Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines.
Coogan, Niall T.; Chimes, Michael A.; Raftery, James; Mocilac, Pavle; Denecke, Melissa A.; The Journal of organic chemistry 80 (2015) 8684–8693; doi:10.1021/acs.joc.5b01380

data_4031342
_publ_section_title
;
 Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8684
_journal_page_last               8693
_journal_paper_doi               10.1021/acs.joc.5b01380
_journal_volume                  80
_journal_year                    2015
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C23 H15 N7'
_chemical_formula_sum            'C23 H15 N7'
_chemical_formula_weight         389.42
_chemical_melting_point_gt       573
_chemical_name_common            PhBTP
_chemical_name_systematic        2,6-bis(6-phenyl-1,2,4-triazin-3-yl)pyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.720(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3429(8)
_cell_length_b                   6.5112(4)
_cell_length_c                   18.4470(9)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    150.02(10)
_cell_measurement_theta_max      29.0560
_cell_measurement_theta_min      3.8950
_cell_volume                     1782.38(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1428
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details
;
  1 omega  -44.00   50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663   77.0000 -150.0000 94

  2 omega  -94.00  -40.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  178.0000    0.0000 54

  3 omega  -86.00  -41.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  -57.0000  150.0000 45

  4 omega   47.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7038  178.0000  120.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0074663000
_diffrn_orient_matrix_UB_12      0.0286084000
_diffrn_orient_matrix_UB_13      0.0381840000
_diffrn_orient_matrix_UB_21      -0.0402707000
_diffrn_orient_matrix_UB_22      0.0588374000
_diffrn_orient_matrix_UB_23      -0.0089396000
_diffrn_orient_matrix_UB_31      -0.0246782000
_diffrn_orient_matrix_UB_32      -0.0870443000
_diffrn_orient_matrix_UB_33      0.0065467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3745
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.194
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.451
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 'hot-box method, dimethylformamide'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0410P)^2^+1.7316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1647
_reflns_number_total             2023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01380_si_003.cif
_cod_data_source_block           PhBTP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>573' was changed to
'573' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031342--4031344.cif.
;
_cod_original_cell_volume        1782.39(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4031342
_chemical_oxdiff_formula         C23H15N7
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C11(H11), C12(H12), C9(H9), C2(H2), C8(H8)
;
_shelx_res_checksum              83007
_shelx_hkl_checksum              26162
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'