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#$Date: 2016-03-22 11:37:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178908 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/37/4113763.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_4113763
loop_
_publ_author_name
'Revital Cohen'
'Boris Rybtchinski'
'Mark Gandelman'
'Haim Rozenberg'
'Jan M. L. Martin'
'David Milstein'
_publ_section_title
;
 Metallacarbenes from Diazoalkanes: An Experimental and Computational
 Study of the Reaction Mechanism
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6532
_journal_page_last               6546
_journal_paper_doi               10.1021/ja028923c
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C20 H35 N P2 Rh'
_chemical_formula_weight         454.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 112.08(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.628(4)
_cell_length_b                   10.970(2)
_cell_length_c                   20.463(4)
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.73
_cell_volume                     4499.0(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_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  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4762
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0292
_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)+(0.0325P)²+1.8015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0652
_reflns_number_gt                3881
_reflns_number_total             4762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028923csi20030124_101934.cif
_cod_data_source_block           m312
_cod_original_cell_volume        4499.0(16)
_cod_database_code               4113763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Rh1 Rh 0.917253(8) 0.145715(16) 0.809979(8) 0.01581(7) Uani 1 1 d .
N1 N 0.98258(8) 0.14811(16) 0.76410(9) 0.0168(4) Uani 1 1 d .
P2 P 0.83819(3) 0.04173(5) 0.72217(3) 0.01696(13) Uani 1 1 d .
C21 C 0.81286(11) 0.1021(2) 0.63161(11) 0.0216(5) Uani 1 1 d .
H21 H 0.8518 0.0910 0.6172 0.026 Uiso 1 1 calc R
C22 C 0.75421(12) 0.0349(2) 0.57720(11) 0.0309(6) Uani 1 1 d .
H22A H 0.7149 0.0427 0.5897 0.046 Uiso 1 1 calc R
H22B H 0.7655 -0.0514 0.5766 0.046 Uiso 1 1 calc R
H22C H 0.7446 0.0704 0.5305 0.046 Uiso 1 1 calc R
C23 C 0.80022(13) 0.2397(2) 0.63124(13) 0.0340(6) Uani 1 1 d .
H23A H 0.7915 0.2724 0.5840 0.051 Uiso 1 1 calc R
H23B H 0.8396 0.2799 0.6654 0.051 Uiso 1 1 calc R
H23C H 0.7615 0.2548 0.6440 0.051 Uiso 1 1 calc R
C24 C 0.84965(12) -0.1226(2) 0.71244(12) 0.0264(5) Uani 1 1 d .
H24 H 0.8058 -0.1580 0.6815 0.032 Uiso 1 1 calc R
C25 C 0.90046(13) -0.1476(2) 0.67865(14) 0.0364(6) Uani 1 1 d .
H25A H 0.9428 -0.1076 0.7062 0.055 Uiso 1 1 calc R
H25B H 0.8836 -0.1156 0.6304 0.055 Uiso 1 1 calc R
H25C H 0.9076 -0.2357 0.6776 0.055 Uiso 1 1 calc R
C26 C 0.87071(16) -0.1823(3) 0.78501(14) 0.0462(8) Uani 1 1 d .
H26A H 0.8713 -0.2711 0.7799 0.069 Uiso 1 1 calc R
H26B H 0.8390 -0.1603 0.8068 0.069 Uiso 1 1 calc R
H26C H 0.9154 -0.1539 0.8149 0.069 Uiso 1 1 calc R
P3 P 0.97555(3) 0.25608(5) 0.90751(3) 0.01753(13) Uani 1 1 d .
C31 C 1.06327(11) 0.2190(2) 0.96275(11) 0.0227(5) Uani 1 1 d .
H31 H 1.0906 0.2380 0.9340 0.027 Uiso 1 1 calc R
C32 C 1.07144(12) 0.0829(2) 0.97951(13) 0.0315(6) Uani 1 1 d .
H32A H 1.1190 0.0621 0.9988 0.047 Uiso 1 1 calc R
H32B H 1.0489 0.0361 0.9363 0.047 Uiso 1 1 calc R
H32C H 1.0517 0.0632 1.0142 0.047 Uiso 1 1 calc R
C33 C 1.09156(12) 0.2950(2) 1.03013(12) 0.0333(6) Uani 1 1 d .
