#------------------------------------------------------------------------------
#$Date: 2022-08-06 13:56:23 +0200 (Sat 06 de Aug de 2022) $
#$Revision: 277124 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/16/7061608.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_7061608
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         'C12 H12 O6'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         252.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 104.542(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.1583(4)
_cell_length_b                   10.1532(2)
_cell_length_c                   26.4824(5)
_cell_measurement_reflns_used    5165
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.1140
_cell_measurement_theta_min      5.0090
_cell_volume                     4726.01(17)
_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      123(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.980
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12047
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.827
_diffrn_reflns_theta_min         3.448
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53626
_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    1.418
_exptl_crystal_description       prism
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4825
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0474
_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)+(0.0718P)²+3.2261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4221
_reflns_number_total             4825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7061608
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.66172(13) -0.0715(2) 0.17498(9) 0.0429(6) Uani 0.796(4) 1 d D . P A 1
H6A1 H 0.672443 -0.127384 0.205185 0.064 Uiso 0.796(4) 1 calc R U P A 1
H4A1 H 0.707078 -0.025089 0.173231 0.064 Uiso 0.796(4) 1 calc R U P A 1
H5A1 H 0.644482 -0.124202 0.144171 0.064 Uiso 0.796(4) 1 calc R U P A 1
O2A1 O 0.6030(3) 0.0226(6) 0.1785(3) 0.0375(5) Uani 0.796(4) 1 d D . P A 1
O1A1 O 0.5282(3) -0.1529(4) 0.1771(3) 0.0491(6) Uani 0.796(4) 1 d D . P A 1
C1A1 C 0.53675(10) -0.0373(2) 0.17904(6) 0.0426(4) Uani 1 1 d . . . . .
C4A7 C 0.5975(5) -0.2115(9) 0.1771(4) 0.047(2) Uani 0.204(4) 1 d D . P A 2
H4A7 H 0.596985 -0.305992 0.175612 0.070 Uiso 0.204(4) 1 calc R U P A 2
H6A7 H 0.612443 -0.176895 0.147463 0.070 Uiso 0.204(4) 1 calc R U P A 2
H5A7 H 0.633025 -0.183178 0.208556 0.070 Uiso 0.204(4) 1 calc R U P A 2
O2A7 O 0.5241(12) -0.165(2) 0.1768(11) 0.056 Uiso 0.204(4) 1 d D U P A 2
O1A7 O 0.5958(16) 0.018(3) 0.1781(14) 0.056 Uiso 0.204(4) 1 d D U P A 2
C2A1 C 0.47544(9) 0.05727(16) 0.18346(6) 0.0327(3) Uani 1 1 d . . . . .
C3A1 C 0.40574(9) 0.00490(15) 0.18642(6) 0.0321(3) Uani 1 1 d . . . . .
H3A1 H 0.398700 -0.085883 0.185481 0.038 Uiso 1 1 calc R U . . .
C4A2 C 0.19204(11) -0.1508(2) 0.18696(8) 0.0498(5) Uani 1 1 d . . . . .
H6A2 H 0.170404 -0.109475 0.212509 0.075 Uiso 1 1 calc R U . . .
H4A2 H 0.197149 -0.243633 0.193799 0.075 Uiso 1 1 calc R U . . .
H5A2 H 0.159386 -0.136549 0.152793 0.075 Uiso 1 1 calc R U . . .
O2A2 O 0.26631(7) -0.09446(12) 0.18963(5) 0.0409(3) Uani 1 1 d . . . . .
C1A2 C 0.27015(9) 0.03645(16) 0.19224(6) 0.0345(3) Uani 1 1 d . . . . .
O1A2 O 0.21791(7) 0.10672(13) 0.19489(6) 0.0509(3) Uani 1 1 d . . . . .
C2A2 C 0.34682(9) 0.08741(15) 0.19075(6) 0.0308(3) Uani 1 1 d . . . . .
C3A2 C 0.35737(9) 0.22354(15) 0.19236(6) 0.0303(3) Uani 1 1 d . . . . .
H3A2 H 0.318020 0.279079 0.195471 0.036 Uiso 1 1 calc R U . . .
C4A3 C 0.39225(12) 0.62943(17) 0.20584(9) 0.0519(5) Uani 1 1 d . . . . .
H6A3 H 0.420548 0.645538 0.241099 0.078 Uiso 1 1 calc R U . . .
H4A3 H 0.343748 0.672562 0.199615 0.078 Uiso 1 1 calc R U . . .
H5A3 H 0.419960 0.663236 0.182192 0.078 Uiso 1 1 calc R U . . .
O2A3 O 0.38089(7) 0.48883(11) 0.19772(5) 0.0408(3) Uani 1 1 d . . . . .
