#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:53:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179429 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/26/4332606.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4332606
loop_
_publ_author_name
'Huang, Jie-Sheng'
'Yu, Guang-Ao'
'Xie, Jin'
'Zhu, Nianyong'
'Che, Chi-Ming'
_publ_section_title
;
 One-Pot Synthesis of Metal Primary Phosphine Complexes from OPCl2R or
 PCl2R. Isolation and Characterization of Primary Alkylphosphine Complexes
 of a Metalloporphyrin
;
_journal_issue                   15
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5724
_journal_page_last               5726
_journal_paper_doi               10.1021/ic060553w
_journal_volume                  45
_journal_year                    2006
_chemical_formula_moiety         'C62 H34 F20 N4 P2 Ru'
_chemical_formula_sum            'C62 H34 F20 N4 P2 Ru'
_chemical_formula_weight         1377.94
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.103(2)
_cell_length_b                   11.570(2)
_cell_length_c                   21.840(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2801.8(9)
_computing_cell_refinement       scalepack
_computing_data_collection       marcontrol
_computing_data_reduction        denzo
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'marresearch IPDS mar300'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19781
_diffrn_reflns_theta_full        25.63
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         5198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0364
_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)+(0.0393P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                3658
_reflns_number_total             5198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic060553wsup1.cif
_cod_data_source_block           complex_1c
_cod_original_cell_volume        2801.8(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4332606
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
Ru1 Ru 0.0000 0.0000 0.0000 0.03150(12) Uani 1 2 d S
P1 P -0.13067(8) -0.12440(7) 0.05046(4) 0.0423(2) Uani 1 1 d .
F1 F 0.1174(2) 0.0378(2) 0.25381(9) 0.0783(7) Uani 1 1 d .
F2 F 0.2454(2) 0.1212(2) 0.35006(8) 0.0824(7) Uani 1 1 d .
F3 F 0.4453(2) 0.2499(2) 0.33400(10) 0.0840(7) Uani 1 1 d .
F4 F 0.5116(2) 0.2978(2) 0.21906(11) 0.0915(8) Uani 1 1 d .
F5 F 0.3851(2) 0.2104(2) 0.12144(9) 0.0710(6) Uani 1 1 d .
F6 F 0.1151(2) -0.4359(2) 0.05698(10) 0.0786(7) Uani 1 1 d .
F7 F 0.2261(3) -0.6413(2) 0.05178(12) 0.0960(8) Uani 1 1 d .
F8 F 0.4079(2) -0.67236(19) -0.02422(12) 0.0857(8) Uani 1 1 d .
F9 F 0.4767(2) -0.4970(2) -0.09561(12) 0.0823(7) Uani 1 1 d .
F10 F 0.3672(2) -0.28981(19) -0.09045(10) 0.0761(7) Uani 1 1 d .
N1 N -0.0073(2) 0.1309(2) 0.06252(10) 0.0354(6) Uani 1 1 d .
N2 N 0.1469(2) -0.0680(2) 0.04891(10) 0.0351(6) Uani 1 1 d .
C1 C -0.0848(3) 0.2231(3) 0.05984(13) 0.0384(7) Uani 1 1 d .
C2 C -0.0576(3) 0.2988(3) 0.11153(14) 0.0519(9) Uani 1 1 d .
H2 H -0.0977 0.3666 0.1208 0.062 Uiso 1 1 calc R
C3 C 0.0369(3) 0.2517(3) 0.14341(14) 0.0515(9) Uani 1 1 d .
H3 H 0.0736 0.2813 0.1793 0.062 Uiso 1 1 calc R
C4 C 0.0720(3) 0.1479(3) 0.11278(12) 0.0378(7) Uani 1 1 d .
C5 C 0.1706(3) 0.0792(3) 0.12889(13) 0.0389(7) Uani 1 1 d .
C6 C 0.2063(3) -0.0211(2) 0.09992(13) 0.0354(7) Uani 1 1 d .
C7 C 0.3041(3) -0.0966(3) 0.11948(14) 0.0457(8) Uani 1 1 d .
