#------------------------------------------------------------------------------
#$Date: 2019-11-02 08:01:22 +0200 (Sat, 02 Nov 2019) $
#$Revision: 221031 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/78/4127868.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_4127868
loop_
_publ_author_name
'Yamamoto, Kensuke'
'Mohara, Yusei'
'Mutoh, Yuichiro'
'Saito, Shinichi'
_publ_section_title
;
 Ruthenium-Catalyzed (Z)-Selective Hydroboration of Terminal
 Alkynes with Naphthalene-1,8-diaminatoborane.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17042
_journal_page_last               17047
_journal_paper_doi               10.1021/jacs.9b06910
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C53 H70 B Cl N4 O P Ru'
_chemical_formula_weight         957.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                93.5660(10)
_cell_angle_beta                 99.4480(10)
_cell_angle_gamma                107.1080(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1502(7)
_cell_length_b                   14.1459(11)
_cell_length_c                   19.8419(15)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.37
_cell_volume                     2404.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.517
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       prism
_exptl_crystal_F_000             1010
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         10720
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0288P)²+1.0896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9609
_reflns_number_total             10720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b06910_si_002.cif
_cod_data_source_block           KY4212
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4127868
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.935
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Ru1 Ru 0.67115(2) 0.24999(2) 0.25550(2) 0.00822(4) Uani 1 1 d . . . . .
Cl1A Cl 0.39624(10) 0.20179(7) 0.20151(4) 0.0127(3) Uani 0.888(7) 1 d . . P A 1
O1A O 1.0007(4) 0.2992(3) 0.3263(2) 0.0187(7) Uani 0.888(7) 1 d . . P A 1
C1A C 0.8698(4) 0.2771(3) 0.2971(2) 0.0137(8) Uani 0.888(7) 1 d . . P A 1
O1B O 0.350(3) 0.2076(16) 0.1893(12) 0.016(4) Uani 0.112(7) 1 d . U P A 2
Cl1B Cl 0.9443(13) 0.2831(6) 0.3094(4) 0.026(5) Uani 0.112(7) 1 d . . P A 2
C1B C 0.471(4) 0.2208(17) 0.2163(12) 0.015(4) Uani 0.112(7) 1 d . U P A 2
C2 C 0.70954(19) 0.19165(12) 0.16195(8) 0.0113(3) Uani 1 1 d . . . . .
P1 P 0.60202(5) 0.28585(3) 0.36394(2) 0.00879(9) Uani 1 1 d . . . . .
N1 N 0.69222(17) 0.09368(10) 0.15089(7) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.7174(2) 0.06209(13) 0.08255(9) 0.0198(4) Uani 1 1 d . . . . .
H3 H 0.625928 0.007896 0.057033 0.024 Uiso 1 1 calc R U . . .
H3A H 0.811008 0.039696 0.086435 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7400(3) 0.15715(14) 0.04824(10) 0.0269(5) Uani 1 1 d . . . . .
H4 H 0.840448 0.176351 0.032165 0.032 Uiso 1 1 calc R U . . .
H4A H 0.654193 0.149563 0.008752 0.032 Uiso 1 1 calc R U . . .
N2 N 0.73854(18) 0.23071(10) 0.10387(7) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.6925(2) 0.02853(12) 0.20370(8) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.5525(2) -0.04174(12) 0.21003(9) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.5579(2) -0.10655(12) 0.25975(9) 0.0160(4) Uani 1 1 d . . . . .
H7 H 0.464048 -0.154808 0.264541 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6961(2) -0.10285(13) 0.30248(9) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.8329(2) -0.03369(13) 0.29384(9) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.928066 -0.030570 0.322948 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8351(2) 0.03126(12) 0.24384(9) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.3999(2) -0.04948(14) 0.16426(10) 0.0214(4) Uani 1 1 d . . . . .
H11 H 0.326177 -0.115885 0.163628 0.032 Uiso 1 1 calc R U . . .
H11A H 0.416744 -0.038623 0.117466 0.032 Uiso 1 1 calc R U . . .
H11B H 0.357458 0.001019 0.181905 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6991(3) -0.17664(15) 0.35368(10) 0.0279(5) Uani 1 1 d . . . . .
H12 H 0.611467 -0.183997 0.377570 0.042 Uiso 1 1 calc R U . . .
H12A H 0.797201 -0.152797 0.387231 0.042 Uiso 1 1 calc R U . . .
H12B H 0.690634 -0.241206 0.329600 0.042 Uiso 1 1 calc R U . . .
C13 C 0.9896(2) 0.09634(13) 0.23184(10) 0.0207(4) Uani 1 1 d . . . . .
H13 H 1.056288 0.128327 0.276102 0.031 Uiso 1 1 calc R U . . .
H13A H 0.972680 0.147526 0.203165 0.031 Uiso 1 1 calc R U . . .
