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#$Date: 2016-03-22 11:08:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178886 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/15/4111548.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_4111548
loop_
_publ_author_name
'Benjamin J. Coe'
'James A. Harris'
'Lathe A. Jones'
'Bruce S. Brunschwig'
'Kai Song'
'Koen Clays'
'Javier Garín'
'Jesús Orduna'
'Simon J. Coles'
'Michael B. Hursthouse'
_publ_section_title
;
 Syntheses and Properties of Two-Dimensional Charged Nonlinear Optical
 Chromophores Incorporating Redox-Switchable cis-Tetraammineruthenium(II)
 Centers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4845
_journal_page_last               4859
_journal_paper_doi               10.1021/ja0424124
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C35 H30 F12 N4 O P2'
_chemical_formula_weight         812.57
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.375(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.1853(7)
_cell_length_b                   10.3325(3)
_cell_length_c                   14.4450(2)
_cell_measurement_reflns_used    10092
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     3383.88(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19666
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.8924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+2.3465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                3048
_reflns_number_total             3742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0424124rom20050105_095444.cif
_cod_data_source_block           03src0108
_cod_database_code               4111548
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C17 C 0.97009(10) 0.88171(19) 0.15730(16) 0.0429(5) Uani 1 1 d .
H17A H 0.9551 0.8216 0.1017 0.064 Uiso 1 1 calc R
H17B H 0.9984 0.9413 0.1452 0.064 Uiso 1 1 calc R
H17C H 0.9372 0.9312 0.1643 0.064 Uiso 1 1 calc R
C18 C 1.0000 0.8071(2) 0.2500 0.0293(5) Uani 1 2 d S
O1 O 1.0000 0.69003(16) 0.2500 0.0338(4) Uani 1 2 d S
C1 C 0.00802(7) 0.44426(15) 0.47424(11) 0.0207(3) Uani 1 1 d .
C2 C 0.04725(7) 0.46013(15) 0.42355(11) 0.0213(3) Uani 1 1 d .
H2 H 0.0647 0.5421 0.4218 0.026 Uiso 1 1 calc R
C3 C 0.06047(7) 0.35416(16) 0.37559(11) 0.0219(3) Uani 1 1 d .
C4 C 0.03454(8) 0.23623(16) 0.38200(13) 0.0276(4) Uani 1 1 d .
H4 H 0.0434 0.1611 0.3520 0.033 Uiso 1 1 calc R
C5 C -0.00457(8) 0.22988(16) 0.43304(13) 0.0281(4) Uani 1 1 d .
H5 H -0.0224 0.1489 0.4363 0.034 Uiso 1 1 calc R
C6 C 0.09757(7) 0.36685(15) 0.31282(12) 0.0220(3) Uani 1 1 d .
C7 C 0.09645(7) 0.48068(16) 0.26080(12) 0.0230(3) Uani 1 1 d .
H7 H 0.0759 0.5541 0.2716 0.028 Uiso 1 1 calc R
C8 C 0.12506(7) 0.48701(15) 0.19374(12) 0.0229(3) Uani 1 1 d .
H8 H 0.1238 0.5648 0.1580 0.028 Uiso 1 1 calc R
C9 C 0.15975(7) 0.27469(16) 0.23154(12) 0.0244(3) Uani 1 1 d .
H9 H 0.1827 0.2045 0.2224 0.029 Uiso 1 1 calc R
C10 C 0.13156(7) 0.26412(16) 0.29937(12) 0.0251(3) Uani 1 1 d .
H10 H 0.1353 0.1870 0.3369 0.030 Uiso 1 1 calc R
C11 C 0.17729(7) 0.38830(16) 0.09678(12) 0.0240(4) Uani 1 1 d .
C12 C 0.20817(7) 0.49617(18) 0.08515(13) 0.0297(4) Uani 1 1 d .
H12 H 0.2172 0.5648 0.1319 0.036 Uiso 1 1 calc R
C13 C 0.22558(8) 0.5012(2) 0.00294(14) 0.0361(4) Uani 1 1 d .
H13 H 0.2473 0.5735 -0.0064 0.043 Uiso 1 1 calc R
C14 C 0.21136(8) 0.4012(2) -0.06529(13) 0.0348(4) Uani 1 1 d .
H14 H 0.2231 0.4060 -0.1215 0.042 Uiso 1 1 calc R
C15 C 0.18025(8) 0.29464(19) -0.05230(13) 0.0324(4) Uani 1 1 d .
H15 H 0.1706 0.2266 -0.0995 0.039 Uiso 1 1 calc R
C16 C 0.16310(7) 0.28726(17) 0.02981(13) 0.0268(4) Uani 1 1 d .
H16 H 0.1420 0.2142 0.0398 0.032 Uiso 1 1 calc R
N1 N -0.01854(6) 0.33121(13) 0.47776(10) 0.0248(3) Uani 1 1 d .
