#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:32:17 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178903 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/32/4113216.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_4113216
loop_
_publ_author_name
'Christine G. Espino'
'Kristin Williams Fiori'
'Mihyong Kim'
'J. Du Bois'
_publ_section_title
;
 Expanding the Scope of C-H Amination through Catalyst Design
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15378
_journal_page_last               15379
_journal_paper_doi               10.1021/ja0446294
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C38 H52 O10 Rh2'
_chemical_formula_sum            'C38 H52 O10 Rh2'
_chemical_formula_weight         874.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.441(6)
_cell_angle_beta                 84.297(7)
_cell_angle_gamma                73.066(7)
_cell_formula_units_Z            1
_cell_length_a                   9.731(4)
_cell_length_b                   9.878(4)
_cell_length_c                   11.256(5)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    159
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.34
_cell_volume                     948.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      159
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type
;
;
_diffrn_measurement_method
;
;
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6182
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G.M. Sheldrick (1996)'
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       rod
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0268
_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)+(0.0292P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0567
_reflns_number_gt                3031
_reflns_number_total             3767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0446294rom20040911_040419.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        948.7(6)
_cod_database_code               4113216
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Rh1 Rh 0.03024(2) 0.10287(2) 1.01112(2) 0.01730(7) Uani 1 1 d .
O1 O 0.20350(18) 0.06627(18) 0.89865(17) 0.0213(4) Uani 1 1 d .
O2 O -0.09774(17) 0.24917(18) 0.85126(17) 0.0221(4) Uani 1 1 d .
O3 O -0.14507(18) 0.12703(19) 1.12380(17) 0.0221(4) Uani 1 1 d .
O4 O 0.15234(17) -0.05284(18) 1.16934(17) 0.0214(4) Uani 1 1 d .
O5 O 0.09341(19) 0.2865(2) 1.05398(19) 0.0271(5) Uani 1 1 d .
C1 C 0.2241(3) -0.0390(3) 0.8558(2) 0.0213(6) Uani 1 1 d .
C2 C 0.3586(3) -0.0605(3) 0.7753(3) 0.0261(6) Uani 1 1 d .
C3 C 0.4888(3) -0.0955(3) 0.8600(3) 0.0334(7) Uani 1 1 d .
H3A H 0.4791 -0.0118 0.8861 0.050 Uiso 1 1 calc R
H3B H 0.5750 -0.1084 0.8113 0.050 Uiso 1 1 calc R
H3C H 0.4939 -0.1881 0.9354 0.050 Uiso 1 1 calc R
C4 C 0.3737(3) -0.1921(3) 0.7316(3) 0.0371(8) Uani 1 1 d .
H4A H 0.3808 -0.2859 0.8063 0.056 Uiso 1 1 calc R
H4B H 0.4586 -0.2028 0.6811 0.056 Uiso 1 1 calc R
H4C H 0.2910 -0.1701 0.6800 0.056 Uiso 1 1 calc R
C5 C 0.3497(3) 0.0929(3) 0.6558(3) 0.0289(6) Uani 1 1 d .
H5A H 0.3563 0.1697 0.6864 0.035 Uiso 1 1 calc R
H5B H 0.4323 0.0769 0.6021 0.035 Uiso 1 1 calc R
C6 C 0.2152(3) 0.1557(3) 0.5725(3) 0.0285(7) Uani 1 1 d .
C7 C 0.2095(3) 0.1212(4) 0.4649(3) 0.0371(7) Uani 1 1 d .
H7 H 0.2914 0.0628 0.4398 0.045 Uiso 1 1 calc R
C8 C 0.0824(4) 0.1737(4) 0.3957(3) 0.0462(9) Uani 1 1 d .
H8 H 0.0783 0.1478 0.3255 0.055 Uiso 1 1 calc R
C9 C -0.0403(3) 0.2654(4) 0.4297(3) 0.0377(8) Uani 1 1 d .
H9 H -0.1253 0.3002 0.3821 0.045 Uiso 1 1 calc R
C10 C -0.0359(3) 0.3043(3) 0.5331(3) 0.0301(7) Uani 1 1 d .
C11 C 0.0931(3) 0.2495(3) 0.6031(3) 0.0277(6) Uani 1 1 d .
H11 H 0.0972 0.2767 0.6725 0.033 Uiso 1 1 calc R
C12 C -0.1666(3) 0.4024(3) 0.5751(3) 0.0315(7) Uani 1 1 d .
H12A H -0.2270 0.4725 0.4994 0.038 Uiso 1 1 calc R
H12B H -0.1349 0.4635 0.6102 0.038 Uiso 1 1 calc R
C13 C -0.2577(3) 0.3081(3) 0.6779(3) 0.0262(6) Uani 1 1 d .
C14 C -0.3238(3) 0.2244(3) 0.6219(3) 0.0342(7) Uani 1 1 d .
