#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:50:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178584 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/95/4069511.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_4069511
loop_
_publ_author_name
'Arquier, Damien'
'Vendier, Laure'
'Miqueu, Karinne'
'Sotiropoulos, Jean-Marc'
'Bastin, Stéphanie'
'Igau, Alain'
_publ_section_title
;
 Crucial Role of the Amidine Moiety in Methylenamino Phosphine-Type
 Ligands for the Synthesis of Tethered \h6-Arene-\h1-PRuthenium(II)
 Complexes: Experimental and Theoretical Studies
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4945
_journal_paper_doi               10.1021/om900231c
_journal_volume                  28
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C29 H47 Cl2 N2 P1 Ru1'
_chemical_formula_sum            'C29 H47 Cl2 N2 P Ru'
_chemical_formula_weight         626.63
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.506(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2054(9)
_cell_length_b                   16.8478(11)
_cell_length_c                   19.3607(19)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    180
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.65
_cell_measurement_wavelength     0.71073
_cell_volume                     2976.9(5)
_computing_cell_refinement       'Stoe IPDS software (Stoe, 1996)'
_computing_data_collection       'Stoe IPDS software (Stoe, 1996)'
_computing_data_reduction        'XRED (Stoe, 1.08, 1996)'
_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    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.0531
_diffrn_reflns_av_unetI/netI     0.041
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23283
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  4
_diffrn_standards_number         200
_exptl_absorpt_coefficient_mu    0.78
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.7782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            'orange yellow'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.0375
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5738
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                4622
_reflns_number_total             5738
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om900231c_si_001.cif
_cod_data_source_block           compound8b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4069511
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.3746(3) 0.67118(17) 0.59580(13) 0.0175(5) Uani 1 1 d .
C2 C 0.2011(3) 0.63757(18) 0.48930(14) 0.0267(6) Uani 1 1 d .
H2 H 0.1479 0.5892 0.4732 0.032 Uiso 1 1 calc R
C3 C 0.0854(3) 0.7020(2) 0.48945(17) 0.0335(7) Uani 1 1 d .
H3A H 0.0221 0.6896 0.5236 0.05 Uiso 1 1 calc R
H3B H 0.0288 0.7051 0.4442 0.05 Uiso 1 1 calc R
H3C H 0.1324 0.7521 0.5006 0.05 Uiso 1 1 calc R
C4 C 0.3063(4) 0.6543(2) 0.43624(16) 0.0381(8) Uani 1 1 d .
H4A H 0.3553 0.7039 0.4471 0.057 Uiso 1 1 calc R
H4B H 0.2524 0.657 0.3904 0.057 Uiso 1 1 calc R
H4C H 0.3775 0.6124 0.4378 0.057 Uiso 1 1 calc R
C5 C 0.2374(4) 0.5437(2) 0.59085(17) 0.0365(7) Uani 1 1 d U
H5 H 0.2985 0.5388 0.6361 0.044 Uiso 1 1 calc R
C6 C 0.2689(5) 0.4706(3) 0.5478(2) 0.0561(10) Uani 1 1 d U
H61 H 0.2282 0.4242 0.5668 0.084 Uiso 1 1 calc R
H62 H 0.3728 0.4641 0.5492 0.084 Uiso 1 1 calc R
H63 H 0.2252 0.4778 0.5004 0.084 Uiso 1 1 calc R
C7 C 0.0794(4) 0.5470(3) 0.6053(2) 0.0528(10) Uani 1 1 d U
H71 H 0.0157 0.5518 0.5621 0.079 Uiso 1 1 calc R
H72 H 0.0663 0.592 0.6343 0.079 Uiso 1 1 calc R
H73 H 0.0563 0.4993 0.6287 0.079 Uiso 1 1 calc R
C8 C 0.4762(3) 0.63700(16) 0.65541(14) 0.0185(5) Uani 1 1 d .
C9 C 0.4861(3) 0.67097(17) 0.72133(13) 0.0184(5) Uani 1 1 d .
