#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/57/4085796.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_4085796
loop_
_publ_author_name
'Esteruelas, Miguel A.'
'Oliván, Montserrat'
'Vélez, Andrea'
_publ_section_title
;
 POP--Rhodium-Promoted C--H and B--H Bond Activation and C--B Bond
 Formation
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              1911
_journal_paper_doi               10.1021/acs.organomet.5b00176
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C45 H55 F2 O P2 Rh'
_chemical_formula_weight         814.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.51
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8677(4)
_cell_length_b                   14.5318(5)
_cell_length_c                   13.0100(5)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     2041.51(13)
_computing_cell_refinement       'APEX2 v2008.4-0, Bruker AXS'
_computing_data_collection       'APEX2 v2008.4-0, Bruker AXS'
_computing_data_reduction
;
  SAINT-Bruker integration program embedded in APEX2 v2008.4-0, Bruker AXS
;
_computing_molecular_graphics    'XP, SHELXTL v. 6.1 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.1 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART APEX CCD system'
_diffrn_measurement_method       'ω rotations with narrow frames'
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24908
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Absorption correction performed with SADABS program. This is based on the
method of Blessing: Blessing, R. H., Acta Crystallogr., Sect. A 1995, 51, 33.

SADABS: Area-Detector Absorption Correction. Bruker-AXS 
within SAINT+ package, v. 6.1 (2000).
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5113
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0230
_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)+(0.0305P)²+0.5751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                4726
_reflns_number_total             5113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00176_si_002.cif
_cod_data_source_block           6-enrique218
_cod_depositor_comments
'Adding full bibliography for 4085793--4085797.cif.'
_cod_original_cell_volume        2041.44(13)
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4085796
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh1 Rh 0.864264(13) 0.7500 0.707886(11) 0.01485(5) Uani 1 2 d S . .
P1 P 0.83324(3) 0.59701(2) 0.68605(3) 0.01627(8) Uani 1 1 d . . .
O O 0.76173(12) 0.7500 0.52429(10) 0.0170(3) Uani 1 2 d S . .
F1 F 0.78021(11) 0.7500 0.91298(11) 0.0351(3) Uani 1 2 d S . .
F2 F 1.15285(11) 0.7500 0.86223(11) 0.0379(3) Uani 1 2 d S . .
C1 C 0.95917(18) 0.7500 0.87491(15) 0.0182(4) Uani 1 2 d S . .
C2 C 0.90749(19) 0.7500 0.95353(17) 0.0223(4) Uani 1 2 d S . .
C3 C 0.9715(2) 0.7500 1.06971(17) 0.0275(4) Uani 1 2 d S . .
H3 H 0.9285 0.7500 1.1172 0.033 Uiso 1 2 calc SR . .
C4 C 1.0992(2) 0.7500 1.11518(17) 0.0294(5) Uani 1 2 d S . .
H4 H 1.1456 0.7500 1.1948 0.035 Uiso 1 2 calc SR . .
C5 C 1.1591(2) 0.7500 1.04371(18) 0.0287(5) Uani 1 2 d S . .
H5 H 1.2470 0.7500 1.0731 0.034 Uiso 1 2 calc SR . .
C6 C 1.08784(19) 0.7500 0.92888(17) 0.0237(4) Uani 1 2 d S . .
C7 C 0.71000(13) 0.55363(10) 0.72625(13) 0.0240(3) Uani 1 1 d . . .
H7 H 0.7412 0.5623 0.8098 0.029 Uiso 1 1 calc R . .
C8 C 0.59554(15) 0.61396(12) 0.67264(18) 0.0422(4) Uani 1 1 d . . .
H8A H 0.5588 0.6052 0.5906 0.063 Uiso 1 1 calc R . .
H8B H 0.6189 0.6787 0.6902 0.063 Uiso 1 1 calc R . .
H8C H 0.5351 0.5969 0.7027 0.063 Uiso 1 1 calc R . .
C9 C 0.67497(15) 0.45194(10) 0.70323(15) 0.0323(4) Uani 1 1 d . . .
H9A H 0.6120 0.4367 0.7309 0.048 Uiso 1 1 calc R . .
H9B H 0.7486 0.4138 0.7423 0.048 Uiso 1 1 calc R . .
