#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/04/4110441.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_4110441
loop_
_publ_author_name
'Sylvain Gatard'
'Remle Çelenligil-Çetin'
'Chengyun Guo'
'Bruce M. Foxman'
'Oleg V. Ozerov'
_publ_section_title
;
 Carbon-Halide Oxidative Addition and Carbon-Carbon Reductive Elimination
 at a (PNP)Rh Center
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2808
_journal_page_last               2809
_journal_paper_doi               10.1021/ja057948j
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C38 H51 Br1 N1 P2 Rh1'
_chemical_formula_sum            'C38 H51 Br N P2 Rh'
_chemical_formula_weight         766.59
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             05-06-23
_audit_creation_method           CRYSTALS_ver_12.80
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5666(13)
_cell_length_b                   14.8684(14)
_cell_length_c                   15.840(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3666.2(8)
_computing_cell_refinement       'CAD4 Express, (Straver, 1992)'
_computing_data_collection       'CAD4 Express, (Straver, 1992)'
_computing_data_reduction        'RC93 (Watkin, Prout & Lilley, 1994)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3848
_diffrn_reflns_theta_full        26.257
_diffrn_reflns_theta_max         26.257
_diffrn_reflns_theta_min         2.617
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
; 
 Azimutal absorption correction (North et al., 1968) 
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.36
_refine_diff_density_max         1.31
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.1163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000440
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.33 0.820 2.85 0.453 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0920
_refine_ls_wR_factor_gt          0.0426
_refine_ls_wR_factor_ref         0.0426
_reflns_limit_h_max              19
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              0
_reflns_limit_l_min              -19
_reflns_number_gt                2360
_reflns_number_total             3848
_reflns_threshold_expression     I>1.96u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.3692(8)
_oxford_structure_analysis_title 'cad4 in P n m a'
_cod_data_source_file            ja057948jsi20051122_041550.cif
_cod_data_source_block           compound_6b
_cod_original_cell_volume        3666.1(9)
_cod_original_sg_symbol_H-M      'P n m a '
_cod_original_formula_sum        'C38 H51 Br1 N1 P2 Rh1'
_cod_database_code               4110441
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,-z+1/2
x,-y+1/2,z
-x,y+1/2,-z
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Rh1 Rh 0.19468(3) 0.7500 -0.47473(3) 0.0300 1.0000 Uani S T
Br1 Br 0.03994(4) 0.7500 -0.43212(5) 0.0523 1.0000 Uani S T
P1 P 0.20346(7) 0.90412(7) -0.48712(8) 0.0430 1.0000 Uani . .
N1 N 0.3057(3) 0.7500 -0.5442(3) 0.0360 1.0000 Uani S T
C1 C 0.3451(3) 0.8323(3) -0.5632(3) 0.0416 1.0000 Uani . .
C2 C 0.3062(3) 0.9129(3) -0.5402(3) 0.0452 1.0000 Uani . .
C3 C 0.3448(4) 0.9961(4) -0.5566(4) 0.0561 1.0000 Uani . .
C4 C 0.4209(4) 1.0030(4) -0.5982(4) 0.0712 1.0000 Uani . .
C7 C 0.4629(5) 1.0926(5) -0.6178(6) 0.0946 1.0000 Uani . .
C8 C 0.2037(3) 0.9874(3) -0.4009(4) 0.0571 1.0000 Uani . .
C9 C 0.1183(4) 0.9858(5) -0.3541(5) 0.0833 1.0000 Uani . .
C10 C 0.2790(4) 0.9781(4) -0.3419(5) 0.0818 1.0000 Uani . .
C11 C 0.1212(3) 0.9454(4) -0.5614(4) 0.0528 1.0000 Uani . .
C12 C 0.1294(5) 1.0436(4) -0.5894(5) 0.0856 1.0000 Uani . .
C13 C 0.1184(5) 0.8845(5) -0.6380(4) 0.0872 1.0000 Uani . .
