#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/45/4124559.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_4124559
loop_
_publ_author_name
'Esteruelas, Miguel A.'
'Oliván, Montserrat'
'Vélez, Andrea'
_publ_section_title
;
 Conclusive Evidence on the Mechanism of the Rhodium-Mediated Decyanative
 Borylation.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12321
_journal_page_last               12329
_journal_paper_doi               10.1021/jacs.5b07357
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C34 H44 F3 O P2 Rh'
_chemical_formula_weight         690.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           31
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.142(3)
_cell_length_b                   7.5379(15)
_cell_length_c                   14.685(3)
_cell_measurement_reflns_used    5915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     1676.1(6)
_computing_cell_refinement       'SAINT+ v. 7.56a (Bruker AXS, 2008)'
_computing_data_collection       'apex2 v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+ v. 7.56a (Bruker AXS, 2008)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.14 (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 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX DUO 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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16918
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.59
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.764
_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            red
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3436
_reflns_number_total             3935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b07357_si_001.cif
_cod_data_source_block           enriquen76a
_cod_original_cell_volume        1676.2(6)
_cod_original_sg_symbol_H-M      Pmn2(1)
_cod_database_code               4124559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, z+1/2'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Rh1 Rh 1.0000 -0.04289(4) 0.47726(3) 0.02368(11) Uani 1 2 d S
P1 P 0.85327(6) -0.05253(11) 0.49781(6) 0.0246(3) Uani 1 1 d .
O1 O 1.0000 -0.1729(5) 0.6130(3) 0.0283(8) Uani 1 2 d S
C1 C 1.0000 0.0790(7) 0.3576(4) 0.0301(11) Uani 1 2 d S
C2 C 1.0000 0.2653(8) 0.3493(5) 0.0383(14) Uani 1 2 d S
H2 H 1.0000 0.3353 0.4031 0.046 Uiso 1 2 calc SR
C3 C 1.0000 0.3508(10) 0.2649(5) 0.0490(17) Uani 1 2 d S
H3 H 1.0000 0.4768 0.2622 0.059 Uiso 1 2 calc SR
C4 C 1.0000 0.2541(11) 0.1863(5) 0.0483(17) Uani 1 2 d S
C5 C 1.0000 0.0696(11) 0.1890(5) 0.0484(17) Uani 1 2 d S
H5 H 1.0000 0.0023 0.1343 0.058 Uiso 1 2 calc SR
C6 C 1.0000 -0.0157(9) 0.2744(5) 0.0410(14) Uani 1 2 d S
H6 H 1.0000 -0.1416 0.2762 0.049 Uiso 1 2 calc SR
C7 C 1.0000 0.3466(17) 0.0957(7) 0.087(4) Uani 1 2 d S
F1 F 0.9265(3) 0.3789(9) 0.0606(4) 0.0511(14) Uiso 0.50 1 d P
F2 F 1.0474(6) 0.2563(14) 0.0309(8) 0.108(3) Uiso 0.50 1 d P
F3 F 1.0583(7) 0.4831(15) 0.0922(8) 0.099(3) Uiso 0.50 1 d P
C8 C 0.7795(3) -0.1844(7) 0.4229(3) 0.0460(11) Uani 1 1 d .
H8 H 0.7224 -0.2076 0.4550 0.055 Uiso 1 1 calc R
C9 C 0.7618(4) -0.0835(10) 0.3343(4) 0.074(2) Uani 1 1 d .
H9A H 0.7219 -0.1531 0.2957 0.111 Uiso 1 1 calc R
H9B H 0.8176 -0.0639 0.3021 0.111 Uiso 1 1 calc R
H9C H 0.7345 0.0311 0.3483 0.111 Uiso 1 1 calc R
C10 C 0.8270(4) -0.3605(7) 0.4050(5) 0.0702(18) Uani 1 1 d .
H10A H 0.8870 -0.3369 0.3834 0.105 Uiso 1 1 calc R
H10B H 0.7946 -0.4278 0.3587 0.105 Uiso 1 1 calc R
H10C H 0.8296 -0.4295 0.4615 0.105 Uiso 1 1 calc R
C11 C 0.7974(3) 0.1629(5) 0.5182(3) 0.0398(10) Uani 1 1 d .
H11 H 0.8001 0.2305 0.4596 0.048 Uiso 1 1 calc R
C12 C 0.6995(3) 0.1562(7) 0.5465(4) 0.0612(15) Uani 1 1 d .
