#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/46/4114612.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_4114612
loop_
_publ_author_name
'Philippe Lainé'
'Fethi Bedioui'
'Philippe Ochsenbein'
'Valérie Marvaud'
'Michel Bonin'
'Edmond Amouyal'
_publ_section_title
;
 A New Class of Functionalized Terpyridyl Ligands as Building Blocks for
 Photosensitized Supramolecular Architectures. Synthesis, Structural, and
 Electronic Characterizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1364
_journal_page_last               1377
_journal_paper_doi               10.1021/ja011069p
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C38 H27 N4, B F4, 0.5(CH3CO2C2H5)'
_chemical_formula_sum            'C40.5 H27 B F4 N4 O'
_chemical_formula_weight         672.47
_chemical_name_common            H3TP+-tpy
_chemical_name_systematic
;
 ?
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                116.59(3)
_cell_angle_beta                 105.55(3)
_cell_angle_gamma                93.46(3)
_cell_formula_units_Z            2
_cell_length_a                   10.446(2)
_cell_length_b                   13.750(2)
_cell_length_c                   14.169(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.34
_cell_measurement_theta_min      17.78
_cell_volume                     1714.4(9)
_computing_cell_refinement       'CAD4 Express '
_computing_data_collection       'CAD4 Express '
_computing_data_reduction        MolEn
_computing_molecular_graphics    SHELXTL-plus
_computing_publication_material  XL
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       CAD4
_diffrn_measurement_method       'Profile fitted 2θ/ω scans'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.064097
_diffrn_orient_matrix_UB_12      -0.007057
_diffrn_orient_matrix_UB_13      -0.042874
_diffrn_orient_matrix_UB_21      0.027512
_diffrn_orient_matrix_UB_22      0.082871
_diffrn_orient_matrix_UB_23      0.037417
_diffrn_orient_matrix_UB_31      0.073897
_diffrn_orient_matrix_UB_32      -0.000786
_diffrn_orient_matrix_UB_33      0.061283
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6370
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         3.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       blocks
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0069(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.744
_refine_ls_goodness_of_fit_obs   1.842
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.745
_refine_ls_restrained_S_obs      1.829
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_obs          0.0601
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2337
_refine_ls_wR_factor_obs         0.2005
_reflns_number_observed          4196
_reflns_number_total             6103
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja011069p_1.cif
_cod_data_source_block           H3TP+-tpy
