#------------------------------------------------------------------------------
#$Date: 2025-12-12 02:54:57 +0100 (Fri 12 de Dec de 2025) $
#$Revision: 304186 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/42/7064216.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_7064216
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         'C10 H10 Br3 N O Te, Br, C H Cl3, C4 H12 N'
_chemical_formula_sum            'C15 H23 Br4 Cl3 N2 O Te'
_chemical_formula_weight         800.94
_chemical_name_systematic
1,1,1-tri-bromo-3-methyl-5-phenyl-1,2-tellurazole-2-anol
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
_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     iterative
_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                 91.967(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1714(10)
_cell_length_b                   9.0498(6)
_cell_length_c                   19.5492(14)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      34.93
_cell_measurement_theta_min      2.48
_cell_volume                     2505.7(3)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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  0.0748
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            66219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.023
_diffrn_reflns_theta_min         2.480
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.894
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.5203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1038 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.6966.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull light yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_description       plate
_exptl_crystal_F_000             1512
_exptl_crystal_preparation
'1,1,1-tri-bromo-3-methyl-5-phenyl-1,2-tellurazole-2-anol was synthesized by allowing 2 equivalents of tetramethylammonium tribromide react with 3-methyl-5-phenyl-1,2-tellurazole-2-oxide in methanol with stirring. The volume was reduced and the product was extracted with DCM and precipitated in hexanes resulting in a light yellow powder.'
_exptl_crystal_recrystallization_method
'1,1,1-tri-bromo-3-methyl-5-phenyl-1,2-tellurazole-2-anol was allowed to slowly evaporate in CHCl3 resulting in platelike yellow crystals'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.619
_refine_diff_density_min         -1.779
_refine_diff_density_rms         0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         10866
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0766P)²+12.0799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7437
_reflns_number_total             10866
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj03688g2.cif
_cod_data_source_block           mo_pm_phiteohbr3chcl3_0m
_cod_database_code               7064216
_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 Ternary CH refined with riding coordinates:
 C11(H11)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,H14b,
 H14c), C15(H15a,H15b,H15c)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method
'Suitable crystals of 1,1,1-tri-bromo-3-methyl-5-phenyl-1,2-tellurazole-2-anol 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-5-49
_olex2_submission_special_instructions 'No special instructions were received'
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
Te1 Te 0.80008(2) 0.21146(3) 0.40679(2) 0.01513(7) Uani 1 1 d . . . . .
Br1 Br 0.83849(4) -0.07214(5) 0.42016(3) 0.02268(11) Uani 1 1 d . . . . .
Br2 Br 0.80151(3) 0.20356(6) 0.27355(2) 0.02218(11) Uani 1 1 d . . . . .
Br3 Br 0.78785(4) 0.50949(5) 0.41193(3) 0.02408(11) Uani 1 1 d . . . . .
O1 O 0.7726(3) 0.2302(4) 0.57850(19) 0.0235(7) Uani 1 1 d . . . . .
H1 H 0.719281 0.201686 0.563852 0.035 Uiso 1 1 calc R U . . .
N1 N 0.8342(3) 0.2315(4) 0.5257(2) 0.0179(7) Uani 1 1 d . . . . .
C1 C 0.9511(3) 0.2451(5) 0.4179(2) 0.0165(7) Uani 1 1 d . . . . .
C2 C 0.9818(3) 0.2703(5) 0.4824(2) 0.0175(8) Uani 1 1 d . . . . .
H2 H 1.047194 0.288222 0.490737 0.021 Uiso 1 1 calc R U . . .
C3 C 0.9202(3) 0.2717(5) 0.5404(3) 0.0193(8) Uani 1 1 d . . . . .
C4 C 0.9533(3) 0.3145(6) 0.6111(3) 0.0214(9) Uani 1 1 d . . . . .
H4A H 1.022235 0.323849 0.612736 0.032 Uiso 1 1 calc R U . . .
H4B H 0.934418 0.238476 0.643592 0.032 Uiso 1 1 calc R U . . .
