#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/65/4066560.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_4066560
loop_
_publ_author_name
'Ho, Hung-An'
'Dunne, James F.'
'Ellern, Arkady'
'Sadow, Aaron D.'
_publ_section_title
;
 Reactions of Tris(oxazolinyl)phenylborato Rhodium(I) with C−X (X =
 Cl, Br, OTf) Bonds: Stereoselective Intermolecular Oxidative Addition
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4105
_journal_paper_doi               10.1021/om100515u
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety
'(C24 H32 B N3 O5 Rh), (C F3 O3 S), 0.5(C H2 Cl2)'
_chemical_formula_sum            'C25.25 H33 B Cl0.5 F3 N3 O8 Rh S'
_chemical_formula_weight         727.05
_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           'APEX2 v2009.11-0'
_cell_angle_alpha                90
_cell_angle_beta                 103.6510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0976(7)
_cell_length_b                   9.3701(4)
_cell_length_c                   21.0690(9)
_cell_measurement_temperature    153.(2)
_cell_volume                     3088.2(2)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            33882
_diffrn_reflns_theta_full        30.58
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.686
_refine_diff_density_min         -1.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         9101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0598P)²+4.6286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                7986
_reflns_number_total             9101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100515u_si_002.cif
_cod_data_source_block           ToMMeRh(CO)2OTf
_cod_original_formula_sum        'C25.25 H33 B Cl0.50 F3 N3 O8 Rh S'
_cod_database_code               4066560
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Rh Rh1 0.219891(11) 0.40266(2) 0.474548(8) 0.02191(6) Uani d . 1
S S1 0.18084(4) 0.75770(8) 0.70110(3) 0.03004(13) Uani d . 1
B B1 0.33264(14) 0.2441(2) 0.37958(11) 0.0170(4) Uani d . 1
C C1 0.3755(2) 0.6423(2) 0.36600(12) 0.0308(5) Uani d . 1
H H1A 0.3381 0.6842 0.3263 0.037 Uiso calc R 1
H H1B 0.43 0.6961 0.3769 0.037 Uiso calc R 1
C C2 0.33187(17) 0.6451(2) 0.42279(12) 0.0273(5) Uani d . 1
C C3 0.3946(2) 0.6667(2) 0.48906(13) 0.0415(7) Uani d . 1
H H3A 0.3648 0.6516 0.5241 0.062 Uiso calc R 1
H H3B 0.4174 0.764 0.4918 0.062 Uiso calc R 1
H H3C 0.4416 0.5981 0.4938 0.062 Uiso calc R 1
C C4 0.2612(2) 0.7562(2) 0.41184(17) 0.0430(7) Uani d . 1
H H4A 0.2167 0.7307 0.3731 0.064 Uiso calc R 1
H H4B 0.2849 0.85 0.4053 0.064 Uiso calc R 1
H H4C 0.2364 0.7597 0.4501 0.064 Uiso calc R 1
C C5 0.33934(13) 0.4179(2) 0.38641(10) 0.0187(4) Uani d . 1