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1714.4(6)
_cod_original_formula_sum        'C40.50 H27 B F4 N4 O'
_cod_database_code               4114612
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.4163(2) 0.5284(2) 0.6326(2) 0.0743(6) Uani 1 d U
C2 C 0.3060(3) 0.4473(2) 0.5885(2) 0.0706(6) Uani 1 d U
C3 C 0.2967(3) 0.3717(2) 0.6282(2) 0.0694(6) Uani 1 d U
H3A H 0.2181(3) 0.3179(2) 0.5995(2) 0.083 Uiso 1 calc R
C4 C 0.4075(2) 0.3798(2) 0.7109(2) 0.0630(6) Uani 1 d U
C5 C 0.5221(3) 0.4610(2) 0.7562(2) 0.0659(6) Uani 1 d U
H5A H 0.5975(3) 0.4655(2) 0.8120(2) 0.079 Uiso 1 calc R
C6 C 0.5214(3) 0.5365(2) 0.7157(2) 0.0690(6) Uani 1 d U
N7 N 0.4043(2) 0.29809(14) 0.75042(15) 0.0606(5) Uani 1 d U
C8 C 0.3345(2) 0.3069(2) 0.8221(2) 0.0632(6) Uani 1 d U
C9 C 0.3271(3) 0.2263(2) 0.8534(2) 0.0678(6) Uani 1 d U
H9A H 0.2794(3) 0.2321(2) 0.9019(2) 0.081 Uiso 1 calc R
C10 C 0.3891(2) 0.1354(2) 0.8145(2) 0.0622(6) Uani 1 d U
C11 C 0.4629(2) 0.1327(2) 0.7450(2) 0.0660(6) Uani 1 d U
H11A H 0.5090(2) 0.0753(2) 0.7204(2) 0.079 Uiso 1 calc R
C12 C 0.4696(2) 0.2118(2) 0.7120(2) 0.0624(5) Uani 1 d U
C13 C 0.3727(2) 0.0454(2) 0.8427(2) 0.0643(6) Uani 1 d U
C14 C 0.4675(3) -0.0226(2) 0.8388(2) 0.0698(6) Uani 1 d U
H14A H 0.5438(3) -0.0095(2) 0.8208(2) 0.084 Uiso 1 calc R
C15 C 0.4487(3) -0.1092(2) 0.8615(2) 0.0805(7) Uani 1 d U
H15A H 0.5121(3) -0.1543(2) 0.8588(2) 0.097 Uiso 1 calc R
C16 C 0.3359(3) -0.1287(2) 0.8881(3) 0.0878(8) Uani 1 d U
H16A H 0.3225(3) -0.1879(2) 0.9019(3) 0.105 Uiso 1 calc R
C17 C 0.2434(3) -0.0618(3) 0.8943(3) 0.0901(8) Uani 1 d U
H17A H 0.1686(3) -0.0750(3) 0.9138(3) 0.108 Uiso 1 calc R
C18 C 0.2602(3) 0.0248(2) 0.8718(2) 0.0782(7) Uani 1 d U
H18A H 0.1966(3) 0.0697(2) 0.8759(2) 0.094 Uiso 1 calc R
C19 C 0.1936(3) 0.4392(3) 0.4934(2) 0.0831(7) Uani 1 d U
C20 C 0.2043(4) 0.5093(3) 0.4496(3) 0.1060(10) Uani 1 d U
H20 H 0.2813(4) 0.5652(3) 0.4803(3) 0.127 Uiso 1 calc R
C21 C 0.0974(6) 0.4944(5) 0.3582(4) 0.1285(14) Uani 1 d U
H21A H 0.1025(6) 0.5393(5) 0.3255(4) 0.154 Uiso 1 calc R
C22 C -0.0145(5) 0.4139(5) 0.3172(3) 0.1273(14) Uani 1 d U
H22A H -0.0882(5) 0.4036(5) 0.2571(3) 0.153 Uiso 1 calc R
C23 C -0.0167(4) 0.3479(4) 0.3662(3) 0.1182(12) Uani 1 d U
H23A H -0.0935(4) 0.2924(4) 0.3373(3) 0.142 Uiso 1 calc R
N24 N 0.0842(3) 0.3587(3) 0.4523(2) 0.1008(8) Uani 1 d U
C25 C 0.6382(3) 0.6302(2) 0.7657(2) 0.0728(6) Uani 1 d U
C26 C 0.6515(3) 0.6943(2) 0.7141(3) 0.0860(8) Uani 1 d U
H26 H 0.5879(3) 0.6780(2) 0.6461(3) 0.103 Uiso 1 calc R
C27 C 0.7603(4) 0.7817(3) 0.7656(3) 0.0979(10) Uani 1 d U
H27A H 0.7719(4) 0.8253(3) 0.7327(3) 0.117 Uiso 1 calc R
C28 C 0.8520(4) 0.8044(3) 0.8662(3) 0.0976(9) Uani 1 d U
H28A H 0.9255(4) 0.8643(3) 0.9031(3) 0.117 Uiso 1 calc R
C29 C 0.8329(3) 0.7366(3) 0.9116(3) 0.0923(8) Uani 1 d U
H29A H 0.8962(3) 0.7514(3) 0.9791(3) 0.111 Uiso 1 calc R