H4C H 0.924934 0.409273 0.623288 0.032 Uiso 1 1 calc R U . . .
C5 C 1.0141(3) 0.2277(5) 0.3603(3) 0.0180(8) Uani 1 1 d . . . . .
C6 C 1.0163(3) 0.3320(6) 0.3075(2) 0.0202(8) Uani 1 1 d . . . . .
H6 H 0.974559 0.414159 0.307046 0.024 Uiso 1 1 calc R U . . .
C7 C 1.0797(4) 0.3144(7) 0.2562(3) 0.0276(10) Uani 1 1 d . . . . .
H7 H 1.083034 0.386976 0.221233 0.033 Uiso 1 1 calc R U . . .
C8 C 1.1387(4) 0.1924(7) 0.2548(3) 0.0317(11) Uani 1 1 d . . . . .
H8 H 1.180730 0.180450 0.218386 0.038 Uiso 1 1 calc R U . . .
C9 C 1.1364(4) 0.0877(6) 0.3065(3) 0.0286(10) Uani 1 1 d . . . . .
H9 H 1.176467 0.003646 0.305585 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0748(3) 0.1068(6) 0.3597(3) 0.0233(9) Uani 1 1 d . . . . .
H10 H 1.074257 0.036778 0.395917 0.028 Uiso 1 1 calc R U . . .
Br4 Br 0.59670(3) 0.15929(6) 0.48824(3) 0.02371(11) Uani 1 1 d . . . . .
Cl1 Cl 0.58547(11) 1.01744(17) 0.30671(8) 0.0353(3) Uani 1 1 d . . . . .
Cl2 Cl 0.58751(11) 0.71775(17) 0.35681(9) 0.0373(3) Uani 1 1 d . . . . .
Cl3 Cl 0.41098(10) 0.84986(19) 0.30958(9) 0.0373(3) Uani 1 1 d . . . . .
C11 C 0.5219(4) 0.8820(6) 0.3508(3) 0.0258(10) Uani 1 1 d . . . . .
H11 H 0.511240 0.918831 0.398165 0.031 Uiso 1 1 calc R U . . .
N2 N 0.6511(3) -0.3410(5) 0.5921(2) 0.0248(8) Uani 1 1 d . . . . .
C12 C 0.5904(4) -0.4475(7) 0.5528(4) 0.0391(15) Uani 1 1 d . . . . .
H12A H 0.532685 -0.397539 0.536223 0.059 Uiso 1 1 calc R U . . .
H12B H 0.573812 -0.529916 0.582614 0.059 Uiso 1 1 calc R U . . .
H12C H 0.624714 -0.485153 0.513795 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6738(5) -0.2156(7) 0.5465(4) 0.0363(13) Uani 1 1 d . . . . .
H13A H 0.713609 -0.144278 0.571774 0.055 Uiso 1 1 calc R U . . .
H13B H 0.615198 -0.167282 0.530535 0.055 Uiso 1 1 calc R U . . .
H13C H 0.707570 -0.252539 0.507044 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7403(5) -0.4171(7) 0.6150(4) 0.0388(15) Uani 1 1 d . . . . .
H14A H 0.771038 -0.458680 0.575238 0.058 Uiso 1 1 calc R U . . .
H14B H 0.725511 -0.496638 0.646939 0.058 Uiso 1 1 calc R U . . .
H14C H 0.782699 -0.345784 0.637968 0.058 Uiso 1 1 calc R U . . .
C15 C 0.6020(7) -0.2833(10) 0.6510(4) 0.054(2) Uani 1 1 d . . . . .
H15A H 0.638577 -0.201878 0.671681 0.081 Uiso 1 1 calc R U . . .
H15B H 0.595088 -0.362156 0.684864 0.081 Uiso 1 1 calc R U . . .
H15C H 0.539418 -0.247297 0.636070 0.081 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'
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'
Cl Cl 0.1484 0.1585 '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'
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 Te1 Br3 168.80(2) . . ?
Br2 Te1 Br1 93.655(18) . . ?