H33A H 1.0645 0.2822 1.0587 0.050 Uiso 1 1 calc R
H33B H 1.0906 0.3815 1.0178 0.050 Uiso 1 1 calc R
H33C H 1.1377 0.2701 1.0571 0.050 Uiso 1 1 calc R
C34 C 0.97704(12) 0.4225(2) 0.89390(12) 0.0268(5) Uani 1 1 d .
H34 H 0.9909 0.4637 0.9408 0.032 Uiso 1 1 calc R
C35 C 1.02651(14) 0.4571(2) 0.85996(14) 0.0419(7) Uani 1 1 d .
H35A H 1.0165 0.4106 0.8163 0.063 Uiso 1 1 calc R
H35B H 1.0719 0.4383 0.8925 0.063 Uiso 1 1 calc R
H35C H 1.0229 0.5445 0.8493 0.063 Uiso 1 1 calc R
C36 C 0.90616(13) 0.4633(2) 0.84882(13) 0.0393(7) Uani 1 1 d .
H36A H 0.9050 0.5522 0.8440 0.059 Uiso 1 1 calc R
H36B H 0.8756 0.4380 0.8715 0.059 Uiso 1 1 calc R
H36C H 0.8924 0.4257 0.8020 0.059 Uiso 1 1 calc R
C4 C 0.84722(10) 0.14265(19) 0.85442(11) 0.0172(5) Uani 1 1 d .
C10 C 0.76290(11) 0.0489(2) 0.74341(11) 0.0274(6) Uani 1 1 d .
H10A H 0.7301 0.1057 0.7108 0.033 Uiso 1 1 calc R
H10B H 0.7421 -0.0328 0.7380 0.033 Uiso 1 1 calc R
C11 C 0.78244(11) 0.0926(2) 0.81885(11) 0.0198(5) Uani 1 1 d .
C12 C 0.73572(11) 0.0858(2) 0.85018(11) 0.0225(5) Uani 1 1 d .
H12 H 0.6934 0.0496 0.8253 0.027 Uiso 1 1 calc R
C13 C 0.75047(11) 0.1317(2) 0.91785(11) 0.0222(5) Uani 1 1 d .
H13 H 0.7184 0.1277 0.9392 0.027 Uiso 1 1 calc R
C14 C 0.81245(11) 0.1830(2) 0.95350(11) 0.0224(5) Uani 1 1 d .
H14 H 0.8225 0.2153 0.9994 0.027 Uiso 1 1 calc R
C15 C 0.86054(11) 0.1883(2) 0.92341(11) 0.0184(5) Uani 1 1 d .
C16 C 0.92868(11) 0.2397(2) 0.96581(11) 0.0240(5) Uani 1 1 d .
H16A H 0.9528 0.1843 1.0054 0.029 Uiso 1 1 calc R
H16B H 0.9241 0.3200 0.9856 0.029 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'
N N 0.0061 0.0033 '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
N1 Rh1 C4 178.18(7) .
N1 Rh1 P2 95.25(5) .
C4 Rh1 P2 83.10(6) .
N1 Rh1 P3 98.70(5) .
C4 Rh1 P3 82.92(7) .
P2 Rh1 P3 165.82(2) .
N1 N1 Rh1 177.3(2) 2_756
C10 P2 C24 103.57(12) .
C10 P2 C21 105.49(11) .
C24 P2 C21 104.13(10) .
C10 P2 Rh1 105.21(8) .
C24 P2 Rh1 119.09(8) .
C21 P2 Rh1 117.74(8) .
C22 C21 C23 111.96(19) .
C22 C21 P2 114.23(16) .
C23 C21 P2 110.07(15) .
C22 C21 H21 106.7 .
C23 C21 H21 106.7 .
P2 C21 H21 106.7 .
C21 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C21 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C21 C23 H23A 109.5 .
C21 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C21 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C25 C24 C26 111.1(2) .
C25 C24 P2 111.97(17) .
C26 C24 P2 108.55(17) .
C25 C24 H24 108.4 .
C26 C24 H24 108.4 .
P2 C24 H24 108.4 .
C24 C25 H25A 109.5 .