H13B H 1.040339 0.055445 0.208451 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7823(2) 0.33380(12) 0.09199(9) 0.0162(4) Uani 1 1 d . . . . .
C15 C 0.9388(2) 0.39104(14) 0.11162(9) 0.0210(4) Uani 1 1 d . . . . .
C16 C 0.9815(3) 0.48844(14) 0.09477(10) 0.0269(5) Uani 1 1 d . . . . .
H16 H 1.086914 0.528986 0.108368 0.032 Uiso 1 1 calc R U . . .
N3 N 0.87377(17) 0.47240(10) 0.25716(7) 0.0129(3) Uani 1 1 d . . . . .
H3B H 0.951(2) 0.4580(14) 0.2770(10) 0.015 Uiso 1 1 d . U . . .
C17 C 0.8741(3) 0.52775(14) 0.05870(10) 0.0303(5) Uani 1 1 d . . . . .
C18 C 0.7207(3) 0.46798(15) 0.03916(10) 0.0282(5) Uani 1 1 d . . . . .
H18 H 0.647023 0.494166 0.013873 0.034 Uiso 1 1 calc R U . . .
C19 C 0.6710(2) 0.37054(14) 0.05542(9) 0.0220(4) Uani 1 1 d . . . . .
C20 C 1.0586(2) 0.34989(16) 0.14940(10) 0.0286(5) Uani 1 1 d . . . . .
H20 H 1.028705 0.328748 0.192616 0.043 Uiso 1 1 calc R U . . .
H20A H 1.160364 0.401466 0.159363 0.043 Uiso 1 1 calc R U . . .
H20B H 1.064757 0.292647 0.120834 0.043 Uiso 1 1 calc R U . . .
C21 C 0.9247(3) 0.63449(15) 0.04267(12) 0.0459(7) Uani 1 1 d . . . . .
H21 H 0.850024 0.642982 0.003889 0.069 Uiso 1 1 calc R U . . .
H21A H 1.028209 0.650277 0.030670 0.069 Uiso 1 1 calc R U . . .
H21B H 0.928513 0.679296 0.083086 0.069 Uiso 1 1 calc R U . . .
C22 C 0.5026(2) 0.30828(16) 0.03561(11) 0.0302(5) Uani 1 1 d . . . . .
H22 H 0.438912 0.350842 0.020753 0.045 Uiso 1 1 calc R U . . .
H22A H 0.468595 0.276623 0.075322 0.045 Uiso 1 1 calc R U . . .
H22B H 0.490467 0.256847 -0.002140 0.045 Uiso 1 1 calc R U . . .
B1 B 0.7259(2) 0.39575(14) 0.23755(9) 0.0124(4) Uani 1 1 d . . . . .
C23 C 0.9016(2) 0.57046(12) 0.24285(8) 0.0128(3) Uani 1 1 d . . . . .
C24 C 1.0485(2) 0.63952(13) 0.25799(9) 0.0175(4) Uani 1 1 d . . . . .
H24 H 1.135533 0.619821 0.277297 0.021 Uiso 1 1 calc R U . . .
C25 C 1.0698(2) 0.73862(13) 0.24501(9) 0.0214(4) Uani 1 1 d . . . . .
H25 H 1.171312 0.785355 0.256378 0.026 Uiso 1 1 calc R U . . .
C26 C 0.9479(2) 0.76933(13) 0.21643(9) 0.0216(4) Uani 1 1 d . . . . .
H26 H 0.965054 0.837179 0.209186 0.026 Uiso 1 1 calc R U . . .
C27 C 0.7958(2) 0.70053(13) 0.19749(9) 0.0174(4) Uani 1 1 d . . . . .
C28 C 0.6668(2) 0.72742(14) 0.16460(10) 0.0226(4) Uani 1 1 d . . . . .
H28 H 0.679889 0.794325 0.155683 0.027 Uiso 1 1 calc R U . . .
C29 C 0.5233(2) 0.65727(15) 0.14561(10) 0.0237(4) Uani 1 1 d . . . . .
H29 H 0.437743 0.676428 0.123777 0.028 Uiso 1 1 calc R U . . .
C30 C 0.5000(2) 0.55780(14) 0.15768(9) 0.0198(4) Uani 1 1 d . . . . .
H30 H 0.399490 0.510470 0.143612 0.024 Uiso 1 1 calc R U . . .
C31 C 0.6220(2) 0.52810(12) 0.18984(8) 0.0144(3) Uani 1 1 d . . . . .
N4 N 0.60529(17) 0.43065(11) 0.20268(7) 0.0138(3) Uani 1 1 d . . . . .
H4B H 0.522(2) 0.3940(15) 0.1890(10) 0.017 Uiso 1 1 d . U . . .
C32 C 0.7731(2) 0.59974(12) 0.21090(8) 0.0135(3) Uani 1 1 d . . . . .
