Solvent-free synthesis of 5-(aryl/alkyl)amino-1,2,4-triazines and α-arylamino-2,2′-bipyridines with greener prospects
Kopchuk, Dmitry S.; Chepchugov, Nikolay V.; Kovalev, Igor S.; Santra, Sougata; Rahman, Matiur; Giri, Kousik; Zyryanov, Grigory V.; Majee, Adinath; Charushin, Valery N.; Chupakhin, Oleg N.; RSC Adv. 7 (2017) 9610–; doi:10.1039/C6RA26305D

data_7227606
_publ_section_title
;
 Solvent-free synthesis of 5-(aryl/alkyl)amino-1,2,4-triazines and
 \a-arylamino-2,2&#x2032;-bipyridines with greener prospects
;
_journal_issue                   16
_journal_name_full               'RSC Adv.'
_journal_page_first              9610
_journal_paper_doi               10.1039/C6RA26305D
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C19 H18 N4 O'
_chemical_formula_sum            'C19 H18 N4 O'
_chemical_formula_weight         318.37
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-16
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-09-20 deposited with the CCDC.
2017-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.5790(8)
_cell_length_b                   9.4791(5)
_cell_length_c                   30.0335(19)
_cell_measurement_reflns_used    1735
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.9670
_cell_measurement_theta_min      2.8630
_cell_volume                     3296.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8913
_diffrn_measurement_details
;
  1 omega  -25.00   16.00   1.0000  159.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000    0.0000 41

  2 omega   12.00   64.00   1.0000  159.8200
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000 -120.0000 52

  3 omega    2.00   69.00   1.0000  159.8200
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000  120.0000 67
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0241768000
_diffrn_orient_matrix_UB_12      0.0186823000
_diffrn_orient_matrix_UB_13      -0.0208752000
_diffrn_orient_matrix_UB_21      -0.0525080000
_diffrn_orient_matrix_UB_22      -0.0185469000
_diffrn_orient_matrix_UB_23      -0.0106835000
_diffrn_orient_matrix_UB_31      -0.0203645000
_diffrn_orient_matrix_UB_32      0.0700258000
_diffrn_orient_matrix_UB_33      0.0027441000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11172
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.78
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                2401
_reflns_number_total             4570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra26305d2.cif
_cod_data_source_block           exp_1074
_cod_original_cell_volume        3296.4(3)
_cod_database_code               7227606
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22