C C6 0.42123(16) 0.0855(2) 0.54751(11) 0.0255(5) Uani d . 1
H H6A 0.4761 0.1302 0.5697 0.031 Uiso calc R 1
H H6B 0.421 -0.0148 0.5623 0.031 Uiso calc R 1
C C7 0.34538(13) 0.1683(2) 0.56203(10) 0.0221(4) Uani d . 1
C C8 0.2793(2) 0.0640(4) 0.57583(16) 0.0401(7) Uani d . 1
H H8A 0.2298 0.1171 0.5829 0.06 Uiso calc R 1
H H8B 0.3045 0.0082 0.615 0.06 Uiso calc R 1
H H8C 0.261 -0.0004 0.5385 0.06 Uiso calc R 1
C C9 0.3726(2) 0.2775(2) 0.61619(12) 0.0355(5) Uani d . 1
H H9A 0.4145 0.3428 0.605 0.053 Uiso calc R 1
H H9B 0.3984 0.2284 0.6572 0.053 Uiso calc R 1
H H9C 0.3226 0.3317 0.6214 0.053 Uiso calc R 1
C C10 0.34847(12) 0.1915(2) 0.45479(10) 0.0177(4) Uani d . 1
C C11 0.10093(14) 0.1156(2) 0.32232(12) 0.0263(5) Uani d . 1
H H11A 0.0524 0.1267 0.3433 0.032 Uiso calc R 1
H H11B 0.0978 0.0199 0.3019 0.032 Uiso calc R 1
C C12 0.09997(13) 0.2323(2) 0.27197(11) 0.0215(4) Uani d . 1
C C13 0.05869(16) 0.3698(2) 0.28793(13) 0.0307(5) Uani d . 1
H H13A 0.0825 0.3952 0.3337 0.046 Uiso calc R 1
H H13B -0.0032 0.3559 0.2807 0.046 Uiso calc R 1
H H13C 0.0702 0.4467 0.2597 0.046 Uiso calc R 1
C C14 0.0616(2) 0.1845(2) 0.20262(12) 0.0342(5) Uani d . 1
H H14A 0.065 0.2626 0.1724 0.051 Uiso calc R 1
H H14B 0.0016 0.1581 0.1983 0.051 Uiso calc R 1
H H14C 0.0933 0.1019 0.1922 0.051 Uiso calc R 1
C C15 0.23242(17) 0.3373(2) 0.23920(12) 0.0332(5) Uani d . 1
H H15A 0.2923 0.3587 0.2599 0.05 Uiso calc R 1
H H15B 0.2009 0.4266 0.2273 0.05 Uiso calc R 1
H H15C 0.2297 0.2801 0.1998 0.05 Uiso calc R 1
C C16 0.23401(12) 0.2120(2) 0.34193(10) 0.0169(4) Uani d . 1
C C17 0.37004(17) 0.0463(2) 0.30326(12) 0.0287(5) Uani d . 1
H H17 0.3139 0.0108 0.2997 0.034 Uiso calc R 1
C C18 0.4240(2) -0.0242(2) 0.27088(13) 0.0399(7) Uani d . 1
H H18 0.4045 -0.107 0.2458 0.048 Uiso calc R 1
C C19 0.5056(2) 0.0255(2) 0.27501(13) 0.0387(7) Uani d . 1
H H19 0.5422 -0.022 0.2524 0.046 Uiso calc R 1
C C20 0.53401(17) 0.1451(2) 0.31243(13) 0.0345(5) Uani d . 1
H H20 0.5905 0.1793 0.316 0.041 Uiso calc R 1
C C21 0.47966(14) 0.2158(2) 0.34503(12) 0.0252(4) Uani d . 1
H H21 0.4999 0.2979 0.3705 0.03 Uiso calc R 1
C C22 0.39666(12) 0.1687(2) 0.34105(10) 0.0184(4) Uani d . 1
C C23 0.1469(2) 0.3213(4) 0.52070(16) 0.0426(7) Uani d . 1
C C24 0.13512(17) 0.5408(2) 0.45117(12) 0.0320(5) Uani d . 1
C C25 0.1741(2) 0.6663(5) 0.6253(2) 0.0604(10) Uani d . 1
C C26 0.0343(8) 0.9394(15) 0.5306(5) 0.042(3) Uani d P 0.25
Cl Cl1 0.06475(13) 0.9705(2) 0.46299(11) 0.0623(5) Uani d P 0.5
F F1 0.0946(2) 0.6115(2) 0.60198(12) 0.0880(11) Uani d . 1
F F2 0.2321(2) 0.5585(4) 0.6355(2) 0.1117(13) Uani d . 1
F F3 0.1891(2) 0.7456(2) 0.57862(12) 0.0900(10) Uani d . 1
N N1 0.29986(12) 0.4943(2) 0.42098(9) 0.0206(2) Uani d . 1
N N2 0.31195(12) 0.2423(2) 0.49817(9) 0.0196(2) Uani d . 1