C33 C 0.76672(19) 0.30975(12) 0.43849(8) 0.0109(3) Uani 1 1 d . . . . .
H33 H 0.855958 0.360521 0.425272 0.013 Uiso 1 1 calc R U . . .
C34 C 0.8230(2) 0.21819(12) 0.45005(8) 0.0132(3) Uani 1 1 d . . . . .
H34 H 0.744545 0.167651 0.468620 0.016 Uiso 1 1 calc R U . . .
H34A H 0.834411 0.188165 0.405558 0.016 Uiso 1 1 calc R U . . .
C35 C 0.9793(2) 0.24814(13) 0.50032(9) 0.0173(4) Uani 1 1 d . . . . .
H35 H 1.012179 0.188332 0.507905 0.021 Uiso 1 1 calc R U . . .
H35A H 1.059395 0.295132 0.480244 0.021 Uiso 1 1 calc R U . . .
C36 C 0.9669(2) 0.29722(13) 0.56920(9) 0.0163(4) Uani 1 1 d . . . . .
H36 H 0.896545 0.247669 0.591992 0.020 Uiso 1 1 calc R U . . .
H36A H 1.070979 0.320613 0.599550 0.020 Uiso 1 1 calc R U . . .
C37 C 0.9046(2) 0.38502(12) 0.55872(9) 0.0145(3) Uani 1 1 d . . . . .
H37 H 0.981318 0.437913 0.541050 0.017 Uiso 1 1 calc R U . . .
H37A H 0.890979 0.412674 0.603510 0.017 Uiso 1 1 calc R U . . .
C38 C 0.74866(19) 0.35425(12) 0.50812(8) 0.0134(3) Uani 1 1 d . . . . .
H38 H 0.712400 0.413073 0.501743 0.016 Uiso 1 1 calc R U . . .
H38A H 0.669672 0.304428 0.526932 0.016 Uiso 1 1 calc R U . . .
C39 C 0.43928(19) 0.17713(11) 0.37624(8) 0.0108(3) Uani 1 1 d . . . . .
H39 H 0.348156 0.177755 0.340903 0.013 Uiso 1 1 calc R U . . .
C40 C 0.4666(2) 0.07719(12) 0.35790(9) 0.0148(3) Uani 1 1 d . . . . .
H40 H 0.500499 0.077093 0.313018 0.018 Uiso 1 1 calc R U . . .
H40A H 0.550428 0.068772 0.393179 0.018 Uiso 1 1 calc R U . . .
C41 C 0.3176(2) -0.00934(12) 0.35408(10) 0.0190(4) Uani 1 1 d . . . . .
H41 H 0.237346 -0.004544 0.315527 0.023 Uiso 1 1 calc R U . . .
H41A H 0.339072 -0.073029 0.344777 0.023 Uiso 1 1 calc R U . . .
C42 C 0.2554(2) -0.00883(13) 0.42093(10) 0.0210(4) Uani 1 1 d . . . . .
H42 H 0.329493 -0.022637 0.458343 0.025 Uiso 1 1 calc R U . . .
H42A H 0.154691 -0.062370 0.415365 0.025 Uiso 1 1 calc R U . . .
C43 C 0.2323(2) 0.09136(13) 0.44076(10) 0.0190(4) Uani 1 1 d . . . . .
H43 H 0.199478 0.090909 0.485889 0.023 Uiso 1 1 calc R U . . .
H43A H 0.148595 0.101359 0.406206 0.023 Uiso 1 1 calc R U . . .
C44 C 0.3829(2) 0.17760(12) 0.44487(9) 0.0160(4) Uani 1 1 d . . . . .
H44 H 0.363705 0.241656 0.455777 0.019 Uiso 1 1 calc R U . . .
H44A H 0.464288 0.170933 0.482142 0.019 Uiso 1 1 calc R U . . .
C45 C 0.52484(18) 0.39112(11) 0.38064(8) 0.0104(3) Uani 1 1 d . . . . .
H45 H 0.495874 0.386134 0.427043 0.012 Uiso 1 1 calc R U . . .
C46 C 0.37605(19) 0.38554(12) 0.32987(9) 0.0132(3) Uani 1 1 d . . . . .
H46 H 0.295977 0.320884 0.330003 0.016 Uiso 1 1 calc R U . . .
H46A H 0.398695 0.389563 0.282840 0.016 Uiso 1 1 calc R U . . .
C47 C 0.3132(2) 0.47070(12) 0.34926(9) 0.0153(3) Uani 1 1 d . . . . .
H47 H 0.222343 0.468548 0.313659 0.018 Uiso 1 1 calc R U . . .
H47A H 0.277184 0.461120 0.393480 0.018 Uiso 1 1 calc R U . . .
