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#$Date: 2022-08-06 13:56:23 +0200 (Sat 06 de Aug de 2022) $
#$Revision: 277124 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/16/7061612.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_7061612
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_absolute_configuration rm
_chemical_formula_moiety         'C14 H22 N2 O3'
_chemical_formula_sum            'C14 H22 N2 O3'
_chemical_formula_weight         266.34
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   16.216(3)
_cell_length_b                   16.216(3)
_cell_length_c                   5.1307(5)
_cell_measurement_reflns_used    1138
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5050
_cell_measurement_theta_min      3.1230
_cell_volume                     1168.4(3)
_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, 2015)'
_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 0.926
_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  0.2058
_diffrn_reflns_av_unetI/netI     0.1297
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3687
_diffrn_reflns_point_group_measured_fraction_full 0.708
_diffrn_reflns_point_group_measured_fraction_max 0.678
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.947
_diffrn_reflns_theta_min         3.147
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08977
_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    1.135
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.342
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.1419
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3939
_refine_ls_wR_factor_ref         0.4401
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.431
_reflns_number_gt                1206
_reflns_number_total             2043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_original_cell_volume        1168.5(5)
_cod_database_code               7061612
_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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
N1C N 0.1678(7) -0.1121(7) 1.2596(15) 0.070(2) Uani 1 1 d . . . . .
H1NC H 0.148082 -0.111189 1.104627 0.084 Uiso 1 1 calc R U . . .
C1C C 0.2609(9) -0.1078(8) 1.2898(17) 0.064(3) Uani 1 1 d . . . . .
H1C H 0.287173 -0.080306 1.460798 0.077 Uiso 1 1 calc R U . . .
C2C C 0.2437(16) -0.2102(10) 1.282(3) 0.100(5) Uani 1 1 d . . . . .
H2C2 H 0.200221 -0.247555 1.420676 0.120 Uiso 1 1 calc R U . . .
H1C2 H 0.215095 -0.239735 1.117057 0.120 Uiso 1 1 calc R U . . .
C3C C 0.3368(15) -0.2081(13) 1.316(3) 0.105(5) Uani 1 1 d . . . . .
H2C3 H 0.326359 -0.272365 1.303776 0.126 Uiso 1 1 calc R U . . .
H1C3 H 0.362687 -0.183314 1.487102 0.126 Uiso 1 1 calc R U . . .
C4C C 0.4071(16) -0.1464(16) 1.109(3) 0.110(6) Uani 1 1 d . . . . .
H1C4 H 0.382831 -0.173903 0.938598 0.132 Uiso 1 1 calc R U . . .
H2C4 H 0.466915 -0.145231 1.135364 0.132 Uiso 1 1 calc R U . . .
C5C C 0.4250(10) -0.0439(13) 1.115(3) 0.088(4) Uani 1 1 d . . . . .
H2C5 H 0.467907 -0.007254 0.974662 0.105 Uiso 1 1 calc R U . . .
H1C5 H 0.454711 -0.013947 1.278804 0.105 Uiso 1 1 calc R U . . .
C6C C 0.3292(8) -0.0450(7) 1.0839(16) 0.058(2) Uani 1 1 d . . . . .
H6C H 0.302348 -0.070952 0.912069 0.070 Uiso 1 1 calc R U . . .
N2C N 0.3451(8) 0.0514(6) 1.1024(16) 0.071(3) Uani 1 1 d . . . . .
H2NC H 0.336869 0.071234 1.250212 0.086 Uiso 1 1 calc R U . . .
C1B C 0.3725(12) 0.1111(9) 0.895(2) 0.081(4) Uani 1 1 d . . . . .
O1B O 0.3749(8) 0.0844(7) 0.6743(16) 0.091(3) Uani 1 1 d . . . . .
O2BA O 0.374(3) 0.1930(19) 0.970(5) 0.078(7) Uani 0.52(5) 1 d D U P A 1
C2BA C 0.405(3) 0.270(2) 0.775(5) 0.080(8) Uani 0.52(5) 1 d D U P A 1
C3BA C 0.414(4) 0.352(2) 0.938(6) 0.108(12) Uani 0.52(5) 1 d D U P A 1
