#------------------------------------------------------------------------------
#$Date: 2025-12-12 02:54:57 +0100 (Fri 12 de Dec de 2025) $
#$Revision: 304186 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/42/7064218.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_7064218
loop_
_publ_author_name
'MacDougall, Phillip'
'Zeng, Mich Wenshi'
'Wang, Jin'
'Ho, Peter Cheng-Wei'
'Vargas-Baca, Ignacio'
_publ_section_title
;
 From Fluorine Chemistry to Noncovalent Interactions: Celebrating Prof.
 Giuseppe Resnati
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03688G
_journal_year                    2026
_chemical_formula_moiety         '2(C10 H10 Br3.5 N O Te), C14 H19 N2'
_chemical_formula_sum            'C34 H39 Br7 N4 O2 Te2'
_chemical_formula_weight         1350.26
_chemical_name_systematic
'1,1,1-tri-bromo-3-methyl-5-phenyl-1,2-tellurazole-2-anol + proton sponge'
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Hygroscopic,Oxygen-sensitive,Light-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-15
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-15 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.617(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.6425(16)
_cell_length_b                   13.1419(9)
_cell_length_c                   13.6360(8)
_cell_measurement_reflns_used    9516
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.76
_cell_measurement_theta_min      2.49
_cell_volume                     4273.1(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            141819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.795
_diffrn_reflns_theta_min         2.486
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.945
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1336 before and 0.0791 after correction.
The Ratio of minimum to maximum transmission is 0.6127.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.099
_exptl_crystal_description       prism
_exptl_crystal_F_000             2544
_exptl_crystal_preparation
'1,1,1-tri-bromo-3-methyl-5-phenyl-1,2-tellurazole-2-anol was predpared, dissoved in THF and 1.2 equivalents of proton sponge in THF was added.'
_exptl_crystal_recrystallization_method
'The resulting solution was filtered and allowed to slowly evaporate yielding yellow crystals'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.744
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6673
_refine_ls_number_restraints     195
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0279P)²+6.9221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5638
_reflns_number_total             6673
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj03688g2.cif
_cod_data_source_block           mo_pm_iteohbr3psponge_0m
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7064218
_shelx_shelxl_version_number     2019/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
3.b Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method
'Suitable crystals were selected and mounted on nylon loops (Hampton, California) or MiTeGen micromounts (Ithaca, New York) with Paratone-N oil on a Bruker APEX-II CCD diffractometer. The crystal was kept at 100.00 K during data collection.'
_olex2_submission_original_sample_id PM-5-63-3
_olex2_submission_special_instructions 'No special instructions were received'
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
Te Te 0.63714(2) 0.19219(2) 0.23880(2) 0.01640(4) Uani 1 1 d . . . . .
Br1 Br 0.67300(2) 0.08042(2) 0.40540(2) 0.03020(6) Uani 1 1 d . . . . .
Br2 Br 0.67660(2) 0.07143(2) 0.12408(2) 0.02382(6) Uani 1 1 d . . . . .
Br3 Br 0.60526(2) 0.33296(2) 0.09460(2) 0.02597(6) Uani 1 1 d . . . . .
Br4 Br 0.500000 0.15557(3) 0.250000 0.03424(9) Uani 1 2 d S T P . .
O1 O 0.57069(8) 0.33182(14) 0.38112(14) 0.0278(4) Uani 1 1 d . . . . .
H1 H 0.546109 0.290188 0.351521 0.042 Uiso 1 1 calc R U . . .
N1 N 0.61888(9) 0.31757(15) 0.34897(15) 0.0223(4) Uani 1 1 d . . . . .
C1 C 0.71313(9) 0.27973(18) 0.28661(17) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.71023(11) 0.35587(19) 0.35032(18) 0.0247(5) Uani 1 1 d . . . . .
H2 H 0.742043 0.398545 0.373016 0.030 Uiso 1 1 calc R U . . .
C3 C 0.66015(11) 0.37630(18) 0.38661(18) 0.0239(5) Uani 1 1 d . . . . .
C4 C 0.65748(13) 0.4590(2) 0.4602(2) 0.0341(6) Uani 1 1 d . . . . .
H4A H 0.627018 0.506020 0.429761 0.051 Uiso 1 1 calc R U . . .
H4B H 0.693152 0.496013 0.477420 0.051 Uiso 1 1 calc R U . . .
H4C H 0.650507 0.429283 0.521817 0.051 Uiso 1 1 calc R U . . .