C48 C 0.4360(2) 0.57274(12) 0.35595(9) 0.0150(3) Uani 1 1 d . . . . .
H48 H 0.393255 0.625040 0.371715 0.018 Uiso 1 1 calc R U . . .
H48A H 0.463409 0.586193 0.310494 0.018 Uiso 1 1 calc R U . . .
C49 C 0.58203(19) 0.57587(12) 0.40732(9) 0.0131(3) Uani 1 1 d . . . . .
H49 H 0.556003 0.566898 0.453483 0.016 Uiso 1 1 calc R U . . .
H49A H 0.661754 0.641600 0.410317 0.016 Uiso 1 1 calc R U . . .
C50 C 0.64740(18) 0.49373(11) 0.38485(9) 0.0115(3) Uani 1 1 d . . . . .
H50 H 0.742239 0.496798 0.418275 0.014 Uiso 1 1 calc R U . . .
H50A H 0.676486 0.503792 0.339313 0.014 Uiso 1 1 calc R U . . .
C51 C 0.1217(2) 0.04674(18) 0.05353(11) 0.0347(5) Uani 1 1 d . . . . .
H51 H 0.205813 0.078935 0.090398 0.042 Uiso 1 1 calc R U . . .
C52 C 0.0865(2) 0.09759(16) -0.00049(13) 0.0353(5) Uani 1 1 d . . . . .
H52 H 0.145844 0.165016 -0.000912 0.042 Uiso 1 1 calc R U . . .
C53 C -0.0356(3) 0.05031(18) -0.05423(11) 0.0347(5) Uani 1 1 d . . . . .
H53 H -0.059821 0.085244 -0.091710 0.042 Uiso 1 1 calc R U . . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
C1B Ru1 B1 94.3(6) .
C1A Ru1 B1 87.04(14) .
C1B Ru1 C2 87.8(6) .
C1A Ru1 C2 93.28(14) .
B1 Ru1 C2 97.52(7) .
C1B Ru1 P1 88.5(6) .
C1A Ru1 P1 90.16(13) .
B1 Ru1 P1 92.41(5) .
C2 Ru1 P1 169.64(4) .
C1A Ru1 Cl1A 176.07(13) .
B1 Ru1 Cl1A 96.85(6) .
C2 Ru1 Cl1A 86.78(5) .
P1 Ru1 Cl1A 89.11(2) .
C1B Ru1 Cl1B 177.7(7) .
B1 Ru1 Cl1B 87.9(2) .
C2 Ru1 Cl1B 91.4(2) .
P1 Ru1 Cl1B 91.9(2) .
O1A C1A Ru1 176.7(5) .
O1B C1B Ru1 175(2) .
N2 C2 N1 107.17(14) .
N2 C2 Ru1 133.23(12) .
N1 C2 Ru1 119.37(11) .
C45 P1 C39 101.78(7) .
C45 P1 C33 101.89(7) .
C39 P1 C33 109.11(7) .
C45 P1 Ru1 122.00(5) .
C39 P1 Ru1 107.85(5) .
C33 P1 Ru1 113.21(5) .
C2 N1 C5 124.95(14) .
C2 N1 C3 113.83(13) .
C5 N1 C3 119.12(13) .
N1 C3 C4 102.14(14) .
N1 C3 H3 111.3 .
C4 C3 H3 111.3 .
N1 C3 H3A 111.3 .
C4 C3 H3A 111.3 .
H3 C3 H3A 109.2 .
N2 C4 C3 102.90(14) .
N2 C4 H4 111.2 .
C3 C4 H4 111.2 .
N2 C4 H4A 111.2 .
C3 C4 H4A 111.2 .
H4 C4 H4A 109.1 .
C2 N2 C14 128.58(14) .
C2 N2 C4 113.68(14) .
C14 N2 C4 117.42(13) .
C6 C5 C10 121.44(15) .
C6 C5 N1 119.42(15) .
C10 C5 N1 118.92(15) .
C7 C6 C5 117.96(16) .
C7 C6 C11 120.10(16) .
C5 C6 C11 121.94(16) .
C8 C7 C6 122.06(16) .
C8 C7 H7 119.0 .
C6 C7 H7 119.0 .
C9 C8 C7 118.43(16) .
C9 C8 C12 120.68(17) .
C7 C8 C12 120.76(16) .
C8 C9 C10 122.02(17) .
C8 C9 H9 119.0 .
C10 C9 H9 119.0 .
C9 C10 C5 117.97(16) .
C9 C10 C13 119.19(16) .
C5 C10 C13 122.72(15) .
C6 C11 H11 109.5 .
C6 C11 H11A 109.5 .
H11 C11 H11A 109.5 .
C6 C11 H11B 109.5 .
H11 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C8 C12 H12 109.5 .
C8 C12 H12A 109.5 .
H12 C12 H12A 109.5 .
