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_7157869
_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         'C25 H19 N3'
_chemical_formula_sum            'C25 H19 N3'
_chemical_formula_weight         361.43
_chemical_name_systematic        2-(benzylamino)-4,5-diphenylnicotinonitrile
_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     dual
_audit_creation_date             2019-11-06
_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                 97.246(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8187(2)
_cell_length_b                   23.8383(6)
_cell_length_c                   13.7274(3)
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9830
_cell_measurement_theta_min      1.8420
_cell_volume                     1888.89(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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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   -140.00   9.00   0.50   10.00    --  -50.40  30.00-150.00  298
  2  \w   -140.00   9.00   0.50   10.00    --  -50.40  60.00 150.00  298
  3  \w   -120.00 -94.00   0.50   10.00    --  -50.40  20.00-180.00   52
  4  \w   -111.00 -69.00   0.50    0.50    --  -90.00  60.00  15.20   84
  5  \w   -163.00 -65.00   0.50    0.50    --  -90.00  60.00  37.44  196
  6  \w   -174.00-130.00   0.50    0.50    --  -90.00  20.00  30.00   88
  7  \w   -178.00 -32.00   0.50    0.50    --  -90.00  30.00 -60.00  292
  8  \w   -177.00-146.00   0.50    0.50    --  -90.00  60.00  15.20   62
  9  \w   -174.00 -32.00   0.50    0.50    --  -90.00  60.00 -21.78  284
 10  \w   -179.00-148.00   0.50    0.50    --  -90.00  20.00 -90.00   62
 11  \w   -119.00 -70.00   0.50    0.50    --  -90.00  56.00 -50.78   98
 12  \w   -174.00-139.00   0.50    0.50    --  -90.00  56.00 -50.78   70
;
_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      -0.0680007000
_diffrn_orient_matrix_UB_12      -0.0084489000
_diffrn_orient_matrix_UB_13      0.1039225000
_diffrn_orient_matrix_UB_21      -0.0052350000
_diffrn_orient_matrix_UB_22      0.0640807000
_diffrn_orient_matrix_UB_23      0.0142337000
_diffrn_orient_matrix_UB_31      -0.2579224000
_diffrn_orient_matrix_UB_32      0.0008657000
_diffrn_orient_matrix_UB_33      -0.0424026000
_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  0.0736
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12778
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.708
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77778
_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    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Hexanes (1:20)'
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0048(7)
_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   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0874P)^2^+0.4560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2990
_reflns_number_total             3300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02591g2.cif
_cod_data_source_block           juliana_unknown_110519
_cod_depositor_comments
'Adding full bibliography for 7157868--7157873.cif.'
_cod_database_code               7157869
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHNO
_diffrn_oxdiff_digest_frames
;
01b0dfda5cc5c33cd071f770f9d4229b83000269a4b
;
_diffrn_oxdiff_digest_hkl
;
019eef70ec04a5e4cf4f6f0df3044e35d6fb92
;
_reflns_odcompleteness_completeness 98.99
_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:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N19(H19), C18(H18), C12(H12), C8(H8), C11(H11), C9(H9), C10(H10), C17(H17),
 C14(H14), C25(H25), C26(H26), C2(H2), C15(H15), C23(H23), C22(H22), C24(H24),
 C16(H16)
;
_shelx_res_checksum              21790
_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id Juliana_unknown_110519
_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 1.918
_oxdiff_exptl_absorpt_empirical_full_min 0.124