#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/13/4031342.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4031342
loop_
_publ_author_name
'Coogan, Niall T.'
'Chimes, Michael A.'
'Raftery, James'
'Mocilac, Pavle'
'Denecke, Melissa A.'
_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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0410P)²+1.7316P] where P=(Fo²+2Fc²)/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 > 2σ(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
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         C23H15N7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N2 N 0.12717(10) 0.8090(2) 0.43765(7) 0.0259(3) Uani 1 1 d . . .
N4 N 0.05601(9) 1.1909(2) 0.45259(7) 0.0231(3) Uani 1 1 d . . .
N1 N 0.0000 0.8883(3) 0.2500 0.0204(4) Uani 1 2 d S T P
N3 N 0.02140(9) 1.0758(2) 0.39108(7) 0.0231(3) Uani 1 1 d . . .
C1 C 0.0000 0.4566(4) 0.2500 0.0237(5) Uani 1 2 d S T P
H1 H 0.0000 0.3107 0.2500 0.028 Uiso 1 2 calc RS T P
C4 C 0.06066(10) 0.8971(3) 0.38440(8) 0.0200(4) Uani 1 1 d . . .
C3 C 0.02835(10) 0.7796(3) 0.31355(8) 0.0203(4) Uani 1 1 d . . .
C7 C 0.16836(10) 1.2588(3) 0.56762(8) 0.0202(4) Uani 1 1 d . . .
C6 C 0.12714(10) 1.1217(3) 0.50442(8) 0.0205(4) Uani 1 1 d . . .
C5 C 0.15979(12) 0.9226(3) 0.49747(9) 0.0263(4) Uani 1 1 d . . .
H5 H 0.2066 0.8688 0.5369 0.032 Uiso 1 1 calc R . .
C10 C 0.24851(11) 1.5248(3) 0.68474(9) 0.0269(4) Uani 1 1 d . . .
H10 H 0.2759 1.6154 0.7244 0.032 Uiso 1 1 calc R . .
C11 C 0.16468(12) 1.5714(3) 0.63785(9) 0.0280(4) Uani 1 1 d . . .
H11 H 0.1344 1.6934 0.6457 0.034 Uiso 1 1 calc R . .
C12 C 0.12523(11) 1.4405(3) 0.57975(9) 0.0252(4) Uani 1 1 d . . .
H12 H 0.0681 1.4743 0.5476 0.030 Uiso 1 1 calc R . .
C9 C 0.29193(11) 1.3460(3) 0.67347(9) 0.0263(4) Uani 1 1 d . . .
H9 H 0.3492 1.3138 0.7056 0.032 Uiso 1 1 calc R . .
C2 C 0.02991(11) 0.5655(3) 0.31613(9) 0.0229(4) Uani 1 1 d . . .
H2 H 0.0511 0.4956 0.3625 0.027 Uiso 1 1 calc R . .
C8 C 0.25258(11) 1.2136(3) 0.61574(9) 0.0239(4) Uani 1 1 d . . .
H8 H 0.2830 1.0910 0.6087 0.029 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 N2 C4 115.25(14) . .
C6 N4 N3 119.34(14) . .
C3 N1 C3 116.4(2) . 2
C4 N3 N4 118.20(13) . .
C2 C1 H1 120.8 . .
C2 C1 H1 120.8 2 .
C2 C1 C2 118.4(2) 2 .
N2 C4 C3 116.24(14) . .
N3 C4 N2 125.46(15) . .
N3 C4 C3 118.29(14) . .
N1 C3 C4 117.24(15) . .
N1 C3 C2 123.72(16) . .
C2 C3 C4 119.04(14) . .
C12 C7 C6 120.78(14) . .
C8 C7 C6 120.93(15) . .
C8 C7 C12 118.27(15) . .
N4 C6 C7 118.01(15) . .
N4 C6 C5 119.45(15) . .
C5 C6 C7 122.54(14) . .
N2 C5 C6 121.69(15) . .
N2 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
C9 C10 C11 119.69(16) . .
C10 C11 H11 119.9 . .
C12 C11 C10 120.13(17) . .
C12 C11 H11 119.9 . .
C7 C12 H12 119.6 . .
C11 C12 C7 120.85(15) . .
C11 C12 H12 119.6 . .
C10 C9 H9 119.8 . .
C10 C9 C8 120.50(15) . .
C8 C9 H9 119.8 . .
C1 C2 C3 118.88(16) . .
C1 C2 H2 120.6 . .
C3 C2 H2 120.6 . .
C7 C8 H8 119.7 . .
C9 C8 C7 120.56(16) . .
C9 C8 H8 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C4 1.351(2) .
N2 C5 1.317(2) .
N4 N3 1.3509(19) .
N4 C6 1.334(2) .
N1 C3 1.3436(19) .
N1 C3 1.3437(19) 2
N3 C4 1.330(2) .
C1 H1 0.9500 .
C1 C2 1.385(2) .
C1 C2 1.385(2) 2
C4 C3 1.487(2) .
C3 C2 1.395(2) .
C7 C6 1.477(2) .
C7 C12 1.401(2) .
C7 C8 1.401(2) .
C6 C5 1.407(2) .
C5 H5 0.9500 .
C10 H10 0.9500 .
C10 C11 1.389(2) .
C10 C9 1.383(2) .
C11 H11 0.9500 .
C11 C12 1.383(2) .
C12 H12 0.9500 .
C9 H9 0.9500 .
C9 C8 1.384(2) .
C2 H2 0.9500 .
C8 H8 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
N2 C4 C3 N1 -147.53(13) .
N2 C4 C3 C2 31.7(2) .
N4 N3 C4 N2 7.2(2) .
N4 N3 C4 C3 -174.22(14) .
N4 C6 C5 N2 6.2(3) .
N1 C3 C2 C1 -0.6(2) .
N3 N4 C6 C7 174.68(13) .
N3 N4 C6 C5 -5.7(2) .
N3 C4 C3 N1 33.8(2) .
N3 C4 C3 C2 -146.93(16) .
C4 N2 C5 C6 -0.2(2) .
C4 C3 C2 C1 -179.82(12) .
C3 N1 C3 C4 179.53(15) 2
C3 N1 C3 C2 0.31(12) 2
C7 C6 C5 N2 -174.14(15) .
C6 N4 N3 C4 -0.6(2) .
C6 C7 C12 C11 -178.52(15) .
C6 C7 C8 C9 178.07(15) .
C5 N2 C4 N3 -6.7(2) .
C5 N2 C4 C3 174.77(15) .
C10 C11 C12 C7 0.6(3) .
C10 C9 C8 C7 0.3(3) .
C11 C10 C9 C8 0.2(3) .
C12 C7 C6 N4 10.8(2) .
C12 C7 C6 C5 -168.87(16) .
C12 C7 C8 C9 -0.2(2) .
C9 C10 C11 C12 -0.6(3) .
C2 C1 C2 C3 0.28(11) 2
C8 C7 C6 N4 -167.50(15) .
C8 C7 C6 C5 12.9(2) .
C8 C7 C12 C11 -0.2(2) .