C24 C25 H25B 109.5 .
H25A C25 H25B 109.5 .
C24 C25 H25C 109.5 .
H25A C25 H25C 109.5 .
H25B C25 H25C 109.5 .
C24 C26 H26A 109.5 .
C24 C26 H26B 109.5 .
H26A C26 H26B 109.5 .
C24 C26 H26C 109.5 .
H26A C26 H26C 109.5 .
H26B C26 H26C 109.5 .
C16 P3 C34 103.84(11) .
C16 P3 C31 105.68(10) .
C34 P3 C31 103.71(10) .
C16 P3 Rh1 104.98(8) .
C34 P3 Rh1 115.46(8) .
C31 P3 Rh1 121.51(8) .
C32 C31 C33 110.94(19) .
C32 C31 P3 110.93(16) .
C33 C31 P3 113.68(16) .
C32 C31 H31 107.0 .
C33 C31 H31 107.0 .
P3 C31 H31 107.0 .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C31 C33 H33A 109.5 .
C31 C33 H33B 109.5 .
H33A C33 H33B 109.5 .
C31 C33 H33C 109.5 .
H33A C33 H33C 109.5 .
H33B C33 H33C 109.5 .
C35 C34 C36 111.6(2) .
C35 C34 P3 111.63(17) .
C36 C34 P3 108.01(17) .
C35 C34 H34 108.5 .
C36 C34 H34 108.5 .
P3 C34 H34 108.5 .
C34 C35 H35A 109.5 .
C34 C35 H35B 109.5 .
H35A C35 H35B 109.5 .
C34 C35 H35C 109.5 .
H35A C35 H35C 109.5 .
H35B C35 H35C 109.5 .
C34 C36 H36A 109.5 .
C34 C36 H36B 109.5 .
H36A C36 H36B 109.5 .
C34 C36 H36C 109.5 .
H36A C36 H36C 109.5 .
H36B C36 H36C 109.5 .
C15 C4 C11 115.89(18) .
C15 C4 Rh1 121.99(16) .
C11 C4 Rh1 122.11(15) .
C11 C10 P2 108.74(15) .
C11 C10 H10A 109.9 .
P2 C10 H10A 109.9 .
C11 C10 H10B 109.9 .
P2 C10 H10B 109.9 .
H10A C10 H10B 108.3 .
C12 C11 C4 122.17(19) .
C12 C11 C10 118.70(19) .
C4 C11 C10 119.11(18) .
C11 C12 C13 120.3(2) .
C11 C12 H12 119.8 .
C13 C12 H12 119.8 .
C14 C13 C12 119.1(2) .
C14 C13 H13 120.5 .
C12 C13 H13 120.5 .
C13 C14 C15 121.3(2) .
C13 C14 H14 119.3 .
C15 C14 H14 119.3 .
C14 C15 C4 121.1(2) .
C14 C15 C16 119.37(19) .
C4 C15 C16 119.46(18) .
C15 C16 P3 108.67(14) .
C15 C16 H16A 110.0 .
P3 C16 H16A 110.0 .
C15 C16 H16B 110.0 .
P3 C16 H16B 110.0 .
H16A C16 H16B 108.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Rh1 N1 1.9687(17) .
Rh1 C4 2.039(2) .
Rh1 P2 2.2680(9) .
Rh1 P3 2.2688(8) .
N1 N1 1.108(3) 2_756
P2 C10 1.838(2) .
P2 C24 1.840(2) .
P2 C21 1.847(2) .
C21 C22 1.527(3) .
C21 C23 1.533(3) .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C25 1.527(3) .
C24 C26 1.528(3) .
C24 H24 1.0000 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
P3 C16 1.842(2) .
P3 C34 1.849(2) .
P3 C31 1.852(2) .
C31 C32 1.527(3) .
C31 C33 1.529(3) .
C31 H31 1.0000 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 C35 1.526(3) .
C34 C36 1.529(3) .
C34 H34 1.0000 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C4 C15 1.422(3) .
C4 C11 1.424(3) .
C10 C11 1.517(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.387(3) .
C12 C13 1.393(3) .
C12 H12 0.9500 .
C13 C14 1.382(3) .
C13 H13 0.9500 .
