#------------------------------------------------------------------------------
#$Date: 2020-10-06 08:51:06 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/81/1558164.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_1558164
loop_
_publ_author_name
'González-Fernández, Rebeca'
'Álvarez, Daniel'
'Crochet, Pascale'
'Cadierno, Victorio'
'Menéndez, M. Isabel'
'López, Ramón'
_publ_section_title
;
 Catalytic hydration of cyanamides with phosphinous acid-based
 ruthenium(ii) and osmium(ii) complexes: scope and mechanistic insights
;
_journal_issue                   12
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              4084
_journal_page_last               4098
_journal_paper_doi               10.1039/D0CY00523A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C16 H29 N2 O1 Cl1 F6 P1 Ru1 Sb1'
_chemical_formula_sum            'C16 H29 Cl F6 N2 O P Ru Sb'
_chemical_formula_weight         668.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-03-11 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.73940(10)
_cell_length_b                   14.7656(2)
_cell_length_c                   14.6955(2)
_cell_measurement_reflns_used    7972
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.4510
_cell_measurement_theta_min      4.2260
_cell_volume                     2420.26(5)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.2640
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12565
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.594
_diffrn_reflns_theta_min         4.232
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    16.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.353
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+2.3911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4053
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cy00523a2.cif
_cod_data_source_block           5a
_cod_depositor_comments
;Adding full bibliography for 1558164--1558165.cif.

 Adding full bibliography for 1558164--1558165.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1558164
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.78339(2) 0.85937(2) 0.07376(2) 0.03523(10) Uani 1 1 d . . . . .
Ru1 Ru 0.82616(2) 0.34424(2) 0.04130(2) 0.02142(9) Uani 1 1 d . . . . .
Cl1 Cl 0.74128(8) 0.46516(7) -0.06789(6) 0.0361(2) Uani 1 1 d . . . . .
P1 P 0.62919(8) 0.30647(7) 0.02092(6) 0.0271(2) Uani 1 1 d . . . . .
F3 F 0.9324(2) 0.8139(3) 0.0751(2) 0.0692(9) Uani 1 1 d . . . . .
N2 N 0.8014(3) 0.1598(2) -0.2094(2) 0.0343(8) Uani 1 1 d . . . . .
O1 O 0.6105(2) 0.2134(2) 0.0705(2) 0.0401(7) Uani 1 1 d . . . . .
F5 F 0.6351(2) 0.9020(3) 0.0772(3) 0.0707(9) Uani 1 1 d . . . . .
F2 F 0.8020(3) 0.7998(2) 0.1901(2) 0.0647(8) Uani 1 1 d . . . . .
C6 C 1.0056(3) 0.4146(3) 0.1082(3) 0.0313(9) Uani 1 1 d . . . . .
H6 H 1.0480 0.4582 0.0838 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5341(3) 0.2981(4) -0.1022(3) 0.0430(11) Uani 1 1 d . . . . .
H15A H 0.5670 0.2527 -0.1358 0.065 Uiso 1 1 calc R U . . .
H15B H 0.5308 0.3570 -0.1337 0.065 Uiso 1 1 calc R U . . .
H15C H 0.4532 0.2801 -0.1038 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8851(3) 0.2845(3) 0.1842(2) 0.0282(8) Uani 1 1 d . . . . .
H3 H 0.8447 0.2409 0.2104 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0023(5) 0.5819(5) 0.2453(6) 0.091(3) Uani 1 1 d . . . . .
H9A H 1.0040 0.5513 0.3049 0.136 Uiso 1 1 calc R U . . .
H9B H 0.9908 0.6471 0.2516 0.136 Uiso 1 1 calc R U . . .
H9C H 1.0784 0.5715 0.2325 0.136 Uiso 1 1 calc R U . . .
F1A F 0.8545(5) 0.9577(4) 0.1608(6) 0.057(2) Uiso 0.564(17) 1 d . . P A 1
F1B F 0.8557(7) 0.9639(6) 0.1191(9) 0.067(3) Uiso 0.436(17) 1 d . . P A 2
C12 C 0.8422(4) 0.1907(4) -0.2889(3) 0.0440(11) Uani 1 1 d . . . . .
H12A H 0.8174 0.2537 -0.3044 0.066 Uiso 1 1 calc R U . . .
H12B H 0.8065 0.1525 -0.3451 0.066 Uiso 1 1 calc R U . . .
H12C H 0.9298 0.1865 -0.2704 0.066 Uiso 1 1 calc R U . . .
N1 N 0.8124(3) 0.2650(2) -0.0767(2) 0.0304(7) Uani 1 1 d . . . . .
C5 C 0.9195(3) 0.4448(3) 0.1538(3) 0.0299(8) Uani 1 1 d . . . . .
C7 C 1.0271(3) 0.3236(3) 0.0995(3) 0.0295(8) Uani 1 1 d . . . . .
