#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:30:24 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060982.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_7060982
loop_
_publ_author_name
'Dolai, Gobinda'
'Roy, Sayanta'
'Sen, Srijit'
'Giri, Rajat Subhra'
'Mandal, Bhubaneswar'
_publ_section_title
;
 Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole
 (TCB-OBt): observation of uncommon intermolecular oxygen--oxygen
 interaction and synthetic application in amidation
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19804
_journal_page_last               19811
_journal_paper_doi               10.1039/D1NJ04048K
_journal_volume                  45
_journal_year                    2021
_chemical_formula_sum            'C13 H6 Cl3 N3 O2'
_chemical_formula_weight         342.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-09-18 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.957(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0723(6)
_cell_length_b                   13.1809(9)
_cell_length_c                   10.5798(8)
_cell_measurement_reflns_used    6307
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.47
_cell_volume                     1404.40(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13230
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocked
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2112
_reflns_number_total             2452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj04048k2.cif
_cod_data_source_block           tcb_hobt_gd_bhm_0m_a
_cod_depositor_comments          'Adding full bibliography for 7060982.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7060982
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.22092(5) 0.64837(5) 0.60985(6) 0.0684(2) Uani 1 1 d . . .
Cl3 Cl 0.68228(6) 0.59340(5) 0.86027(7) 0.0740(3) Uani 1 1 d . . .
Cl2 Cl 0.52087(8) 0.96830(5) 0.73531(9) 0.0881(3) Uani 1 1 d . . .
O2 O 0.48534(14) 0.48094(10) 0.62773(13) 0.0485(4) Uani 1 1 d . . .
O1 O 0.3753(2) 0.47131(12) 0.81104(17) 0.0723(5) Uani 1 1 d . . .
N1 N 0.46256(17) 0.37814(13) 0.61343(15) 0.0481(4) Uani 1 1 d . . .
N2 N 0.54883(18) 0.31076(15) 0.66302(18) 0.0580(5) Uani 1 1 d . . .
C8 C 0.35606(19) 0.33384(15) 0.55648(16) 0.0411(4) Uani 1 1 d . . .
N3 N 0.50238(19) 0.22127(15) 0.63914(18) 0.0602(5) Uani 1 1 d . . .
C1 C 0.45424(18) 0.63198(15) 0.73530(16) 0.0407(4) Uani 1 1 d . . .
C6 C 0.56744(19) 0.67332(16) 0.79086(18) 0.0453(5) Uani 1 1 d . . .
C7 C 0.43042(19) 0.52058(15) 0.73609(18) 0.0440(5) Uani 1 1 d . . .
C9 C 0.3837(2) 0.23163(15) 0.57373(18) 0.0464(5) Uani 1 1 d . . .
C2 C 0.36295(18) 0.69769(16) 0.68010(18) 0.0459(5) Uani 1 1 d . . .
C5 C 0.5904(2) 0.77671(17) 0.79095(19) 0.0520(5) Uani 1 1 d . . .
H5 H 0.6676 0.8036 0.8268 0.062 Uiso 1 1 calc R . .
C13 C 0.2441(2) 0.36907(18) 0.4920(2) 0.0540(5) Uani 1 1 d . . .
H13 H 0.2274 0.4378 0.4803 0.065 Uiso 1 1 calc R . .
C10 C 0.2944(3) 0.15793(17) 0.5275(2) 0.0567(6) Uani 1 1 d . . .
H10 H 0.3100 0.0890 0.5392 0.068 Uiso 1 1 calc R . .
C3 C 0.3818(2) 0.80099(17) 0.6803(2) 0.0537(5) Uani 1 1 d . . .
H3 H 0.3193 0.8443 0.6435 0.064 Uiso 1 1 calc R . .
C4 C 0.4957(2) 0.83854(16) 0.7365(2) 0.0528(5) Uani 1 1 d . . .
C12 C 0.1605(2) 0.2957(2) 0.4470(2) 0.0620(6) Uani 1 1 d . . .
H12 H 0.0843 0.3151 0.4024 0.074 Uiso 1 1 calc R . .
C11 C 0.1849(2) 0.19185(19) 0.4654(2) 0.0613(6) Uani 1 1 d . . .
H11 H 0.1238 0.1450 0.4339 0.074 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N1 O2 C7 113.14(14) . . ?
N2 N1 C8 113.03(17) . . ?
N2 N1 O2 120.02(16) . . ?
C8 N1 O2 126.90(16) . . ?
N3 N2 N1 107.31(17) . . ?
N1 C8 C9 101.80(17) . . ?
N1 C8 C13 134.87(19) . . ?
C9 C8 C13 123.31(19) . . ?
N2 N3 C9 108.42(18) . . ?
C6 C1 C2 117.95(18) . . ?
C6 C1 C7 121.15(17) . . ?
C2 C1 C7 120.90(17) . . ?
C5 C6 C1 121.64(19) . . ?
C5 C6 Cl3 119.48(16) . . ?
C1 C6 Cl3 118.88(16) . . ?
O1 C7 O2 123.49(19) . . ?
O1 C7 C1 128.97(19) . . ?
O2 C7 C1 107.53(15) . . ?
N3 C9 C8 109.44(18) . . ?
N3 C9 C10 130.6(2) . . ?
C8 C9 C10 120.0(2) . . ?
C3 C2 C1 121.88(18) . . ?
C3 C2 Cl1 119.11(16) . . ?
C1 C2 Cl1 119.01(16) . . ?
C4 C5 C6 118.00(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C12 C13 C8 115.2(2) . . ?
C12 C13 H13 122.4 . . ?
C8 C13 H13 122.4 . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 122.4(2) . . ?
C5 C4 Cl2 119.26(17) . . ?
C3 C4 Cl2 118.30(18) . . ?
C13 C12 C11 122.5(2) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C10 C11 C12 122.0(2) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
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
Cl1 C2 1.728(2) . ?
Cl3 C6 1.720(2) . ?
Cl2 C4 1.729(2) . ?
O2 N1 1.382(2) . ?
O2 C7 1.384(2) . ?
O1 C7 1.172(2) . ?
N1 N2 1.343(2) . ?
N1 C8 1.354(2) . ?
N2 N3 1.292(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.388(3) . ?
N3 C9 1.378(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.385(3) . ?
C1 C7 1.488(3) . ?
C6 C5 1.382(3) . ?
C9 C10 1.406(3) . ?
C2 C3 1.375(3) . ?
C5 C4 1.374(3) . ?
C5 H5 0.9300 . ?
C13 C12 1.364(3) . ?
C13 H13 0.9300 . ?
C10 C11 1.350(4) . ?
C10 H10 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C12 C11 1.403(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
