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#$Date: 2025-08-20 16:06:16 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/26/4072681.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_4072681
loop_
_publ_author_name
'Praetorius, Jeremy M.'
'Kotyk, Matthew W.'
'Webb, Jonathan D.'
'Wang, Ruiyao'
'Crudden, Cathleen M.'
_publ_section_title
;
 Rhodium N-Heterocyclic Carbene Carboxylato Complexes:  Synthesis,
 Structure Determination, and Catalytic Activity in the Hydroformylation
 of Alkenes
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1057
_journal_paper_doi               10.1021/om060942y
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C31 H39 N2 O4 Rh'
_chemical_formula_weight         606.55
_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                 111.0870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5386(8)
_cell_length_b                   17.4011(15)
_cell_length_c                   9.7950(9)
_cell_measurement_temperature    180(2)
_cell_volume                     1516.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8984
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8159
_exptl_absorpt_correction_type   'Empirical (Bruker SADABS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.3985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                2573
_reflns_number_total             2765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om060942ysi20061012_090249.cif
_cod_data_source_block           cc12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4072681
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
N1 N 0.23221(17) 0.18831(9) 0.54712(17) 0.0320(3) Uani 1 1 d .
Rh1 Rh 0.48213(2) 0.2500 0.44608(2) 0.03478(11) Uani 1 2 d S
O1 O 0.6334(3) 0.2500 0.6559(3) 0.0960(12) Uani 1 2 d S
O2 O 0.8137(4) 0.2997(3) 0.6240(5) 0.0782(12) Uani 0.50 1 d P
O3 O 0.7118(4) 0.2500 0.2966(4) 0.0818(9) Uani 1 2 d S
O4 O 0.2471(4) 0.2500 0.1495(3) 0.0720(8) Uani 1 2 d S
C1 C 0.3081(3) 0.2500 0.5254(3) 0.0296(5) Uani 1 2 d S
C2 C 0.1094(2) 0.21182(13) 0.5814(2) 0.0412(5) Uani 1 1 d .
H2 H 0.046(3) 0.1777(16) 0.598(3) 0.055(7) Uiso 1 1 d .
C3 C 0.2780(2) 0.10897(11) 0.5485(2) 0.0340(4) Uani 1 1 d .
C4 C 0.2102(2) 0.06391(12) 0.4247(2) 0.0398(5) Uani 1 1 d .
C5 C 0.2559(3) -0.01278(14) 0.4325(3) 0.0504(6) Uani 1 1 d .
H5 H 0.215(3) -0.0381(16) 0.364(3) 0.046(7) Uiso 1 1 d .
C6 C 0.3633(3) -0.04177(14) 0.5567(3) 0.0524(6) Uani 1 1 d .
H7 H 0.395(3) -0.0907(16) 0.555(3) 0.058(7) Uiso 1 1 d .
C7 C 0.4252(3) 0.00348(14) 0.6777(3) 0.0497(6) Uani 1 1 d .
H7 H 0.500(3) -0.0170(16) 0.759(3) 0.061(7) Uiso 1 1 d .
C8 C 0.3844(2) 0.08020(13) 0.6775(2) 0.0410(5) Uani 1 1 d .
C9 C 0.0879(3) 0.09438(15) 0.2893(3) 0.0542(6) Uani 1 1 d .
H9 H 0.090(2) 0.1489(14) 0.295(2) 0.044(6) Uiso 1 1 d .
C10 C -0.0665(4) 0.0672(3) 0.2867(5) 0.1005(14) Uani 1 1 d D
H10B H -0.064(5) 0.0122(12) 0.271(4) 0.107(7) Uiso 1 1 d D
H10A H -0.145(3) 0.091(2) 0.208(3) 0.107(7) Uiso 1 1 d D
H10C H -0.086(5) 0.082(2) 0.374(3) 0.107(7) Uiso 1 1 d D
C11 C 0.1147(5) 0.0725(2) 0.1496(3) 0.0892(12) Uani 1 1 d D
H11A H 0.105(4) 0.0167(11) 0.134(3) 0.097(7) Uiso 1 1 d D
H11C H 0.213(3) 0.089(2) 0.151(4) 0.097(7) Uiso 1 1 d D
H11B H 0.037(3) 0.100(2) 0.076(3) 0.097(7) Uiso 1 1 d D
C12 C 0.4481(3) 0.12897(16) 0.8140(3) 0.0597(7) Uani 1 1 d .