H12A H 0.6744 0.2760 0.5440 0.092 Uiso 1 1 calc R
H12B H 0.6948 0.1100 0.6087 0.092 Uiso 1 1 calc R
H12C H 0.6670 0.0785 0.5048 0.092 Uiso 1 1 calc R
C13 C 0.8516(4) 0.2683(6) 0.5881(4) 0.0550(14) Uani 1 1 d .
H13A H 0.8549 0.2014 0.6452 0.082 Uiso 1 1 calc R
H13B H 0.8231 0.3830 0.5992 0.082 Uiso 1 1 calc R
H13C H 0.9113 0.2878 0.5644 0.082 Uiso 1 1 calc R
C14 C 0.8435(2) -0.1754(5) 0.6052(3) 0.0256(7) Uani 1 1 d .
C15 C 0.7633(3) -0.2284(6) 0.6414(3) 0.0382(9) Uani 1 1 d .
H15 H 0.7106 -0.2006 0.6094 0.046 Uiso 1 1 calc R
C16 C 0.7575(3) -0.3213(7) 0.7231(4) 0.0465(12) Uani 1 1 d .
H16 H 0.7018 -0.3556 0.7472 0.056 Uiso 1 1 calc R
C17 C 0.8351(3) -0.3622(6) 0.7681(3) 0.0419(10) Uani 1 1 d .
H17 H 0.8318 -0.4228 0.8247 0.050 Uiso 1 1 calc R
C18 C 0.9176(2) -0.3181(6) 0.7339(3) 0.0320(9) Uani 1 1 d .
C19 C 0.9198(2) -0.2235(5) 0.6530(3) 0.0259(7) Uani 1 1 d .
C20 C 1.0000 -0.3764(10) 0.7873(4) 0.0397(14) Uani 1 2 d S
C21 C 1.0000 -0.2818(14) 0.8788(5) 0.068(2) Uani 1 2 d S
H21A H 1.0578 -0.2963 0.9079 0.102 Uiso 0.50 1 calc PR
H21B H 0.9541 -0.3330 0.9179 0.102 Uiso 0.50 1 calc PR
H21C H 0.9881 -0.1553 0.8696 0.102 Uiso 0.50 1 calc PR
C22 C 1.0000 -0.5779(14) 0.7993(7) 0.074(3) Uani 1 2 d S
H22A H 1.0151 -0.6347 0.7413 0.111 Uiso 0.50 1 calc PR
H22B H 0.9413 -0.6171 0.8188 0.111 Uiso 0.50 1 calc PR
H22C H 1.0437 -0.6110 0.8455 0.111 Uiso 0.50 1 calc PR
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 O1 178.6(2) . .
C1 Rh1 P1 97.71(2) . 4_755
O1 Rh1 P1 82.24(2) . 4_755
C1 Rh1 P1 97.71(2) . .
O1 Rh1 P1 82.24(2) . .
P1 Rh1 P1 164.09(5) 4_755 .
C14 P1 C11 105.45(19) . .
C14 P1 C8 101.0(2) . .
C11 P1 C8 106.8(2) . .
C14 P1 Rh1 102.23(12) . .
C11 P1 Rh1 116.44(15) . .
C8 P1 Rh1 122.24(17) . .
C19 O1 C19 120.0(4) 4_755 .
C19 O1 Rh1 119.76(19) 4_755 .
C19 O1 Rh1 119.76(19) . .
C2 C1 C6 115.3(6) . .
C2 C1 Rh1 122.6(5) . .
C6 C1 Rh1 122.1(4) . .
C3 C2 C1 122.5(7) . .
C3 C2 H2 118.8 . .
C1 C2 H2 118.8 . .
C4 C3 C2 120.2(7) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 120.6(6) . .
C3 C4 C7 120.1(8) . .
C5 C4 C7 119.3(8) . .
C4 C5 C6 118.8(7) . .
C4 C5 H5 120.6 . .
C6 C5 H5 120.6 . .
C5 C6 C1 122.6(6) . .
C5 C6 H6 118.7 . .
C1 C6 H6 118.7 . .
F1 C7 F1 125.8(9) . 4_755
F1 C7 F3 114.6(9) . .
F1 C7 F3 42.0(5) 4_755 .
F1 C7 F3 42.0(5) . 4_755
F1 C7 F3 114.6(9) 4_755 4_755
F3 C7 F3 81.2(12) . 4_755
F1 C7 F2 49.1(5) . 4_755
F1 C7 F2 106.1(11) 4_755 4_755
F3 C7 F2 133.6(10) . 4_755
F3 C7 F2 90.5(7) 4_755 4_755
F1 C7 F2 106.1(11) . .
