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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/7/06/16/7061607.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_7061607
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      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   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                 105.678(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5550(2)
_cell_length_b                   18.3095(5)
_cell_length_c                   7.8064(3)
_cell_measurement_reflns_used    2385
_cell_measurement_temperature    246(15)
_cell_measurement_theta_max      75.6400
_cell_measurement_theta_min      4.8310
_cell_volume                     1039.67(6)
_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      246(15)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4916
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.705
_diffrn_reflns_theta_min         4.831
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88028
_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    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0454
_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)+(0.0701P)²+0.0769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1819
_reflns_number_total             2132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           1-cis
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061607
_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+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
C4A C 0.8794(3) -0.09717(10) 0.4581(3) 0.0833(5) Uani 1 1 d . . . . .
H6A H 0.780813 -0.131178 0.414166 0.125 Uiso 1 1 calc R U . . .
H4A H 0.963363 -0.116692 0.563103 0.125 Uiso 1 1 calc R U . . .
H5A H 0.942986 -0.089048 0.368660 0.125 Uiso 1 1 calc R U . . .
O2A O 0.80590(16) -0.02920(7) 0.50038(15) 0.0740(3) Uani 1 1 d . . . . .
C1A C 0.6849(2) 0.00307(9) 0.3636(2) 0.0642(4) Uani 1 1 d . . . . .
O1A O 0.6387(2) -0.02298(9) 0.21876(18) 0.1034(5) Uani 1 1 d . . . . .
C2A C 0.6218(2) 0.07274(10) 0.4185(2) 0.0731(4) Uani 1 1 d . . . . .
H2A H 0.675795 0.088422 0.534127 0.088 Uiso 1 1 calc R U . . .
C3A C 0.4946(2) 0.11491(10) 0.3169(2) 0.0710(4) Uani 1 1 d . . . . .
H3A H 0.464912 0.159058 0.361153 0.085 Uiso 1 1 calc R U . . .
O1H O 0.40574(18) 0.09426(7) 0.14662(17) 0.0813(4) Uani 1 1 d . . . . .
N1H N 0.29028(18) 0.14776(7) 0.05665(19) 0.0689(4) Uani 1 1 d . . . . .
N2H N 0.3580(2) 0.20419(9) -0.0142(3) 0.0843(5) Uani 1 1 d . . . . .
N3H N 0.2190(2) 0.24090(8) -0.1110(2) 0.0821(4) Uani 1 1 d . . . . .
C1H C 0.1043(2) 0.14456(8) 0.00375(19) 0.0578(3) Uani 1 1 d . . . . .
C2H C 0.0601(2) 0.20597(8) -0.1038(2) 0.0634(4) Uani 1 1 d . . . . .
C3H C -0.1243(3) 0.22254(10) -0.1863(2) 0.0750(4) Uani 1 1 d . . . . .
H3H H -0.156962 0.263404 -0.258677 0.090 Uiso 1 1 calc R U . . .
C4H C -0.2537(2) 0.17617(12) -0.1558(2) 0.0792(5) Uani 1 1 d . . . . .
H4H H -0.377239 0.185878 -0.208874 0.095 Uiso 1 1 calc R U . . .
C5H C -0.2065(2) 0.11420(11) -0.0470(2) 0.0773(5) Uani 1 1 d . . . . .
H5H H -0.299645 0.084036 -0.030661 0.093 Uiso 1 1 calc R U . . .
C6H C -0.0275(2) 0.09686(9) 0.0359(2) 0.0670(4) Uani 1 1 d . . . . .
H6H H 0.004193 0.056055 0.108697 0.080 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 114.90(13) . . ?
O1A C1A O2A 122.84(15) . . ?
O1A C1A C2A 126.29(16) . . ?
O2A C1A C2A 110.87(14) . . ?
C3A C2A C1A 125.16(16) . . ?
C2A C3A O1H 120.56(14) . . ?
C3A O1H N1H 112.12(12) . . ?
N2H N1H C1H 112.88(14) . . ?
N2H N1H O1H 120.12(14) . . ?
C1H N1H O1H 126.07(13) . . ?
N3H N2H N1H 107.43(14) . . ?
N2H N3H C2H 108.22(14) . . ?
N1H C1H C2H 102.10(13) . . ?
N1H C1H C6H 134.68(15) . . ?
C2H C1H C6H 123.23(15) . . ?
N3H C2H C1H 109.35(15) . . ?
N3H C2H C3H 130.63(16) . . ?
C1H C2H C3H 120.01(15) . . ?
C4H C3H C2H 117.12(17) . . ?
C3H C4H C5H 122.10(17) . . ?
C6H C5H C4H 122.02(16) . . ?
C5H C6H C1H 115.52(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 1.341(2) . ?
C1A O1A 1.189(2) . ?
C1A C2A 1.466(2) . ?
C2A C3A 1.318(3) . ?
C3A O1H 1.371(2) . ?
O1H N1H 1.3720(18) . ?
N1H N2H 1.337(2) . ?
N1H C1H 1.355(2) . ?
N2H N3H 1.303(2) . ?
N3H C2H 1.375(2) . ?
C1H C2H 1.389(2) . ?
C1H C6H 1.397(2) . ?
C2H C3H 1.400(2) . ?
C3H C4H 1.364(3) . ?
C4H C5H 1.405(3) . ?
C5H C6H 1.369(3) . ?