H12 H 0.457(3) 0.1775(15) 0.790(3) 0.050(7) Uiso 1 1 d .
C13 C 0.3493(6) 0.1238(3) 0.9063(4) 0.0940(13) Uani 1 1 d .
H13C H 0.351(4) 0.074(2) 0.938(4) 0.094(13) Uiso 1 1 d .
H13B H 0.394(4) 0.157(2) 0.974(5) 0.109(14) Uiso 1 1 d .
H13A H 0.246(5) 0.139(3) 0.852(5) 0.119(16) Uiso 1 1 d .
C14 C 0.6114(5) 0.1095(3) 0.9055(4) 0.0908(13) Uani 1 1 d .
H14C H 0.614(4) 0.064(3) 0.950(4) 0.102(14) Uiso 1 1 d .
H14B H 0.654(4) 0.142(2) 0.982(4) 0.099(12) Uiso 1 1 d .
H14A H 0.679(4) 0.108(2) 0.839(4) 0.102(13) Uiso 1 1 d .
C15 C 0.7659(4) 0.2500 0.6950(5) 0.0596(9) Uani 1 2 d S
C16 C 0.8716(6) 0.2500 0.8479(7) 0.126(3) Uani 1 2 d SD
H16B H 0.824(8) 0.2500 0.924(6) 0.176(17) Uiso 1 2 d SD
H16A H 0.947(4) 0.208(2) 0.865(6) 0.176(17) Uiso 1 1 d D
C17 C 0.6347(4) 0.2500 0.3614(4) 0.0530(8) Uani 1 2 d S
C18 C 0.3390(4) 0.2500 0.2643(4) 0.0457(7) Uani 1 2 d S
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'
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
C1 N1 C2 110.44(17) . .
C1 N1 C3 125.53(16) . .
C2 N1 C3 123.81(17) . .
C18 Rh1 C17 89.75(15) . .
C18 Rh1 O1 176.60(12) . .
C17 Rh1 O1 93.66(15) . .
C18 Rh1 C1 86.95(12) . .
C17 Rh1 C1 176.70(13) . .
O1 Rh1 C1 89.65(11) . .
C15 O1 Rh1 127.8(3) . .
C15 O2 O2 48.0(2) . 4_565
N1 C1 N1 104.9(2) . 4_565
N1 C1 Rh1 127.25(11) . .
N1 C1 Rh1 127.25(11) 4_565 .
C2 C2 N1 107.10(11) 4_565 .
C4 C3 C8 122.99(19) . .
C4 C3 N1 119.03(17) . .
C8 C3 N1 117.92(18) . .
C3 C4 C5 116.9(2) . .
C3 C4 C9 122.4(2) . .
C5 C4 C9 120.6(2) . .
C6 C5 C4 121.2(2) . .
C7 C6 C5 120.5(2) . .
C6 C7 C8 121.2(2) . .
C7 C8 C3 117.2(2) . .
C7 C8 C12 120.9(2) . .
C3 C8 C12 121.9(2) . .
C4 C9 C11 111.9(3) . .
C4 C9 C10 109.8(2) . .
C11 C9 C10 112.1(3) . .
C8 C12 C13 110.7(3) . .
C8 C12 C14 113.2(3) . .
C13 C12 C14 110.9(3) . .
O1 C15 O2 111.7(3) . 4_565
O1 C15 O2 111.7(3) . .
O2 C15 O2 84.1(5) 4_565 .
O1 C15 C16 126.2(4) . .
O2 C15 C16 107.6(3) 4_565 .
O2 C15 C16 107.6(3) . .
O3 C17 Rh1 172.2(4) . .