H9 H 0.4227 0.7117 0.7299 0.022 Uiso 1 1 calc R
C10 C 0.5903(3) 0.64414(19) 0.77429(15) 0.0259(6) Uani 1 1 d .
H10 H 0.5967 0.6674 0.8182 0.031 Uiso 1 1 calc R
C11 C 0.6843(3) 0.58368(19) 0.76284(16) 0.0286(7) Uani 1 1 d .
H11 H 0.754 0.5663 0.7987 0.034 Uiso 1 1 calc R
C12 C 0.6748(3) 0.5486(2) 0.69752(17) 0.0320(7) Uani 1 1 d .
H12 H 0.7378 0.5074 0.6896 0.038 Uiso 1 1 calc R
C13 C 0.5714(3) 0.57528(19) 0.64427(16) 0.0275(6) Uani 1 1 d .
H13 H 0.5652 0.5518 0.6005 0.033 Uiso 1 1 calc R
C14 C 0.4738(3) 0.88806(17) 0.53315(14) 0.0208(6) Uani 1 1 d .
H14 H 0.518 0.9383 0.5505 0.025 Uiso 1 1 calc R
C15 C 0.5743(4) 0.8540(2) 0.48460(16) 0.0356(7) Uani 1 1 d .
H15A H 0.5437 0.8009 0.4717 0.053 Uiso 1 1 calc R
H15B H 0.673 0.853 0.5078 0.053 Uiso 1 1 calc R
H15C H 0.5697 0.8864 0.4436 0.053 Uiso 1 1 calc R
C16 C 0.3261(3) 0.9090(2) 0.49241(16) 0.0309(7) Uani 1 1 d .
H16A H 0.341 0.9394 0.452 0.046 Uiso 1 1 calc R
H16B H 0.2701 0.9396 0.5214 0.046 Uiso 1 1 calc R
H16C H 0.274 0.8611 0.4782 0.046 Uiso 1 1 calc R
C17 C 0.6524(3) 0.80700(17) 0.64749(14) 0.0198(6) Uani 1 1 d .
H17 H 0.649 0.7833 0.6935 0.024 Uiso 1 1 calc R
C18 C 0.7347(3) 0.74705(19) 0.60681(16) 0.0280(7) Uani 1 1 d .
H18A H 0.8011 0.7749 0.5811 0.042 Uiso 1 1 calc R
H18B H 0.6656 0.7179 0.5751 0.042 Uiso 1 1 calc R
H18C H 0.7888 0.711 0.6388 0.042 Uiso 1 1 calc R
C19 C 0.7368(3) 0.88491(18) 0.66080(16) 0.0273(6) Uani 1 1 d .
H19A H 0.8298 0.8746 0.6879 0.041 Uiso 1 1 calc R
H19B H 0.6815 0.9208 0.6857 0.041 Uiso 1 1 calc R
H19C H 0.7521 0.9083 0.6171 0.041 Uiso 1 1 calc R
C20 C 0.1027(3) 0.94817(18) 0.64677(14) 0.0207(6) Uani 1 1 d .
C21 C 0.1227(3) 0.95664(17) 0.72087(14) 0.0209(6) Uani 1 1 d .
H21 H 0.1212 1.007 0.7405 0.025 Uiso 1 1 calc R
C22 C 0.1446(3) 0.89037(17) 0.76417(14) 0.0200(6) Uani 1 1 d .
H22 H 0.1576 0.8973 0.8122 0.024 Uiso 1 1 calc R
C23 C 0.1476(3) 0.81197(16) 0.73609(14) 0.0180(6) Uani 1 1 d .
C24 C 0.1292(3) 0.80408(17) 0.66326(13) 0.0181(5) Uani 1 1 d .
H24 H 0.1327 0.7538 0.6437 0.022 Uiso 1 1 calc R
C25 C 0.1050(3) 0.87166(17) 0.61858(14) 0.0201(6) Uani 1 1 d .
