Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.
Stephens, David E.; Lakey-Beitia, Johant; Burch, Jessica E.; Arman, Hadi D.; Larionov, Oleg V.; Chemical communications (Cambridge, England) 52 (2016) 9945–9948; doi:10.1039/c6cc04816a

data_7124818
_publ_section_title
;
 Mechanistic insights into the potassium tert-butoxide-mediated synthesis
 of N-heterobiaryls.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9945
_journal_page_last               9948
_journal_paper_doi               10.1039/c6cc04816a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(C11 H8 N)'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_chemical_name_systematic        5,5'-Diphenyl-2,2'-bipyridine
_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     direct
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.528(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.260(12)
_cell_length_b                   5.434(3)
_cell_length_c                   16.088(9)
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.5
_cell_volume                     1658.7(16)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
scan:
	Number of images: 246
	           Slice: -125.0000 - -2.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 270.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 184
	           Slice: -68.0000 - 24.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 92
	           Slice: 0.0000 - 46.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 64
	           Slice: -45.0000 - -13.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 62
	           Slice: 19.0000 - 50.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.9568
	          2theta: -35.0367
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.006354
_diffrn_orient_matrix_UB_12      -0.064037
_diffrn_orient_matrix_UB_13      -0.016251
_diffrn_orient_matrix_UB_21      -0.156145
_diffrn_orient_matrix_UB_22      0.038233
_diffrn_orient_matrix_UB_23      -0.089604
_diffrn_orient_matrix_UB_31      0.023926
_diffrn_orient_matrix_UB_32      -0.009879
_diffrn_orient_matrix_UB_33      -0.045910
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8978
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.704
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.5500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2142
_reflns_number_total             2904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04816a2.cif
_cod_data_source_block           cd1338a
_cod_database_code               7124818
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: C21A(0.5) H21A(0.5) C21B(0.5) H21B(0.5) H20A(0.5) H20(0.5)
 C22A(0.5) H22A(0.5) C22B(0.5) H22B(0.5) C18B(0.5) H18B(0.5) C18A(0.5)
 H18A(0.5) C19B(0.5) H19B(0.5) C19A(0.5) H19A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C21A(H21A), C15(H15), C21B(H21B), C13(H13), C20(H20A), C20(H20), C14(H14),
 C2(H2), C11(H11), C9(H9), C4(H4), C3(H3), C10(H10), C7(H7), C8(H8), C22A(H22A),
  C22B(H22B), C18B(H18B), C18A(H18A), C19B(H19B), C19A(H19A)
;
_shelx_res_checksum              15502
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-26
_olex2_date_sample_submission    2015-06-25
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'