#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:50:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178584 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/95/4069512.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_4069512
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         'C19 H33 Cl2 N2 P1 Ru1'
_chemical_formula_sum            'C19 H33 Cl2 N2 P Ru'
_chemical_formula_weight         492.41
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 95.056(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8481(8)
_cell_length_b                   9.0226(6)
_cell_length_c                   26.7241(18)
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    180
_cell_measurement_theta_max      32.1126
_cell_measurement_theta_min      2.8333
_cell_measurement_wavelength     0.71073
_cell_volume                     2605.5(3)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford-Diffraction XCALIBUR'
_diffrn_measurement_method       ω-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  0.0534
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18799
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.9362
_exptl_absorpt_correction_T_min  0.8645
_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
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.49
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.97
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.97
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                3837
_reflns_number_total             5308
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om900231c_si_001.cif
_cod_data_source_block           compound9b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4069512
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
C1 C 0.2451(3) 0.3813(4) 0.64049(13) 0.0186(8) Uani 1 1 d .
C2 C 0.4325(4) 0.4556(5) 0.69283(15) 0.0311(10) Uani 1 1 d .
H2 H 0.4014 0.3768 0.7136 0.037 Uiso 1 1 calc R
C3 C 0.4296(5) 0.5998(6) 0.72315(18) 0.0518(14) Uani 1 1 d .
H3A H 0.45 0.6818 0.7025 0.078 Uiso 1 1 calc R
H3B H 0.4886 0.5939 0.752 0.078 Uiso 1 1 calc R
H3C H 0.3482 0.6141 0.7339 0.078 Uiso 1 1 calc R
C4 C 0.5620(4) 0.4106(6) 0.68126(18) 0.0450(12) Uani 1 1 d .
H4A H 0.5584 0.3174 0.6638 0.067 Uiso 1 1 calc R
H4B H 0.614 0.401 0.7121 0.067 Uiso 1 1 calc R
H4C H 0.5954 0.4849 0.6606 0.067 Uiso 1 1 calc R
C5 C 0.3805(4) 0.5708(5) 0.60732(15) 0.0292(10) Uani 1 1 d .
H5 H 0.4568 0.6205 0.6206 0.035 Uiso 1 1 calc R
C8 C 0.2201(3) 0.2757(4) 0.68246(13) 0.0187(8) Uani 1 1 d .
C9 C 0.2562(3) 0.1238(4) 0.67859(14) 0.0220(9) Uani 1 1 d .
H9 H 0.3085 0.0938 0.6548 0.026 Uiso 1 1 calc R
C10 C 0.2106(4) 0.0223(5) 0.71168(14) 0.0276(9) Uani 1 1 d .
H10 H 0.2266 -0.0778 0.7073 0.033 Uiso 1 1 calc R
C11 C 0.1413(4) 0.0647(5) 0.75140(14) 0.0312(10) Uani 1 1 d .
H11 H 0.1157 -0.005 0.7739 0.037 Uiso 1 1 calc R
C12 C 0.1119(4) 0.2154(5) 0.75605(14) 0.0309(10) Uani 1 1 d .
H12 H 0.0652 0.2451 0.7819 0.037 Uiso 1 1 calc R
C13 C 0.1515(3) 0.3235(4) 0.72249(14) 0.0247(9) Uani 1 1 d .
H13 H 0.133 0.4233 0.7265 0.03 Uiso 1 1 calc R
C14 C 0.0608(3) 0.1575(4) 0.54258(13) 0.0201(8) Uani 1 1 d .
H14 H -0.0098 0.0894 0.5391 0.024 Uiso 1 1 calc R
C15 C 0.1791(4) 0.0627(5) 0.54938(15) 0.0301(10) Uani 1 1 d .
H15A H 0.1871 0.0061 0.5194 0.045 Uiso 1 1 calc R
H15B H 0.1741 -0.0033 0.5773 0.045 Uiso 1 1 calc R
H15C H 0.2497 0.1262 0.5556 0.045 Uiso 1 1 calc R
C16 C 0.0584(4) 0.2471(5) 0.49439(14) 0.0319(10) Uani 1 1 d .
H16A H 0.1196 0.3242 0.4983 0.048 Uiso 1 1 calc R
H16B H -0.022 0.2905 0.4872 0.048 Uiso 1 1 calc R
H16C H 0.0763 0.1834 0.4672 0.048 Uiso 1 1 calc R
C17 C -0.0809(4) 0.4003(4) 0.57854(14) 0.0253(9) Uani 1 1 d .
H17 H -0.0574 0.4503 0.5482 0.03 Uiso 1 1 calc R
C18 C -0.0953(4) 0.5201(5) 0.61778(15) 0.0366(11) Uani 1 1 d .
H18A H -0.1426 0.6009 0.6027 0.055 Uiso 1 1 calc R
H18B H -0.015 0.5551 0.6305 0.055 Uiso 1 1 calc R
H18C H -0.1372 0.4796 0.6448 0.055 Uiso 1 1 calc R
C19 C -0.2035(4) 0.3213(5) 0.56423(16) 0.0365(11) Uani 1 1 d .
H19A H -0.2261 0.2639 0.5923 0.055 Uiso 1 1 calc R
H19B H -0.1946 0.2569 0.5362 0.055 Uiso 1 1 calc R
H19C H -0.2667 0.3933 0.5553 0.055 Uiso 1 1 calc R
N1 N 0.1691(3) 0.3844(3) 0.59962(11) 0.0224(7) Uani 1 1 d .
N2 N 0.3476(3) 0.4646(3) 0.64678(11) 0.0225(7) Uani 1 1 d .
P1 P 0.04483(9) 0.27152(11) 0.59860(3) 0.0176(2) Uani 1 1 d .