H14A H -0.2489 0.1559 0.5943 0.051 Uiso 1 1 calc R
H14B H -0.3849 0.2977 0.5490 0.051 Uiso 1 1 calc R
H14C H -0.3794 0.1666 0.6869 0.051 Uiso 1 1 calc R
C15 C -0.3770(3) 0.4183(3) 0.7221(3) 0.0395(8) Uani 1 1 d .
H15A H -0.4313 0.3606 0.7888 0.059 Uiso 1 1 calc R
H15B H -0.4395 0.4902 0.6498 0.059 Uiso 1 1 calc R
H15C H -0.3348 0.4728 0.7555 0.059 Uiso 1 1 calc R
C16 C -0.1614(3) 0.1934(3) 0.7960(2) 0.0196(6) Uani 1 1 d .
C17 C 0.1655(3) 0.3732(3) 0.9987(3) 0.0298(7) Uani 1 1 d .
C18 C 0.2072(4) 0.4040(4) 0.8613(3) 0.0520(10) Uani 1 1 d .
H18A H 0.2684 0.3114 0.8552 0.078 Uiso 1 1 calc R
H18B H 0.2576 0.4817 0.8318 0.078 Uiso 1 1 calc R
H18C H 0.1225 0.4389 0.8083 0.078 Uiso 1 1 calc R
C19 C 0.2157(3) 0.4545(4) 1.0648(4) 0.0478(9) Uani 1 1 d .
H19A H 0.1824 0.4250 1.1523 0.072 Uiso 1 1 calc R
H19B H 0.1783 0.5634 1.0192 0.072 Uiso 1 1 calc R
H19C H 0.3188 0.4274 1.0655 0.072 Uiso 1 1 calc R
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'
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
O4 Rh1 O3 90.70(7) . .
O4 Rh1 O1 88.69(7) . .
O3 Rh1 O1 176.37(7) . .
O4 Rh1 O2 176.38(6) . .
O3 Rh1 O2 88.74(7) . .
O1 Rh1 O2 91.64(8) . .
O4 Rh1 O5 86.17(7) . .
O3 Rh1 O5 88.80(7) . .
O1 Rh1 O5 94.73(7) . .
O2 Rh1 O5 97.39(7) . .
O4 Rh1 Rh1 88.64(5) . 2_557
O3 Rh1 Rh1 89.00(5) . 2_557
O1 Rh1 Rh1 87.41(5) . 2_557
O2 Rh1 Rh1 87.78(5) . 2_557
O5 Rh1 Rh1 174.34(5) . 2_557
C1 O1 Rh1 119.65(16) . .
C16 O2 Rh1 118.84(15) . .
C1 O3 Rh1 118.28(16) 2_557 .
C16 O4 Rh1 119.21(16) 2_557 .
C17 O5 Rh1 133.7(2) . .
O3 C1 O1 125.7(2) 2_557 .
O3 C1 C2 118.4(2) 2_557 .
O1 C1 C2 115.9(2) . .
C1 C2 C4 111.2(2) . .
C1 C2 C3 107.7(2) . .
C4 C2 C3 110.0(2) . .
C1 C2 C5 108.7(2) . .
C4 C2 C5 110.6(2) . .
C3 C2 C5 108.6(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 . .
C6 C5 C2 115.2(2) . .
C6 C5 H5A 108.5 . .
C2 C5 H5A 108.5 . .
C6 C5 H5B 108.5 . .
C2 C5 H5B 108.5 . .
H5A C5 H5B 107.5 . .
C11 C6 C7 118.4(3) . .
C11 C6 C5 119.9(3) . .
C7 C6 C5 121.7(3) . .
C8 C7 C6 119.9(3) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C7 C8 C9 120.8(3) . .
C7 C8 H8 119.6 . .
C9 C8 H8 119.6 . .
C10 C9 C8 120.2(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 118.5(3) . .
C9 C10 C12 122.4(3) . .
C11 C10 C12 119.1(3) . .
C6 C11 C10 122.1(3) . .
C6 C11 H11 119.0 . .
C10 C11 H11 119.0 . .
C10 C12 C13 113.8(2) . .
C10 C12 H12A 108.8 . .
C13 C12 H12A 108.8 . .
C10 C12 H12B 108.8 . .
C13 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C14 C13 C16 110.5(2) . .
C14 C13 C15 109.8(2) . .
C16 C13 C15 108.1(2) . .
C14 C13 C12 110.7(2) . .
C16 C13 C12 108.9(2) . .
C15 C13 C12 108.8(2) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O4 C16 O2 125.5(2) 2_557 .
O4 C16 C13 117.7(2) 2_557 .
O2 C16 C13 116.8(2) . .
O5 C17 C19 121.2(3) . .
O5 C17 C18 121.4(3) . .
C19 C17 C18 117.4(3) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 O4 2.0286(18) .
Rh1 O3 2.0374(18) .
Rh1 O1 2.0403(18) .