H25 H 0.0908 0.8648 0.5705 0.024 Uiso 1 1 calc R
C26 C 0.0765(3) 1.02080(19) 0.60207(15) 0.0299(7) Uani 1 1 d .
H26A H 0.0958 1.0088 0.5557 0.045 Uiso 1 1 calc R
H26B H 0.1405 1.0626 0.6211 0.045 Uiso 1 1 calc R
H26C H -0.0235 1.0374 0.6009 0.045 Uiso 1 1 calc R
C27 C 0.1478(3) 0.73915(17) 0.78147(14) 0.0221(6) Uani 1 1 d .
H27 H 0.1827 0.6943 0.7559 0.026 Uiso 1 1 calc R
C28 C -0.0119(3) 0.7224(2) 0.79196(18) 0.0344(7) Uani 1 1 d .
H28A H -0.0493 0.7662 0.816 0.052 Uiso 1 1 calc R
H28B H -0.0162 0.6749 0.819 0.052 Uiso 1 1 calc R
H28C H -0.07 0.7157 0.7474 0.052 Uiso 1 1 calc R
C29 C 0.2434(4) 0.7446(2) 0.85166(16) 0.0354(8) Uani 1 1 d .
H29A H 0.3412 0.7593 0.8447 0.053 Uiso 1 1 calc R
H29B H 0.2452 0.6941 0.8747 0.053 Uiso 1 1 calc R
H29C H 0.204 0.784 0.8799 0.053 Uiso 1 1 calc R
N1 N 0.3764(2) 0.74446(13) 0.57573(11) 0.0164(5) Uani 1 1 d .
N2 N 0.2813(3) 0.61812(14) 0.55880(12) 0.0245(5) Uani 1 1 d .
P1 P 0.45833(7) 0.82615(4) 0.61102(3) 0.01428(14) Uani 1 1 d .
Cl1 Cl 0.50222(7) 0.86741(4) 0.78490(3) 0.02221(15) Uani 1 1 d .
Cl2 Cl 0.43277(7) 1.01090(4) 0.67076(4) 0.02581(16) Uani 1 1 d .
Ru1 Ru 0.31064(2) 0.888071(13) 0.688873(10) 0.01388(8) 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 0 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 '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
N1 C1 N2 119.7(2)
N1 C1 C8 124.4(2)
N2 C1 C8 115.8(2)
N2 C2 C3 114.9(2)
N2 C2 C4 111.5(2)
C3 C2 C4 112.1(3)
N2 C5 C7 111.5(3)
N2 C5 C6 111.8(3)
C7 C5 C6 112.5(3)
C9 C8 C13 118.8(2)
C9 C8 C1 120.5(2)
C13 C8 C1 120.5(2)
C10 C9 C8 120.1(3)
C11 C10 C9 120.8(3)
C10 C11 C12 119.8(3)
C13 C12 C11 119.7(3)
C12 C13 C8 120.8(3)
C15 C14 C16 110.0(2)
C15 C14 P1 114.1(2)
C16 C14 P1 113.18(19)
C19 C17 C18 112.1(2)
C19 C17 P1 110.9(2)
C18 C17 P1 115.58(19)
C25 C20 C21 118.4(3)
C25 C20 C26 122.4(3)
C21 C20 C26 119.2(3)
C25 C20 Ru1 70.59(15)
C21 C20 Ru1 71.67(14)
C26 C20 Ru1 130.42(19)
C22 C21 C20 120.9(3)
C22 C21 Ru1 72.32(15)
C20 C21 Ru1 70.93(14)
C21 C22 C23 121.3(2)
C21 C22 Ru1 71.39(15)