H9C H 0.6419 0.4402 0.6218 0.048 Uiso 1 1 calc R . .
C10 C 0.95216(13) 0.50570(10) 0.73534(12) 0.0227(3) Uani 1 1 d . . .
H10 H 0.9124 0.4457 0.7020 0.027 Uiso 1 1 calc R . .
C11 C 1.00389(15) 0.49880(11) 0.86415(13) 0.0316(3) Uani 1 1 d . . .
H11A H 1.0696 0.4523 0.8909 0.047 Uiso 1 1 calc R . .
H11B H 0.9374 0.4812 0.8863 0.047 Uiso 1 1 calc R . .
H11C H 1.0378 0.5585 0.8977 0.047 Uiso 1 1 calc R . .
C12 C 1.05508(15) 0.52549(12) 0.69720(15) 0.0357(4) Uani 1 1 d . . .
H12A H 1.0960 0.5835 0.7308 0.054 Uiso 1 1 calc R . .
H12B H 1.0197 0.5304 0.6147 0.054 Uiso 1 1 calc R . .
H12C H 1.1157 0.4753 0.7217 0.054 Uiso 1 1 calc R . .
C13 C 0.76610(12) 0.58644(9) 0.53173(11) 0.0173(3) Uani 1 1 d . . .
C14 C 0.74521(12) 0.50189(9) 0.47568(12) 0.0204(3) Uani 1 1 d . . .
H14 H 0.7680 0.4466 0.5184 0.025 Uiso 1 1 calc R . .
C15 C 0.69196(13) 0.49737(9) 0.35911(12) 0.0212(3) Uani 1 1 d . . .
H15 H 0.6784 0.4394 0.3222 0.025 Uiso 1 1 calc R . .
C16 C 0.65843(12) 0.57744(10) 0.29632(11) 0.0191(3) Uani 1 1 d . . .
H16 H 0.6200 0.5736 0.2162 0.023 Uiso 1 1 calc R . .
C17 C 0.67968(11) 0.66398(9) 0.34783(11) 0.0162(2) Uani 1 1 d . . .
C18 C 0.73389(11) 0.66622(8) 0.46503(11) 0.0154(2) Uani 1 1 d . . .
C19 C 0.64382(17) 0.7500 0.27444(15) 0.0169(4) Uani 1 2 d S . .
C20 C 0.50266(18) 0.7500 0.20383(17) 0.0227(4) Uani 1 2 d S . .
H20A H 0.4782 0.8070 0.1598 0.034 Uiso 0.50 1 d PR . .
H20B H 0.4603 0.7500 0.2543 0.034 Uiso 1 2 d SR . .
H20C H 0.4796 0.6971 0.1524 0.034 Uiso 0.50 1 d PR . .
C21 C 0.7112(2) 0.7500 0.19527(17) 0.0236(4) Uani 1 2 d S . .
H21A H 0.6911 0.6934 0.1502 0.035 Uiso 0.50 1 d PR . .
H21B H 0.8009 0.7500 0.2405 0.035 Uiso 1 2 d SR . .
H21C H 0.6845 0.8034 0.1448 0.035 Uiso 0.50 1 d PR . .
C34 C 0.2308(2) 0.7500 0.64023(19) 0.0301(5) Uani 1 2 d S . .
H34 H 0.2741 0.7500 0.7202 0.036 Uiso 1 2 calc SR . .
C35 C 0.1029(2) 0.7500 0.59082(19) 0.0306(5) Uani 1 2 d S . .
H35 H 0.0578 0.7500 0.6365 0.037 Uiso 1 2 calc SR . .
C36 C 0.0415(2) 0.7500 0.4752(2) 0.0373(5) Uani 1 2 d S . .
H36 H -0.0465 0.7500 0.4411 0.045 Uiso 1 2 calc SR . .
C37 C 0.1059(2) 0.7500 0.4074(2) 0.0356(5) Uani 1 2 d S . .
H37 H 0.0623 0.7500 0.3275 0.043 Uiso 1 2 calc SR . .
C38 C 0.2335(2) 0.7500 0.4566(2) 0.0309(5) Uani 1 2 d S . .
H38 H 0.2783 0.7500 0.4108 0.037 Uiso 1 2 calc SR . .
C39 C 0.2960(2) 0.7500 0.5730(2) 0.0324(5) Uani 1 2 d S . .