C14 C 0.2543(4) 0.7500 -0.3625(4) 0.0373 1.0000 Uani S T
C15 C 0.2063(5) 0.750000(7) -0.2901(4) 0.0484 1.0000 Uani S T
C16 C 0.2465(6) 0.750000(7) -0.2114(5) 0.0644 1.0000 Uani S T
C17 C 0.3336(6) 0.750000(7) -0.2044(5) 0.0590 1.0000 Uani S T
C18 C 0.3822(5) 0.750000(7) -0.2773(5) 0.0530 1.0000 Uani S T
C19 C 0.3434(4) 0.750000(7) -0.3561(5) 0.0409 1.0000 Uani S T
C20 C 0.1668(10) 1.250000(7) -0.4240(10) 0.1018 1.0000 Uani S T
C21 C 0.1608(11) 1.250000(7) -0.3392(9) 0.1146 1.0000 Uani S T
C22 C 0.2360(10) 1.250000(7) -0.2940(8) 0.1116 1.0000 Uani S T
C23 C 0.3130(9) 1.250000(7) -0.3335(7) 0.0997 1.0000 Uani S T
C24 C 0.3183(9) 1.250000(7) -0.4171(9) 0.1035 1.0000 Uani S T
C25 C 0.2452(14) 1.250000(7) -0.4630(7) 0.1164 1.0000 Uani S T
C50 C 0.4425(7) 0.9289(7) -0.6442(7) 0.054(3) 0.5000 Uiso . .
C51 C 0.4706(8) 0.9220(8) -0.5937(8) 0.059(3) 0.5000 Uiso . .
C60 C 0.4365(7) 0.8374(7) -0.5754(7) 0.049(2) 0.5000 Uiso . .
C61 C 0.4071(7) 0.8461(7) -0.6284(7) 0.049(2) 0.5000 Uiso . .
H31 H 0.3171 1.0494 -0.5378 0.0732 1.0000 Uiso R .
H71 H 0.5152 1.0831 -0.6474 0.1249 1.0000 Uiso R .
H72 H 0.4253 1.1279 -0.6514 0.1249 1.0000 Uiso R .
H73 H 0.4744 1.1231 -0.5663 0.1249 1.0000 Uiso R .
H81 H 0.2085 1.0449 -0.4266 0.0743 1.0000 Uiso R .
H91 H 0.1193 1.0291 -0.3099 0.1111 1.0000 Uiso R .
H92 H 0.0733 0.9999 -0.3924 0.1111 1.0000 Uiso R .
H93 H 0.1089 0.9277 -0.3309 0.1111 1.0000 Uiso R .
H101 H 0.2751 1.0230 -0.2994 0.1079 1.0000 Uiso R .
H102 H 0.3313 0.9854 -0.3722 0.1079 1.0000 Uiso R .
H103 H 0.2779 0.9203 -0.3164 0.1079 1.0000 Uiso R .
H111 H 0.0674 0.9398 -0.5337 0.0698 1.0000 Uiso R .
H121 H 0.0841 1.0572 -0.6274 0.1143 1.0000 Uiso R .
H122 H 0.1830 1.0525 -0.6168 0.1143 1.0000 Uiso R .
H123 H 0.1258 1.0819 -0.5415 0.1143 1.0000 Uiso R .
H131 H 0.0760 0.9061 -0.6761 0.1147 1.0000 Uiso R .
H132 H 0.1728 0.8842 -0.6652 0.1147 1.0000 Uiso R .
H133 H 0.1042 0.8252 -0.6208 0.1147 1.0000 Uiso R .
H141 H 0.3779 0.7500 -0.4056 0.0492 1.0000 Uiso RS .
H142 H 0.4431 0.7500 -0.2737 0.0669 1.0000 Uiso RS .
H143 H 0.3606 0.7500 -0.1506 0.0713 1.0000 Uiso RS .
H144 H 0.2123 0.7500 -0.1617 0.0775 1.0000 Uiso RS .
H145 H 0.1454 0.7500 -0.2933 0.0595 1.0000 Uiso RS .
H251 H 0.3726 1.2500 -0.4445 0.1310 1.0000 Uiso RS .
H252 H 0.3645 1.2500 -0.3014 0.1219 1.0000 Uiso RS .
H253 H 0.2343 1.2500 -0.2341 0.1347 1.0000 Uiso RS .
H254 H 0.1064 1.2500 -0.3121 0.1385 1.0000 Uiso RS .
H255 H 0.1157 1.2500 -0.4568 0.1236 1.0000 Uiso RS .
H256 H 0.2475 1.2500 -0.5230 0.1368 1.0000 Uiso RS .
H501 H 0.4839 0.9351 -0.6879 0.0648 0.5000 Uiso R .
H511 H 0.5309 0.9263 -0.6020 0.0706 0.5000 Uiso R .
H601 H 0.4717 0.7853 -0.5725 0.0627 0.5000 Uiso R .