C23 C22 Ru1 71.87(14)
C24 C23 C22 117.6(2)
C24 C23 C27 119.9(2)
C22 C23 C27 121.9(2)
C24 C23 Ru1 69.31(14)
C22 C23 Ru1 71.09(14)
C27 C23 Ru1 138.42(18)
C23 C24 C25 121.4(3)
C23 C24 Ru1 73.94(15)
C25 C24 Ru1 71.16(15)
C20 C25 C24 120.4(2)
C20 C25 Ru1 72.49(15)
C24 C25 Ru1 70.88(14)
C23 C27 C29 115.3(2)
C23 C27 C28 107.3(2)
C29 C27 C28 110.2(2)
C1 N1 P1 133.23(19)
C1 N2 C5 121.3(2)
C1 N2 C2 122.1(2)
C5 N2 C2 115.9(2)
N1 P1 C14 102.09(12)
N1 P1 C17 111.81(12)
C14 P1 C17 103.54(13)
N1 P1 Ru1 110.66(8)
C14 P1 Ru1 112.12(9)
C17 P1 Ru1 115.59(9)
C24 Ru1 C25 37.96(10)
C24 Ru1 C20 67.52(11)
C25 Ru1 C20 36.92(11)
C24 Ru1 C21 78.59(10)
C25 Ru1 C21 66.53(10)
C20 Ru1 C21 37.40(10)
C24 Ru1 C22 66.15(10)
C25 Ru1 C22 78.48(10)
C20 Ru1 C22 66.67(10)
C21 Ru1 C22 36.28(10)
C24 Ru1 C23 36.75(10)
C25 Ru1 C23 67.37(10)
C20 Ru1 C23 79.69(10)
C21 Ru1 C23 66.51(10)
C22 Ru1 C23 37.04(10)
C24 Ru1 P1 93.14(7)
C25 Ru1 P1 93.97(7)
C20 Ru1 P1 119.97(7)
C21 Ru1 P1 157.35(7)
C22 Ru1 P1 154.92(8)
C23 Ru1 P1 118.00(7)
C24 Ru1 Cl2 151.48(7)
C25 Ru1 Cl2 113.53(8)
C20 Ru1 Cl2 87.20(8)
C21 Ru1 Cl2 89.37(8)
C22 Ru1 Cl2 116.80(8)
C23 Ru1 Cl2 153.81(7)
P1 Ru1 Cl2 88.19(3)
C24 Ru1 Cl1 122.58(7)
C25 Ru1 Cl1 160.24(8)
C20 Ru1 Cl1 148.74(7)
C21 Ru1 Cl1 112.03(7)
C22 Ru1 Cl1 89.61(7)
C23 Ru1 Cl1 93.64(7)
P1 Ru1 Cl1 90.24(2)
Cl2 Ru1 Cl1 85.87(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.295(4)
C1 N2 1.375(3)
C1 C8 1.502(4)
C2 N2 1.484(3)
C2 C3 1.521(4)
C2 C4 1.527(5)
C5 N2 1.479(4)
C5 C7 1.518(5)
C5 C6 1.536(6)
C8 C9 1.391(4)
C8 C13 1.395(4)
C9 C10 1.385(4)
C10 C11 1.373(5)
C11 C12 1.388(5)
C12 C13 1.384(4)
C14 C15 1.515(4)
C14 C16 1.522(4)
C14 P1 1.854(3)
C17 C19 1.530(4)
C17 C18 1.540(4)
C17 P1 1.861(3)
C20 C25 1.401(4)
C20 C21 1.429(4)
C20 C26 1.500(4)
C20 Ru1 2.224(2)
C21 C22 1.395(4)
C21 Ru1 2.234(3)
C22 C23 1.430(4)
C22 Ru1 2.246(3)
C23 C24 1.404(4)
C23 C27 1.509(4)
C23 Ru1 2.256(2)
C24 C25 1.430(4)
C24 Ru1 2.196(2)
C25 Ru1 2.200(2)
C27 C29 1.522(4)
C27 C28 1.536(4)
N1 P1 1.672(2)
P1 Ru1 2.3967(7)
Cl1 Ru1 2.4148(7)
Cl2 Ru1 2.4026(7)