N2 N 0.15502(5) 0.38369(12) 0.17812(10) 0.0215(3) Uani 1 1 d .
F1 F 0.14288(6) 0.94565(12) 0.25336(9) 0.0500(3) Uani 1 1 d .
F2 F 0.10962(6) 0.98755(12) 0.09006(10) 0.0516(3) Uani 1 1 d .
F3 F 0.20755(5) 0.98416(11) 0.17705(9) 0.0450(3) Uani 1 1 d .
F4 F 0.16608(6) 0.82460(13) 0.06736(9) 0.0516(3) Uani 1 1 d .
F5 F 0.19894(5) 0.78216(11) 0.23074(8) 0.0404(3) Uani 1 1 d .
F6 F 0.10118(5) 0.78575(11) 0.14438(10) 0.0500(3) Uani 1 1 d .
P1 P 0.154179(19) 0.88461(4) 0.15989(3) 0.02700(15) Uani 1 1 d .
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'
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'
O O 0.0106 0.0060 '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
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O1 C18 C17 121.03(12) . 2_755
O1 C18 C17 121.03(12) . .
C17 C18 C17 117.9(2) 2_755 .
N1 C1 C2 122.95(14) . .
N1 C1 C1 116.19(17) . 5_566
C2 C1 C1 120.84(18) . 5_566
C3 C2 C1 119.02(15) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C4 C3 C2 118.04(14) . .
C4 C3 C6 120.05(14) . .
C2 C3 C6 121.76(14) . .
C3 C4 C5 118.95(15) . .
C3 C4 H4 120.5 . .
C5 C4 H4 120.5 . .
N1 C5 C4 123.66(15) . .
N1 C5 H5 118.2 . .
C4 C5 H5 118.2 . .
C7 C6 C10 117.99(14) . .
C7 C6 C3 120.10(14) . .
C10 C6 C3 121.80(14) . .
C8 C7 C6 120.08(15) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
N2 C8 C7 120.70(15) . .
N2 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
N2 C9 C10 120.58(15) . .
N2 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C6 119.93(15) . .
C9 C10 H10 120.0 . .
C6 C10 H10 120.0 . .
C16 C11 C12 122.42(15) . .
C16 C11 N2 117.97(14) . .
C12 C11 N2 119.47(15) . .
C11 C12 C13 118.00(17) . .
C11 C12 H12 121.0 . .
C13 C12 H12 121.0 . .
C14 C13 C12 120.35(17) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C15 C14 C13 120.60(16) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C16 119.88(17) . .
C14 C15 H15 120.1 . .
C16 C15 H15 120.1 . .
C11 C16 C15 118.75(16) . .
C11 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
C5 N1 C1 117.34(14) . .
C9 N2 C8 120.51(14) . .
C9 N2 C11 120.58(13) . .
C8 N2 C11 118.67(13) . .
F4 P1 F6 90.23(8) . .
F4 P1 F1 179.40(8) . .
F6 P1 F1 90.34(7) . .
F4 P1 F2 90.49(7) . .
F6 P1 F2 90.30(7) . .
F1 P1 F2 89.68(7) . .
F4 P1 F3 90.49(7) . .
F6 P1 F3 179.22(8) . .
F1 P1 F3 88.94(7) . .
F2 P1 F3 90.01(7) . .
F4 P1 F5 89.97(7) . .
F6 P1 F5 89.88(6) . .
F1 P1 F5 89.85(7) . .
F2 P1 F5 179.50(7) . .
F3 P1 F5 89.80(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C17 C18 1.495(2) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 O1 1.210(3) .
C18 C17 1.495(2) 2_755
C1 N1 1.343(2) .
C1 C2 1.395(2) .
C1 C1 1.494(3) 5_566
C2 C3 1.391(2) .
C2 H2 0.9500 .
C3 C4 1.388(2) .
C3 C6 1.487(2) .
C4 C5 1.389(2) .
C4 H4 0.9500 .
C5 N1 1.334(2) .
C5 H5 0.9500 .
C6 C7 1.391(2) .
C6 C10 1.397(2) .
C7 C8 1.374(2) .
C7 H7 0.9500 .
C8 N2 1.353(2) .
C8 H8 0.9500 .
C9 N2 1.347(2) .
C9 C10 1.379(2) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C16 1.383(2) .
C11 C12 1.384(2) .
C11 N2 1.4538(19) .
C12 C13 1.392(2) .
C12 H12 0.9500 .
C13 C14 1.385(3) .
C13 H13 0.9500 .
C14 C15 1.383(3) .
C14 H14 0.9500 .
C15 C16 1.388(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
F1 P1 1.5976(12) .
F2 P1 1.5980(12) .
F3 P1 1.6009(11) .
F4 P1 1.5879(12) .
F5 P1 1.6026(11) .
F6 P1 1.5928(11) .