H39 H 0.3840 0.7500 0.6071 0.039 Uiso 1 2 calc SR . .
C40 C 0.6100(11) 0.4539(13) 0.0259(11) 0.053(3) Uani 0.50 1 d PU . 1
H40 H 0.6857 0.4220 0.0443 0.064 Uiso 0.50 1 calc PR . 1
C41 C 0.5189(19) 0.4162(6) 0.0501(7) 0.051(3) Uani 0.50 1 d PU A 1
H41 H 0.5320 0.3574 0.0849 0.062 Uiso 0.50 1 calc PR A 1
C42 C 0.4086(15) 0.4605(13) 0.0257(10) 0.051(3) Uani 0.50 1 d PU . 1
H42 H 0.3464 0.4331 0.0437 0.061 Uiso 0.50 1 calc PR . 1
C43 C 0.6118(9) 0.4943(15) -0.0034(11) 0.054(3) Uani 0.50 1 d PU . 2
H43 H 0.6907 0.4907 -0.0057 0.065 Uiso 0.50 1 calc PR . 2
C44 C 0.5743(17) 0.4235(9) 0.0443(8) 0.056(3) Uani 0.50 1 d PU B 2
H44 H 0.6260 0.3714 0.0740 0.067 Uiso 0.50 1 calc PR B 2
C45 C 0.461(2) 0.4291(10) 0.0484(8) 0.055(3) Uani 0.50 1 d PU . 2
H45 H 0.4334 0.3811 0.0817 0.066 Uiso 0.50 1 calc PR . 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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'
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
C1 Rh1 O 179.45(6) . .
C1 Rh1 P1 97.273(11) . .
O Rh1 P1 82.782(10) . .
C1 Rh1 P1 97.273(11) . 4_575
O Rh1 P1 82.781(10) . 4_575
P1 Rh1 P1 161.611(18) . 4_575
C13 P1 C10 104.01(6) . .
C13 P1 C7 104.17(6) . .
C10 P1 C7 103.65(7) . .
C13 P1 Rh1 101.24(4) . .
C10 P1 Rh1 127.15(5) . .
C7 P1 Rh1 113.99(5) . .
C18 O C18 120.09(14) . 4_575
C18 O Rh1 119.82(7) . .
C18 O Rh1 119.82(7) 4_575 .
C6 C1 C2 110.77(17) . .
C6 C1 Rh1 123.83(14) . .
C2 C1 Rh1 125.40(15) . .
F1 C2 C3 115.87(18) . .
F1 C2 C1 117.73(17) . .
C3 C2 C1 126.40(19) . .
C4 C3 C2 118.5(2) . .
C4 C3 H3 120.8 . .
C2 C3 H3 120.8 . .
C3 C4 C5 119.40(19) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 118.2(2) . .
C6 C5 H5 120.9 . .
C4 C5 H5 120.9 . .
C5 C6 F2 115.44(18) . .
C5 C6 C1 126.79(19) . .
F2 C6 C1 117.77(17) . .
C8 C7 C9 110.38(13) . .
C8 C7 P1 109.46(10) . .
C9 C7 P1 117.04(10) . .
C8 C7 H7 106.4 . .
C9 C7 H7 106.4 . .
P1 C7 H7 106.4 . .
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 . .
C12 C10 C11 110.94(13) . .
C12 C10 P1 110.58(10) . .
C11 C10 P1 109.20(10) . .
C12 C10 H10 108.7 . .
C11 C10 H10 108.7 . .
P1 C10 H10 108.7 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C18 117.39(12) . .
C14 C13 P1 123.20(10) . .
C18 C13 P1 119.42(10) . .
C15 C14 C13 121.06(13) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
C14 C15 C16 119.82(12) . .
C14 C15 H15 120.1 . .
C16 C15 H15 120.1 . .
C15 C16 C17 121.57(12) . .
C15 C16 H16 119.2 . .
C17 C16 H16 119.2 . .
C18 C17 C16 117.20(12) . .
C18 C17 C19 123.46(12) . .
C16 C17 C19 119.34(12) . .
C17 C18 C13 122.91(11) . .
C17 C18 O 121.30(11) . .
C13 C18 O 115.78(11) . .
C17 C19 C17 110.37(15) 4_575 .