C8 C12 H12B 109.5 .
H12 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C10 C13 H13 109.5 .
C10 C13 H13A 109.5 .
H13 C13 H13A 109.5 .
C10 C13 H13B 109.5 .
H13 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C19 C14 C15 122.10(16) .
C19 C14 N2 119.11(16) .
C15 C14 N2 118.48(16) .
C16 C15 C14 117.75(18) .
C16 C15 C20 120.56(18) .
C14 C15 C20 121.69(16) .
C17 C16 C15 121.8(2) .
C17 C16 H16 119.1 .
C15 C16 H16 119.1 .
C23 N3 B1 124.64(15) .
C23 N3 H3B 115.9(13) .
B1 N3 H3B 119.4(13) .
C18 C17 C16 118.59(18) .
C18 C17 C21 121.3(2) .
C16 C17 C21 120.1(2) .
C17 C18 C19 122.1(2) .
C17 C18 H18 119.0 .
C19 C18 H18 119.0 .
C18 C19 C14 117.63(19) .
C18 C19 C22 121.02(18) .
C14 C19 C22 121.33(17) .
C15 C20 H20 109.5 .
C15 C20 H20A 109.5 .
H20 C20 H20A 109.5 .
C15 C20 H20B 109.5 .
H20 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C17 C21 H21 109.5 .
C17 C21 H21A 109.5 .
H21 C21 H21A 109.5 .
C17 C21 H21B 109.5 .
H21 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C19 C22 H22 109.5 .
C19 C22 H22A 109.5 .
H22 C22 H22A 109.5 .
C19 C22 H22B 109.5 .
H22 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
N4 B1 N3 113.23(15) .
N4 B1 Ru1 118.59(13) .
N3 B1 Ru1 128.16(14) .
C24 C23 N3 122.49(16) .
C24 C23 C32 119.29(15) .
N3 C23 C32 118.22(15) .
C23 C24 C25 120.37(17) .
C23 C24 H24 119.8 .
C25 C24 H24 119.8 .
C26 C25 C24 121.48(17) .
C26 C25 H25 119.3 .
C24 C25 H25 119.3 .
C25 C26 C27 120.38(17) .
C25 C26 H26 119.8 .
C27 C26 H26 119.8 .
C28 C27 C26 122.64(17) .
C28 C27 C32 118.94(17) .
C26 C27 C32 118.41(17) .
C29 C28 C27 120.19(17) .
C29 C28 H28 119.9 .
C27 C28 H28 119.9 .
C28 C29 C30 121.42(18) .
C28 C29 H29 119.3 .
C30 C29 H29 119.3 .
C31 C30 C29 120.52(17) .
C31 C30 H30 119.7 .
C29 C30 H30 119.7 .
C30 C31 N4 122.79(16) .
C30 C31 C32 119.48(16) .
N4 C31 C32 117.73(15) .
C31 N4 B1 125.46(15) .
C31 N4 H4B 114.1(15) .
B1 N4 H4B 120.4(15) .
C23 C32 C27 119.99(15) .
C23 C32 C31 120.53(15) .
C27 C32 C31 119.44(16) .
C38 C33 C34 108.43(13) .
C38 C33 P1 118.24(11) .
C34 C33 P1 113.16(11) .
C38 C33 H33 105.3 .
C34 C33 H33 105.3 .
P1 C33 H33 105.3 .
C35 C34 C33 110.64(13) .
C35 C34 H34 109.5 .
C33 C34 H34 109.5 .
C35 C34 H34A 109.5 .
C33 C34 H34A 109.5 .
H34 C34 H34A 108.1 .
C36 C35 C34 110.94(14) .
C36 C35 H35 109.5 .
C34 C35 H35 109.5 .
C36 C35 H35A 109.5 .
C34 C35 H35A 109.5 .
H35 C35 H35A 108.0 .
C37 C36 C35 110.79(14) .
C37 C36 H36 109.5 .
C35 C36 H36 109.5 .
C37 C36 H36A 109.5 .
C35 C36 H36A 109.5 .
H36 C36 H36A 108.1 .
C36 C37 C38 111.63(14) .
C36 C37 H37 109.3 .
C38 C37 H37 109.3 .
C36 C37 H37A 109.3 .
C38 C37 H37A 109.3 .
H37 C37 H37A 108.0 .
C37 C38 C33 110.13(14) .
C37 C38 H38 109.6 .
C33 C38 H38 109.6 .
C37 C38 H38A 109.6 .
C33 C38 H38A 109.6 .
H38 C38 H38A 108.1 .
C44 C39 C40 110.22(13) .
C44 C39 P1 118.10(11) .
C40 C39 P1 112.49(11) .
C44 C39 H39 104.9 .
C40 C39 H39 104.9 .
P1 C39 H39 104.9 .
C41 C40 C39 110.59(14) .