Cl1 Cl -0.01979(9) -0.07347(11) 0.63616(3) 0.0277(2) Uani 1 1 d .
Cl2 Cl -0.15415(9) 0.19821(12) 0.69349(4) 0.0300(2) Uani 1 1 d .
Ru1 Ru 0.05602(3) 0.15059(3) 0.676070(10) 0.01762(10) Uani 1 1 d .
C6 C 0.4098(4) 0.4910(6) 0.55989(16) 0.0435(12) Uani 1 1 d .
H6A H 0.4702 0.4151 0.5682 0.065 Uiso 1 1 calc R
H6B H 0.4422 0.5605 0.5372 0.065 Uiso 1 1 calc R
H6C H 0.3358 0.4468 0.5442 0.065 Uiso 1 1 calc R
C7 C 0.2832(4) 0.6915(5) 0.59742(19) 0.0433(12) Uani 1 1 d .
H7A H 0.2122 0.6512 0.5781 0.065 Uiso 1 1 calc R
H7B H 0.317 0.771 0.5791 0.065 Uiso 1 1 calc R
H7C H 0.2592 0.7284 0.6288 0.065 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 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 123.2(3)
N1 C1 C8 119.4(3)
N2 C1 C8 117.4(3)
N2 C2 C4 111.4(3)
N2 C2 C3 110.7(3)
C4 C2 C3 113.3(4)
N2 C5 C6 111.6(3)
N2 C5 C7 112.2(3)
C6 C5 C7 112.8(4)
C13 C8 C9 120.6(3)
C13 C8 C1 120.4(3)
C9 C8 C1 118.7(3)
C13 C8 Ru1 74.2(2)
C9 C8 Ru1 73.5(2)
C1 C8 Ru1 118.9(2)
C10 C9 C8 117.9(3)
C10 C9 Ru1 71.6(2)
C8 C9 Ru1 67.5(2)
C9 C10 C11 122.9(4)
C9 C10 Ru1 71.2(2)
C11 C10 Ru1 75.2(2)
C12 C11 C10 118.1(4)
C12 C11 Ru1 70.8(2)
C10 C11 Ru1 68.1(2)
C11 C12 C13 121.8(4)
C11 C12 Ru1 73.0(2)
C13 C12 Ru1 69.4(2)
C12 C13 C8 118.4(4)
C12 C13 Ru1 73.4(2)
C8 C13 Ru1 67.2(2)
C16 C14 C15 110.3(3)
C16 C14 P1 113.4(3)
C15 C14 P1 110.6(2)
C18 C17 C19 111.4(3)
C18 C17 P1 111.5(3)
C19 C17 P1 112.7(3)
C1 N1 P1 116.4(3)
C1 N2 C2 121.6(3)
C1 N2 C5 121.3(3)
C2 N2 C5 117.1(3)
N1 P1 C17 101.23(17)
N1 P1 C14 102.62(16)
C17 P1 C14 103.75(17)
N1 P1 Ru1 106.78(11)
C17 P1 Ru1 122.29(13)
C14 P1 Ru1 117.37(12)
C8 Ru1 C9 39.00(14)
C8 Ru1 C10 68.73(15)
C9 Ru1 C10 37.24(14)
C8 Ru1 C13 38.60(14)
C9 Ru1 C13 69.04(14)
C10 Ru1 C13 79.90(15)
C8 Ru1 C12 68.12(14)
C9 Ru1 C12 79.33(15)
C10 Ru1 C12 65.88(16)
C13 Ru1 C12 37.17(14)
C8 Ru1 C11 80.54(14)
C9 Ru1 C11 66.97(15)
C10 Ru1 C11 36.68(15)
C13 Ru1 C11 66.89(15)
C12 Ru1 C11 36.18(15)
C8 Ru1 P1 78.37(10)
C9 Ru1 P1 93.04(10)
C10 Ru1 P1 127.72(11)
C13 Ru1 P1 98.86(10)
C12 Ru1 P1 135.28(11)
C11 Ru1 P1 158.28(11)
C8 Ru1 Cl1 138.07(11)
C9 Ru1 Cl1 102.84(10)
C10 Ru1 Cl1 88.12(11)
C13 Ru1 Cl1 167.71(11)
C12 Ru1 Cl1 134.11(11)
C11 Ru1 Cl1 101.72(11)
P1 Ru1 Cl1 90.61(3)
C8 Ru1 Cl2 134.32(11)
C9 Ru1 Cl2 166.48(10)
C10 Ru1 Cl2 135.59(11)
C13 Ru1 Cl2 99.88(11)
C12 Ru1 Cl2 87.15(11)
C11 Ru1 Cl2 102.01(11)
P1 Ru1 Cl2 96.44(4)
Cl1 Ru1 Cl2 86.73(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.309(4)
C1 N2 1.340(4)
C1 C8 1.514(5)
C2 N2 1.473(5)
C2 C4 1.521(6)
C2 C3 1.535(6)
C5 N2 1.491(5)
C5 C6 1.516(6)
C5 C7 1.523(6)
C8 C13 1.423(5)
C8 C9 1.431(5)
C8 Ru1 2.102(3)
C9 C10 1.394(5)
C9 Ru1 2.181(4)
C10 C11 1.406(6)
C10 Ru1 2.185(4)
C11 C12 1.405(6)
C11 Ru1 2.276(4)
C12 C13 1.417(5)
C12 Ru1 2.247(4)
C13 Ru1 2.195(4)
C14 C16 1.519(5)
C14 C15 1.539(5)
C14 P1 1.837(4)
C17 C18 1.523(5)
C17 C19 1.528(6)
C17 P1 1.836(4)
N1 P1 1.688(3)
P1 Ru1 2.3339(10)
Cl1 Ru1 2.3971(10)
Cl2 Ru1 2.4056(10)
