#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019473.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019473
loop_
_publ_author_name
'Krause, Jeanette A.'
'Zhao, Daoli'
'Chatterjee, Sayandev'
'Falcon, Roland'
'Stoltz, Kristen'
'Warren, John C.'
'Wiswell, Sara E.'
'Connick, William B.'
'Collins, Sibrina N.'
_publ_section_title
;
 In-house and synchrotron X-ray diffraction studies of
 2-phenyl-1,10-phenanthroline, protonated salts, complexes with gold(III)
 and copper(II), and an orthometallation product with palladium(II)
;
_journal_coeditor_code           GZ3246
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              260
_journal_page_last               266
_journal_paper_doi               10.1107/S2053229614001843
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H13 N2 +, C F3 S O3 -'
_chemical_formula_moiety         'C18 H13 N2 +, C F3 S O3 -'
_chemical_formula_sum            'C19 H13 F3 N2 O3 S'
_chemical_formula_weight         406.37
_chemical_name_systematic
;
2-Phenyl-1,10-phenanthrolin-1-ium trifluoromethanesulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.848(2)
_cell_angle_beta                 95.687(2)
_cell_angle_gamma                100.439(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6682(2)
_cell_length_b                   10.7446(4)
_cell_length_c                   11.1174(4)
_cell_measurement_reflns_used    4788
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.65
_cell_measurement_theta_min      4.16
_cell_volume                     860.48(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART6000 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7396
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.87
_diffrn_reflns_theta_min         4.16
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.194
_exptl_absorpt_correction_T_max  0.8982
_exptl_absorpt_correction_T_min  0.7944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0352
_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/[σ²(Fo²)+(0.0628P)²+0.2088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2658
_reflns_number_total             2976
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            gz3246sup1.cif
_cod_data_source_block           III
_cod_database_code               2019473
_cod_database_fobs_code          2019473
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.82129(19) 0.37096(14) 0.24790(13) 0.0278(3) Uani d . 1 1
H H1 0.801(3) 0.444(2) 0.2719(19) 0.033 Uiso d . 1 1
N N2 0.75786(18) 0.48085(13) 0.48577(12) 0.0263(3) Uani d . 1 1
C C1 0.8476(2) 0.32438(17) 0.12979(16) 0.0320(4) Uani d . 1 1
H H1A 0.8439 0.3771 0.0732 0.038 Uiso calc R 1 1
C C2 0.8804(2) 0.19852(18) 0.08934(17) 0.0354(4) Uani d . 1 1