H611 H 0.4244 0.7964 -0.6621 0.0617 0.5000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Rh -1.1178 0.9187 19.2957 0.7515 14.3501 8.2176 4.7343 25.8749 1.2892 98.6062
5.3280 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
P1 5_565 Rh1 Br1 94.60(3) yes
P1 5_565 Rh1 P1 168.08(6) yes
Br1 . Rh1 P1 94.60(3) yes
P1 5_565 Rh1 N1 84.50(3) yes
Br1 . Rh1 N1 163.17(14) yes
P1 . Rh1 N1 84.50(3) yes
P1 5_565 Rh1 C14 92.75(4) yes
Br1 . Rh1 C14 101.93(19) yes
P1 . Rh1 C14 92.75(4) yes
N1 . Rh1 C14 94.9(2) yes
Rh1 . P1 C2 99.43(15) yes
Rh1 . P1 C8 127.24(18) yes
C2 . P1 C8 107.1(2) yes
Rh1 . P1 C11 110.14(18) yes
C2 . P1 C11 107.0(2) yes
C8 . P1 C11 104.5(3) yes
C1 5_565 N1 Rh1 119.0(3) yes
C1 5_565 N1 C1 121.6(5) yes
Rh1 . N1 C1 119.0(3) yes
N1 . C1 C2 120.3(4) yes
N1 . C1 C60 120.6(6) yes
C2 . C1 C60 114.9(6) yes
N1 . C1 C61 125.2(6) yes
C2 . C1 C61 111.1(6) yes
P1 . C2 C1 116.3(3) yes
P1 . C2 C3 122.0(4) yes
C1 . C2 C3 121.7(4) yes
C2 . C3 C4 122.1(5) yes
C2 . C3 H31 118.9 no
C4 . C3 H31 119.0 no
C3 . C4 C7 122.8(6) yes
C3 . C4 C50 114.4(7) yes
C7 . C4 C50 119.6(7) yes
C3 . C4 C51 112.5(7) yes
C7 . C4 C51 121.1(7) yes
C4 . C7 H71 109.9 no
C4 . C7 H72 109.5 no
H71 . C7 H72 109.5 no
C4 . C7 H73 109.0 no
H71 . C7 H73 109.5 no
H72 . C7 H73 109.5 no
P1 . C8 C9 110.4(4) yes
P1 . C8 C10 113.6(4) yes
C9 . C8 C10 112.1(5) yes
P1 . C8 H81 106.7 no
C9 . C8 H81 107.0 no
C10 . C8 H81 106.7 no
C8 . C9 H91 109.5 no
C8 . C9 H92 109.2 no
H91 . C9 H92 109.5 no
C8 . C9 H93 109.7 no
H91 . C9 H93 109.5 no
H92 . C9 H93 109.5 no
C8 . C10 H101 108.9 no
C8 . C10 H102 110.0 no
H101 . C10 H102 109.5 no
C8 . C10 H103 109.4 no
H101 . C10 H103 109.5 no
H102 . C10 H103 109.5 no
P1 . C11 C12 116.4(4) yes
P1 . C11 C13 109.4(4) yes
C12 . C11 C13 109.9(6) yes
P1 . C11 H111 106.7 no
C12 . C11 H111 106.9 no
C13 . C11 H111 107.0 no
C11 . C12 H121 109.0 no
C11 . C12 H122 109.8 no
H121 . C12 H122 109.5 no
C11 . C12 H123 109.7 no
H121 . C12 H123 109.5 no
H122 . C12 H123 109.5 no
C11 . C13 H131 109.1 no
C11 . C13 H132 109.8 no
H131 . C13 H132 109.5 no
C11 . C13 H133 109.4 no
H131 . C13 H133 109.5 no
H132 . C13 H133 109.5 no
Rh1 . C14 C15 119.3(5) yes
Rh1 . C14 C19 121.7(5) yes
C15 . C14 C19 118.9(6) yes
C14 . C15 C16 120.2(7) yes
C14 . C15 H145 120.0 no
C16 . C15 H145 119.8 no
C15 . C16 C17 121.3(8) yes
C15 . C16 H144 119.2 no
C17 . C16 H144 119.5 no
C16 . C17 C18 118.6(8) yes
C16 . C17 H143 120.9 no
C18 . C17 H143 120.5 no
C17 . C18 C19 121.0(7) yes
C17 . C18 H142 119.8 no
C19 . C18 H142 119.3 no
C14 . C19 C18 120.0(7) yes
