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_7157873
_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         'C22 H20 N4 O3 S'
_chemical_formula_sum            'C22 H20 N4 O3 S'
_chemical_formula_weight         420.48
_chemical_name_systematic
5-((4-methoxyphenyl)thio)-4-(4-nitrophenyl)-2-(propylamino)nicotinonitrile
_chemical_properties_physical    estable
_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             2019-09-09
_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                 92.3040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1835(2)
_cell_length_b                   24.2903(4)
_cell_length_c                   6.05870(10)
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.5800
_cell_measurement_theta_min      1.7820
_cell_volume                     2085.66(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 0.970
_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   -139.00   8.00   0.50    0.50    --  -50.50  40.00  30.00  294
  2  \w   -139.00   8.00   0.50    0.50    --  -50.50  40.00  90.00  294
  3  \w   -175.00 -85.00   0.50    0.50    --  -90.00  30.00  90.00  180
  4  \w   -175.00 -53.00   0.50    0.50    --  -90.00  60.00 116.67  244
  5  \w    -73.00 -45.00   0.50    0.50    --  -90.00  20.00  30.00   56
  6  \w   -100.00 -74.00   0.50    0.50    --  -90.00  58.00  48.64   52
  7  \w   -179.00-113.00   0.50    0.50    --  -90.00  58.00  48.64  132
  8  \w   -171.00 -94.00   0.50    0.50    --  -90.00  20.00  30.00  154
  9  \w   -142.00-116.00   0.50    0.50    --  -90.00  60.00  90.31   52
 10  \w   -128.00 -31.00   0.50    0.50    --  -90.00  20.00-180.00  194
 11  \w   -176.00-151.00   0.50    0.50    --  -90.00  60.00  90.31   50
;
_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      0.0239590000
_diffrn_orient_matrix_UB_12      0.0608241000
_diffrn_orient_matrix_UB_13      0.0478120000
_diffrn_orient_matrix_UB_21      -0.1044796000
_diffrn_orient_matrix_UB_22      0.0155150000
_diffrn_orient_matrix_UB_23      -0.0426592000
_diffrn_orient_matrix_UB_31      -0.0182015000
_diffrn_orient_matrix_UB_32      -0.0091298000
_diffrn_orient_matrix_UB_33      0.2461936000
_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  0.0407
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13201
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.825
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52800
_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    1.339
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_preparation       Re-crystalliaztion
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Hexane (1:20)'
_exptl_crystal_size_max          0.734
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0015(3)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0627P)^2^+0.4760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3558
_reflns_number_total             3903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02591g2.cif
_cod_data_source_block           juliana_no2phsphome_090919
_cod_depositor_comments
'Adding full bibliography for 7157868--7157873.cif.'
_cod_database_code               7157873
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C22H20N4O3S
_diffrn_oxdiff_digest_frames
;
014cb06e4044d5f02b1acac148db54e12100042f763
;
_diffrn_oxdiff_digest_hkl
;
012cee91ea051d19f824f6c691bdbd8e9d4096
;
_reflns_odcompleteness_completeness 99.35
_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:
 C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 N25(H25), C5(H5), C22(H22), C8(H8), C12(H12), C18(H18), C21(H21), C11(H11),
 C9(H9), C19(H19)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              52926
_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id NO2PhSPhOMe
_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 4.212
_oxdiff_exptl_absorpt_empirical_full_min 0.191