#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/51/7025193.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_7025193
loop_
_publ_author_name
'Bozic-Weber, Biljana'
'Constable, Edwin C.'
'Housecroft, Catherine E.'
'Neuburger, Markus'
'Price, Jason R.'
_publ_section_title
;
 Sticky complexes: carboxylic acid-functionalized
 N-phenylpyridin-2-ylmethanimine ligands as anchoring domains for copper
 and ruthenium dye-sensitized solar cells.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3585
_journal_page_last               3594
_journal_paper_doi               10.1039/b925623g
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C28 H24 Cu N4 O4, F6 P, 2(C3 H7 N O)'
_chemical_formula_sum            'C34 H38 Cu F6 N6 O6 P'
_chemical_formula_weight         835.22
_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
_cell_angle_alpha                90
_cell_angle_beta                 97.370(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2661(13)
_cell_length_b                   16.4632(13)
_cell_length_c                   12.4427(7)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    123
_cell_measurement_theta_max      23
_cell_measurement_theta_min      4
_cell_volume                     3710.8(4)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.100
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27891
_diffrn_reflns_theta_full        27.509
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.245
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.93
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     423
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.000669
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.513 0.451 0.325
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0814
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0548
_reflns_limit_h_max              23
_reflns_limit_h_min              -23
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2701
_reflns_number_total             4262
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      540.22
_oxford_refine_ls_r_factor_ref   0.0684
_oxford_refine_ls_scale          0.05946(14)
_oxford_reflns_number_all        4251
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            b925623g.txt
_cod_data_source_block           jp167
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C34 H38 Cu1 F6 N6 O6 P1'
_cod_database_code               7025193
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.0000 0.71660(4) 0.2500 0.0244 1.0000 Uani S T
N1 N 0.08869(16) 0.64712(18) 0.2275(2) 0.0261 1.0000 Uani . .
N2 N 0.02157(16) 0.76536(16) 0.1080(2) 0.0237 1.0000 Uani . .
O1 O -0.13944(15) 1.04878(18) -0.1857(2) 0.0369 1.0000 Uani . .
O2 O -0.18093(18) 1.0732(2) -0.0282(2) 0.0483 1.0000 Uani . .
C1 C 0.0992(3) 0.5778(3) 0.4013(3) 0.0393 1.0000 Uani . .
C2 C 0.1204(2) 0.5869(2) 0.2892(3) 0.0287 1.0000 Uani . .
C3 C 0.1714(2) 0.5346(3) 0.2508(3) 0.0336 1.0000 Uani . .
C4 C 0.1895(2) 0.5451(3) 0.1466(3) 0.0396 1.0000 Uani . .
C5 C 0.1580(2) 0.6080(2) 0.0840(4) 0.0326 1.0000 Uani . .
C6 C 0.10720(19) 0.6575(2) 0.1268(3) 0.0268 1.0000 Uani . .
C7 C 0.0709(2) 0.7255(2) 0.0656(3) 0.0285 1.0000 Uani . .
C8 C -0.01603(18) 0.8324(2) 0.0551(3) 0.0221 1.0000 Uani . .
C9 C -0.0065(2) 0.8594(2) -0.0489(3) 0.0296 1.0000 Uani . .
C10 C -0.04792(19) 0.9244(2) -0.0937(3) 0.0268 1.0000 Uani . .
C11 C -0.09721(18) 0.9644(2) -0.0373(3) 0.0238 1.0000 Uani . .
C12 C -0.1057(2) 0.9380(3) 0.0670(3) 0.0373 1.0000 Uani . .
C13 C -0.0653(2) 0.8732(3) 0.1123(3) 0.0351 1.0000 Uani . .
C14 C -0.1414(2) 1.0329(2) -0.0874(3) 0.0280 1.0000 Uani . .
N3 N -0.29183(19) 1.2630(2) -0.2615(3) 0.0373 1.0000 Uani . .
C15 C -0.3336(2) 1.3183(3) -0.2036(3) 0.0373 1.0000 Uani . .
C16 C -0.3011(4) 1.2698(4) -0.3782(4) 0.0762 1.0000 Uani . .
C17 C -0.2510(2) 1.2043(3) -0.2125(4) 0.0459 1.0000 Uani . .
O3 O -0.2443(3) 1.2007(3) -0.1004(4) 0.0297 0.5000 Uani . .
O4 O -0.2201(3) 1.1523(4) -0.2781(5) 0.0422 0.5000 Uani . .