F1 C7 F2 49.1(5) 4_755 .
F3 C7 F2 90.5(7) . .
F3 C7 F2 133.6(10) 4_755 .
F2 C7 F2 63.1(11) 4_755 .
F1 C7 C4 117.1(4) . .
F1 C7 C4 117.1(4) 4_755 .
F3 C7 C4 112.7(9) . .
F3 C7 C4 112.7(9) 4_755 .
F2 C7 C4 112.6(9) 4_755 .
F2 C7 C4 112.6(9) . .
F3 F1 F2 144.3(11) 4_755 4_755
F3 F1 C7 75.0(10) 4_755 .
F2 F1 C7 71.3(8) 4_755 .
F1 F2 C7 59.6(7) 4_755 .
F1 F2 F2 111.1(6) 4_755 4_755
C7 F2 F2 58.5(5) . 4_755
F1 F3 C7 62.9(9) 4_755 .
F1 F3 F3 104.2(7) 4_755 4_755
C7 F3 F3 49.4(6) . 4_755
C9 C8 C10 111.5(5) . .
C9 C8 P1 110.1(4) . .
C10 C8 P1 106.5(3) . .
C9 C8 H8 109.6 . .
C10 C8 H8 109.6 . .
P1 C8 H8 109.6 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C13 C11 C12 110.5(4) . .
C13 C11 P1 108.5(3) . .
C12 C11 P1 117.0(3) . .
C13 C11 H11 106.8 . .
C12 C11 H11 106.8 . .
P1 C11 H11 106.8 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 C19 117.2(3) . .
C15 C14 P1 123.1(3) . .
C19 C14 P1 119.7(3) . .
C14 C15 C16 122.1(4) . .
C14 C15 H15 119.0 . .
C16 C15 H15 119.0 . .
C17 C16 C15 118.0(4) . .
C17 C16 H16 121.0 . .
C15 C16 H16 121.0 . .
C16 C17 C18 122.6(4) . .
C16 C17 H17 118.7 . .
C18 C17 H17 118.7 . .
C19 C18 C17 117.1(4) . .
C19 C18 C20 124.3(3) . .
C17 C18 C20 118.5(4) . .
C18 C19 C14 122.9(3) . .
C18 C19 O1 121.4(3) . .
C14 C19 O1 115.7(3) . .
C21 C20 C22 111.3(7) . .
C21 C20 C18 108.5(4) . 4_755
C22 C20 C18 110.0(4) . 4_755
C21 C20 C18 108.5(4) . .
C22 C20 C18 110.0(4) . .
C18 C20 C18 108.5(5) 4_755 .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 C1 1.983(6) .
Rh1 O1 2.221(4) .
Rh1 P1 2.2434(10) 4_755
Rh1 P1 2.2434(10) .
P1 C14 1.835(4) .
P1 C11 1.855(4) .
P1 C8 1.856(4) .
O1 C19 1.402(4) 4_755
O1 C19 1.402(4) .
C1 C2 1.409(8) .
C1 C6 1.415(9) .
C2 C3 1.398(9) .
C2 H2 0.9500 .
C3 C4 1.365(12) .
C3 H3 0.9500 .
C4 C5 1.392(11) .
C4 C7 1.502(10) .
C5 C6 1.409(9) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 F1 1.250(7) .
C7 F1 1.250(7) 4_755
C7 F3 1.357(14) .
C7 F3 1.357(14) 4_755
C7 F2 1.372(14) 4_755
C7 F2 1.372(14) .
F1 F3 0.941(11) 4_755
F1 F2 1.096(11) 4_755
F2 F1 1.096(11) 4_755
F2 F2 1.436(19) 4_755
F3 F1 0.941(11) 4_755
F3 F3 1.77(2) 4_755
C8 C9 1.532(8) .
C8 C10 1.532(8) .
C8 H8 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C13 1.536(7) .
C11 C12 1.540(7) .
C11 H11 1.0000 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.384(5) .
C14 C19 1.399(5) .
C15 C16 1.392(6) .
C15 H15 0.9500 .
C16 C17 1.383(6) .
C16 H16 0.9500 .
C17 C18 1.386(5) .
C17 H17 0.9500 .
C18 C19 1.386(5) .
C18 C20 1.538(5) .
C20 C21 1.522(10) .
C20 C22 1.529(12) .
C20 C18 1.538(5) 4_755
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