N N3 0.19437(12) 0.2576(2) 0.28459(9) 0.0195(2) Uani d . 1
O O2 0.40903(11) 0.09233(17) 0.47687(8) 0.0211(2) Uani d . 1
O O1 0.39095(11) 0.49114(18) 0.35630(8) 0.0250(2) Uani d . 1
O O3 0.18337(10) 0.13560(18) 0.37029(8) 0.0224(2) Uani d . 1
O O4 0.0988(2) 0.2790(4) 0.54711(17) 0.0744(10) Uani d . 1
O O5 0.07947(14) 0.6176(2) 0.43782(12) 0.0477(5) Uani d . 1
O O6 0.11155(17) 0.8592(2) 0.6862(2) 0.0768(10) Uani d . 1
O O7 0.16909(18) 0.6484(4) 0.74428(12) 0.0624(8) Uani d . 1
O O8 0.26407(12) 0.8219(2) 0.71254(11) 0.0405(5) Uani d . 1
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'
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'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C23 Rh1 C24 . . 84.79(13)
C23 Rh1 N2 . . 94.64(11)
C24 Rh1 N2 . . 177.76(10)
C23 Rh1 N1 . . 178.84(12)
C24 Rh1 N1 . . 94.47(11)
N2 Rh1 N1 . . 86.07(7)
O7 S1 O8 . . 117.21(15)
O7 S1 O6 . . 113.9(2)
O8 S1 O6 . . 113.76(16)
O7 S1 C25 . . 103.8(2)
O8 S1 C25 . . 101.98(17)
O6 S1 C25 . . 103.8(2)
C22 B1 C10 . . 112.70(17)
C22 B1 C16 . . 109.80(17)
C10 B1 C16 . . 109.30(17)
C22 B1 C5 . . 116.26(18)
C10 B1 C5 . . 103.00(17)
C16 B1 C5 . . 105.27(17)
O1 C1 C2 . . 104.6(2)
O1 C1 H1A . . 110.8
C2 C1 H1A . . 110.8
O1 C1 H1B . . 110.8
C2 C1 H1B . . 110.8
H1A C1 H1B . . 108.9
N1 C2 C4 . . 113.6(2)
N1 C2 C1 . . 100.53(18)
C4 C2 C1 . . 111.1(2)
N1 C2 C3 . . 107.2(2)
C4 C2 C3 . . 110.9(2)
C1 C2 C3 . . 113.0(2)
C2 C3 H3A . . 109.5
C2 C3 H3B . . 109.5
H3A C3 H3B . . 109.5
C2 C3 H3C . . 109.5
H3A C3 H3C . . 109.5
H3B C3 H3C . . 109.5
C2 C4 H4A . . 109.5
C2 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C2 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
N1 C5 O1 . . 115.1(2)
N1 C5 B1 . . 124.8(2)
O1 C5 B1 . . 120.09(18)
O2 C6 C7 . . 105.02(17)
O2 C6 H6A . . 110.7
C7 C6 H6A . . 110.7
O2 C6 H6B . . 110.7
C7 C6 H6B . . 110.7
H6A C6 H6B . . 108.8
N2 C7 C9 . . 110.0(2)
N2 C7 C8 . . 110.5(2)
C9 C7 C8 . . 112.3(2)
N2 C7 C6 . . 100.90(17)
C9 C7 C6 . . 112.8(2)
C8 C7 C6 . . 109.7(2)
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C7 C9 H9A . . 109.5
C7 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C7 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
N2 C10 O2 . . 115.1(2)
N2 C10 B1 . . 126.0(2)
O2 C10 B1 . . 118.77(17)
O3 C11 C12 . . 104.20(17)
O3 C11 H11A . . 110.9
C12 C11 H11A . . 110.9
O3 C11 H11B . . 110.9
C12 C11 H11B . . 110.9
H11A C11 H11B . . 108.9
N3 C12 C14 . . 112.6(2)
N3 C12 C11 . . 98.46(17)
C14 C12 C11 . . 113.3(2)
N3 C12 C13 . . 107.7(2)
C14 C12 C13 . . 111.3(2)
C11 C12 C13 . . 112.8(2)
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C12 C14 H14A . . 109.5
