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_4031343
_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
'C30 H18 N8, C1.79 H4.19 N0.52 O0.6, 0.4(C3 H7 N1 O1)'
_chemical_formula_sum            'C33 H25 N9 O'
_chemical_formula_weight         563.62
_chemical_melting_point_gt       573
_chemical_name_common            PhBTPhen
_chemical_name_systematic
2,9-bis(6-phenyl-1,2,4-triazin-3-yl)-1,10-phenanthroline
_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             2015-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.922(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.786(3)
_cell_length_b                   6.1087(5)
_cell_length_c                   32.530(4)
_cell_measurement_reflns_used    1226
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      23.3070
_cell_measurement_theta_min      3.9080
_cell_volume                     5272.0(10)
_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      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   25.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8601   57.0000  -90.0000 63

  2 omega   -7.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8601   37.0000 -120.0000 85

  3 omega   34.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -99.0000    0.0000 27

  4 omega  -50.00   16.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -57.0000  120.0000 66
;
_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      -0.0256513000
_diffrn_orient_matrix_UB_12      0.0049619000
_diffrn_orient_matrix_UB_13      -0.0090051000
_diffrn_orient_matrix_UB_21      -0.0075062000
_diffrn_orient_matrix_UB_22      -0.0050610000
_diffrn_orient_matrix_UB_23      0.0200476000
_diffrn_orient_matrix_UB_31      0.0007657000
_diffrn_orient_matrix_UB_32      0.1158993000
_diffrn_orient_matrix_UB_33      0.0012585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.1140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3777
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.255
_diffrn_reflns_theta_max         23.255
_diffrn_reflns_theta_min         3.422
_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  0.80608
_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    1.420
_exptl_crystal_description       plate
_exptl_crystal_F_000             2352
_exptl_crystal_recrystallization_method 'hot box, dimethyl formamide'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.00097(19)
_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   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     410
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.1048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+31.5517P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2177
_refine_ls_wR_factor_ref         0.2377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2584
_reflns_number_total             3777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01380_si_004.cif
_cod_data_source_block           PhBTPhen
_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        5272.1(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4031343
_chemical_oxdiff_formula         C30H16N8
_chemical_oxdiff_usercomment     PhBTPhen
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.827(3) 0.173(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O1R-C1R \\sim O1S-C1S
 with sigma of 0.02
4. Rigid bond restraints
 C8, C7, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1R) = Uanis(O1S)
6. Rigid body (RIGU) restrains
 C11, C9, C8, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(O1R)=Sof(C1R)=Sof(H1R)=Sof(N1R)=Sof(C2R)=Sof(H2RA)=Sof(H2RB)=Sof(H2RC)=
 Sof(C3R)=Sof(H3RA)=Sof(H3RB)=Sof(H3RC)=1-FVAR(1)
 Sof(O1S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=
 Sof(H2SC)=Sof(C1S)=Sof(H1S)=FVAR(1)
8.a Aromatic/amide H refined with riding coordinates:
 C30(H30), C5(H5), C8(H8), C10(H10), C4(H4), C11(H11), C17(H17), C29(H29),
 C7(H7), C15(H15), C23(H23), C18(H18), C21(H21), C19(H19), C28(H28), C20(H20),
 C27(H27), C26(H26), C1S(H1S), C1R(H1R)
8.b Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C2S(H2SA,H2SB,H2SC), C2R(H2RA,H2RB,H2RC), C3R(H3RA,H3RB,
 H3RC)
;
_shelx_res_checksum              85922
_shelx_hkl_checksum              44984
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'