564
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0400
_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)+(0.0337P)²+0.7093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2973
_reflns_number_total             3461
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00235j3.cif
_cod_data_source_block           8d_170K
_cod_depositor_comments
'Adding full bibliography for 7157911--7157921.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157912
_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   0.832
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl1 Cl 0.23058(4) 0.04646(2) 0.64336(4) 0.03360(11) Uani 1 1 d . . . . .
C1 C 0.67332(16) 0.08286(8) 0.76016(16) 0.0294(3) Uani 1 1 d . . . . .
C2 C 0.82523(16) 0.09752(8) 0.75340(16) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.94397(16) 0.10225(7) 0.88717(16) 0.0265(3) Uani 1 1 d . . . . .
H3 H 1.047263 0.110988 0.883497 0.032 Uiso 1 1 calc R U . . .
C4 C 0.91452(16) 0.09440(7) 1.02769(16) 0.0263(3) Uani 1 1 d . . . . .
C5 C 0.76250(17) 0.08144(9) 1.03229(17) 0.0318(3) Uani 1 1 d . . . . .
H5 H 0.740763 0.076804 1.127054 0.038 Uiso 1 1 calc R U . . .
C6 C 0.64332(17) 0.07534(9) 0.89902(17) 0.0337(3) Uani 1 1 d . . . . .
H6 H 0.540316 0.065925 0.902823 0.040 Uiso 1 1 calc R U . . .
C7 C 1.04298(16) 0.09655(7) 1.16903(16) 0.0267(3) Uani 1 1 d . . . . .
C8 C 1.31742(17) 0.13009(9) 1.29814(18) 0.0343(3) Uani 1 1 d . . . . .
H8 H 1.313104 0.087346 1.365029 0.041 Uiso 1 1 calc R U . . .
C9 C 1.4542(2) 0.11928(11) 1.2347(2) 0.0480(4) Uani 1 1 d . . . . .
H9A H 1.437322 0.075223 1.170936 0.072 Uiso 1 1 calc R U . . .
H9B H 1.549429 0.113449 1.318172 0.072 Uiso 1 1 calc R U . . .
H9C H 1.464278 0.162156 1.173825 0.072 Uiso 1 1 calc R U . . .
C10 C 1.3307(2) 0.19928(11) 1.3907(2) 0.0564(5) Uani 1 1 d . . . . .
H10A H 1.328066 0.242050 1.325392 0.085 Uiso 1 1 calc R U . . .
H10B H 1.429047 0.198836 1.471608 0.085 Uiso 1 1 calc R U . . .
H10C H 1.243803 0.201948 1.435303 0.085 Uiso 1 1 calc R U . . .
N1 N 0.85017(14) 0.10850(7) 0.61039(14) 0.0308(3) Uani 1 1 d G . . . .
H1A H 0.789986 0.079392 0.536395 0.046 Uiso 1 1 d G U . . .
H1B H 0.951797 0.102820 0.613382 0.046 Uiso 1 1 d G U . . .
N2 N 1.17301(14) 0.13078(7) 1.17190(14) 0.0313(3) Uani 1 1 d . . . . .
H2 H 1.173905 0.156415 1.091123 0.038 Uiso 1 1 calc R U . . .
N3 N 1.02564(15) 0.06321(7) 1.29067(14) 0.0309(3) Uani 1 1 d . . . . .
H3A H 1.101797 0.063637 1.375491 0.037 Uiso 1 1 calc R U . . .
H3B H 0.937940 0.040564 1.286866 0.037 Uiso 1 1 calc R U . . .
O1 O 0.56368(12) 0.07568(7) 0.62518(12) 0.0401(3) Uani 1 1 d . . . . .
H1 H 0.477861 0.065372 0.639982 0.060 Uiso 1 1 calc R U . . .
C1S C 0.7646(3) 0.26383(19) 0.3372(3) 0.0541(8) Uani 0.744(5) 1 d D U P A 1
H1S1 H 0.732481 0.313552 0.296869 0.065 Uiso 0.744(5) 1 calc R U P A 1
H1S2 H 0.702031 0.227621 0.265033 0.065 Uiso 0.744(5) 1 calc R U P A 1
C2S C 0.9314(4) 0.25303(16) 0.3489(4) 0.0581(9) Uani 0.744(5) 1 d D U P A 1
H2S1 H 0.993900 0.288420 0.421088 0.087 Uiso 0.744(5) 1 calc R U P A 1
H2S2 H 0.948263 0.260533 0.249256 0.087 Uiso 0.744(5) 1 calc R U P A 1
H2S3 H 0.962409 0.203003 0.383916 0.087 Uiso 0.744(5) 1 calc R U P A 1
O1S O 0.73374(15) 0.25558(7) 0.48202(15) 0.0440(3) Uani 1 1 d D U . . .