H7 H 1.0833 0.3057 0.0683 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8181(5) 0.0633(4) -0.1848(4) 0.0564(13) Uani 1 1 d . . . . .
H13A H 0.9040 0.0494 -0.1611 0.085 Uiso 1 1 calc R U . . .
H13B H 0.7801 0.0267 -0.2419 0.085 Uiso 1 1 calc R U . . .
H13C H 0.7813 0.0492 -0.1351 0.085 Uiso 1 1 calc R U . . .
C11 C 0.8108(3) 0.2166(3) -0.1377(3) 0.0293(8) Uani 1 1 d . . . . .
C2 C 0.9663(3) 0.2551(3) 0.1367(3) 0.0297(8) Uani 1 1 d . . . . .
C16 C 0.6453(5) 0.1291(3) 0.0380(4) 0.0547(13) Uani 1 1 d . . . . .
H16A H 0.5913 0.1154 -0.0262 0.082 Uiso 1 1 calc R U . . .
H16B H 0.6405 0.0805 0.0821 0.082 Uiso 1 1 calc R U . . .
H16C H 0.7277 0.1338 0.0360 0.082 Uiso 1 1 calc R U . . .
C4 C 0.8630(3) 0.3784(3) 0.1934(2) 0.0285(8) Uani 1 1 d . . . . .
H4 H 0.8092 0.3964 0.2267 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5487(4) 0.3813(4) 0.0750(3) 0.0427(11) Uani 1 1 d . . . . .
H14A H 0.4652 0.3611 0.0592 0.064 Uiso 1 1 calc R U . . .
H14B H 0.5508 0.4429 0.0507 0.064 Uiso 1 1 calc R U . . .
H14C H 0.5860 0.3809 0.1447 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7799(4) 0.5678(4) 0.1758(4) 0.0528(12) Uani 1 1 d . . . . .
H10A H 0.7145 0.5446 0.1215 0.079 Uiso 1 1 calc R U . . .
H10B H 0.7729 0.6338 0.1794 0.079 Uiso 1 1 calc R U . . .
H10C H 0.7752 0.5404 0.2352 0.079 Uiso 1 1 calc R U . . .
C8 C 0.8988(4) 0.5442(3) 0.1622(4) 0.0426(10) Uani 1 1 d . . . . .
H8 H 0.9019 0.5740 0.1019 0.051 Uiso 1 1 calc R U . . .
C1 C 0.9920(4) 0.1567(3) 0.1275(3) 0.0411(10) Uani 1 1 d . . . . .
H1A H 1.0718 0.1421 0.1711 0.062 Uiso 1 1 calc R U . . .
H1B H 0.9893 0.1438 0.0614 0.062 Uiso 1 1 calc R U . . .
H1C H 0.9317 0.1200 0.1439 0.062 Uiso 1 1 calc R U . . .
F6 F 0.7116(3) 0.7554(3) 0.0089(3) 0.0799(11) Uani 1 1 d . . . . .
F4A F 0.7724(6) 0.9340(8) -0.0277(6) 0.077(2) Uiso 0.564(17) 1 d . . P A 1
F4B F 0.7579(7) 0.8950(8) -0.0548(7) 0.064(3) Uiso 0.436(17) 1 d . . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 '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
_geom_angle_publ_flag
F1B Sb1 F6 171.2(5) . . ?
F4A Sb1 F6 100.0(4) . . ?
F1B Sb1 F5 92.1(3) . . ?
F4A Sb1 F5 89.4(2) . . ?
F6 Sb1 F5 90.87(15) . . ?
F1B Sb1 F3 88.4(3) . . ?
F4A Sb1 F3 93.0(2) . . ?
F6 Sb1 F3 88.95(16) . . ?
F5 Sb1 F3 177.55(16) . . ?
F1B Sb1 F2 99.2(4) . . ?
F4A Sb1 F2 170.7(4) . . ?
F6 Sb1 F2 89.13(17) . . ?
F5 Sb1 F2 88.74(15) . . ?
F3 Sb1 F2 88.82(14) . . ?
F1B Sb1 F4B 92.3(4) . . ?
F6 Sb1 F4B 79.2(4) . . ?
F5 Sb1 F4B 94.3(3) . . ?
F3 Sb1 F4B 88.1(3) . . ?
F2 Sb1 F4B 168.0(4) . . ?
F4A Sb1 F1A 89.6(3) . . ?
F6 Sb1 F1A 170.1(3) . . ?
F5 Sb1 F1A 86.7(2) . . ?
F3 Sb1 F1A 93.1(2) . . ?
F2 Sb1 F1A 81.2(3) . . ?
N1 Ru1 C3 119.96(14) . . ?
N1 Ru1 C4 157.91(15) . . ?
C3 Ru1 C4 37.95(15) . . ?
N1 Ru1 C2 92.44(14) . . ?
C3 Ru1 C2 37.39(13) . . ?
C4 Ru1 C2 67.90(14) . . ?