Rh1 O2 2.0484(18) .
Rh1 O5 2.3042(19) .
Rh1 Rh1 2.3817(9) 2_557
O1 C1 1.271(3) .
O2 C16 1.274(3) .
O3 C1 1.263(3) 2_557
O4 C16 1.261(3) 2_557
O5 C17 1.204(3) .
C1 O3 1.263(3) 2_557
C1 C2 1.528(3) .
C2 C4 1.529(4) .
C2 C3 1.535(4) .
C2 C5 1.559(4) .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 C6 1.512(4) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C11 1.386(4) .
C6 C7 1.392(4) .
C7 C8 1.379(4) .
C7 H7 0.9300 .
C8 C9 1.396(4) .
C8 H8 0.9300 .
C9 C10 1.371(4) .
C9 H9 0.9300 .
C10 C11 1.396(4) .
C10 C12 1.520(4) .
C11 H11 0.9300 .
C12 C13 1.552(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.517(4) .
C13 C16 1.534(3) .
C13 C15 1.537(4) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 O4 1.261(3) 2_557
C17 C19 1.489(4) .
C17 C18 1.490(4) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
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
O4 Rh1 O1 C1 89.08(18) . .
O3 Rh1 O1 C1 8.6(13) . .
O2 Rh1 O1 C1 -87.31(18) . .
O5 Rh1 O1 C1 175.13(18) . .
Rh1 Rh1 O1 C1 0.39(17) 2_557 .
O4 Rh1 O2 C16 -8.1(12) . .
O3 Rh1 O2 C16 -89.28(17) . .
O1 Rh1 O2 C16 87.11(17) . .
O5 Rh1 O2 C16 -177.91(17) . .
Rh1 Rh1 O2 C16 -0.23(17) 2_557 .
O4 Rh1 O3 C1 -89.46(18) . 2_557
O1 Rh1 O3 C1 -9.0(13) . 2_557
O2 Rh1 O3 C1 86.96(18) . 2_557
O5 Rh1 O3 C1 -175.62(18) . 2_557
Rh1 Rh1 O3 C1 -0.84(17) 2_557 2_557
O3 Rh1 O4 C16 89.93(18) . 2_557
O1 Rh1 O4 C16 -86.49(18) . 2_557
O2 Rh1 O4 C16 8.8(12) . 2_557
O5 Rh1 O4 C16 178.67(18) . 2_557
Rh1 Rh1 O4 C16 0.94(17) 2_557 2_557
O4 Rh1 O5 C17 112.7(2) . .
O3 Rh1 O5 C17 -156.5(2) . .
O1 Rh1 O5 C17 24.4(3) . .
O2 Rh1 O5 C17 -67.9(3) . .
Rh1 Rh1 O5 C17 136.4(4) 2_557 .
Rh1 O1 C1 O3 0.2(3) . 2_557
Rh1 O1 C1 C2 -178.53(16) . .
O3 C1 C2 C4 0.0(3) 2_557 .
O1 C1 C2 C4 178.8(2) . .
O3 C1 C2 C3 -120.6(3) 2_557 .
O1 C1 C2 C3 58.2(3) . .
O3 C1 C2 C5 122.0(2) 2_557 .
O1 C1 C2 C5 -59.2(3) . .
C1 C2 C5 C6 -54.8(3) . .
C4 C2 C5 C6 67.6(3) . .
C3 C2 C5 C6 -171.6(2) . .
C2 C5 C6 C11 86.7(3) . .
C2 C5 C6 C7 -92.9(3) . .
C11 C6 C7 C8 -3.2(4) . .
C5 C6 C7 C8 176.4(3) . .
C6 C7 C8 C9 1.9(5) . .
C7 C8 C9 C10 -0.1(5) . .
C8 C9 C10 C11 -0.4(4) . .
C8 C9 C10 C12 -179.4(2) . .
C7 C6 C11 C10 2.8(4) . .
C5 C6 C11 C10 -176.8(2) . .
C9 C10 C11 C6 -1.0(4) . .
C12 C10 C11 C6 178.0(2) . .
C9 C10 C12 C13 91.0(3) . .
C11 C10 C12 C13 -88.0(3) . .
C10 C12 C13 C14 -64.9(3) . .
C10 C12 C13 C16 56.8(3) . .
C10 C12 C13 C15 174.4(2) . .
Rh1 O2 C16 O4 -0.5(3) . 2_557
Rh1 O2 C16 C13 179.11(16) . .
C14 C13 C16 O4 -1.3(3) . 2_557
C15 C13 C16 O4 118.9(2) . 2_557
C12 C13 C16 O4 -123.0(2) . 2_557
C14 C13 C16 O2 179.1(2) . .
C15 C13 C16 O2 -60.7(3) . .
C12 C13 C16 O2 57.3(3) . .
Rh1 O5 C17 C19 -165.48(19) . .
Rh1 O5 C17 C18 14.8(4) . .