H7 H 0.3588 -0.0843 0.1525 0.055 Uiso 1 1 calc R
C8 C 0.3019(3) -0.1876(3) 0.08164(14) 0.0456(8) Uani 1 1 d .
H8 H 0.3543 -0.2503 0.0839 0.055 Uiso 1 1 calc R
C9 C 0.2035(3) -0.1707(3) 0.03653(12) 0.0361(7) Uani 1 1 d .
C10 C 0.1733(3) -0.2424(3) -0.01294(13) 0.0372(7) Uani 1 1 d .
C11 C 0.2474(3) 0.1207(3) 0.18371(13) 0.0402(7) Uani 1 1 d .
C12 C 0.2160(3) 0.0999(3) 0.24304(14) 0.0494(8) Uani 1 1 d .
C13 C 0.2812(4) 0.1429(3) 0.29351(14) 0.0558(10) Uani 1 1 d .
C14 C 0.3807(4) 0.2089(3) 0.28542(17) 0.0588(10) Uani 1 1 d .
C15 C 0.4142(3) 0.2325(3) 0.22710(18) 0.0579(10) Uani 1 1 d .
C16 C 0.3479(3) 0.1872(3) 0.17757(14) 0.0476(8) Uani 1 1 d .
C17 C 0.2390(3) -0.3548(3) -0.01569(14) 0.0406(7) Uani 1 1 d .
C18 C 0.2060(3) -0.4476(3) 0.01936(15) 0.0492(8) Uani 1 1 d .
C19 C 0.2612(4) -0.5534(3) 0.01673(17) 0.0585(10) Uani 1 1 d .
C20 C 0.3528(3) -0.5695(3) -0.02159(17) 0.0548(9) Uani 1 1 d .
C21 C 0.3886(3) -0.4815(3) -0.05675(16) 0.0543(10) Uani 1 1 d .
C22 C 0.3314(3) -0.3746(3) -0.05422(15) 0.0483(8) Uani 1 1 d .
C23 C -0.1906(3) -0.0823(3) 0.12281(14) 0.0441(8) Uani 1 1 d .
C24 C -0.2984(3) -0.0189(3) 0.12342(15) 0.0494(8) Uani 1 1 d .
C25 C -0.3330(4) 0.0263(3) 0.17867(17) 0.0648(11) Uani 1 1 d .
H25 H -0.4052 0.0668 0.1794 0.078 Uiso 1 1 calc R
C26 C -0.2636(4) 0.0131(3) 0.23288(18) 0.0696(11) Uani 1 1 d .
C27 C -0.1598(4) -0.0500(3) 0.23125(15) 0.0578(9) Uani 1 1 d .
H27 H -0.1131 -0.0599 0.2674 0.069 Uiso 1 1 calc R
C28 C -0.1208(3) -0.1003(3) 0.17745(15) 0.0479(8) Uani 1 1 d .
C29 C -0.3796(3) -0.0007(3) 0.06662(16) 0.0639(10) Uani 1 1 d .
H29A H -0.3443 -0.0365 0.0322 0.096 Uiso 1 1 calc R
H29B H -0.3890 0.0806 0.0591 0.096 Uiso 1 1 calc R
H29C H -0.4570 -0.0346 0.0725 0.096 Uiso 1 1 calc R
C30 C -0.3013(5) 0.0673(5) 0.29226(19) 0.112(2) Uani 1 1 d .
H30A H -0.3756 0.1087 0.2848 0.168 Uiso 1 1 calc R
H30B H -0.2397 0.1197 0.3075 0.168 Uiso 1 1 calc R
H30C H -0.3124 0.0077 0.3221 0.168 Uiso 1 1 calc R
C31 C -0.0091(3) -0.1743(3) 0.17997(16) 0.0601(10) Uani 1 1 d .