C41 C40 H40 109.5 .
C39 C40 H40 109.5 .
C41 C40 H40A 109.5 .
C39 C40 H40A 109.5 .
H40 C40 H40A 108.1 .
C42 C41 C40 111.51(14) .
C42 C41 H41 109.3 .
C40 C41 H41 109.3 .
C42 C41 H41A 109.3 .
C40 C41 H41A 109.3 .
H41 C41 H41A 108.0 .
C41 C42 C43 111.47(14) .
C41 C42 H42 109.3 .
C43 C42 H42 109.3 .
C41 C42 H42A 109.3 .
C43 C42 H42A 109.3 .
H42 C42 H42A 108.0 .
C42 C43 C44 111.19(15) .
C42 C43 H43 109.4 .
C44 C43 H43 109.4 .
C42 C43 H43A 109.4 .
C44 C43 H43A 109.4 .
H43 C43 H43A 108.0 .
C39 C44 C43 110.23(14) .
C39 C44 H44 109.6 .
C43 C44 H44 109.6 .
C39 C44 H44A 109.6 .
C43 C44 H44A 109.6 .
H44 C44 H44A 108.1 .
C46 C45 C50 110.40(13) .
C46 C45 P1 113.61(11) .
C50 C45 P1 113.00(11) .
C46 C45 H45 106.4 .
C50 C45 H45 106.4 .
P1 C45 H45 106.4 .
C45 C46 C47 110.87(13) .
C45 C46 H46 109.5 .
C47 C46 H46 109.5 .
C45 C46 H46A 109.5 .
C47 C46 H46A 109.5 .
H46 C46 H46A 108.1 .
C48 C47 C46 112.20(14) .
C48 C47 H47 109.2 .
C46 C47 H47 109.2 .
C48 C47 H47A 109.2 .
C46 C47 H47A 109.2 .
H47 C47 H47A 107.9 .
C47 C48 C49 110.28(14) .
C47 C48 H48 109.6 .
C49 C48 H48 109.6 .
C47 C48 H48A 109.6 .
C49 C48 H48A 109.6 .
H48 C48 H48A 108.1 .
C48 C49 C50 110.39(13) .
C48 C49 H49 109.6 .
C50 C49 H49 109.6 .
C48 C49 H49A 109.6 .
C50 C49 H49A 109.6 .
H49 C49 H49A 108.1 .
C49 C50 C45 110.00(13) .
C49 C50 H50 109.7 .
C45 C50 H50 109.7 .
C49 C50 H50A 109.7 .
C45 C50 H50A 109.7 .
H50 C50 H50A 108.2 .
C53 C51 C52 120.0(2) 2
C53 C51 H51 120.0 2
C52 C51 H51 120.0 .
C51 C52 C53 119.8(2) .
C51 C52 H52 120.1 .
C53 C52 H52 120.1 .
C51 C53 C52 120.2(2) 2
C51 C53 H53 119.9 2
C52 C53 H53 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 C1B 1.78(3) .
Ru1 C1A 1.787(4) .
Ru1 B1 2.0424(19) .
Ru1 C2 2.1081(16) .
Ru1 P1 2.4057(4) .
Ru1 Cl1A 2.4404(9) .
Ru1 Cl1B 2.446(11) .
O1A C1A 1.182(6) .
O1B C1B 1.11(5) .
C2 N2 1.341(2) .
C2 N1 1.347(2) .
P1 C45 1.8602(16) .
P1 C39 1.8602(16) .
P1 C33 1.8653(16) .
N1 C5 1.438(2) .
N1 C3 1.476(2) .
C3 C4 1.520(2) .
C3 H3 0.9900 .
C3 H3A 0.9900 .
C4 N2 1.474(2) .
C4 H4 0.9900 .
C4 H4A 0.9900 .
N2 C14 1.440(2) .
C5 C6 1.402(2) .
C5 C10 1.401(2) .
C6 C7 1.393(2) .
C6 C11 1.506(2) .
C7 C8 1.387(3) .
C7 H7 0.9500 .
C8 C9 1.388(2) .
C8 C12 1.504(2) .
C9 C10 1.392(2) .
C9 H9 0.9500 .
C10 C13 1.509(2) .
C11 H11 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C12 H12 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C13 H13 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 C19 1.397(3) .
C14 C15 1.398(3) .
C15 C16 1.395(3) .
C15 C20 1.504(3) .
C16 C17 1.388(3) .
C16 H16 0.9500 .
N3 C23 1.391(2) .
N3 B1 1.439(2) .
N3 H3B 0.84(2) .
C17 C18 1.385(3) .
C17 C21 1.514(3) .
C18 C19 1.395(3) .
C18 H18 0.9500 .
C19 C22 1.505(3) .
C20 H20 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C21 H21 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C22 H22 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
B1 N4 1.433(2) .