C14 C15 1.395(3) .
C14 H14 0.9500 .
C15 C16 1.510(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
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_4
C4 Rh1 N1 N1 -11(4) 2_756
P2 Rh1 N1 N1 14.0(18) 2_756
P3 Rh1 N1 N1 -163.5(18) 2_756
N1 Rh1 P2 C10 -170.09(10) .
C4 Rh1 P2 C10 9.15(11) .
P3 Rh1 P2 C10 -0.47(14) .
N1 Rh1 P2 C24 74.47(10) .
C4 Rh1 P2 C24 -106.29(11) .
P3 Rh1 P2 C24 -115.91(12) .
N1 Rh1 P2 C21 -52.98(10) .
C4 Rh1 P2 C21 126.25(10) .
P3 Rh1 P2 C21 116.63(12) .
C10 P2 C21 C22 -56.61(19) .
C24 P2 C21 C22 52.11(19) .
Rh1 P2 C21 C22 -173.57(14) .
C10 P2 C21 C23 70.33(18) .
C24 P2 C21 C23 179.05(16) .
Rh1 P2 C21 C23 -46.62(18) .
C10 P2 C24 C25 167.20(17) .
C21 P2 C24 C25 57.08(19) .
Rh1 P2 C24 C25 -76.49(17) .
C10 P2 C24 C26 -69.7(2) .
C21 P2 C24 C26 -179.85(18) .
Rh1 P2 C24 C26 46.6(2) .
N1 Rh1 P3 C16 -169.70(10) .
C4 Rh1 P3 C16 11.14(10) .
P2 Rh1 P3 C16 20.77(13) .
N1 Rh1 P3 C34 76.63(10) .
C4 Rh1 P3 C34 -102.53(11) .
P2 Rh1 P3 C34 -92.91(12) .
N1 Rh1 P3 C31 -50.21(10) .
C4 Rh1 P3 C31 130.62(11) .
P2 Rh1 P3 C31 140.25(11) .
C16 P3 C31 C32 71.04(18) .
C34 P3 C31 C32 179.95(16) .
Rh1 P3 C31 C32 -48.10(18) .
C16 P3 C31 C33 -54.80(19) .
C34 P3 C31 C33 54.11(19) .
Rh1 P3 C31 C33 -173.94(14) .
C16 P3 C34 C35 167.59(17) .
C31 P3 C34 C35 57.32(19) .
Rh1 P3 C34 C35 -78.07(17) .
C16 P3 C34 C36 -69.34(18) .
C31 P3 C34 C36 -179.61(16) .
Rh1 P3 C34 C36 45.00(19) .
N1 Rh1 C4 C15 -160(2) .
P2 Rh1 C4 C15 174.90(18) .
P3 Rh1 C4 C15 -7.47(17) .
N1 Rh1 C4 C11 21(3) .
P2 Rh1 C4 C11 -3.91(17) .
P3 Rh1 C4 C11 173.72(18) .
C24 P2 C10 C11 112.16(18) .
C21 P2 C10 C11 -138.72(17) .
Rh1 P2 C10 C11 -13.56(19) .
C15 C4 C11 C12 -1.7(3) .
Rh1 C4 C11 C12 177.20(17) .
C15 C4 C11 C10 176.4(2) .
Rh1 C4 C11 C10 -4.7(3) .
P2 C10 C11 C12 -169.42(18) .
P2 C10 C11 C4 12.4(3) .
C4 C11 C12 C13 1.9(3) .
C10 C11 C12 C13 -176.2(2) .
C11 C12 C13 C14 -0.6(3) .
C12 C13 C14 C15 -0.8(3) .
C13 C14 C15 C4 0.9(3) .
C13 C14 C15 C16 -177.0(2) .
C11 C4 C15 C14 0.3(3) .
Rh1 C4 C15 C14 -178.58(16) .
C11 C4 C15 C16 178.2(2) .
Rh1 C4 C15 C16 -0.6(3) .
C14 C15 C16 P3 -171.37(17) .
C4 C15 C16 P3 10.7(3) .
C34 P3 C16 C15 107.32(17) .
C31 P3 C16 C15 -143.87(16) .
Rh1 P3 C16 C15 -14.29(17) .