H H2A 0.8968 0.1638 0.0046 0.042 Uiso calc R 1 1
C C3 0.8890(2) 0.12466(17) 0.17333(17) 0.0337(4) Uani d . 1 1
H H3A 0.9116 0.0386 0.1462 0.040 Uiso calc R 1 1
C C4 0.8646(2) 0.17512(16) 0.29892(16) 0.0289(4) Uani d . 1 1
C C5 0.8277(2) 0.30197(16) 0.33458(15) 0.0265(3) Uani d . 1 1
C C6 0.8778(2) 0.10544(17) 0.39261(17) 0.0323(4) Uani d . 1 1
H H6A 0.9027 0.0197 0.3703 0.039 Uiso calc R 1 1
C C7 0.8553(2) 0.16056(17) 0.51205(17) 0.0324(4) Uani d . 1 1
H H7A 0.8684 0.1139 0.5732 0.039 Uiso calc R 1 1
C C8 0.8121(2) 0.28787(17) 0.54848(16) 0.0288(4) Uani d . 1 1
C C9 0.7979(2) 0.36027(16) 0.46050(15) 0.0258(3) Uani d . 1 1
C C10 0.7793(2) 0.34725(17) 0.67040(16) 0.0316(4) Uani d . 1 1
H H10A 0.7877 0.3034 0.7342 0.038 Uiso calc R 1 1
C C11 0.7354(2) 0.46834(17) 0.69647(16) 0.0311(4) Uani d . 1 1
H H11A 0.7110 0.5080 0.7780 0.037 Uiso calc R 1 1
C C12 0.7264(2) 0.53452(16) 0.60124(15) 0.0266(3) Uani d . 1 1
C C13 0.6835(2) 0.66778(16) 0.62633(15) 0.0272(4) Uani d . 1 1
C C14 0.6588(2) 0.73704(18) 0.74594(16) 0.0342(4) Uani d . 1 1
H H14A 0.6665 0.6981 0.8134 0.041 Uiso calc R 1 1
C C15 0.6233(3) 0.86216(19) 0.76683(17) 0.0385(4) Uani d . 1 1
H H15A 0.6072 0.9085 0.8486 0.046 Uiso calc R 1 1
C C16 0.6112(2) 0.92001(18) 0.66934(17) 0.0362(4) Uani d . 1 1
H H16A 0.5878 1.0061 0.6841 0.043 Uiso calc R 1 1
C C17 0.6335(2) 0.85149(17) 0.54991(17) 0.0342(4) Uani d . 1 1
H H17A 0.6237 0.8905 0.4826 0.041 Uiso calc R 1 1
C C18 0.6698(2) 0.72677(16) 0.52804(15) 0.0296(4) Uani d . 1 1
H H18A 0.6854 0.6809 0.4460 0.035 Uiso calc R 1 1
S S1 0.81504(5) 0.69060(4) 0.14034(4) 0.02846(15) Uani d . 1 1
O O1 0.82534(18) 0.61105(12) 0.01695(12) 0.0398(3) Uani d . 1 1
F F1 0.60625(17) 0.82031(13) 0.04384(11) 0.0519(3) Uani d . 1 1
F F2 0.57104(16) 0.81289(12) 0.23124(11) 0.0504(3) Uani d . 1 1
F F3 0.46595(16) 0.64175(12) 0.07531(12) 0.0553(3) Uani d . 1 1
O O2 0.78871(19) 0.61981(13) 0.23348(12) 0.0413(3) Uani d . 1 1
O O3 0.94529(17) 0.81352(12) 0.18409(11) 0.0367(3) Uani d . 1 1
C C19 0.6034(2) 0.74334(18) 0.12102(16) 0.0340(4) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 N1 C5 123.25(15)
C1 N1 H1 120.3(15)
C5 N1 H1 116.4(15)
C12 N2 C9 118.16(14)
N1 C1 C2 119.86(16)
N1 C1 H1A 120.1
C2 C1 H1A 120.1
C3 C2 C1 119.26(16)
C3 C2 H2A 120.4
C1 C2 H2A 120.4
C2 C3 C4 120.78(16)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
C3 C4 C5 117.80(15)
C3 C4 C6 123.76(15)
C5 C4 C6 118.44(15)
N1 C5 C4 119.02(15)
N1 C5 C9 119.48(15)
C4 C5 C9 121.50(15)
C7 C6 C4 120.67(15)
C7 C6 H6A 119.7
C4 C6 H6A 119.7
C6 C7 C8 121.38(16)
C6 C7 H7A 119.3
C8 C7 H7A 119.3
C9 C8 C10 116.17(15)
C9 C8 C7 120.19(15)
C10 C8 C7 123.63(15)
N2 C9 C8 124.57(15)
N2 C9 C5 117.66(14)
C8 C9 C5 117.76(15)
