Efficient synthetic approach to <i>m</i>-terphenyl derivatives <i>via</i> arylation of azolium salts.
Kar, Subarna; Ramachandran, Arya; Rit, Arnab; Chemical communications (Cambridge, England) 61 (2025) 16802–16805; doi:10.1039/d5cc05201g

data_7134998
_publ_section_title
;
 Efficient synthetic approach to <i>m</i>-terphenyl derivatives <i>via</i>
 arylation of azolium salts.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16802
_journal_page_last               16805
_journal_paper_doi               10.1039/d5cc05201g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C21 H21 Br N2 O'
_chemical_formula_weight         397.31
_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   mixed
_atom_sites_solution_primary     'Intrinsic Phasing'
_audit_creation_method
;FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-09-09 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.338(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9547(13)
_cell_length_b                   10.2165(11)
_cell_length_c                   16.1046(15)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    302.15
_cell_measurement_theta_max      25.3395
_cell_measurement_theta_min      2.4231
_cell_measurement_wavelength     0.71073
_cell_volume                     1957.1(3)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_collection       'Bruker Instrument Service v8.5.4.0'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.391
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   0.000 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   0.000 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Omega scan: start=   0.9; len= 106.0; end= 106.9 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   1.167 deg phi=   0.000 deg chi= -44.500 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start=   0.9; len= 106.0; end= 106.9 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   1.167 deg phi= 144.000 deg chi= -44.500 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start=   0.9; len= 106.0; end= 106.9 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   1.167 deg phi= 288.000 deg chi= -44.500 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  45.0; end= 369.6 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   0.583 deg phi= 360.000 deg chi=  68.500 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start= 300.0; len= 208.0; end= 508.0 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   1.167 deg omega= 266.259 deg chi=  24.000 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start= 228.0; len= 184.0; end= 412.0 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   1.167 deg omega= 359.885 deg chi= -44.500 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start=   0.9; len= 106.0; end= 106.9 at [Counterclockwise Eulerian 
angles: dx= 40.00 mm theta=   1.167 deg phi= 216.000 deg chi= -44.500 deg] 
measure for 4.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 50.00 mm theta=   0.000 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
;
_diffrn_measurement_device       'FIXED CHI diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            68687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         2.423
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_target            Mo
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.111
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0384
_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/[\s^2^(Fo^2^)+(0.0509P)^2^+1.1455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3144
_reflns_number_total             4002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05201g2.cif
_cod_data_source_block           oetme_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134998.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7134998
_shelx_shelxl_version_number     2019/3
_exptl_bruker_absorpt_correction_t_ratio 0.8072
_shelx_estimated_absorpt_t_min   0.700
_shelx_estimated_absorpt_t_max   0.909
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_measurement_bruker_total_exposure_time 7428.0
_diffrn_reflns_bruker_av_norm_i  2117.069
_diffrn_reflns_bruker_number_gt  38374
_computing_bruker_data_scaling
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_geom_details
; All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
_shelx_res_checksum              55477
_shelx_hkl_checksum              21214