C23 C24 1.382(2) .
C23 C32 1.425(2) .
C24 C25 1.404(2) .
C24 H24 0.9500 .
C25 C26 1.364(3) .
C25 H25 0.9500 .
C26 C27 1.418(3) .
C26 H26 0.9500 .
C27 C28 1.416(3) .
C27 C32 1.428(2) .
C28 C29 1.369(3) .
C28 H28 0.9500 .
C29 C30 1.402(3) .
C29 H29 0.9500 .
C30 C31 1.380(2) .
C30 H30 0.9500 .
C31 N4 1.386(2) .
C31 C32 1.431(2) .
N4 H4B 0.78(2) .
C33 C38 1.536(2) .
C33 C34 1.545(2) .
C33 H33 1.0000 .
C34 C35 1.530(2) .
C34 H34 0.9900 .
C34 H34A 0.9900 .
C35 C36 1.530(2) .
C35 H35 0.9900 .
C35 H35A 0.9900 .
C36 C37 1.524(2) .
C36 H36 0.9900 .
C36 H36A 0.9900 .
C37 C38 1.531(2) .
C37 H37 0.9900 .
C37 H37A 0.9900 .
C38 H38 0.9900 .
C38 H38A 0.9900 .
C39 C44 1.534(2) .
C39 C40 1.539(2) .
C39 H39 1.0000 .
C40 C41 1.528(2) .
C40 H40 0.9900 .
C40 H40A 0.9900 .
C41 C42 1.527(3) .
C41 H41 0.9900 .
C41 H41A 0.9900 .
C42 C43 1.530(3) .
C42 H42 0.9900 .
C42 H42A 0.9900 .
C43 C44 1.534(2) .
C43 H43 0.9900 .
C43 H43A 0.9900 .
C44 H44 0.9900 .
C44 H44A 0.9900 .
C45 C46 1.533(2) .
C45 C50 1.539(2) .
C45 H45 1.0000 .
C46 C47 1.534(2) .
C46 H46 0.9900 .
C46 H46A 0.9900 .
C47 C48 1.529(2) .
C47 H47 0.9900 .
C47 H47A 0.9900 .
C48 C49 1.529(2) .
C48 H48 0.9900 .
C48 H48A 0.9900 .
C49 C50 1.529(2) .
C49 H49 0.9900 .
C49 H49A 0.9900 .
C50 H50 0.9900 .
C50 H50A 0.9900 .
C51 C53 1.369(3) 2
C51 C52 1.374(3) .
C51 H51 0.9500 .
C52 C53 1.383(3) .
C52 H52 0.9500 .
C53 H53 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N2 C2 N1 C5 166.15(15) . .
Ru1 C2 N1 C5 -18.6(2) . .
N2 C2 N1 C3 2.9(2) . .
Ru1 C2 N1 C3 178.08(12) . .
C2 N1 C3 C4 -5.1(2) . .
C5 N1 C3 C4 -169.42(16) . .
N1 C3 C4 N2 4.91(19) . .
N1 C2 N2 C14 -172.49(16) . .
Ru1 C2 N2 C14 13.2(3) . .
N1 C2 N2 C4 0.8(2) . .
Ru1 C2 N2 C4 -173.46(14) . .
C3 C4 N2 C2 -3.9(2) . .
C3 C4 N2 C14 170.25(16) . .
C2 N1 C5 C6 107.58(19) . .
C3 N1 C5 C6 -89.9(2) . .
C2 N1 C5 C10 -77.7(2) . .
C3 N1 C5 C10 84.7(2) . .
C10 C5 C6 C7 2.7(2) . .
N1 C5 C6 C7 177.27(15) . .
C10 C5 C6 C11 -176.22(16) . .
N1 C5 C6 C11 -1.7(2) . .
C5 C6 C7 C8 0.3(3) . .
C11 C6 C7 C8 179.26(16) . .
C6 C7 C8 C9 -1.6(3) . .
C6 C7 C8 C12 -177.45(17) . .
C7 C8 C9 C10 -0.1(3) . .
C12 C8 C9 C10 175.77(17) . .
C8 C9 C10 C5 3.0(3) . .
C8 C9 C10 C13 -173.06(16) . .
C6 C5 C10 C9 -4.3(3) . .
N1 C5 C10 C9 -178.87(15) . .
C6 C5 C10 C13 171.57(16) . .
N1 C5 C10 C13 -3.0(2) . .
C2 N2 C14 C19 -104.1(2) . .
C4 N2 C14 C19 82.8(2) . .
C2 N2 C14 C15 82.2(2) . .
C4 N2 C14 C15 -90.9(2) . .
C19 C14 C15 C16 1.4(3) . .
N2 C14 C15 C16 174.95(15) . .
C19 C14 C15 C20 -178.40(17) . .
N2 C14 C15 C20 -4.8(3) . .
