Expanding the versatility of trihalophenols as molecular templates to achieve a series of [2+2] cycloaddition reaction involving 1,2-bis(2-pyridyl)ethylene
Andren, Max; Unruh, Daniel K.; Krueger, Herman R.; Groeneman, Ryan H.; New Journal of Chemistry 48 (2024) 10584–10587; doi:10.1039/D4NJ01769B

data_7063222
_publ_section_title
;
 Expanding the versatility of trihalophenols as molecular templates to
 achieve a series of [2+2] cycloaddition reaction involving
 1,2-bis(2-pyridyl)ethylene
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10584
_journal_page_last               10587
_journal_paper_doi               10.1039/D4NJ01769B
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H3 Br3 O)'
_chemical_formula_sum            'C24 H16 Br6 N2 O2'
_chemical_formula_weight         843.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-04 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.3530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.2907(6)
_cell_length_b                   4.0298(2)
_cell_length_c                   22.1448(7)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    290.00
_cell_measurement_theta_max      28.012
_cell_measurement_theta_min      2.776
_cell_volume                     1309.33(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35054
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         2.777
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    9.225
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.5660.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_description       irregular
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0299
_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/[\s^2^(Fo^2^)+(0.0288P)^2^+1.3713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2497
_reflns_number_total             3113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01769b2.cif
_cod_data_source_block           C6H2Br3OH_22BPE
_cod_depositor_comments
'Adding full bibliography for 7063222--7063224.cif.'
_cod_database_code               7063222
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.526
_shelx_estimated_absorpt_t_min   0.198
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              52524
_shelx_hkl_checksum              28915
_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'