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#$Date: 2022-08-06 14:56:23 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277124 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/16/7061609.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_7061609
loop_
_publ_author_name
'Opačak, Saša'
'Perić, Berislav'
'Gojšić, Tomislav'
'Čikoš, Ana'
'Vikić-Topić, Dražen'
'Kirin, Srećko I.'
_publ_section_title
;
 Tandem amide coupling and hydroamination: unexpected benzotriazole oxide
 addition to the propiolic acid triple bond
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13275
_journal_page_last               13285
_journal_paper_doi               10.1039/D2NJ02587F
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C8 H10 O5'
_chemical_formula_sum            'C8 H10 O5'
_chemical_formula_weight         186.16
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8849(7)
_cell_length_b                   30.166(4)
_cell_length_c                   7.806(4)
_cell_measurement_reflns_used    402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.0630
_cell_measurement_theta_min      6.4720
_cell_volume                     898.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2359
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        62.428
_diffrn_reflns_theta_max         62.428
_diffrn_reflns_theta_min         2.930
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0959
_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)+(0.1467P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2331
_refine_ls_wR_factor_ref         0.2928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                680
_reflns_number_total             1384
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061609
_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.
;
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
C4A1 C 0.676(2) 0.2466(2) 0.3853(10) 0.095(2) Uani 1 1 d . . . . .
H6A1 H 0.919541 0.252062 0.386692 0.143 Uiso 1 1 calc R U . . .
H4A1 H 0.597371 0.264887 0.470995 0.143 Uiso 1 1 calc R U . . .
H5A1 H 0.542569 0.253341 0.271907 0.143 Uiso 1 1 calc R U . . .
O2A1 O 0.6274(11) 0.20111(14) 0.4245(6) 0.0858(14) Uani 1 1 d . . . . .
C1A1 C 0.7012(15) 0.1713(2) 0.3098(8) 0.0729(17) Uani 1 1 d . . . . .
O1A1 O 0.8116(12) 0.18157(14) 0.1797(5) 0.0907(15) Uani 1 1 d . . . . .
C2A1 C 0.6395(14) 0.12653(18) 0.3622(7) 0.0695(17) Uani 1 1 d . . . . .
H2A1 H 0.540081 0.122227 0.460462 0.083 Uiso 1 1 calc R U . . .
C3A1 C 0.7180(14) 0.09174(19) 0.2767(7) 0.0681(17) Uani 1 1 d . . . . .
H3A1 H 0.820958 0.095578 0.179326 0.082 Uiso 1 1 calc R U . . .
O1 O 0.6514(11) 0.05031(12) 0.3282(5) 0.0785(14) Uani 1 1 d . . . . .
C3A2 C 0.7381(14) 0.0151(2) 0.2396(7) 0.0676(16) Uani 1 1 d . . . . .
H3A2 H 0.834465 0.019680 0.140601 0.081 Uiso 1 1 calc R U . . .
C2A2 C 0.6901(15) -0.02551(19) 0.2895(7) 0.0725(18) Uani 1 1 d . . . . .
H2A2 H 0.599013 -0.029979 0.390199 0.087 Uiso 1 1 calc R U . . .
C1A2 C 0.7746(14) -0.06373(18) 0.1925(7) 0.0677(16) Uani 1 1 d . . . . .
O1A2 O 0.8854(12) -0.06233(14) 0.0565(5) 0.0878(15) Uani 1 1 d . . . . .
O2A2 O 0.7240(10) -0.10168(13) 0.2706(5) 0.0785(13) Uani 1 1 d . . . . .
C4A2 C 0.8060(17) -0.14212(19) 0.1893(8) 0.0852(19) Uani 1 1 d . . . . .
H6A2 H 0.641342 -0.146509 0.082547 0.128 Uiso 1 1 calc R U . . .
H4A2 H 0.792697 -0.166586 0.266479 0.128 Uiso 1 1 calc R U . . .
H5A2 H 1.038572 -0.140271 0.164720 0.128 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C1A1 O2A1 C4A1 116.8(5) . . ?
O1A1 C1A1 O2A1 122.7(6) . . ?
O1A1 C1A1 C2A1 125.4(5) . . ?
O2A1 C1A1 C2A1 111.8(5) . . ?
C3A1 C2A1 C1A1 122.5(5) . . ?
C2A1 C3A1 O1 120.9(5) . . ?
C3A2 O1 C3A1 119.8(4) . . ?
C2A2 C3A2 O1 121.5(5) . . ?
C3A2 C2A2 C1A2 122.0(5) . . ?
O1A2 C1A2 O2A2 122.4(5) . . ?
O1A2 C1A2 C2A2 125.4(5) . . ?
O2A2 C1A2 C2A2 112.2(4) . . ?
C1A2 O2A2 C4A2 117.7(4) . . ?
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
C4A1 O2A1 1.425(7) . ?
O2A1 C1A1 1.338(7) . ?
C1A1 O1A1 1.215(6) . ?
C1A1 C2A1 1.443(8) . ?
C2A1 C3A1 1.310(7) . ?
C3A1 O1 1.353(7) . ?
O1 C3A2 1.344(6) . ?
C3A2 C2A2 1.309(7) . ?
C2A2 C1A2 1.451(7) . ?
C1A2 O1A2 1.218(6) . ?
C1A2 O2A2 1.329(6) . ?
O2A2 C4A2 1.438(6) . ?
