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_2242155
_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          'C17 H11 N3'
_chemical_formula_moiety         'C17 H11 N3'
_chemical_formula_sum            'C17 H11 N3'
_chemical_formula_weight         257.29
_chemical_name_systematic
;
4-(Pyridin-3-ylethynyl)-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
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.799(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7436(3)
_cell_length_b                   34.146(3)
_cell_length_c                   10.7528(9)
_cell_measurement_reflns_used    1697
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6940
_cell_measurement_theta_min      3.5340
_cell_volume                     1369.7(2)
_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
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>Olex2.solve</i> (Bourhis <i>et al.</i>,  2015)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Agilent SuperNova (single source at offset, Eos detector)
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4235
_diffrn_reflns_theta_full        23.248
_diffrn_reflns_theta_max         23.248
_diffrn_reflns_theta_min         3.051
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
TITL
CELL    3.7436   34.1460   10.7528     90.00     94.80     90.00
SPGR P21/c
C101 0.682 0.490 0.308 !       7.17 eA-3
C102 0.586 1.002 0.205 !       6.79 eA-3
C103 0.068 0.502 0.430 !       6.07 eA-3
Q104 0.395 0.485 0.183 !       1.12 eA-3
C105 0.219 0.999 0.111 !       1.07 eA-3
C106 0.776 0.024 0.181 !       0.89 eA-3
Q107 0.807 0.970 0.039 !       0.82 eA-3
Q108 0.392 0.471 0.262 !       0.81 eA-3
C109 0.294 0.485 0.371 !       0.81 eA-3
C110 0.710 0.522 0.298 !       0.79 eA-3
C111 0.103 0.008 0.148 !       0.79 eA-3
Q112 0.366 0.469 0.366 !       0.77 eA-3
C113 0.887 0.478 0.280 !       0.74 eA-3
Q114 0.113 0.134 0.374 !       0.69 eA-3
Q115 0.429 0.264 0.295 !       0.67 eA-3
Q116 0.328 0.405 0.488 !       0.66 eA-3
C117 0.788 0.459 0.346 !       0.66 eA-3
Q118 0.963 0.412 0.129 !       0.65 eA-3
Q119 0.917 0.447 0.084 !       0.62 eA-3
Q120 0.406 0.633 0.107 !       0.61 eA-3
Q121 0.729 0.396 0.441 !       0.60 eA-3
Q122 0.451 0.033 0.320 !       0.59 eA-3
C123 0.655 0.515 0.376 !       0.58 eA-3
Q124 0.063 0.124 0.423 !       0.58 eA-3
Q125 0.376 0.399 0.084 !       0.57 eA-3
Q126 0.508 0.788 0.329 !       0.56 eA-3
Q127 0.805 0.439 0.398 !       0.55 eA-3
Q128 0.729 0.845 0.080 !       0.55 eA-3
Q129 0.752 0.697 0.243 !       0.55 eA-3
Q130 0.763 0.328 0.455 !       0.54 eA-3
Q131 0.073 0.876 0.455 !       0.53 eA-3
Q132 0.873 0.930 0.571 !       0.52 eA-3
Q133 0.127 0.070 0.429 !       0.52 eA-3
Q134 0.929 0.734 0.400 !       0.52 eA-3
Q135 0.324 0.703 0.238 !       0.51 eA-3
Q136 0.675 0.109 0.460 !       0.51 eA-3
C137 0.310 0.976 0.013 !       0.51 eA-3
Q138 0.323 0.961 0.053 !       0.51 eA-3
Q139 0.922 0.763 0.335 !       0.51 eA-3
Q140 0.142 0.802 0.140 !       0.50 eA-3
;
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0828
_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^)+(0.0696P)^2^+4.7923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2083
_reflns_number_gt                1645
_reflns_number_total             1926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zs2378sup1.cif
_cod_data_source_block           II
_cod_database_code               2242155
_cod_database_fobs_code          2242155
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.992
_shelx_fab_checksum              5165