P1 P 0.0000 0.36217(9) 0.2500 0.0325 1.0000 Uani DS TU
F1 F -0.0833(9) 0.3568(5) 0.1800(8) 0.0417 0.5000 Uani D U
F2 F 0.0777(10) 0.3667(5) 0.3149(10) 0.0570 0.5000 Uani D U
F3 F 0.0074(4) 0.4540(3) 0.2143(4) 0.0641 0.5000 Uani D U
F4 F 0.0375(3) 0.3338(3) 0.1431(5) 0.0519 0.5000 Uani D U
F5 F -0.0044(4) 0.2692(3) 0.2812(4) 0.0534 0.5000 Uani D U
F6 F -0.0333(3) 0.3885(4) 0.3519(5) 0.0703 0.5000 Uani D U
H11 H 0.1401 0.5562 0.4473 0.0590 1.0000 Uiso R .
H12 H 0.0869 0.6300 0.4290 0.0596 1.0000 Uiso R .
H13 H 0.0578 0.5418 0.4010 0.0594 1.0000 Uiso R .
H31 H 0.1932 0.4930 0.2941 0.0393 1.0000 Uiso R .
H41 H 0.2236 0.5093 0.1195 0.0461 1.0000 Uiso R .
H51 H 0.1690 0.6163 0.0129 0.0422 1.0000 Uiso R .
H71 H 0.0834 0.7390 -0.0033 0.0344 1.0000 Uiso R .
H91 H 0.0274 0.8325 -0.0874 0.0362 1.0000 Uiso R .
H101 H -0.0430 0.9424 -0.1632 0.0314 1.0000 Uiso R .
H121 H -0.1387 0.9643 0.1064 0.0450 1.0000 Uiso R .
H131 H -0.0712 0.8573 0.1831 0.0429 1.0000 Uiso R .
H151 H -0.3196 1.3126 -0.1269 0.0578 1.0000 Uiso R .
H152 H -0.3254 1.3739 -0.2246 0.0582 1.0000 Uiso R .
H153 H -0.3855 1.3075 -0.2199 0.0582 1.0000 Uiso R .
H161 H -0.2766 1.2250 -0.4083 0.1170 1.0000 Uiso R .
H162 H -0.2798 1.3204 -0.3977 0.1171 1.0000 Uiso R .
H163 H -0.3529 1.2691 -0.4061 0.1170 1.0000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 5_555 Cu1 N2 5_555 81.68(12) yes
N1 5_555 Cu1 N1 . 111.46(17) yes
N2 5_555 Cu1 N1 . 126.24(12) yes
N1 5_555 Cu1 N2 . 126.24(12) yes
N2 5_555 Cu1 N2 . 133.29(16) yes
N1 . Cu1 N2 . 81.68(12) yes
Cu1 . N1 C2 . 129.2(3) yes
Cu1 . N1 C6 . 110.8(2) yes
C2 . N1 C6 . 118.9(3) yes
Cu1 . N2 C7 . 112.5(2) yes
Cu1 . N2 C8 . 125.3(2) yes
C7 . N2 C8 . 122.2(3) yes
C2 . C1 H11 . 108.7 no
C2 . C1 H12 . 110.1 no
H11 . C1 H12 . 108.7 no
C2 . C1 H13 . 110.9 no
H11 . C1 H13 . 109.1 no
H12 . C1 H13 . 109.4 no
C1 . C2 N1 . 117.5(3) yes
C1 . C2 C3 . 121.3(3) yes
N1 . C2 C3 . 121.3(4) yes
C2 . C3 C4 . 119.4(4) yes
C2 . C3 H31 . 120.7 no
C4 . C3 H31 . 119.9 no
C3 . C4 C5 . 119.3(4) yes
C3 . C4 H41 . 120.0 no
C5 . C4 H41 . 120.7 no
C4 . C5 C6 . 118.4(4) yes
C4 . C5 H51 . 121.1 no
C6 . C5 H51 . 120.5 no
C5 . C6 N1 . 122.7(3) yes
C5 . C6 C7 . 121.9(4) yes
N1 . C6 C7 . 115.4(3) yes
C6 . C7 N2 . 118.2(3) yes
C6 . C7 H71 . 120.5 no
N2 . C7 H71 . 121.3 no
N2 . C8 C9 . 124.5(3) yes
N2 . C8 C13 . 116.5(3) yes
C9 . C8 C13 . 119.0(3) yes
C8 . C9 C10 . 119.5(4) yes
C8 . C9 H91 . 119.2 no
C10 . C9 H91 . 121.3 no
C9 . C10 C11 . 121.5(3) yes
