Crystal structures of three 4-substituted-2,2'-bipyridines synthesized by Sonogashira and Suzuki–Miyaura cross-coupling reactions
Luong Thi Thu, Thuy; Nguyen Bich, Ngan; Nguyen, Hien; Van Meervelt, Luc; Acta Crystallographica Section E 73 (2017) 610–615; doi:10.1107/S2056989017004662

data_2242156
_publ_section_title
;
 Crystal structures of three 4-substituted-2,2'-bipyridines synthesized by
 Sonogashira and Suzuki--Miyaura cross-coupling reactions
;
_journal_coeditor_code           ZS2378
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              610
_journal_page_last               615
_journal_paper_doi               10.1107/S2056989017004662
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C18 H13 N3'
_chemical_formula_moiety         'C18 H13 N3'
_chemical_formula_sum            'C18 H13 N3'
_chemical_formula_weight         271.31
_chemical_melting_point_gt       398
_chemical_melting_point_lt       400
_chemical_name_systematic
;
4-(Indol-4-yl)-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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.552(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6951(6)
_cell_length_b                   12.0142(7)
_cell_length_c                   12.0376(9)
_cell_measurement_reflns_used    4854
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.0890
_cell_measurement_theta_min      3.5340
_cell_volume                     1321.28(16)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Agilent SuperNova (single source at offset, Eos detector)
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8569
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.7137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                2363
_reflns_number_total             2692
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            zs2378sup1.cif
_cod_data_source_block           III
_cod_original_cell_volume        1321.28(15)
_cod_database_code               2242156
_cod_database_fobs_code          2242156