#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:03:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178766 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/20/4102062.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_4102062
loop_
_publ_author_name
'Benjamin J. Coe'
'John Fielden'
'Simon P. Foxon'
'Bruce S. Brunschwig'
'Inge Asselberghs'
'Koen Clays'
'Anna Samoc'
'Marek Samoc'
_publ_section_title
;
 Combining Very Large Quadratic and cubic Nonlinear Optical Responses in
 Extended, Tris-Chelate Metallochromophores with Six π-Conjugated
 Pyridinium Substituents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3496
_journal_page_last               3513
_journal_paper_doi               10.1021/ja910538s
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C36 H28 N4, 2(C3 H7 N O), 2 (F6 P)'
_chemical_formula_sum            'C42 H42 F12 N6 O2 P2'
_chemical_formula_weight         952.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-03-18 # Formatted by publCIF
;
_cell_angle_alpha                90.000
_cell_angle_beta                 109.478(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   9.1252(13)
_cell_length_b                   17.637(2)
_cell_length_c                   13.683(2)
_cell_measurement_reflns_used    5399
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5849
_cell_measurement_theta_min      2.6203
_cell_volume                     2076.1(5)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11) 
;
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1992)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Oxford Diffraction XCalibur 2'
_diffrn_measurement_method       'phi and omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11919
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_correction_T_min  0.9410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0561
_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)+(0.1030P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                3259
_reflns_number_total             4694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910538s_si_002.cif
_cod_data_source_block           '[Ph2bbpe2+][PF6]2.2DMF'
_cod_database_code               4102062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.94175(8) 0.15552(4) 0.44566(5) 0.0253(2) Uani 1 1 d . . .
F1 F 1.05057(19) 0.08568(10) 0.49322(14) 0.0487(5) Uani 1 1 d . . .
F2 F 1.0850(2) 0.21056(10) 0.46855(15) 0.0532(5) Uani 1 1 d . . .
O1 O 0.4351(2) 0.33051(13) 0.62362(15) 0.0465(6) Uani 1 1 d . . .
F3 F 0.9299(3) 0.17346(12) 0.55565(17) 0.0701(7) Uani 1 1 d . . .
N3 N 0.3847(2) 0.30146(11) 0.77039(15) 0.0247(5) Uani 1 1 d . . .
F6 F 0.7985(2) 0.09983(10) 0.42136(18) 0.0688(7) Uani 1 1 d . . .
F5 F 0.8298(2) 0.22454(10) 0.39819(19) 0.0735(7) Uani 1 1 d . . .
N1 N 0.9826(2) 0.07832(11) 1.07894(15) 0.0228(4) Uani 1 1 d . . .
N2 N -0.0853(2) 0.08159(10) 0.74284(14) 0.0192(4) Uani 1 1 d . . .
F4 F 0.9546(4) 0.13662(12) 0.33665(16) 0.0899(9) Uani 1 1 d . . .
C3 C 0.7852(3) 0.01502(13) 0.94342(16) 0.0193(5) Uani 1 1 d . . .
H3 H 0.7589 -0.0233 0.8938 0.023 Uiso 1 1 calc R . .
C5 C 0.6709(3) 0.06277(13) 0.95533(17) 0.0213(5) Uani 1 1 d . . .
C6 C 0.5098(3) 0.05346(13) 0.88991(17) 0.0208(5) Uani 1 1 d . . .
H6 H 0.4880 0.0223 0.8320 0.025 Uiso 1 1 calc R . .
C13 C -0.2507(3) 0.07752(14) 0.69264(16) 0.0211(5) Uani 1 1 d . . .
C4 C 0.9378(3) 0.02489(12) 1.00573(16) 0.0186(5) Uani 1 1 d . . .
C9 C 0.1664(3) 0.03748(13) 0.76090(17) 0.0207(5) Uani 1 1 d . . .
H9 H 0.2312 0.0067 0.7381 0.025 Uiso 1 1 calc R . .
C10 C 0.0109(3) 0.03736(13) 0.71000(17) 0.0221(5) Uani 1 1 d . . .
H10 H -0.0303 0.0067 0.6520 0.026 Uiso 1 1 calc R . .
C11 C 0.1270(3) 0.12970(13) 0.87688(17) 0.0207(5) Uani 1 1 d . . .
H11 H 0.1660 0.1620 0.9334 0.025 Uiso 1 1 calc R . .
C18 C -0.3368(3) 0.14352(15) 0.67268(19) 0.0268(6) Uani 1 1 d . . .
H18 H -0.2885 0.1905 0.6886 0.032 Uiso 1 1 calc R . .
C8 C 0.2291(3) 0.08366(12) 0.84732(16) 0.0193(5) Uani 1 1 d . . .
C7 C 0.3924(3) 0.08733(13) 0.90889(17) 0.0208(5) Uani 1 1 d . . .
H7 H 0.4179 0.1168 0.9686 0.025 Uiso 1 1 calc R . .
C15 C -0.4787(3) 0.00372(16) 0.62513(18) 0.0294(6) Uani 1 1 d . . .
H15 H -0.5269 -0.0432 0.6081 0.035 Uiso 1 1 calc R . .
C14 C -0.3200(3) 0.00751(14) 0.66970(17) 0.0240(5) Uani 1 1 d . . .
H14 H -0.2604 -0.0365 0.6841 0.029 Uiso 1 1 calc R . .
C1 C 0.8718(3) 0.12362(15) 1.08936(19) 0.0280(6) Uani 1 1 d . . .
H1 H 0.9011 0.1611 1.1399 0.034 Uiso 1 1 calc R . .
C12 C -0.0273(3) 0.12837(13) 0.82518(17) 0.0203(5) Uani 1 1 d . . .
H12 H -0.0937 0.1595 0.8460 0.024 Uiso 1 1 calc R . .