O4 C18 Rh1 179.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.354(2) .
N1 C2 1.391(3) .
N1 C3 1.447(3) .
Rh1 C18 1.813(4) .
Rh1 C17 1.917(3) .
Rh1 O1 2.043(3) .
Rh1 C1 2.070(3) .
O1 C15 1.181(4) .
O2 C15 1.292(5) .
O2 O2 1.730(9) 4_565
O3 C17 1.132(4) .
O4 C18 1.151(4) .
C1 N1 1.354(2) 4_565
C2 C2 1.329(5) 4_565
C3 C4 1.392(3) .
C3 C8 1.398(3) .
C4 C5 1.398(3) .
C4 C9 1.513(3) .
C5 C6 1.374(4) .
C6 C7 1.368(4) .
C7 C8 1.390(3) .
C8 C12 1.514(3) .
C9 C11 1.528(4) .
C9 C10 1.538(5) .
C12 C13 1.525(5) .
C12 C14 1.529(5) .
C15 O2 1.292(5) 4_565
C15 C16 1.474(7) .
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
C18 Rh1 O1 C15 180.000(5) . .
C17 Rh1 O1 C15 0.000(1) . .
C1 Rh1 O1 C15 180.0 . .
C2 N1 C1 N1 0.3(3) . 4_565
C3 N1 C1 N1 -174.36(12) . 4_565
C2 N1 C1 Rh1 -171.40(16) . .
C3 N1 C1 Rh1 13.9(3) . .
C18 Rh1 C1 N1 85.0(2) . .
C17 Rh1 C1 N1 85.0(2) . .
O1 Rh1 C1 N1 -95.0(2) . .
C18 Rh1 C1 N1 -85.0(2) . 4_565
C17 Rh1 C1 N1 -85.0(2) . 4_565
O1 Rh1 C1 N1 95.0(2) . 4_565
C1 N1 C2 C2 -0.19(17) . 4_565
C3 N1 C2 C2 174.58(14) . 4_565
C1 N1 C3 C4 -101.0(2) . .
C2 N1 C3 C4 85.1(2) . .
C1 N1 C3 C8 81.9(3) . .
C2 N1 C3 C8 -92.1(2) . .
C8 C3 C4 C5 -1.7(3) . .
N1 C3 C4 C5 -178.68(19) . .
C8 C3 C4 C9 175.9(2) . .
N1 C3 C4 C9 -1.1(3) . .
C3 C4 C5 C6 -0.2(3) . .
C9 C4 C5 C6 -177.8(2) . .
C4 C5 C6 C7 1.8(4) . .
C5 C6 C7 C8 -1.7(4) . .
C6 C7 C8 C3 -0.2(4) . .
C6 C7 C8 C12 177.2(2) . .
C4 C3 C8 C7 1.9(3) . .
N1 C3 C8 C7 178.89(19) . .
C4 C3 C8 C12 -175.5(2) . .
N1 C3 C8 C12 1.5(3) . .
C3 C4 C9 C11 134.1(3) . .
C5 C4 C9 C11 -48.5(3) . .
C3 C4 C9 C10 -100.8(3) . .
C5 C4 C9 C10 76.7(3) . .
C7 C8 C12 C13 -89.5(3) . .
C3 C8 C12 C13 87.7(3) . .
C7 C8 C12 C14 35.6(4) . .
C3 C8 C12 C14 -147.1(3) . .
Rh1 O1 C15 O2 -46.1(3) . 4_565
Rh1 O1 C15 O2 46.1(3) . .
Rh1 O1 C15 C16 180.000(2) . .
O2 O2 C15 O1 -111.0(4) 4_565 .
O2 O2 C15 C16 106.6(3) 4_565 .
C18 Rh1 C17 O3 0.000(5) . .
O1 Rh1 C17 O3 180.000(5) . .
C1 Rh1 C17 O3 0.000(10) . .
C17 Rh1 C18 O4 180.00(3) . .
O1 Rh1 C18 O4 0.00(3) . .
C1 Rh1 C18 O4 0.00(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139103785