C11 C10 C8 119.77(15)
C11 C10 H10A 120.1
C8 C10 H10A 120.1
C10 C11 C12 119.82(15)
C10 C11 H11A 120.1
C12 C11 H11A 120.1
N2 C12 C11 121.48(15)
N2 C12 C13 116.88(14)
C11 C12 C13 121.64(14)
C14 C13 C18 118.69(15)
C14 C13 C12 121.89(15)
C18 C13 C12 119.42(14)
C15 C14 C13 120.46(16)
C15 C14 H14A 119.8
C13 C14 H14A 119.8
C16 C15 C14 120.44(16)
C16 C15 H15A 119.8
C14 C15 H15A 119.8
C15 C16 C17 119.56(16)
C15 C16 H16A 120.2
C17 C16 H16A 120.2
C18 C17 C16 120.52(16)
C18 C17 H17A 119.7
C16 C17 H17A 119.7
C17 C18 C13 120.33(15)
C17 C18 H18A 119.8
C13 C18 H18A 119.8
O1 S1 O3 115.13(8)
O1 S1 O2 115.22(8)
O3 S1 O2 114.60(8)
O1 S1 C19 104.23(8)
O3 S1 C19 102.96(8)
O2 S1 C19 102.26(8)
F3 C19 F2 107.36(15)
F3 C19 F1 108.06(15)
F2 C19 F1 107.10(14)
F3 C19 S1 111.83(13)
F2 C19 S1 110.79(12)
F1 C19 S1 111.48(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.329(2)
N1 C5 1.360(2)
N1 H1 0.81(2)
N2 C12 1.331(2)
N2 C9 1.351(2)
C1 C2 1.389(2)
C1 H1A 0.9500
C2 C3 1.376(3)
C2 H2A 0.9500
C3 C4 1.407(2)
C3 H3A 0.9500
C4 C5 1.407(2)
C4 C6 1.436(2)
C5 C9 1.439(2)
C6 C7 1.350(2)
C6 H6A 0.9500
C7 C8 1.432(2)
C7 H7A 0.9500
C8 C9 1.405(2)
C8 C10 1.411(2)
C10 C11 1.369(2)
C10 H10A 0.9500
C11 C12 1.421(2)
C11 H11A 0.9500
C12 C13 1.490(2)
C13 C14 1.397(2)
C13 C18 1.401(2)
C14 C15 1.386(3)
C14 H14A 0.9500
C15 C16 1.384(3)
C15 H15A 0.9500
C16 C17 1.387(2)
C16 H16A 0.9500
C17 C18 1.383(2)
C17 H17A 0.9500
C18 H18A 0.9500
S1 O1 1.4366(12)
S1 O3 1.4404(13)
S1 O2 1.4425(13)
S1 C19 1.8238(19)
F1 C19 1.335(2)
F2 C19 1.334(2)
F3 C19 1.324(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 1_555 0.81(2) 2.06(2) 2.773(2) 147(2) n
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
C5 N1 C1 C2 1.2(3)
N1 C1 C2 C3 -1.3(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 1.3(2)
C2 C3 C4 C6 -177.75(16)
C1 N1 C5 C4 0.2(2)
C1 N1 C5 C9 179.88(14)
C3 C4 C5 N1 -1.4(2)
C6 C4 C5 N1 177.62(14)
C3 C4 C5 C9 178.93(14)
C6 C4 C5 C9 -2.0(2)
C3 C4 C6 C7 179.05(15)
C5 C4 C6 C7 0.0(2)
C4 C6 C7 C8 2.0(3)
C6 C7 C8 C9 -2.1(3)
C6 C7 C8 C10 177.06(16)
C12 N2 C9 C8 -1.3(2)
C12 N2 C9 C5 178.63(13)
C10 C8 C9 N2 0.8(2)
C7 C8 C9 N2 -179.99(15)
C10 C8 C9 C5 -179.07(13)
C7 C8 C9 C5 0.1(2)
N1 C5 C9 N2 2.4(2)
C4 C5 C9 N2 -178.00(14)
N1 C5 C9 C8 -177.74(14)
C4 C5 C9 C8 1.9(2)
C9 C8 C10 C11 0.4(2)
C7 C8 C10 C11 -178.73(16)
C8 C10 C11 C12 -1.2(2)
C9 N2 C12 C11 0.4(2)
C9 N2 C12 C13 179.70(14)
C10 C11 C12 N2 0.8(2)
C10 C11 C12 C13 -178.47(15)
N2 C12 C13 C14 -176.04(14)
C11 C12 C13 C14 3.2(2)
N2 C12 C13 C18 3.1(2)
C11 C12 C13 C18 -177.67(15)
C18 C13 C14 C15 -0.7(3)
C12 C13 C14 C15 178.46(16)
C13 C14 C15 C16 0.2(3)
C14 C15 C16 C17 0.5(3)
C15 C16 C17 C18 -0.8(3)
C16 C17 C18 C13 0.3(3)
C14 C13 C18 C17 0.4(2)
C12 C13 C18 C17 -178.77(15)