H2B3 H 0.353175 0.333912 1.013986 0.163 Uiso 0.52(5) 1 calc R U P A 1
H3B3 H 0.459945 0.366172 1.073060 0.163 Uiso 0.52(5) 1 calc R U P A 1
H1B3 H 0.433740 0.406592 0.828935 0.163 Uiso 0.52(5) 1 calc R U P A 1
C4BA C 0.496(3) 0.293(3) 0.653(8) 0.091(8) Uani 0.52(5) 1 d D U P A 1
H1B4 H 0.513403 0.343012 0.527963 0.136 Uiso 0.52(5) 1 calc R U P A 1
H2B4 H 0.544494 0.313289 0.784177 0.136 Uiso 0.52(5) 1 calc R U P A 1
H3B4 H 0.489525 0.237433 0.566585 0.136 Uiso 0.52(5) 1 calc R U P A 1
C5BA C 0.325(3) 0.238(3) 0.575(6) 0.083(8) Uani 0.52(5) 1 d D U P A 1
H3B5 H 0.267329 0.223953 0.662801 0.124 Uiso 0.52(5) 1 calc R U P A 1
H1B5 H 0.341409 0.288459 0.451362 0.124 Uiso 0.52(5) 1 calc R U P A 1
H2B5 H 0.316821 0.182508 0.486054 0.124 Uiso 0.52(5) 1 calc R U P A 1
O2BB O 0.416(3) 0.202(2) 0.967(6) 0.085(9) Uani 0.48(5) 1 d D U P A 2
C2BB C 0.452(4) 0.283(2) 0.786(6) 0.088(9) Uani 0.48(5) 1 d D U P A 2
C3BB C 0.490(4) 0.368(2) 0.968(7) 0.116(14) Uani 0.48(5) 1 d D U P A 2
H5B3 H 0.439499 0.363748 1.074894 0.174 Uiso 0.48(5) 1 calc R U P A 2
H6B3 H 0.538917 0.369497 1.076368 0.174 Uiso 0.48(5) 1 calc R U P A 2
H4B3 H 0.516514 0.425889 0.866709 0.174 Uiso 0.48(5) 1 calc R U P A 2
C4BB C 0.528(3) 0.288(3) 0.619(10) 0.117(14) Uani 0.48(5) 1 d D U P A 2
H4B4 H 0.549385 0.341587 0.503122 0.176 Uiso 0.48(5) 1 calc R U P A 2
H5B4 H 0.579715 0.296155 0.726245 0.176 Uiso 0.48(5) 1 calc R U P A 2
H6B4 H 0.503811 0.230709 0.519749 0.176 Uiso 0.48(5) 1 calc R U P A 2
C5BB C 0.367(4) 0.274(3) 0.630(9) 0.111(12) Uani 0.48(5) 1 d D U P A 2
H6B5 H 0.319458 0.270353 0.747021 0.167 Uiso 0.48(5) 1 calc R U P A 2
H4B5 H 0.388088 0.327867 0.517472 0.167 Uiso 0.48(5) 1 calc R U P A 2
H5B5 H 0.340560 0.216673 0.526092 0.167 Uiso 0.48(5) 1 calc R U P A 2
C1A C 0.1137(9) -0.1174(12) 1.459(2) 0.084(4) Uani 1 1 d . . . . .
O1A O 0.1377(7) -0.1168(9) 1.6894(17) 0.103(4) Uani 1 1 d . . . . .
C2A C 0.0242(11) -0.1220(13) 1.387(2) 0.088(4) Uani 1 1 d . . . . .
C3A C -0.0463(16) -0.127(2) 1.311(4) 0.123(6) Uani 1 1 d . . . . .
H3A H -0.102165 -0.130450 1.251010 0.148 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 N1C C1C 123.3(9) . . ?
N1C C1C C6C 110.3(8) . . ?
N1C C1C C2C 108.3(11) . . ?
C6C C1C C2C 112.9(11) . . ?
C3C C2C C1C 109.5(13) . . ?
C2C C3C C4C 110.5(12) . . ?
C3C C4C C5C 111.9(13) . . ?
C4C C5C C6C 109.8(13) . . ?
N2C C6C C1C 111.0(8) . . ?
N2C C6C C5C 110.0(10) . . ?
C1C C6C C5C 109.3(9) . . ?
C1B N2C C6C 122.4(8) . . ?
O1B C1B O2BB 123.9(17) . . ?
O1B C1B N2C 122.2(11) . . ?
O2BB C1B N2C 112.1(14) . . ?
O1B C1B O2BA 128.1(15) . . ?
N2C C1B O2BA 108.2(13) . . ?
C1B O2BA C2BA 117(2) . . ?
C4BA C2BA O2BA 112(3) . . ?
C4BA C2BA C3BA 112(3) . . ?
O2BA C2BA C3BA 101.9(19) . . ?
C4BA C2BA C5BA 112.1(19) . . ?
O2BA C2BA C5BA 107(2) . . ?
C3BA C2BA C5BA 111(3) . . ?
C1B O2BB C2BB 124(2) . . ?
C4BB C2BB O2BB 111(3) . . ?
C4BB C2BB C3BB 111(3) . . ?
O2BB C2BB C3BB 103(2) . . ?
C4BB C2BB C5BB 113(3) . . ?
O2BB C2BB C5BB 108(3) . . ?
C3BB C2BB C5BB 111(3) . . ?
O1A C1A N1C 122.7(13) . . ?
O1A C1A C2A 122.5(12) . . ?
N1C C1A C2A 114.8(11) . . ?
C3A C2A C1A 175.0(15) . . ?
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
N1C C1A 1.321(16) . ?
N1C C1C 1.483(16) . ?
C1C C6C 1.501(15) . ?
C1C C2C 1.541(17) . ?
C2C C3C 1.50(3) . ?
C3C C4C 1.51(3) . ?
C4C C5C 1.54(3) . ?
C5C C6C 1.554(17) . ?
C6C N2C 1.454(14) . ?
N2C C1B 1.355(15) . ?
C1B O1B 1.220(15) . ?
C1B O2BB 1.33(3) . ?
C1B O2BA 1.37(3) . ?
O2BA C2BA 1.48(2) . ?
C2BA C4BA 1.46(5) . ?
C2BA C3BA 1.51(3) . ?
C2BA C5BA 1.53(5) . ?
O2BB C2BB 1.47(2) . ?
C2BB C4BB 1.47(5) . ?
C2BB C3BB 1.52(3) . ?
C2BB C5BB 1.53(5) . ?
C1A O1A 1.245(18) . ?
C1A C2A 1.46(2) . ?
C2A C3A 1.17(3) . ?
