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_4031344
_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         'C8 H9 N3 O'
_chemical_formula_sum            'C8 H9 N3 O'
_chemical_formula_weight         163.18
_chemical_melting_point          381
_chemical_name_common            E-INPH
_chemical_name_systematic        '(1E,2E)-2-hydrazono-1-phenylethanone oxime'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Wed Apr 08 14:44:53 2015'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_cell_angle_alpha                72.166(5)
_cell_angle_beta                 86.199(4)
_cell_angle_gamma                73.290(4)
_cell_formula_units_Z            4
_cell_length_a                   8.2989(4)
_cell_length_b                   10.3062(5)
_cell_length_c                   10.3246(5)
_cell_measurement_reflns_used    6123
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.4742
_cell_measurement_theta_min      4.6930
_cell_volume                     804.90(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
  1 omega   65.61  218.61   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   73.8669   49.2094 153

  2 phi    -16.98  311.22   1.0006    8.0000
omega____ theta____ kappa____ phi______ frames
 229.2097  112.0000   73.8669     -     328

  3 phi    -25.36  284.83   1.0006    8.0000
omega____ theta____ kappa____ phi______ frames
 154.2097  110.0000   73.8669     -     310

  4 omega  116.73  266.73   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8669  329.2088 150

  5 phi    -11.22  144.88   1.0006    8.0000
omega____ theta____ kappa____ phi______ frames
 134.1594  105.0000   73.8669     -     156

  6 omega   81.26  209.26   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   73.8669  169.2088 128

  7 omega  118.71  268.71   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669   74.2100 150

  8 omega   94.52  215.52   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.8669  279.2081 121

  9 omega   84.43  219.43   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669  139.2094 135

 10 omega   97.45  225.45   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.8669    4.2094 128

 11 omega  108.63  237.63   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8669  254.2100 129

 12 phi    175.98  328.17   1.0012    4.5000
omega____ theta____ kappa____ phi______ frames
 321.0197  -15.0000   73.8669     -     152

 13 omega  149.14  265.14   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669  204.2094 116

 14 phi      7.22  102.28   1.0006    8.0000
omega____ theta____ kappa____ phi______ frames
 184.2097  113.0000   73.8669     -     95

 15 omega  -84.83  -12.83   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -62.0000   73.8669  -18.2900 72

 16 omega   42.13  114.13   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       70.5000   73.8669  -25.7900 72

 17 omega  179.14  250.14   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       95.0000   73.8669   74.2100 71

 18 phi    -13.17   93.90   1.0006    8.0000
omega____ theta____ kappa____ phi______ frames
 108.8197  110.0000   73.8669     -     107

 19 omega   91.80  191.80   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669  304.2088 100

;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      0.1618904000
_diffrn_orient_matrix_UB_12      0.0476549000
_diffrn_orient_matrix_UB_13      -0.0300205000
_diffrn_orient_matrix_UB_21      -0.1060507000
_diffrn_orient_matrix_UB_22      0.1564946000
_diffrn_orient_matrix_UB_23      -0.0364778000
_diffrn_orient_matrix_UB_31      0.0114846000
_diffrn_orient_matrix_UB_32      -0.0038181000
_diffrn_orient_matrix_UB_33      0.1495021000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9382
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         74.65
_diffrn_reflns_theta_min         4.70
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.8077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method
'difusion = dichloromethane vs. diethylether'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0629P)^2^+0.1531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2733
_reflns_number_total             3111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01380_si_002.cif
_cod_data_source_block           EINPH
_cod_depositor_comments
'Adding full bibliography for 4031342--4031344.cif.'
_cod_database_code               4031344