C9 . C10 H101 . 120.6 no
C11 . C10 H101 . 117.9 no
C10 . C11 C12 . 118.8(3) yes
C10 . C11 C14 . 120.5(3) yes
C12 . C11 C14 . 120.7(3) yes
C11 . C12 C13 . 120.3(4) yes
C11 . C12 H121 . 120.1 no
C13 . C12 H121 . 119.6 no
C8 . C13 C12 . 120.9(4) yes
C8 . C13 H131 . 120.4 no
C12 . C13 H131 . 118.7 no
C11 . C14 O2 . 118.1(3) yes
C11 . C14 O1 . 119.2(3) yes
O2 . C14 O1 . 122.7(4) yes
C15 . N3 C16 . 116.9(3) yes
C15 . N3 C17 . 122.4(4) yes
C16 . N3 C17 . 120.5(4) yes
N3 . C15 H151 . 110.2 no
N3 . C15 H152 . 110.6 no
H151 . C15 H152 . 109.3 no
N3 . C15 H153 . 110.4 no
H151 . C15 H153 . 108.7 no
H152 . C15 H153 . 107.6 no
N3 . C16 H161 . 109.3 no
N3 . C16 H162 . 108.8 no
H161 . C16 H162 . 110.1 no
N3 . C16 H163 . 110.1 no
H161 . C16 H163 . 109.5 no
H162 . C16 H163 . 109.1 no
N3 . C17 O3 . 117.9(4) yes
N3 . C17 O4 . 116.0(4) yes
O3 . C17 O4 . 126.1(4) yes
F1 . P1 F2 . 179.7(3) yes
F1 . P1 F3 . 90.5(3) yes
F2 . P1 F3 . 89.7(3) yes
F1 . P1 F4 . 90.5(3) yes
F2 . P1 F4 . 89.3(3) yes
F3 . P1 F4 . 89.1(3) yes
F1 . P1 F5 . 90.3(3) yes
F2 . P1 F5 . 89.5(3) yes
F3 . P1 F5 . 176.9(3) yes
F4 . P1 F5 . 87.9(2) yes
F1 . P1 F6 . 90.8(3) yes
F2 . P1 F6 . 89.3(3) yes
F3 . P1 F6 . 91.0(3) yes
F4 . P1 F6 . 178.6(3) yes
F5 . P1 F6 . 91.9(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 5_555 2.032(3) yes
Cu1 N2 5_555 2.025(3) yes
Cu1 N1 . 2.032(3) yes
Cu1 N2 . 2.025(3) yes
N1 C2 . 1.339(5) yes
N1 C6 . 1.351(5) yes
N2 C7 . 1.282(5) yes
N2 C8 . 1.416(4) yes
O1 C14 . 1.256(4) yes
O2 C14 . 1.282(5) yes
C1 C2 . 1.502(6) yes
C1 H11 . 0.950 no
C1 H12 . 0.962 no
C1 H13 . 0.960 no
C2 C3 . 1.397(6) yes
C3 C4 . 1.388(6) yes
C3 H31 . 0.929 no
C4 C5 . 1.378(6) yes
C4 H41 . 0.951 no
C5 C6 . 1.390(5) yes
C5 H51 . 0.942 no
C6 C7 . 1.464(5) yes
C7 H71 . 0.942 no
C8 C9 . 1.400(5) yes
C8 C13 . 1.390(5) yes
C9 C10 . 1.385(5) yes
C9 H91 . 0.941 no
C10 C11 . 1.379(5) yes
C10 H101 . 0.929 no
C11 C12 . 1.396(5) yes
C11 C14 . 1.476(5) yes
C12 C13 . 1.376(5) yes
C12 H121 . 0.931 no
C13 H131 . 0.938 no
N3 C15 . 1.439(5) yes
N3 C16 . 1.444(6) yes
N3 C17 . 1.321(5) yes
C15 H151 . 0.960 no
C15 H152 . 0.968 no
C15 H153 . 0.961 no
C16 H161 . 0.964 no
C16 H162 . 0.964 no
C16 H163 . 0.966 no
C17 O3 . 1.386(7) yes
C17 O4 . 1.354(8) yes
P1 F1 . 1.656(17) yes
P1 F2 . 1.54(2) yes
P1 F3 . 1.586(5) yes
P1 F4 . 1.640(6) yes
P1 F5 . 1.584(4) yes
P1 F6 . 1.537(6) yes
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 H121 O1 6_575 125 0.93 2.60 3.223(6) yes