H31A H 0.0252 -0.1762 0.2212 0.090 Uiso 1 1 calc R
H31B H 0.0484 -0.1426 0.1533 0.090 Uiso 1 1 calc R
H31C H -0.0299 -0.2514 0.1670 0.090 Uiso 1 1 calc R
H1A H -0.089(2) -0.233(2) 0.0586(11) 0.034(7) Uiso 1 1 d .
H1B H -0.232(3) -0.156(3) 0.0177(12) 0.049(9) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ru Ru -1.2594 0.8363 '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'
F F 0.0171 0.0103 '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'
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'
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
N1 Ru1 N1 180.00(16) 3 .
N1 Ru1 N2 89.69(9) 3 3
N1 Ru1 N2 90.31(9) . 3
N1 Ru1 N2 90.31(9) 3 .
N1 Ru1 N2 89.69(9) . .
N2 Ru1 N2 180.00(18) 3 .
N1 Ru1 P1 84.66(7) 3 .
N1 Ru1 P1 95.34(7) . .
N2 Ru1 P1 89.19(7) 3 .
N2 Ru1 P1 90.81(7) . .
N1 Ru1 P1 95.34(7) 3 3
N1 Ru1 P1 84.66(7) . 3
N2 Ru1 P1 90.81(7) 3 3
N2 Ru1 P1 89.19(7) . 3
P1 Ru1 P1 180.00(6) . 3
C23 P1 Ru1 120.42(11) . .
C23 P1 H1A 106.0(11) . .
Ru1 P1 H1A 114.6(11) . .
C23 P1 H1B 101.6(12) . .
Ru1 P1 H1B 115.7(12) . .
H1A P1 H1B 94.9(16) . .
C1 N1 C4 107.1(2) . .
C1 N1 Ru1 126.53(19) . .
C4 N1 Ru1 126.14(19) . .
C6 N2 C9 107.1(2) . .
C6 N2 Ru1 127.07(19) . .
C9 N2 Ru1 125.82(18) . .
N1 C1 C10 124.8(3) . 3
N1 C1 C2 109.4(3) . .
C10 C1 C2 125.7(3) 3 .
C3 C2 C1 106.5(3) . .
C3 C2 H2 126.7 . .
C1 C2 H2 126.7 . .
C2 C3 C4 108.7(3) . .
C2 C3 H3 125.7 . .
C4 C3 H3 125.7 . .
C5 C4 N1 125.5(3) . .
C5 C4 C3 126.3(3) . .
N1 C4 C3 108.2(3) . .
C4 C5 C6 127.3(3) . .
C4 C5 C11 115.1(3) . .
C6 C5 C11 117.6(3) . .
N2 C6 C5 124.1(3) . .
N2 C6 C7 108.9(2) . .
C5 C6 C7 126.9(3) . .
C8 C7 C6 107.8(3) . .
C8 C7 H7 126.1 . .
C6 C7 H7 126.1 . .
C7 C8 C9 107.7(3) . .
C7 C8 H8 126.2 . .
C9 C8 H8 126.2 . .
N2 C9 C10 125.0(3) . .
N2 C9 C8 108.6(2) . .
C10 C9 C8 126.4(3) . .
C9 C10 C1 127.2(3) . 3
C9 C10 C17 116.9(3) . .
C1 C10 C17 115.8(3) 3 .
C16 C11 C12 115.9(3) . .
C16 C11 C5 122.0(3) . .
C12 C11 C5 121.9(3) . .
F1 C12 C13 116.9(3) . .
F1 C12 C11 120.4(3) . .
C13 C12 C11 122.7(3) . .
F2 C13 C14 120.4(3) . .
F2 C13 C12 120.0(4) . .
C14 C13 C12 119.6(3) . .
F3 C14 C13 120.1(4) . .
F3 C14 C15 120.4(4) . .
C13 C14 C15 119.5(3) . .
F4 C15 C14 119.6(3) . .
F4 C15 C16 120.9(4) . .
C14 C15 C16 119.5(4) . .
F5 C16 C11 119.6(3) . .
F5 C16 C15 117.6(3) . .
C11 C16 C15 122.8(3) . .
C18 C17 C22 115.9(3) . .