C17 C19 C20 109.01(10) 4_575 .
C17 C19 C20 109.01(10) . .
C17 C19 C21 109.32(10) 4_575 .
C17 C19 C21 109.32(10) . .
C20 C19 C21 109.78(15) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 106.4 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 112.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
H21A C21 H21B 107.1 . .
C19 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 111.8 . .
C35 C34 C39 120.0(2) . .
C35 C34 H34 120.0 . .
C39 C34 H34 120.0 . .
C36 C35 C34 119.4(2) . .
C36 C35 H35 120.3 . .
C34 C35 H35 120.3 . .
C35 C36 C37 121.0(2) . .
C35 C36 H36 119.5 . .
C37 C36 H36 119.5 . .
C38 C37 C36 119.6(2) . .
C38 C37 H37 120.2 . .
C36 C37 H37 120.2 . .
C37 C38 C39 119.8(2) . .
C37 C38 H38 120.1 . .
C39 C38 H38 120.1 . .
C38 C39 C34 120.3(2) . .
C38 C39 H39 119.9 . .
C34 C39 H39 119.9 . .
C41 C40 C42 119.4(9) . 3_665
C41 C40 H40 120.3 . .
C42 C40 H40 120.3 3_665 .
C40 C41 C42 122.1(8) . .
C40 C41 H41 119.0 . .
C42 C41 H41 119.0 . .
C41 C42 C40 118.6(9) . 3_665
C41 C42 H42 120.7 . .
C40 C42 H42 120.7 3_665 .
C44 C43 C45 122.1(9) . 3_665
C44 C43 H43 118.9 . .
C45 C43 H43 118.9 3_665 .
C45 C44 C43 118.9(10) . .
C45 C44 H44 120.6 . .
C43 C44 H44 120.6 . .
C44 C45 C43 119.0(10) . 3_665
C44 C45 H45 120.5 . .
C43 C45 H45 120.5 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 C1 1.9898(19) .
Rh1 O 2.1850(13) .
Rh1 P1 2.2521(3) .
Rh1 P1 2.2521(3) 4_575
P1 C13 1.8335(13) .
P1 C10 1.8474(14) .
P1 C7 1.8560(14) .
O C18 1.4051(13) .
O C18 1.4051(13) 4_575
F1 C2 1.378(2) .
F2 C6 1.379(2) .
C1 C6 1.391(3) .
C1 C2 1.394(3) .
C2 C3 1.382(3) .
C3 C4 1.379(3) .
C3 H3 0.9500 .
C4 C5 1.386(3) .
C4 H4 0.9500 .
C5 C6 1.378(3) .
C5 H5 0.9500 .
C7 C8 1.521(2) .
C7 C9 1.531(2) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C12 1.524(2) .
C10 C11 1.530(2) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.3974(18) .
C13 C18 1.4029(18) .
C14 C15 1.3815(19) .
C14 H14 0.9500 .
C15 C16 1.3820(19) .
C15 H15 0.9500 .
C16 C17 1.3978(18) .
C16 H16 0.9500 .
C17 C18 1.3877(18) .
C17 C19 1.5226(16) .
C19 C17 1.5226(16) 4_575
C19 C20 1.541(3) .
C19 C21 1.544(3) .
C20 H20A 0.9800 .
C20 H20B 0.9781 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9789 .
C21 H21C 0.9800 .
C34 C35 1.382(3) .
C34 C39 1.388(3) .
C34 H34 0.9500 .
C35 C36 1.373(3) .
C35 H35 0.9500 .
C36 C37 1.386(3) .
C36 H36 0.9500 .
C37 C38 1.378(3) .
C37 H37 0.9500 .
C38 C39 1.382(3) .
C38 H38 0.9500 .
C39 H39 0.9500 .
C40 C41 1.361(10) .
C40 C42 1.387(11) 3_665
C40 H40 0.9500 .
C41 C42 1.372(10) .
C41 H41 0.9500 .
C42 C40 1.387(11) 3_665
C42 H42 0.9500 .
C43 C44 1.367(11) .
C43 C45 1.383(11) 3_665
C43 H43 0.9500 .
C44 C45 1.367(9) .
C44 H44 0.9500 .
C45 C43 1.383(11) 3_665
C45 H45 0.9500 .