N30 N 0.7282(2) 0.6512(2) 0.8631(2) 0.0834(6) Uani 1 d U
C31 C 0.2657(2) 0.4016(2) 0.8638(2) 0.0654(6) Uani 1 d U
C32 C 0.3355(3) 0.5124(2) 0.9228(2) 0.0718(6) Uani 1 d U
H32A H 0.4276(3) 0.5294(2) 0.9337(2) 0.086 Uiso 1 calc R
C33 C 0.2683(3) 0.5963(2) 0.9646(2) 0.0838(8) Uani 1 d U
H33A H 0.3154(3) 0.6699(2) 1.0046(2) 0.101 Uiso 1 calc R
C34 C 0.1315(4) 0.5721(3) 0.9477(3) 0.0930(9) Uani 1 d U
H34A H 0.0862(4) 0.6292(3) 0.9759(3) 0.112 Uiso 1 calc R
C35 C 0.0622(3) 0.4633(3) 0.8891(3) 0.0911(8) Uani 1 d U
H35A H -0.0304(3) 0.4472(3) 0.8771(3) 0.109 Uiso 1 calc R
C36 C 0.1283(3) 0.3775(2) 0.8478(2) 0.0781(7) Uani 1 d U
H36A H 0.0810(3) 0.3041(2) 0.8096(2) 0.094 Uiso 1 calc R
C37 C 0.5413(3) 0.2050(2) 0.6330(2) 0.0660(6) Uani 1 d U
C38 C 0.6807(3) 0.2221(3) 0.6677(3) 0.0883(8) Uani 1 d U
H38A H 0.7295(3) 0.2397(3) 0.7406(3) 0.106 Uiso 1 calc R
C39 C 0.7484(4) 0.2128(4) 0.5923(3) 0.1117(11) Uani 1 d U
H39A H 0.8426(4) 0.2232(4) 0.6148(3) 0.134 Uiso 1 calc R
C40 C 0.6763(4) 0.1884(3) 0.4852(3) 0.1030(10) Uani 1 d U
H40A H 0.7219(4) 0.1852(3) 0.4361(3) 0.124 Uiso 1 calc R
C41 C 0.5388(4) 0.1690(3) 0.4509(3) 0.0926(9) Uani 1 d U
H41A H 0.4902(4) 0.1499(3) 0.3775(3) 0.111 Uiso 1 calc R
C42 C 0.4709(3) 0.1773(2) 0.5237(2) 0.0815(7) Uani 1 d U
H42A H 0.3765(3) 0.1641(2) 0.4994(2) 0.098 Uiso 1 calc R
B43 B 0.8488(3) 0.0964(3) 0.8415(3) 0.0819(9) Uani 1 d .
F44 F 0.7879(3) 0.1533(2) 0.9171(3) 0.1534(10) Uani 1 d .
F45 F 0.9327(2) 0.0404(2) 0.8792(2) 0.1297(8) Uani 1 d .
F46 F 0.9245(2) 0.1715(2) 0.8284(2) 0.1215(7) Uani 1 d .
F47 F 0.7487(2) 0.0224(2) 0.7426(2) 0.1143(6) Uani 1 d .
C48 C 1.0000 0.0000 0.5000 0.227(7) Uani 1 d SU
O49 O 1.0073(8) 0.0722(7) 0.3928(5) 0.298(4) Uani 1 d U
C50 C 1.0406(9) 0.0609(8) 0.4968(7) 0.209(3) Uani 1 d U
C52 C 1.1280(8) 0.1354(6) 0.5813(6) 0.198(3) Uani 1 d U
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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'
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
C6 N1 C2 119.4(2) . .
N1 C2 C3 121.9(2) . .
N1 C2 C19 117.4(2) . .
C3 C2 C19 120.7(3) . .
C4 C3 C2 117.4(2) . .
C3 C4 C5 121.8(2) . .
C3 C4 N7 118.9(2) . .
C5 C4 N7 119.3(2) . .
C4 C5 C6 117.5(2) . .
N1 C6 C5 122.0(2) . .
N1 C6 C25 117.8(2) . .
C5 C6 C25 120.2(2) . .
C8 N7 C12 121.2(2) . .
C8 N7 C4 120.1(2) . .
C12 N7 C4 118.6(2) . .
N7 C8 C9 119.1(2) . .
N7 C8 C31 120.4(2) . .
C9 C8 C31 120.5(2) . .
C8 C9 C10 121.9(2) . .
C11 C10 C9 116.7(2) . .
C11 C10 C13 122.0(2) . .
C9 C10 C13 121.4(2) . .
C12 C11 C10 122.0(2) . .
C11 C12 N7 119.1(2) . .
C11 C12 C37 121.8(2) . .
N7 C12 C37 119.0(2) . .
C18 C13 C14 118.5(2) . .
C18 C13 C10 120.6(2) . .
C14 C13 C10 120.9(2) . .
C15 C14 C13 120.5(2) . .
C16 C15 C14 119.8(3) . .
C17 C16 C15 120.6(2) . .
C16 C17 C18 120.5(3) . .
C17 C18 C13 120.2(3) . .
N24 C19 C20 122.6(3) . .
N24 C19 C2 116.0(3) . .
C20 C19 C2 121.4(3) . .