C1A3 C 0.44095(9) 0.42120(16) 0.19150(6) 0.0344(3) Uani 1 1 d . . . . .
O1A3 O 0.50054(8) 0.46939(13) 0.18831(5) 0.0452(3) Uani 1 1 d . . . . .
C2A3 C 0.42676(9) 0.27603(15) 0.18930(6) 0.0311(3) Uani 1 1 d . . . . .
C3A3 C 0.48579(9) 0.19304(16) 0.18456(5) 0.0325(3) Uani 1 1 d . . . . .
H3A3 H 0.532028 0.228393 0.182130 0.039 Uiso 1 1 calc R U . . .
C4A4 C 0.57702(9) 0.18936(17) 0.05111(7) 0.0392(4) Uani 1 1 d . . . . .
H6A4 H 0.597531 0.139724 0.082334 0.059 Uiso 1 1 calc R U . . .
H4A4 H 0.611578 0.258923 0.048299 0.059 Uiso 1 1 calc R U . . .
H5A4 H 0.570068 0.132393 0.021355 0.059 Uiso 1 1 calc R U . . .
O2A4 O 0.50425(6) 0.24540(11) 0.05316(4) 0.0336(3) Uani 1 1 d . . . . .
C1A4 C 0.45028(8) 0.15842(14) 0.05578(5) 0.0286(3) Uani 1 1 d . . . . .
O1A4 O 0.45870(7) 0.04083(11) 0.05608(5) 0.0377(3) Uani 1 1 d . . . . .
C2A4 C 0.37818(8) 0.22482(14) 0.05924(5) 0.0264(3) Uani 1 1 d . . . . .
C3A4 C 0.31611(8) 0.14668(14) 0.06106(5) 0.0279(3) Uani 1 1 d . . . . .
H3A4 H 0.320159 0.055481 0.059879 0.034 Uiso 1 1 calc R U . . .
C4A5 C 0.05660(11) 0.1063(2) 0.07525(10) 0.0621(6) Uani 1 1 d . . . . .
H6A5 H 0.046246 0.037507 0.049559 0.093 Uiso 1 1 calc R U . . .
H4A5 H 0.012904 0.162509 0.070609 0.093 Uiso 1 1 calc R U . . .
H5A5 H 0.067820 0.068128 0.109499 0.093 Uiso 1 1 calc R U . . .
O2A5 O 0.12113(6) 0.18269(13) 0.06933(5) 0.0421(3) Uani 1 1 d . . . . .
C1A5 C 0.18335(9) 0.11498(16) 0.06728(6) 0.0333(3) Uani 1 1 d . . . . .
O1A5 O 0.18766(7) -0.00364(12) 0.06776(5) 0.0449(3) Uani 1 1 d . . . . .
C2A5 C 0.24798(8) 0.20369(15) 0.06464(5) 0.0283(3) Uani 1 1 d . . . . .
C3A5 C 0.24209(8) 0.33997(15) 0.06605(5) 0.0290(3) Uani 1 1 d . . . . .
H3A5 H 0.196430 0.378735 0.067881 0.035 Uiso 1 1 calc R U . . .
C4A6 C 0.35077(10) 0.77316(16) 0.06947(8) 0.0417(4) Uani 1 1 d . . . . .
H6A6 H 0.324269 0.802700 0.035296 0.062 Uiso 1 1 calc R U . . .
H4A6 H 0.400368 0.812659 0.079036 0.062 Uiso 1 1 calc R U . . .
H5A6 H 0.322658 0.798252 0.094181 0.062 Uiso 1 1 calc R U . . .
O2A6 O 0.35834(6) 0.63076(10) 0.06929(5) 0.0350(3) Uani 1 1 d . . . . .
C1A6 C 0.29418(9) 0.56443(15) 0.06622(6) 0.0337(3) Uani 1 1 d . . . . .
O1A6 O 0.23423(8) 0.61564(13) 0.06447(7) 0.0622(4) Uani 1 1 d . . . . .
C2A6 C 0.30435(8) 0.41870(14) 0.06473(5) 0.0281(3) Uani 1 1 d . . . . .
C3A6 C 0.37248(8) 0.36153(14) 0.06142(5) 0.0271(3) Uani 1 1 d . . . . .
H3A6 H 0.414090 0.414200 0.060665 0.033 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 112.0(4) . . ?
O1A7 C1A1 O2A7 126.7(15) . . ?
O1A1 C1A1 O2A1 123.6(3) . . ?
O1A1 C1A1 C2A1 123.2(3) . . ?
O1A7 C1A1 C2A1 112.6(15) . . ?
O2A7 C1A1 C2A1 120.8(9) . . ?
O2A1 C1A1 C2A1 113.1(3) . . ?
C1A1 O2A7 C4A7 100.1(16) . . ?
C3A3 C2A1 C3A1 119.81(15) . . ?
