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_7157868
_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         'C26 H21 N3 O S'
_chemical_formula_sum            'C26 H21 N3 O S'
_chemical_formula_weight         423.52
_chemical_name_systematic
2-(benzylamino)-5-((4-methoxyphenyl)thio)-4-phenylnicotinonitrile
_chemical_properties_physical    'Air stable'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-19
_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                74.382(2)
_cell_angle_beta                 74.161(3)
_cell_angle_gamma                69.175(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9364(3)
_cell_length_b                   10.9906(3)
_cell_length_c                   12.2832(3)
_cell_measurement_reflns_used    10817
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.6770
_cell_measurement_theta_min      3.8440
_cell_volume                     1064.71(6)
_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 0.992
_diffrn_measured_fraction_theta_max 0.978
_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   8.00   0.50    0.50    --  -51.00  20.00  90.00  296
  2  \w   -140.00   8.00   0.50    0.50    --  -51.00  50.00  30.00  296
  3  \w   -140.00   8.00   0.50    0.50    --  -51.00  60.00-120.00  296
  4  \w   -140.00   8.00   0.50    0.50    --  -51.00  60.00 -90.00  296
  5  \w   -140.00   8.00   0.50    0.50    --  -51.00  50.00 150.00  296
  6  \w   -179.00 -31.00   0.50    0.50    --  -90.00  20.00  60.00  296
  7  \w   -179.00 -31.00   0.50    0.50    --  -90.00  60.00  53.95  296
  8  \w   -179.00 -31.00   0.50    0.50    --  -90.00  58.00  96.00  296
  9  \w   -179.00 -31.00   0.50    0.50    --  -90.00  20.00-150.00  296
 10  \w   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 -70.32  296
 11  \w   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 -90.91  296
 12  \w   -179.00 -31.00   0.50    0.50    --  -90.00  30.00 120.00  296
 13  \w   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 171.65  296
 14  \w   -179.00 -96.00   0.50    0.50    --  -90.00  30.00  30.00  166
 15  \w   -179.00-101.00   0.50    0.50    --  -90.00  30.00 -60.00  156
 16  \w   -171.00 -55.00   0.50    0.50    --  -90.00  51.00-146.73  232
 17  \w   -178.00-152.00   0.50    0.50    --  -90.00  58.00  45.81   52
 18  \w   -177.00 -31.00   0.50    0.50    --  -90.00  60.00 -29.89  292
;
_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      0.1124553000
_diffrn_orient_matrix_UB_12      -0.0965317000
_diffrn_orient_matrix_UB_13      -0.0803275000
_diffrn_orient_matrix_UB_21      0.0001414000
_diffrn_orient_matrix_UB_22      -0.1176017000
_diffrn_orient_matrix_UB_23      0.1022367000
_diffrn_orient_matrix_UB_31      -0.1508130000
_diffrn_orient_matrix_UB_32      -0.0140715000
_diffrn_orient_matrix_UB_33      -0.0271792000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17453
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.011
_diffrn_reflns_theta_min         3.811
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68813
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Hexanes (1:20)'
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0148(9)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0609P)^2^+0.5996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3914
_reflns_number_total             3933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02591g2.cif
_cod_data_source_block           juliana_ph_sphome_091919
_cod_depositor_comments
'Adding full bibliography for 7157868--7157873.cif.'
_cod_database_code               7157868
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHNOS
_diffrn_oxdiff_digest_frames
;
01c2d46f9d46201984e028b6f55387b932000467836
;
_diffrn_oxdiff_digest_hkl
;
01568560828477c5e60783c49bfcb279c902b0
;
_reflns_odcompleteness_completeness 99.27
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N22(H22), C5(H5), C11(H11), C19(H19), C12(H12), C8(H8), C18(H18), C29(H29),
 C10(H10), C15(H15), C16(H16), C28(H28), C25(H25), C9(H9), C27(H27), C26(H26)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              48026
_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id Ph_SPhOMe
_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 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.285