C12 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C12 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N3 C15 H15A . . 109.5
N3 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
N3 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
N3 C16 O3 . . 112.1(2)
N3 C16 B1 . . 127.0(2)
O3 C16 B1 . . 120.83(18)
C18 C17 C22 . . 121.5(3)
C18 C17 H17 . . 119.2
C22 C17 H17 . . 119.2
C19 C18 C17 . . 120.4(3)
C19 C18 H18 . . 119.8
C17 C18 H18 . . 119.8
C18 C19 C20 . . 119.4(2)
C18 C19 H19 . . 120.3
C20 C19 H19 . . 120.3
C19 C20 C21 . . 120.1(3)
C19 C20 H20 . . 119.9
C21 C20 H20 . . 119.9
C22 C21 C20 . . 121.5(3)
C22 C21 H21 . . 119.2
C20 C21 H21 . . 119.2
C21 C22 C17 . . 117.0(2)
C21 C22 B1 . . 123.2(2)
C17 C22 B1 . . 119.7(2)
O4 C23 Rh1 . . 175.3(3)
O5 C24 Rh1 . . 175.0(3)
F3 C25 F2 . . 107.6(4)
F3 C25 F1 . . 105.7(4)
F2 C25 F1 . . 109.3(4)
F3 C25 S1 . . 114.7(3)
F2 C25 S1 . . 108.6(3)
F1 C25 S1 . . 110.8(3)
Cl1 C26 Cl1 . 3_576 115.1(7)
Cl1 C26 C26 . 3_576 62.7(6)
Cl1 C26 C26 3_576 3_576 52.4(7)
C26 Cl1 C26 . 3_576 64.9(7)
C5 N1 C2 . . 109.0(2)
C5 N1 Rh1 . . 121.69(15)
C2 N1 Rh1 . . 128.72(15)
C10 N2 C7 . . 109.80(18)
C10 N2 Rh1 . . 120.94(15)
C7 N2 Rh1 . . 129.26(14)
C16 N3 C15 . . 126.1(2)
C16 N3 C12 . . 111.61(18)
C15 N3 C12 . . 122.03(18)
C10 O2 C6 . . 107.19(16)
C5 O1 C1 . . 106.52(18)
C16 O3 C11 . . 107.96(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Rh1 C23 . 1.856(3)
Rh1 C24 . 1.861(3)
Rh1 N2 . 2.0862(18)
Rh1 N1 . 2.087(2)
S1 O7 . 1.412(3)
S1 O8 . 1.436(2)
S1 O6 . 1.443(3)
S1 C25 . 1.794(4)
B1 C22 . 1.617(3)
B1 C10 . 1.621(3)
B1 C16 . 1.627(3)
B1 C5 . 1.636(3)
C1 O1 . 1.460(3)
C1 C2 . 1.524(4)
C1 H1A . 0.99
C1 H1B . 0.99
C2 N1 . 1.501(3)
C2 C4 . 1.519(4)
C2 C3 . 1.531(4)
C3 H3A . 0.98
C3 H3B . 0.98
C3 H3C . 0.98
C4 H4A . 0.98
C4 H4B . 0.98
C4 H4C . 0.98
C5 N1 . 1.291(3)
C5 O1 . 1.346(3)
C6 O2 . 1.456(3)
C6 C7 . 1.537(3)
C6 H6A . 0.99
C6 H6B . 0.99
C7 N2 . 1.496(3)
C7 C9 . 1.518(3)
C7 C8 . 1.522(4)
C8 H8A . 0.98
C8 H8B . 0.98
C8 H8C . 0.98
C9 H9A . 0.98
C9 H9B . 0.98
C9 H9C . 0.98
C10 N2 . 1.289(3)
C10 O2 . 1.348(3)
C11 O3 . 1.478(3)
C11 C12 . 1.521(3)
C11 H11A . 0.99
C11 H11B . 0.99
C12 N3 . 1.499(3)
C12 C14 . 1.514(3)
C12 C13 . 1.523(3)
C13 H13A . 0.98
C13 H13B . 0.98
C13 H13C . 0.98
C14 H14A . 0.98
C14 H14B . 0.98
C14 H14C . 0.98
C15 N3 . 1.457(3)
C15 H15A . 0.98
C15 H15B . 0.98
C15 H15C . 0.98
C16 N3 . 1.298(3)
C16 O3 . 1.328(3)
C17 C18 . 1.392(3)
C17 C22 . 1.404(3)
C17 H17 . 0.95
C18 C19 . 1.377(5)
C18 H18 . 0.95
C19 C20 . 1.385(5)
C19 H19 . 0.95
C20 C21 . 1.400(3)
C20 H20 . 0.95
C21 C22 . 1.391(3)
C21 H21 . 0.95
C23 O4 . 1.127(4)
C24 O5 . 1.132(3)
C25 F3 . 1.299(5)
C25 F2 . 1.357(6)
C25 F1 . 1.358(5)
C26 Cl1 . 1.639(12)
C26 Cl1 3_576 1.837(14)
C26 C26 3_576 1.87(2)
Cl1 C26 3_576 1.837(14)