C5 C 0.76090(10) 0.25508(18) 0.24437(18) 0.0227(5) Uani 1 1 d . . . . .
C6 C 0.77250(12) 0.3147(2) 0.1687(2) 0.0318(6) Uani 1 1 d . . . . .
H6 H 0.750777 0.373887 0.146259 0.038 Uiso 1 1 calc R U . . .
C7 C 0.81589(12) 0.2883(2) 0.1253(2) 0.0370(6) Uani 1 1 d . . . . .
H7 H 0.823116 0.328719 0.072254 0.044 Uiso 1 1 calc R U . . .
C8 C 0.84827(11) 0.2045(2) 0.1584(2) 0.0320(6) Uani 1 1 d . . . . .
H8 H 0.878137 0.187470 0.128951 0.038 Uiso 1 1 calc R U . . .
C9 C 0.83758(11) 0.1444(2) 0.2347(2) 0.0352(6) Uani 1 1 d . . . . .
H9 H 0.860222 0.086515 0.258068 0.042 Uiso 1 1 calc R U . . .
C10 C 0.79359(11) 0.1692(2) 0.2772(2) 0.0320(6) Uani 1 1 d . . . . .
H10 H 0.785775 0.127301 0.328738 0.038 Uiso 1 1 calc R U . . .
N2 N 0.51099(8) 0.13229(14) 0.66274(14) 0.0193(4) Uani 1 1 d . . . . .
H2A H 0.500000 0.115(5) 0.750000 0.072(18) Uiso 1 2 d S . P . .
C11 C 0.51395(9) 0.24349(16) 0.66687(16) 0.0175(4) Uani 1 1 d . . . . .
C12 C 0.500000 0.2936(2) 0.750000 0.0168(6) Uani 1 2 d S T P . .
C13 C 0.500000 0.4022(2) 0.750000 0.0187(6) Uani 1 2 d S T P . .
C14 C 0.51551(10) 0.45519(18) 0.67063(19) 0.0227(4) Uani 1 1 d . . . . .
H14 H 0.515926 0.527471 0.670939 0.027 Uiso 1 1 calc R U . . .
C15 C 0.52981(10) 0.40406(19) 0.59402(19) 0.0249(5) Uani 1 1 d . . . . .
H15 H 0.540679 0.440796 0.542067 0.030 Uiso 1 1 calc R U . . .
C16 C 0.52858(10) 0.29747(18) 0.59145(18) 0.0234(5) Uani 1 1 d . . . . .
H16 H 0.537939 0.262394 0.537046 0.028 Uiso 1 1 calc R U . . .
C17 C 0.56463(11) 0.08428(19) 0.6566(2) 0.0266(5) Uani 1 1 d . . . . .
H17A H 0.562327 0.010533 0.665439 0.040 Uiso 1 1 calc R U . . .
H17B H 0.595411 0.111931 0.710137 0.040 Uiso 1 1 calc R U . . .
H17C H 0.571519 0.098720 0.590310 0.040 Uiso 1 1 calc R U . . .
C18 C 0.46331(11) 0.09615(19) 0.58009(19) 0.0264(5) Uani 1 1 d . . . . .
H18A H 0.470247 0.113258 0.514360 0.040 Uiso 1 1 calc R U . . .
H18B H 0.428647 0.129129 0.586206 0.040 Uiso 1 1 calc R U . . .
H18C H 0.459590 0.022217 0.585181 0.040 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 0.0033 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'
Br Br -0.2901 2.4595 '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'
Te Te -0.5308 1.6751 '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
Br1 Te Br3 169.611(10) . . ?
Br1 Te Br4 90.181(8) . . ?
Br2 Te Br1 94.768(10) . . ?
Br2 Te Br3 93.753(10) . . ?
Br2 Te Br4 117.570(9) . . ?
Br3 Te Br4 91.134(8) . . ?
N1 Te Br1 85.25(5) . . ?
N1 Te Br2 168.56(5) . . ?
N1 Te Br3 85.22(5) . . ?
N1 Te Br4 73.86(5) . . ?
C1 Te Br1 87.73(6) . . ?
C1 Te Br2 94.59(6) . . ?
C1 Te Br3 85.67(6) . . ?
C1 Te Br4 147.83(6) . . ?
C1 Te N1 73.97(8) . . ?
N1 O1 H1 109.5 . . ?
O1 N1 Te 128.19(15) . . ?