Br2 Te1 Br3 93.854(18) . . ?
N1 Te1 Br1 86.72(10) . . ?
N1 Te1 Br2 167.43(10) . . ?
N1 Te1 Br3 84.15(10) . . ?
C1 Te1 Br1 85.80(12) . . ?
C1 Te1 Br2 93.60(12) . . ?
C1 Te1 Br3 85.45(12) . . ?
C1 Te1 N1 73.88(16) . . ?
N1 O1 H1 109.5 . . ?
O1 N1 Te1 128.6(3) . . ?
C3 N1 Te1 113.5(3) . . ?
C3 N1 O1 116.9(4) . . ?
C2 C1 Te1 113.9(3) . . ?
C2 C1 C5 123.7(4) . . ?
C5 C1 Te1 122.1(3) . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.5(4) . . ?
C3 C2 H2 118.3 . . ?
N1 C3 C2 114.2(4) . . ?
N1 C3 C4 122.8(4) . . ?
C2 C3 C4 123.0(4) . . ?
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 121.5(4) . . ?
C10 C5 C1 118.9(4) . . ?
C10 C5 C6 119.6(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.1(5) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(5) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.5(5) . . ?
C9 C10 H10 119.7 . . ?
Cl1 C11 Cl3 110.7(3) . . ?
Cl1 C11 H11 108.5 . . ?
Cl2 C11 Cl1 110.1(3) . . ?
Cl2 C11 Cl3 110.6(3) . . ?
Cl2 C11 H11 108.5 . . ?
Cl3 C11 H11 108.5 . . ?
C12 N2 C14 108.9(4) . . ?
C13 N2 C12 108.6(5) . . ?
C13 N2 C14 109.5(5) . . ?
C15 N2 C12 110.8(6) . . ?
C15 N2 C13 108.6(5) . . ?
C15 N2 C14 110.3(5) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Te1 Br1 2.6348(6) . ?
Te1 Br2 2.6065(6) . ?
Te1 Br3 2.7047(6) . ?
Te1 N1 2.364(4) . ?
Te1 C1 2.166(4) . ?
O1 H1 0.8400 . ?
O1 N1 1.375(5) . ?
N1 C3 1.295(6) . ?
C1 C2 1.339(6) . ?
C1 C5 1.468(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.454(7) . ?
C3 C4 1.496(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.401(7) . ?
C5 C10 1.393(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(7) . ?
C10 H10 0.9500 . ?
Cl1 C11 1.764(6) . ?
Cl2 C11 1.755(6) . ?
Cl3 C11 1.766(6) . ?
C11 H11 1.0000 . ?
N2 C12 1.487(7) . ?
N2 C13 1.484(7) . ?
N2 C14 1.494(7) . ?
N2 C15 1.463(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
Te1 N1 C3 C2 -10.4(5) . . . . ?
Te1 N1 C3 C4 170.1(4) . . . . ?
Te1 C1 C2 C3 1.4(6) . . . . ?
Te1 C1 C5 C6 73.1(5) . . . . ?
Te1 C1 C5 C10 -109.0(4) . . . . ?
O1 N1 C3 C2 179.8(4) . . . . ?
O1 N1 C3 C4 0.3(7) . . . . ?
C1 C2 C3 N1 6.7(7) . . . . ?
C1 C2 C3 C4 -173.8(5) . . . . ?
C1 C5 C6 C7 177.0(4) . . . . ?
C1 C5 C10 C9 -179.1(5) . . . . ?
C2 C1 C5 C6 -112.8(5) . . . . ?
C2 C1 C5 C10 65.2(6) . . . . ?
C5 C1 C2 C3 -173.1(4) . . . . ?
C5 C6 C7 C8 2.4(7) . . . . ?
C6 C5 C10 C9 -1.1(7) . . . . ?
C6 C7 C8 C9 -1.8(8) . . . . ?
C7 C8 C9 C10 -0.3(8) . . . . ?
C8 C9 C10 C5 1.8(8) . . . . ?
C10 C5 C6 C7 -0.9(7) . . . . ?