C19 C20 C21 118.3(4) . .
C22 C21 C20 119.3(4) . .
C21 C22 C23 118.5(4) . .
N24 C23 C22 123.8(4) . .
C23 N24 C19 117.5(3) . .
N30 C25 C26 122.2(3) . .
N30 C25 C6 116.7(2) . .
C26 C25 C6 121.1(3) . .
C27 C26 C25 118.5(3) . .
C28 C27 C26 119.5(3) . .
C27 C28 C29 118.7(3) . .
N30 C29 C28 123.0(3) . .
C29 N30 C25 118.1(3) . .
C36 C31 C32 119.3(2) . .
C36 C31 C8 118.0(2) . .
C32 C31 C8 122.5(2) . .
C33 C32 C31 120.1(3) . .
C34 C33 C32 120.4(3) . .
C35 C34 C33 119.7(3) . .
C34 C35 C36 120.8(3) . .
C35 C36 C31 119.6(3) . .
C38 C37 C42 119.3(2) . .
C38 C37 C12 119.2(2) . .
C42 C37 C12 121.4(2) . .
C37 C38 C39 119.3(3) . .
C40 C39 C38 120.2(3) . .
C41 C40 C39 120.1(3) . .
C40 C41 C42 120.3(3) . .
C41 C42 C37 120.7(3) . .
F44 B43 F45 110.3(3) . .
F44 B43 F46 108.2(3) . .
F45 B43 F46 108.8(3) . .
F44 B43 F47 108.1(3) . .
F45 B43 F47 109.9(3) . .
F46 B43 F47 111.6(3) . .
C50 C48 C50 179.998(3) 2_756 .
C50 C48 C52 145.1(5) 2_756 .
C50 C48 C52 34.9(5) . .
C50 C48 C52 34.9(5) 2_756 2_756
C50 C48 C52 145.1(5) . 2_756
C52 C48 C52 180.000(1) . 2_756
C48 C50 C52 119.2(9) . .
C48 C50 O49 123.7(8) . .
C52 C50 O49 117.1(9) . .
C48 C50 C50 0.001(2) . 2_756
C52 C50 C50 119.2(9) . 2_756
O49 C50 C50 123.7(8) . 2_756
C50 C52 C48 25.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.333(4) .
N1 C2 1.340(4) .
C2 C3 1.396(3) .
C2 C19 1.486(4) .
C3 C4 1.366(4) .
C4 C5 1.369(4) .
C4 N7 1.465(3) .
C5 C6 1.394(3) .
C6 C25 1.476(4) .
N7 C8 1.369(3) .
N7 C12 1.375(3) .
C8 C9 1.372(3) .
C8 C31 1.487(3) .
C9 C10 1.399(3) .
C10 C11 1.394(3) .
C10 C13 1.474(3) .
C11 C12 1.368(3) .
C12 C37 1.478(3) .
C13 C18 1.398(3) .
C13 C14 1.398(4) .
C14 C15 1.382(3) .
C15 C16 1.375(4) .
C16 C17 1.366(5) .
C17 C18 1.377(4) .
C19 N24 1.336(4) .
C19 C20 1.373(4) .
C20 C21 1.388(6) .
C21 C22 1.354(7) .
C22 C23 1.368(6) .
C23 N24 1.324(4) .
C25 N30 1.337(4) .
C25 C26 1.396(4) .
C26 C27 1.368(5) .
C27 C28 1.370(5) .
C28 C29 1.380(5) .
C29 N30 1.329(4) .
C31 C36 1.386(4) .
C31 C32 1.397(4) .
C32 C33 1.372(4) .
C33 C34 1.378(5) .
C34 C35 1.373(5) .
C35 C36 1.381(4) .
C37 C38 1.374(4) .
C37 C42 1.382(4) .
C38 C39 1.397(4) .
C39 C40 1.373(5) .
C40 C41 1.353(5) .
C41 C42 1.371(4) .
B43 F44 1.356(4) .
B43 F45 1.358(4) .
B43 F46 1.370(4) .
B43 F47 1.379(4) .
C48 C50 0.941(10) 2_756
C48 C50 0.941(10) .
C48 C52 1.881(7) .
C48 C52 1.881(7) 2_756
O49 C50 1.502(11) .
C50 C52 1.233(9) .
C50 C50 1.88(2) 2_756