C3 N1 Te 114.80(16) . . ?
C3 N1 O1 116.9(2) . . ?
C2 C1 Te 114.27(18) . . ?
C2 C1 C5 126.7(2) . . ?
C5 C1 Te 118.96(16) . . ?
C1 C2 H2 118.5 . . ?
C1 C2 C3 122.9(2) . . ?
C3 C2 H2 118.5 . . ?
N1 C3 C2 114.0(2) . . ?
N1 C3 C4 123.0(2) . . ?
C2 C3 C4 123.0(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 120.3(2) . . ?
C6 C5 C10 119.2(2) . . ?
C10 C5 C1 120.5(2) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 N2 H2A 99(3) . . ?
C11 N2 C17 112.93(18) . . ?
C11 N2 C18 111.75(18) . . ?
C17 N2 H2A 111.7(14) . . ?
C17 N2 C18 111.47(19) . . ?
C18 N2 H2A 109.3(11) . . ?
C12 C11 N2 118.2(2) . . ?
C16 C11 N2 120.5(2) . . ?
C16 C11 C12 121.3(2) . . ?
C11 C12 C11 125.0(3) . 2_656 ?
C11 C12 C13 117.51(14) 2_656 . ?
C11 C12 C13 117.51(14) . . ?
C14 C13 C12 119.42(15) 2_656 . ?
C14 C13 C12 119.42(15) . . ?
C14 C13 C14 121.2(3) 2_656 . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
Te Br1 2.6620(3) . ?
Te Br2 2.5844(3) . ?
Te Br3 2.6695(3) . ?
Te Br4 3.4549(3) . ?
Te N1 2.3486(19) . ?
Te C1 2.154(2) . ?
O1 H1 0.8400 . ?
O1 N1 1.378(3) . ?
N1 C3 1.277(3) . ?
C1 C2 1.339(3) . ?
C1 C5 1.471(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.466(3) . ?
C3 C4 1.492(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.382(4) . ?
C5 C10 1.394(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(4) . ?
C10 H10 0.9500 . ?
N2 H2A 1.305(10) . ?
N2 C11 1.464(3) . ?
N2 C17 1.486(3) . ?
N2 C18 1.486(3) . ?
C11 C12 1.426(3) . ?
C11 C16 1.370(3) . ?
C12 C13 1.427(4) . ?
C13 C14 1.418(3) . ?
C13 C14 1.418(3) 2_656 ?
C14 H14 0.9500 . ?
C14 C15 1.361(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Te N1 C3 C2 2.2(3) . . . . ?
Te N1 C3 C4 -178.40(19) . . . . ?
Te C1 C2 C3 1.5(3) . . . . ?
Te C1 C5 C6 102.3(2) . . . . ?
Te C1 C5 C10 -75.1(3) . . . . ?
O1 N1 C3 C2 179.1(2) . . . . ?
O1 N1 C3 C4 -1.5(3) . . . . ?
C1 C2 C3 N1 -2.6(4) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C1 C5 C6 C7 -176.7(2) . . . . ?
C1 C5 C10 C9 178.0(2) . . . . ?
C2 C1 C5 C6 -74.5(3) . . . . ?
C2 C1 C5 C10 108.2(3) . . . . ?
C5 C1 C2 C3 178.4(2) . . . . ?
C5 C6 C7 C8 -1.4(4) . . . . ?
C6 C5 C10 C9 0.5(4) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C5 -1.1(4) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
N2 C11 C12 C11 3.48(13) . . . 2_656 ?
N2 C11 C12 C13 -176.52(13) . . . . ?
N2 C11 C16 C15 178.1(2) . . . . ?
C11 C12 C13 C14 177.83(15) 2_656 . . . ?
C11 C12 C13 C14 177.83(15) . . . 2_656 ?
C11 C12 C13 C14 -2.17(15) 2_656 . . 2_656 ?
C11 C12 C13 C14 -2.17(15) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C13 C14 C15 -179.3(3) 2_656 . . . ?
C14 C15 C16 C11 -1.2(4) . . . . ?
C16 C11 C12 C11 -177.9(2) . . . 2_656 ?
C16 C11 C12 C13 2.1(2) . . . . ?
C17 N2 C11 C12 -123.9(2) . . . . ?
C17 N2 C11 C16 57.5(3) . . . . ?
C18 N2 C11 C12 109.4(2) . . . . ?
C18 N2 C11 C16 -69.1(3) . . . . ?