C2 C 0.7174(3) 0.11866(14) 1.03052(19) 0.0248(5) Uani 1 1 d . . .
H2 H 0.6453 0.1522 1.0409 0.030 Uiso 1 1 calc R . .
C19 C 0.2284(3) 0.27629(16) 0.7168(2) 0.0332(6) Uani 1 1 d . . .
H19A H 0.1929 0.2972 0.6481 0.050 Uiso 1 1 calc R . .
H19B H 0.1615 0.2929 0.7538 0.050 Uiso 1 1 calc R . .
H19C H 0.2265 0.2219 0.7127 0.050 Uiso 1 1 calc R . .
C21 C 0.4736(3) 0.32672(15) 0.7182(2) 0.0314(6) Uani 1 1 d . . .
H21 H 0.5733 0.3429 0.7564 0.038 Uiso 1 1 calc R . .
C16 C -0.5670(3) 0.06883(18) 0.60544(18) 0.0331(6) Uani 1 1 d . . .
H16 H -0.6746 0.0658 0.5765 0.040 Uiso 1 1 calc R . .
C17 C -0.4954(3) 0.13828(16) 0.62879(19) 0.0314(6) Uani 1 1 d . . .
H17 H -0.5552 0.1822 0.6147 0.038 Uiso 1 1 calc R . .
C20 C 0.4398(4) 0.29423(17) 0.8823(2) 0.0414(7) Uani 1 1 d . . .
H20A H 0.5438 0.3137 0.9099 0.062 Uiso 1 1 calc R . .
H20B H 0.4390 0.2418 0.9008 0.062 Uiso 1 1 calc R . .
H20C H 0.3731 0.3225 0.9103 0.062 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
F4 P1 F2 89.99(13) . . ?
F4 P1 F3 179.24(14) . . ?
F2 P1 F3 90.16(11) . . ?
F4 P1 F6 89.25(14) . . ?
F2 P1 F6 179.22(13) . . ?
F3 P1 F6 90.60(13) . . ?
F4 P1 F1 89.42(13) . . ?
F2 P1 F1 91.88(11) . . ?
F3 P1 F1 89.83(12) . . ?
F6 P1 F1 87.96(10) . . ?
F4 P1 F5 90.91(14) . . ?
F2 P1 F5 89.24(11) . . ?
F3 P1 F5 89.84(13) . . ?
F6 P1 F5 90.93(11) . . ?
F1 P1 F5 178.84(11) . . ?
C21 N3 C19 120.7(2) . . ?
C21 N3 C20 122.7(2) . . ?
C19 N3 C20 116.6(2) . . ?
C1 N1 C4 116.7(2) . . ?
C12 N2 C10 120.6(2) . . ?
C12 N2 C13 119.04(19) . . ?
C10 N2 C13 120.34(19) . . ?
C4 C3 C5 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C5 C3 H3 120.3 . . ?
C2 C5 C3 117.5(2) . . ?
C2 C5 C6 122.3(2) . . ?
C3 C5 C6 120.2(2) . . ?
C7 C6 C5 123.1(2) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C14 C13 C18 121.6(2) . . ?
C14 C13 N2 118.9(2) . . ?
C18 C13 N2 119.4(2) . . ?
N1 C4 C3 123.1(2) . . ?
N1 C4 C4 116.3(2) . 3_757 ?
C3 C4 C4 120.7(2) . 3_757 ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 N2 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
N2 C10 H10 119.7 . . ?
C12 C11 C8 121.3(2) . . ?
C12 C11 H11 119.3 . . ?
C8 C11 H11 119.3 . . ?
C17 C18 C13 118.5(3) . . ?
C17 C18 H18 120.7 . . ?
C13 C18 H18 120.7 . . ?
C9 C8 C11 117.5(2) . . ?
C9 C8 C7 124.9(2) . . ?
C11 C8 C7 117.6(2) . . ?
C6 C7 C8 127.4(2) . . ?
C6 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
N1 C1 C2 124.5(2) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C11 C12 N2 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
N2 C12 H12 120.1 . . ?
C1 C2 C5 118.7(2) . . ?
C1 C2 H2 120.6 . . ?
C5 C2 H2 120.6 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C21 N3 125.2(3) . . ?
O1 C21 H21 117.4 . . ?
N3 C21 H21 117.4 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F4 1.571(2) . ?
P1 F2 1.5734(18) . ?
P1 F3 1.576(2) . ?
P1 F6 1.5792(19) . ?
P1 F1 1.5798(18) . ?
P1 F5 1.583(2) . ?
O1 C21 1.224(3) . ?
N3 C21 1.325(3) . ?
N3 C19 1.439(3) . ?
N3 C20 1.449(3) . ?
N1 C1 1.333(3) . ?
N1 C4 1.336(3) . ?
N2 C12 1.354(3) . ?
N2 C10 1.358(3) . ?
N2 C13 1.436(3) . ?
C3 C4 1.380(3) . ?
C3 C5 1.391(3) . ?
C3 H3 0.9300 . ?
C5 C2 1.385(3) . ?
C5 C6 1.454(3) . ?
C6 C7 1.325(3) . ?
C6 H6 0.9300 . ?
C13 C14 1.375(3) . ?
C13 C18 1.380(3) . ?
C4 C4 1.485(4) 3_757 ?
C9 C10 1.356(3) . ?
C9 C8 1.392(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.349(3) . ?
C11 C8 1.394(3) . ?
C11 H11 0.9300 . ?
C18 C17 1.373(4) . ?
C18 H18 0.9300 . ?
C8 C7 1.449(3) . ?
C7 H7 0.9300 . ?
C15 C14 1.373(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C1 C2 1.373(4) . ?
C1 H1 0.9300 . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