C14 C15 C16 C17 -1.1(3) . .
C20 C15 C16 C17 178.66(17) . .
C15 C16 C17 C18 0.0(3) . .
C15 C16 C17 C21 178.82(17) . .
C16 C17 C18 C19 0.9(3) . .
C21 C17 C18 C19 -177.88(18) . .
C17 C18 C19 C14 -0.7(3) . .
C17 C18 C19 C22 177.94(18) . .
C15 C14 C19 C18 -0.5(3) . .
N2 C14 C19 C18 -174.05(15) . .
C15 C14 C19 C22 -179.12(17) . .
N2 C14 C19 C22 7.4(3) . .
C23 N3 B1 N4 -1.7(2) . .
C23 N3 B1 Ru1 179.95(12) . .
B1 N3 C23 C24 -174.80(16) . .
B1 N3 C23 C32 4.7(2) . .
N3 C23 C24 C25 -177.51(15) . .
C32 C23 C24 C25 3.0(3) . .
C23 C24 C25 C26 -0.9(3) . .
C24 C25 C26 C27 -1.5(3) . .
C25 C26 C27 C28 -176.81(17) . .
C25 C26 C27 C32 1.8(3) . .
C26 C27 C28 C29 178.07(17) . .
C32 C27 C28 C29 -0.5(3) . .
C27 C28 C29 C30 -0.3(3) . .
C28 C29 C30 C31 0.6(3) . .
C29 C30 C31 N4 -179.68(16) . .
C29 C30 C31 C32 0.0(3) . .
C30 C31 N4 B1 -178.07(17) . .
C32 C31 N4 B1 2.3(2) . .
N3 B1 N4 C31 -2.0(2) . .
Ru1 B1 N4 C31 176.56(12) . .
C24 C23 C32 C27 -2.6(2) . .
N3 C23 C32 C27 177.85(14) . .
C24 C23 C32 C31 175.21(15) . .
N3 C23 C32 C31 -4.3(2) . .
C28 C27 C32 C23 178.91(16) . .
C26 C27 C32 C23 0.2(2) . .
C28 C27 C32 C31 1.1(2) . .
C26 C27 C32 C31 -177.59(16) . .
C30 C31 C32 C23 -178.63(15) . .
N4 C31 C32 C23 1.1(2) . .
C30 C31 C32 C27 -0.8(2) . .
N4 C31 C32 C27 178.88(14) . .
C45 P1 C33 C38 34.84(14) . .
C39 P1 C33 C38 -72.25(13) . .
Ru1 P1 C33 C38 167.65(10) . .
C45 P1 C33 C34 163.16(11) . .
C39 P1 C33 C34 56.07(13) . .
Ru1 P1 C33 C34 -64.03(12) . .
C38 C33 C34 C35 -59.68(17) . .
P1 C33 C34 C35 167.08(11) . .
C33 C34 C35 C36 57.80(18) . .
C34 C35 C36 C37 -54.80(19) . .
C35 C36 C37 C38 55.22(19) . .
C36 C37 C38 C33 -58.19(18) . .
C34 C33 C38 C37 59.39(17) . .
P1 C33 C38 C37 -170.10(11) . .
C45 P1 C39 C44 -55.74(14) . .
C33 P1 C39 C44 51.43(15) . .
Ru1 P1 C39 C44 174.77(11) . .
C45 P1 C39 C40 174.09(12) . .
C33 P1 C39 C40 -78.74(13) . .
Ru1 P1 C39 C40 44.60(13) . .
C44 C39 C40 C41 57.82(18) . .
P1 C39 C40 C41 -168.10(12) . .
C39 C40 C41 C42 -55.9(2) . .
C40 C41 C42 C43 54.5(2) . .
C41 C42 C43 C44 -54.9(2) . .
C40 C39 C44 C43 -58.21(18) . .
P1 C39 C44 C43 170.59(12) . .
C42 C43 C44 C39 56.8(2) . .
C39 P1 C45 C46 -62.06(13) . .
C33 P1 C45 C46 -174.75(11) . .
Ru1 P1 C45 C46 57.92(13) . .
C39 P1 C45 C50 171.15(11) . .
C33 P1 C45 C50 58.47(13) . .
Ru1 P1 C45 C50 -68.87(12) . .
C50 C45 C46 C47 -55.44(18) . .
P1 C45 C46 C47 176.43(11) . .
C45 C46 C47 C48 54.32(19) . .
C46 C47 C48 C49 -55.22(19) . .
C47 C48 C49 C50 57.75(18) . .
C48 C49 C50 C45 -59.73(17) . .
C46 C45 C50 C49 58.47(17) . .
P1 C45 C50 C49 -173.07(11) . .
C53 C51 C52 C53 -0.3(4) 2 .
C51 C52 C53 C51 0.3(4) . 2