C18 C17 C10 120.7(3) . .
C22 C17 C10 123.3(3) . .
F6 C18 C19 117.9(3) . .
F6 C18 C17 119.5(3) . .
C19 C18 C17 122.6(3) . .
F7 C19 C20 119.6(3) . .
F7 C19 C18 120.6(4) . .
C20 C19 C18 119.8(4) . .
F8 C20 C21 119.8(4) . .
F8 C20 C19 120.3(4) . .
C21 C20 C19 119.9(3) . .
F9 C21 C20 120.4(3) . .
F9 C21 C22 119.6(4) . .
C20 C21 C22 120.0(3) . .
F10 C22 C17 119.6(3) . .
F10 C22 C21 118.6(3) . .
C17 C22 C21 121.8(3) . .
C28 C23 C24 120.1(3) . .
C28 C23 P1 119.3(3) . .
C24 C23 P1 120.0(2) . .
C25 C24 C23 118.6(3) . .
C25 C24 C29 118.8(3) . .
C23 C24 C29 122.5(3) . .
C26 C25 C24 122.3(4) . .
C26 C25 H25 118.8 . .
C24 C25 H25 118.8 . .
C27 C26 C25 117.9(3) . .
C27 C26 C30 120.9(4) . .
C25 C26 C30 121.2(4) . .
C26 C27 C28 122.9(3) . .
C26 C27 H27 118.6 . .
C28 C27 H27 118.6 . .
C27 C28 C23 118.1(3) . .
C27 C28 C31 119.7(3) . .
C23 C28 C31 122.2(3) . .
C24 C29 H29A 109.5 . .
C24 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C24 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C26 C30 H30A 109.5 . .
C26 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C26 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C28 C31 H31A 109.5 . .
C28 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C28 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 N1 2.043(2) 3
Ru1 N1 2.043(2) .
Ru1 N2 2.059(2) 3
Ru1 N2 2.059(2) .
Ru1 P1 2.3575(10) .
Ru1 P1 2.3575(10) 3
P1 C23 1.813(3) .
P1 H1A 1.35(3) .
P1 H1B 1.35(3) .
F1 C12 1.341(4) .
F2 C13 1.341(4) .
F3 C14 1.337(4) .
F4 C15 1.339(4) .
F5 C16 1.341(4) .
F6 C18 1.341(4) .
F7 C19 1.343(4) .
F8 C20 1.341(4) .
F9 C21 1.340(4) .
F10 C22 1.333(4) .
N1 C1 1.370(4) .
N1 C4 1.385(3) .
N2 C6 1.377(3) .
N2 C9 1.378(4) .
C1 C10 1.400(4) 3
C1 C2 1.448(4) .
C2 C3 1.344(4) .
C2 H2 0.9300 .
C3 C4 1.438(4) .
C3 H3 0.9300 .
C4 C5 1.384(4) .
C5 C6 1.389(4) .
C5 C11 1.511(4) .
C6 C7 1.440(4) .
C7 C8 1.337(4) .
C7 H7 0.9300 .
C8 C9 1.446(4) .
C8 H8 0.9300 .
C9 C10 1.389(4) .
C10 C1 1.400(4) 3
C10 C17 1.494(4) .
C11 C16 1.368(5) .
C11 C12 1.380(4) .
C12 C13 1.379(4) .
C13 C14 1.362(5) .
C14 C15 1.373(5) .
C15 C16 1.380(4) .
C17 C18 1.379(5) .
C17 C22 1.380(4) .
C18 C19 1.372(5) .
C19 C20 1.363(5) .
C20 C21 1.348(5) .
C21 C22 1.392(5) .
C23 C28 1.404(4) .
C23 C24 1.405(5) .
C24 C25 1.387(5) .
C24 C29 1.509(5) .
C25 C26 1.387(5) .
C25 H25 0.9300 .
C26 C27 1.366(5) .
C26 C30 1.519(5) .
C27 C28 1.400(5) .
C27 H27 0.9300 .
C28 C31 1.505(5) .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
