Synthesis of multi-substituted pyridines from ylidenemalononitriles and their emission properties.
de Souza, Juliana M.; Abdiaj, Irini; Chen, Jiaqi; Hanson, Kenneth; de Oliveira, Kleber T.; McQuade, D. Tyler; Organic & biomolecular chemistry 19 (2021) 1991–1999; doi:10.1039/d0ob02591g

data_7157870
_publ_section_title
;
 Synthesis of multi-substituted pyridines from ylidenemalononitriles and
 their emission properties.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1991
_journal_page_last               1999
_journal_paper_doi               10.1039/d0ob02591g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 N4'
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33
_chemical_name_systematic
2'-(benzylamino)-[3,4'-bipyridine]-3'-carbonitrile
_chemical_properties_physical    Air-stable
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-11
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3651(2)
_cell_length_b                   11.1837(2)
_cell_length_c                   23.1292(4)
_cell_measurement_reflns_used    7003
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1130
_cell_measurement_theta_min      1.8720
_cell_volume                     2939.81(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -88.00 -63.00   0.50    0.50    --  -60.00  50.00 120.00   50
  2  \w   -119.00  -1.00   0.50    0.50    --  -60.00  50.00  30.00  236
  3  \w    -52.00  -3.00   0.50    0.50    --  -60.00  50.00 120.00   98
  4  \w   -149.00 -32.00   0.50    0.50    --  -90.00  30.00-180.00  234
  5  \w   -149.00-107.00   0.50    0.50    --  -90.00  60.00  29.22   84
  6  \w   -123.00 -92.00   0.50    0.50    --  -90.00  59.00 -60.99   62
  7  \w   -129.00-101.00   0.50    0.50    --  -90.00  60.00 -21.86   56
  8  \w   -149.00 -95.00   0.50    0.50    --  -90.00  60.00  41.89  108
  9  \w    -85.00 -60.00   0.50    0.50    --  -90.00  59.00 -60.99   50
 10  \w   -149.00-123.00   0.50    0.50    --  -90.00  60.00  -3.71   52
 11  \w   -149.00 -75.00   0.50    0.50    --  -90.00  60.00   7.21  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1217907000
_diffrn_orient_matrix_UB_12      -0.0190620000
_diffrn_orient_matrix_UB_13      0.0278249000
_diffrn_orient_matrix_UB_21      -0.0580532000
_diffrn_orient_matrix_UB_22      0.0086896000
_diffrn_orient_matrix_UB_23      -0.0600909000
_diffrn_orient_matrix_UB_31      0.0133223000
_diffrn_orient_matrix_UB_32      -0.1360200000
_diffrn_orient_matrix_UB_33      -0.0076140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14134
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.071
_diffrn_reflns_theta_min         3.822
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Choloroform/Hexane (1:20)'
_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0061(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0662P)^2^+1.0318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2647
_reflns_number_total             2771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02591g2.cif
_cod_data_source_block           juliana_py_cyc_py_h_11111_run2_7-12
_cod_depositor_comments
'Adding full bibliography for 7157868--7157873.cif.'
_cod_database_code               7157870
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C18H14N4
_diffrn_oxdiff_digest_frames
;
017f2a7cb918b0ab9459a1c2471a5fed0e011785ad9
;
_diffrn_oxdiff_digest_hkl
;
019dd09a34cddcea02f2594e03c849da6a5374
;
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C14(H14), C2(H2), C1(H1), C18(H18), C17(H17), C7(H7), C15(H15),
 C10(H10), C16(H16), C8(H8), C9(H9)
;
_shelx_res_checksum              51516
_olex2_exptl_crystal_mounting_method MiTeGen
_olex2_submission_original_sample_id Py_CyC_Py_H
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.372
_oxdiff_exptl_absorpt_empirical_full_min 0.176