H1S H 0.765568 0.214338 0.518842 0.066 Uiso 1 1 calc R U . A 1
C1S' C 0.8469(10) 0.2783(5) 0.4086(9) 0.054(2) Uani 0.256(5) 1 d D U P A 2
H1S3 H 0.952089 0.265281 0.472744 0.065 Uiso 0.256(5) 1 calc R U P A 2
H1S4 H 0.842325 0.332349 0.395872 0.065 Uiso 0.256(5) 1 calc R U P A 2
C2S' C 0.8192(12) 0.2431(6) 0.2598(9) 0.067(3) Uani 0.256(5) 1 d D U P A 2
H2S4 H 0.820953 0.189658 0.272044 0.100 Uiso 0.256(5) 1 calc R U P A 2
H2S5 H 0.900596 0.257948 0.213777 0.100 Uiso 0.256(5) 1 calc R U P A 2
H2S6 H 0.717539 0.258341 0.194260 0.100 Uiso 0.256(5) 1 calc R U P A 2
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
O1 C1 C6 123.80(13) . . ?
O1 C1 C2 116.00(13) . . ?
C6 C1 C2 120.19(13) . . ?
C3 C2 C1 118.91(13) . . ?
C3 C2 N1 122.42(12) . . ?
C1 C2 N1 118.65(13) . . ?
C2 C3 C4 121.14(13) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.14(13) . . ?
C5 C4 C7 120.25(13) . . ?
C3 C4 C7 120.56(12) . . ?
C6 C5 C4 120.15(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.44(13) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N2 C7 N3 121.12(13) . . ?
N2 C7 C4 119.81(13) . . ?
N3 C7 C4 119.06(12) . . ?
N2 C8 C10 110.48(14) . . ?
N2 C8 C9 108.89(13) . . ?
C10 C8 C9 112.58(15) . . ?
N2 C8 H8 108.3 . . ?
C10 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 N1 H1A 113.5 . . ?
C2 N1 H1B 112.2 . . ?
H1A N1 H1B 109.5 . . ?
C7 N2 C8 125.97(13) . . ?
C7 N2 H2 117.0 . . ?
C8 N2 H2 117.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 O1 H1 109.5 . . ?
O1S C1S C2S 111.9(2) . . ?
O1S C1S H1S1 109.2 . . ?
C2S C1S H1S1 109.2 . . ?
O1S C1S H1S2 109.2 . . ?
C2S C1S H1S2 109.2 . . ?
H1S1 C1S H1S2 107.9 . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S' C2S' 111.0(7) . . ?
O1S C1S' H1S3 109.4 . . ?
C2S' C1S' H1S3 109.4 . . ?
O1S C1S' H1S4 109.4 . . ?
C2S' C1S' H1S4 109.4 . . ?
H1S3 C1S' H1S4 108.0 . . ?
C1S' C2S' H2S4 109.5 . . ?
C1S' C2S' H2S5 109.5 . . ?
H2S4 C2S' H2S5 109.5 . . ?
C1S' C2S' H2S6 109.5 . . ?
H2S4 C2S' H2S6 109.5 . . ?
H2S5 C2S' H2S6 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 1.3551(17) . ?
C1 C6 1.386(2) . ?
C1 C2 1.4069(19) . ?
C2 C3 1.3840(19) . ?
C2 N1 1.4107(18) . ?
C3 C4 1.399(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C7 1.4743(19) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.3160(18) . ?
C7 N3 1.3211(18) . ?
C8 N2 1.4751(18) . ?
C8 C10 1.506(3) . ?
C8 C9 1.513(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N2 H2 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
O1 H1 0.8400 . ?
C1S O1S 1.444(3) . ?
C1S C2S 1.482(4) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
O1S C1S' 1.431(6) . ?
O1S H1S 0.8400 . ?
C1S' C2S' 1.468(8) . ?
C1S' H1S3 0.9900 . ?
C1S' H1S4 0.9900 . ?
C2S' H2S4 0.9800 . ?
C2S' H2S5 0.9800 . ?
C2S' H2S6 0.9800 . ?
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 -177.17(13) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
O1 C1 C2 N1 4.3(2) . . . . ?
C6 C1 C2 N1 -176.85(14) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
N1 C2 C3 C4 177.05(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C7 177.49(13) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C7 C4 C5 C6 -176.37(14) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
O1 C1 C6 C5 178.18(15) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C5 C4 C7 N2 -158.33(14) . . . . ?
C3 C4 C7 N2 24.3(2) . . . . ?
C5 C4 C7 N3 22.4(2) . . . . ?
C3 C4 C7 N3 -154.99(14) . . . . ?
N3 C7 N2 C8 7.1(2) . . . . ?
C4 C7 N2 C8 -172.15(13) . . . . ?
C10 C8 N2 C7 -99.85(19) . . . . ?
C9 C8 N2 C7 136.02(16) . . . . ?
