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_7157872
_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         'C16 H14 F3 N3 S'
_chemical_formula_sum            'C16 H14 F3 N3 S'
_chemical_formula_weight         337.36
_chemical_name_systematic
2-(benzylamino)-4-methyl-5-((2,2,2-trifluoroethyl)thio)nicotinonitrile
_chemical_properties_physical    estable
_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             2019-11-12
_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                94.122(2)
_cell_angle_beta                 94.410(2)
_cell_angle_gamma                102.197(2)
_cell_formula_units_Z            4
_cell_length_a                   5.33630(10)
_cell_length_b                   11.5026(2)
_cell_length_c                   25.9164(5)
_cell_measurement_reflns_used    6654
_cell_measurement_temperature    99.96(12)
_cell_measurement_theta_max      69.7450
_cell_measurement_theta_min      1.7110
_cell_volume                     1543.92(5)
_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      99.96(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.932
_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   -110.00 -75.00   0.50    0.50    --  -51.00  50.00 -30.00   70
  2  \w    -93.00   7.00   0.50    0.50    --  -51.00  20.00-150.00  200
  3  \w   -139.00 -98.00   0.50    0.50    --  -51.00  30.00 -60.00   82
  4  \w    -67.00   8.00   0.50    0.50    --  -51.00  50.00 -30.00  150
  5  \w    -76.00 -10.00   0.50    0.50    --  -51.00  50.00  90.00  132
  6  \w   -130.00-105.00   0.50    0.50    --  -51.00  20.00-150.00   50
  7  \w   -140.00 -79.00   0.50    0.50    --  -51.00  50.00  90.00  122
  8  \w    -90.00 -65.00   0.50    0.50    --  -51.00  30.00 -60.00   50
  9  \w   -122.00 -88.00   0.50    0.50    --  -90.00  60.00  49.48   68
 10  \w   -178.00 -85.00   0.50    0.50    --  -90.00  40.00 -90.00  186
 11  \w   -179.00-139.00   0.50    0.50    --  -90.00  60.00  49.48   80
 12  \w   -173.00 -77.00   0.50    0.50    --  -90.00  60.00 104.51  192
 13  \w   -179.00-152.00   0.50    0.50    --  -90.00  59.00 -76.72   54
 14  \w   -127.00 -56.00   0.50    0.50    --  -90.00  59.00 -76.72  142
 15  \w    -67.00 -41.00   0.50    0.50    --  -90.00  60.00  -0.67   52
 16  \w   -179.00 -36.00   0.50    0.50    --  -90.00  20.00-150.00  286
 17  \w   -132.00 -32.00   0.50    0.50    --  -90.00  60.00  88.34  200
 18  \w    -95.00 -60.00   0.50    0.50    --  -90.00  60.00 -34.42   70
 19  \w   -179.00 -36.00   0.50    0.50    --  -90.00  30.00  60.00  286
 20  \w   -179.00-146.00   0.50    0.50    --  -90.00  60.00-124.50   66
 21  \w   -108.00 -83.00   0.50    0.50    --  -90.00  60.00-124.50   50
 22  \w   -176.00-135.00   0.50    0.50    --  -90.00  60.00-155.14   82
 23  \w   -171.00-146.00   0.50    0.50    --  -90.00  59.00-117.16   50
 24  \w   -170.00-101.00   0.50    0.50    --  -90.00  60.00 -34.42  138
 25  \w    -99.00 -74.00   0.50    0.50    --  -90.00  60.00  -0.67   50
 26  \w    -69.00 -33.00   0.50    0.50    --  -90.00  60.00 104.51   72
 27  \w   -175.00-123.00   0.50    0.50    --  -90.00  60.00  -0.67  104
;
_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      -0.0627341000
_diffrn_orient_matrix_UB_12      -0.1323812000
_diffrn_orient_matrix_UB_13      0.0109823000
_diffrn_orient_matrix_UB_21      -0.0684461000
_diffrn_orient_matrix_UB_22      -0.0368658000
_diffrn_orient_matrix_UB_23      -0.0585602000
_diffrn_orient_matrix_UB_31      0.2817840000
_diffrn_orient_matrix_UB_32      -0.0068446000
_diffrn_orient_matrix_UB_33      -0.0058263000
_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  0.0802
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12450
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        66.574
_diffrn_reflns_theta_max         66.574
_diffrn_reflns_theta_min         3.435
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.184
_exptl_absorpt_correction_type   none
_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    1.451
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Hexane (1:20)'
_exptl_crystal_size_max          0.637
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.0005(6)
_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   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1294P)^2^+0.2242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4729
_reflns_number_total             5099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02591g2.cif
_cod_data_source_block           juliana_py_cyc_me_sch2cf3_111119_rint_25
_cod_depositor_comments
'Adding full bibliography for 7157868--7157873.cif.'
_cod_database_code               7157872
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C16H14F3N3S
_diffrn_oxdiff_digest_frames
;
01be539f0f459408a7aa382d01968aec2003084ccca
;
_diffrn_oxdiff_digest_hkl
;
0132ef6ac3f112d8c9b7f354507ccdd167657a
;
_reflns_odcompleteness_completeness 93.13
_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:
 C00Q(H00B,H00C), C6(H6A,H6B), C15(H15A,H15B), C013(H01D,H01E)
2.b Aromatic/amide H refined with riding coordinates:
 N00A(H00A), N2(H2), C5(H5), C12(H12), C8(H8), C00T(H00T), C00W(H00W),
 C00Y(H00Y), C11(H11), C10(H10), C017(H017), C9(H9), C019(H019), C01A(H01F)
2.c Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              8399
_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.151
_oxdiff_exptl_absorpt_empirical_full_min 0.205