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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/7/06/16/7061606.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_7061606
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         'C10 H9 N3 O3'
_chemical_formula_sum            'C10 H9 N3 O3'
_chemical_formula_weight         219.20
_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   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                94.916(7)
_cell_angle_beta                 97.452(8)
_cell_angle_gamma                113.275(9)
_cell_formula_units_Z            2
_cell_length_a                   6.3645(7)
_cell_length_b                   7.7209(6)
_cell_length_c                   11.7329(11)
_cell_measurement_reflns_used    1910
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9580
_cell_measurement_theta_min      3.8230
_cell_volume                     519.19(9)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.974
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3967
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.073
_diffrn_reflns_theta_min         3.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59071
_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    1.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0430
_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)+(0.0516P)²+0.0641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1720
_reflns_number_total             2098
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           1-trans
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_database_code               7061606
_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, -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
C4A C -0.2386(4) 0.2194(3) 0.59773(19) 0.0827(6) Uani 1 1 d . . . . .
H6A H -0.150620 0.195112 0.662394 0.124 Uiso 1 1 calc R U . . .
H4A H -0.401437 0.145714 0.595086 0.124 Uiso 1 1 calc R U . . .
H5A H -0.207128 0.352589 0.606572 0.124 Uiso 1 1 calc R U . . .
O2A O -0.1736(2) 0.16681(19) 0.49164(11) 0.0731(4) Uani 1 1 d . . . . .
C1A C 0.0474(3) 0.2565(2) 0.48082(15) 0.0609(4) Uani 1 1 d . . . . .
O1A O 0.1927(3) 0.3727(2) 0.55626(13) 0.0929(5) Uani 1 1 d . . . . .
C2A C 0.0847(3) 0.1969(2) 0.36608(15) 0.0608(4) Uani 1 1 d . . . . .
H2A H -0.038805 0.103109 0.314014 0.073 Uiso 1 1 calc R U . . .
C3A C 0.2881(3) 0.2728(2) 0.33546(14) 0.0570(4) Uani 1 1 d . . . . .
H3A H 0.413954 0.365681 0.386730 0.068 Uiso 1 1 calc R U . . .
O1H O 0.3135(2) 0.21256(16) 0.22516(10) 0.0636(3) Uani 1 1 d . . . . .
N1H N 0.5146(2) 0.33500(19) 0.19511(12) 0.0544(3) Uani 1 1 d . . . . .
N2H N 0.6834(3) 0.2766(2) 0.18348(15) 0.0679(4) Uani 1 1 d . . . . .
N3H N 0.8450(3) 0.4111(2) 0.14459(16) 0.0716(4) Uani 1 1 d . . . . .
C1H C 0.5596(3) 0.5087(2) 0.16284(12) 0.0474(3) Uani 1 1 d . . . . .
C2H C 0.7756(3) 0.5569(2) 0.13134(14) 0.0534(4) Uani 1 1 d . . . . .
C3H C 0.8860(3) 0.7325(3) 0.09343(16) 0.0641(4) Uani 1 1 d . . . . .
H3H H 1.030007 0.767253 0.070687 0.077 Uiso 1 1 calc R U . . .
C4H C 0.7735(3) 0.8500(2) 0.09130(16) 0.0645(4) Uani 1 1 d . . . . .
H4H H 0.843733 0.968453 0.067728 0.077 Uiso 1 1 calc R U . . .
C5H C 0.5545(3) 0.7976(2) 0.12367(17) 0.0638(4) Uani 1 1 d . . . . .
H5H H 0.484221 0.882623 0.120989 0.077 Uiso 1 1 calc R U . . .
C6H C 0.4411(3) 0.6259(2) 0.15897(15) 0.0578(4) Uani 1 1 d . . . . .
H6H H 0.294662 0.590062 0.179037 0.069 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'
N N 0.0311 0.0180 '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
C1A O2A C4A 117.25(15) . . ?
O1A C1A O2A 123.05(18) . . ?
O1A C1A C2A 125.82(18) . . ?
O2A C1A C2A 111.12(15) . . ?
C3A C2A C1A 121.26(16) . . ?
C2A C3A O1H 118.94(15) . . ?
N1H O1H C3A 111.98(12) . . ?
N2H N1H C1H 112.89(13) . . ?
N2H N1H O1H 119.20(14) . . ?
C1H N1H O1H 127.55(13) . . ?
N3H N2H N1H 107.25(14) . . ?
N2H N3H C2H 108.25(14) . . ?
N1H C1H C2H 102.28(13) . . ?
N1H C1H C6H 134.18(15) . . ?
C2H C1H C6H 123.54(15) . . ?
N3H C2H C1H 109.33(14) . . ?
N3H C2H C3H 130.82(16) . . ?
C1H C2H C3H 119.86(15) . . ?
C4H C3H C2H 117.14(16) . . ?
C3H C4H C5H 121.83(16) . . ?
C6H C5H C4H 122.27(17) . . ?
C5H C6H C1H 115.34(16) . . ?
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
C4A O2A 1.437(2) . ?
O2A C1A 1.328(2) . ?
C1A O1A 1.200(2) . ?
C1A C2A 1.464(3) . ?
C2A C3A 1.306(2) . ?
C3A O1H 1.388(2) . ?
O1H N1H 1.3689(17) . ?
N1H N2H 1.337(2) . ?
N1H C1H 1.355(2) . ?
N2H N3H 1.305(2) . ?
N3H C2H 1.376(2) . ?
C1H C2H 1.384(2) . ?
C1H C6H 1.389(2) . ?
C2H C3H 1.401(2) . ?
C3H C4H 1.359(3) . ?
C4H C5H 1.403(3) . ?
C5H C6H 1.365(2) . ?