N1 Ru1 C5 153.17(12) . . ?
C3 Ru1 C5 67.76(15) . . ?
C4 Ru1 C5 36.97(14) . . ?
C2 Ru1 C5 80.32(15) . . ?
N1 Ru1 C7 92.32(13) . . ?
C3 Ru1 C7 66.52(13) . . ?
C4 Ru1 C7 78.22(13) . . ?
C2 Ru1 C7 37.36(14) . . ?
C5 Ru1 C7 66.32(14) . . ?
N1 Ru1 C6 116.27(13) . . ?
C3 Ru1 C6 78.21(14) . . ?
C4 Ru1 C6 66.09(13) . . ?
C2 Ru1 C6 66.17(15) . . ?
C5 Ru1 C6 37.34(13) . . ?
C7 Ru1 C6 35.39(15) . . ?
N1 Ru1 P1 86.60(9) . . ?
C3 Ru1 P1 91.81(10) . . ?
C4 Ru1 P1 93.36(10) . . ?
C2 Ru1 P1 116.92(10) . . ?
C5 Ru1 P1 119.77(9) . . ?
C7 Ru1 P1 154.24(11) . . ?
C6 Ru1 P1 157.09(10) . . ?
N1 Ru1 Cl1 87.29(10) . . ?
C3 Ru1 Cl1 152.29(11) . . ?
C4 Ru1 Cl1 114.72(11) . . ?
C2 Ru1 Cl1 158.62(10) . . ?
C5 Ru1 Cl1 90.35(11) . . ?
C7 Ru1 Cl1 121.27(11) . . ?
C6 Ru1 Cl1 94.85(11) . . ?
P1 Ru1 Cl1 84.41(3) . . ?
O1 P1 C14 99.27(19) . . ?
O1 P1 C15 105.5(2) . . ?
C14 P1 C15 103.8(2) . . ?
O1 P1 Ru1 114.99(11) . . ?
C14 P1 Ru1 116.05(16) . . ?
C15 P1 Ru1 115.28(13) . . ?
C11 N2 C12 118.0(4) . . ?
C11 N2 C13 116.6(4) . . ?
C12 N2 C13 116.5(4) . . ?
C16 O1 P1 119.9(3) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 Ru1 71.8(2) . . ?
C5 C6 Ru1 69.8(2) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 Ru1 73.1(2) . . ?
C4 C3 Ru1 71.7(2) . . ?
C11 N1 Ru1 174.8(3) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 C8 122.6(3) . . ?
C6 C5 C8 119.6(3) . . ?
C4 C5 Ru1 70.0(2) . . ?
C6 C5 Ru1 72.8(2) . . ?
C8 C5 Ru1 131.0(3) . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 Ru1 72.8(2) . . ?
C2 C7 Ru1 69.9(2) . . ?
N1 C11 N2 176.2(4) . . ?
C3 C2 C7 117.5(4) . . ?
C3 C2 C1 121.9(4) . . ?
C7 C2 C1 120.6(3) . . ?
C3 C2 Ru1 69.5(2) . . ?
C7 C2 Ru1 72.7(2) . . ?
C1 C2 Ru1 130.2(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 Ru1 73.0(2) . . ?
C3 C4 Ru1 70.4(2) . . ?
C5 C8 C10 114.7(4) . . ?
C5 C8 C9 108.2(4) . . ?
C10 C8 C9 110.2(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 F1B 1.787(9) . ?
Sb1 F4A 1.826(7) . ?
Sb1 F6 1.864(3) . ?
Sb1 F5 1.867(3) . ?
Sb1 F3 1.868(3) . ?
Sb1 F2 1.874(3) . ?
Sb1 F4B 1.893(8) . ?
Sb1 F1A 1.943(7) . ?
Ru1 N1 2.056(3) . ?
Ru1 C3 2.181(3) . ?
Ru1 C4 2.199(3) . ?
Ru1 C2 2.228(4) . ?
Ru1 C5 2.238(4) . ?
Ru1 C7 2.266(3) . ?
Ru1 C6 2.278(4) . ?
Ru1 P1 2.3056(9) . ?
Ru1 Cl1 2.3996(10) . ?
P1 O1 1.602(3) . ?
P1 C14 1.793(4) . ?
P1 C15 1.809(4) . ?
N2 C11 1.324(5) . ?
N2 C12 1.467(5) . ?
N2 C13 1.469(6) . ?
O1 C16 1.438(6) . ?
C6 C7 1.381(6) . ?
C6 C5 1.446(5) . ?
C3 C2 1.414(5) . ?
C3 C4 1.424(6) . ?
C9 C8 1.534(8) . ?
N1 C11 1.142(5) . ?
C5 C4 1.407(5) . ?
C5 C8 1.499(6) . ?
C7 C2 1.440(5) . ?
C2 C1 1.498(6) . ?
C10 C8 1.511(6) . ?