C3A3 C2A1 C1A1 122.58(16) . . ?
C3A1 C2A1 C1A1 117.61(15) . . ?
C2A2 C3A1 C2A1 120.33(14) . . ?
C1A2 O2A2 C4A2 115.60(14) . . ?
O1A2 C1A2 O2A2 124.27(16) . . ?
O1A2 C1A2 C2A2 123.33(15) . . ?
O2A2 C1A2 C2A2 112.39(14) . . ?
C3A1 C2A2 C3A2 119.91(15) . . ?
C3A1 C2A2 C1A2 122.43(14) . . ?
C3A2 C2A2 C1A2 117.64(14) . . ?
C2A3 C3A2 C2A2 119.88(15) . . ?
C1A3 O2A3 C4A3 115.78(14) . . ?
O1A3 C1A3 O2A3 125.03(15) . . ?
O1A3 C1A3 C2A3 123.00(16) . . ?
O2A3 C1A3 C2A3 111.97(14) . . ?
C3A2 C2A3 C3A3 120.18(14) . . ?
C3A2 C2A3 C1A3 121.74(15) . . ?
C3A3 C2A3 C1A3 118.08(14) . . ?
C2A1 C3A3 C2A3 119.88(15) . . ?
C1A4 O2A4 C4A4 115.46(12) . . ?
O1A4 C1A4 O2A4 124.30(14) . . ?
O1A4 C1A4 C2A4 123.94(14) . . ?
O2A4 C1A4 C2A4 111.75(12) . . ?
C3A4 C2A4 C3A6 119.86(13) . . ?
C3A4 C2A4 C1A4 118.36(13) . . ?
C3A6 C2A4 C1A4 121.77(13) . . ?
C2A4 C3A4 C2A5 120.54(13) . . ?
C1A5 O2A5 C4A5 116.43(15) . . ?
O1A5 C1A5 O2A5 124.52(15) . . ?
O1A5 C1A5 C2A5 123.52(15) . . ?
O2A5 C1A5 C2A5 111.96(14) . . ?
C3A5 C2A5 C3A4 119.49(13) . . ?
C3A5 C2A5 C1A5 122.16(14) . . ?
C3A4 C2A5 C1A5 118.34(14) . . ?
C2A5 C3A5 C2A6 120.19(14) . . ?
C1A6 O2A6 C4A6 114.95(12) . . ?
O1A6 C1A6 O2A6 123.82(15) . . ?
O1A6 C1A6 C2A6 123.15(15) . . ?
O2A6 C1A6 C2A6 113.03(13) . . ?
C3A6 C2A6 C3A5 120.22(14) . . ?
C3A6 C2A6 C1A6 122.26(13) . . ?
C3A5 C2A6 C1A6 117.51(13) . . ?
C2A6 C3A6 C2A4 119.68(13) . . ?
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 1.453(5) . ?
O2A1 C1A1 1.350(6) . ?
O1A1 C1A1 1.182(5) . ?
C1A1 O1A7 1.22(3) . ?
C1A1 O2A7 1.32(3) . ?
C1A1 C2A1 1.497(2) . ?
C4A7 O2A7 1.411(18) . ?
C2A1 C3A3 1.391(2) . ?
C2A1 C3A1 1.393(2) . ?
C3A1 C2A2 1.386(2) . ?
C4A2 O2A2 1.450(2) . ?
O2A2 C1A2 1.332(2) . ?
C1A2 O1A2 1.203(2) . ?
C1A2 C2A2 1.495(2) . ?
C2A2 C3A2 1.395(2) . ?
C3A2 C2A3 1.389(2) . ?
C4A3 O2A3 1.451(2) . ?
O2A3 C1A3 1.333(2) . ?
C1A3 O1A3 1.210(2) . ?
C1A3 C2A3 1.495(2) . ?
C2A3 C3A3 1.394(2) . ?
C4A4 O2A4 1.4522(18) . ?
O2A4 C1A4 1.3337(18) . ?
C1A4 O1A4 1.2034(19) . ?
C1A4 C2A4 1.496(2) . ?
C2A4 C3A4 1.389(2) . ?
C2A4 C3A6 1.394(2) . ?
C3A4 C2A5 1.391(2) . ?
C4A5 O2A5 1.446(2) . ?
O2A5 C1A5 1.335(2) . ?
C1A5 O1A5 1.207(2) . ?
C1A5 C2A5 1.495(2) . ?
C2A5 C3A5 1.389(2) . ?
C3A5 C2A6 1.392(2) . ?
C4A6 O2A6 1.4526(18) . ?
O2A6 C1A6 1.3303(19) . ?
C1A6 O1A6 1.197(2) . ?
C1A6 C2A6 1.493(2) . ?
C2A6 C3A6 1.389(2) . ?