C14 . C19 H141 120.3 no
C18 . C19 H141 119.7 no
C21 . C20 C25 120.8(13) yes
C21 . C20 H255 119.2 no
C25 . C20 H255 120.0 no
C20 . C21 C22 117.5(14) yes
C20 . C21 H254 120.9 no
C22 . C21 H254 121.6 no
C21 . C22 C23 121.0(12) yes
C21 . C22 H253 119.8 no
C23 . C22 H253 119.3 no
C22 . C23 C24 121.2(12) yes
C22 . C23 H252 120.0 no
C24 . C23 H252 118.8 no
C23 . C24 C25 119.0(13) yes
C23 . C24 H251 120.7 no
C25 . C24 H251 120.3 no
C20 . C25 C24 120.5(11) yes
C20 . C25 H256 119.1 no
C24 . C25 H256 120.4 no
C4 . C50 C61 121.9(10) yes
C4 . C50 H501 118.6 no
C51 . C50 H501 108.8 no
C60 . C50 H501 124.5 no
C61 . C50 H501 119.5 no
C4 . C51 C60 124.2(10) yes
C4 . C51 H511 118.1 no
C50 . C51 H511 110.0 no
C60 . C51 H511 117.7 no
C61 . C51 H511 127.7 no
C1 . C60 C51 116.9(9) yes
C1 . C60 H601 121.5 no
C51 . C60 H601 121.6 no
C50 . C60 H601 129.3 no
C61 . C60 H601 115.1 no
C1 . C61 C50 122.2(9) yes
C51 . C61 H611 124.6 no
C1 . C61 H611 119.1 no
C50 . C61 H611 118.8 no
C60 . C61 H611 104.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Rh1 P1 5_565 2.3040(11) yes
Rh1 Br1 . 2.5015(8) yes
Rh1 P1 . 2.3040(11) yes
Rh1 N1 . 2.048(5) yes
Rh1 C14 . 2.006(6) yes
P1 C2 . 1.811(5) yes
P1 C8 . 1.844(5) yes
P1 C11 . 1.843(5) yes
N1 C1 5_565 1.402(5) yes
N1 C1 . 1.402(5) yes
C1 C2 . 1.392(6) yes
C1 C60 . 1.437(11) yes
C1 C61 . 1.428(11) yes
C2 C3 . 1.399(7) yes
C3 C4 . 1.360(8) yes
C3 H31 . 0.950 no
C4 C7 . 1.515(8) yes
C4 C50 . 1.364(12) yes
C4 C51 . 1.433(13) yes
C7 H71 . 0.950 no
C7 H72 . 0.950 no
C7 H73 . 0.950 no
C8 C9 . 1.523(8) yes
C8 C10 . 1.506(9) yes
C8 H81 . 0.950 no
C9 H91 . 0.950 no
C9 H92 . 0.950 no
C9 H93 . 0.950 no
C10 H101 . 0.950 no
C10 H102 . 0.950 no
C10 H103 . 0.950 no
C11 C12 . 1.531(8) yes
C11 C13 . 1.515(9) yes
C11 H111 . 0.950 no
C12 H121 . 0.950 no
C12 H122 . 0.950 no
C12 H123 . 0.950 no
C13 H131 . 0.950 no
C13 H132 . 0.950 no
C13 H133 . 0.950 no
C14 C15 . 1.369(9) yes
C14 C19 . 1.390(9) yes
C15 C16 . 1.395(10) yes
C15 H145 . 0.950 no
C16 C17 . 1.360(12) yes
C16 H144 . 0.950 no
C17 C18 . 1.381(11) yes
C17 H143 . 0.950 no
C18 C19 . 1.386(10) yes
C18 H142 . 0.950 no
C19 H141 . 0.950 no
C20 C21 . 1.346(17) yes
C20 C25 . 1.37(2) yes
C20 H255 . 0.950 no
C21 C22 . 1.373(19) yes
C21 H254 . 0.950 no
C22 C23 . 1.351(17) yes
C22 H253 . 0.950 no
C23 C24 . 1.327(16) yes
C23 H252 . 0.950 no
C24 C25 . 1.351(19) yes
C24 H251 . 0.950 no
C25 H256 . 0.950 no
C50 C61 . 1.373(15) yes
C50 H501 . 0.950 no
C51 C60 . 1.396(16) yes
C51 H511 . 0.950 no
C60 H601 . 0.950 no
C61 H611 . 0.950 no
