#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/61/7026134.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_7026134
loop_
_publ_author_name
'Langer, Jens'
'Fabra, María José'
'García-Orduña, Pilar'
'Lahoz, Fernando J.'
'Görls, Helmar'
'Oro, Luis A.'
'Westerhausen, Matthias'
_publ_section_title
;
 An iridium-mediated C-H activation/CO2-carboxylation reaction of
 1,1-bisdiphenylphosphinomethane.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7813
_journal_page_last               7821
_journal_paper_doi               10.1039/c0dt00230e
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C33 H41 Li O4 P2'
_chemical_formula_weight         570.54
_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                 106.354(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2326(6)
_cell_length_b                   9.2525(2)
_cell_length_c                   21.7101(7)
_cell_measurement_temperature    183(2)
_cell_volume                     3128.76(17)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10804
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0640P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                2844
_reflns_number_total             3572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00230e.txt
_cod_data_source_block           FO3498
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'NONE' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7026134
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
Li Li 0.5000 0.4427(4) 0.7500 0.0302(7) Uani 1 2 d S
P1 P 0.46818(2) 0.17213(3) 0.680272(15) 0.01962(12) Uani 1 1 d .
O1 O 0.62977(7) 0.47867(11) 0.75248(5) 0.0347(3) Uani 1 1 d .
O2 O 0.48184(7) 0.58643(11) 0.67160(5) 0.0345(3) Uani 1 1 d .
C1 C 0.5000 0.0709(2) 0.7500 0.0247(4) Uani 1 2 d S
H1 H 0.5000 -0.033(3) 0.7500 0.046(7) Uiso 1 2 d S
C2 C 0.36495(9) 0.09477(14) 0.63151(6) 0.0219(3) Uani 1 1 d .
C3 C 0.30026(10) 0.18306(17) 0.59510(7) 0.0308(3) Uani 1 1 d .
H3 H 0.3114(12) 0.280(2) 0.5934(8) 0.042(5) Uiso 1 1 d .
C4 C 0.22117(11) 0.12723(19) 0.56033(8) 0.0381(4) Uani 1 1 d .
H4 H 0.1800(14) 0.190(2) 0.5369(10) 0.057(6) Uiso 1 1 d .
C5 C 0.20564(10) -0.01859(18) 0.56135(7) 0.0332(4) Uani 1 1 d .
H5 H 0.1535(12) -0.0605(19) 0.5377(8) 0.041(5) Uiso 1 1 d .
C6 C 0.26898(11) -0.10854(17) 0.59705(8) 0.0376(4) Uani 1 1 d .
H6 H 0.2590(13) -0.206(2) 0.5982(9) 0.051(5) Uiso 1 1 d .
C7 C 0.34745(11) -0.05312(17) 0.63169(8) 0.0338(4) Uani 1 1 d .
H7 H 0.3912(12) -0.1140(19) 0.6572(8) 0.038(5) Uiso 1 1 d .
C8 C 0.53426(9) 0.11567(14) 0.62753(6) 0.0231(3) Uani 1 1 d .
C9 C 0.60639(10) 0.03050(17) 0.65088(8) 0.0328(3) Uani 1 1 d .
H9 H 0.6208(12) -0.0051(19) 0.6946(9) 0.043(5) Uiso 1 1 d .
C10 C 0.65988(12) -0.0047(2) 0.61277(9) 0.0442(4) Uani 1 1 d .
H10 H 0.7112(14) -0.060(2) 0.6327(10) 0.057(6) Uiso 1 1 d .
C11 C 0.64179(12) 0.0450(2) 0.55086(9) 0.0451(5) Uani 1 1 d .
H11 H 0.6764(14) 0.022(2) 0.5248(10) 0.058(6) Uiso 1 1 d .
C12 C 0.57051(13) 0.1307(2) 0.52668(8) 0.0428(4) Uani 1 1 d .
H12 H 0.5544(13) 0.164(2) 0.4847(10) 0.052(6) Uiso 1 1 d .
C13 C 0.51690(11) 0.16646(17) 0.56438(7) 0.0321(3) Uani 1 1 d .
H13 H 0.4680(12) 0.2245(18) 0.5467(8) 0.031(4) Uiso 1 1 d .
C14 C 0.62998(13) 0.6104(2) 0.71800(10) 0.0484(5) Uani 1 1 d .
H14B H 0.6858(14) 0.623(2) 0.7092(9) 0.053(6) Uiso 1 1 d .
H14A H 0.6181(13) 0.686(2) 0.7457(9) 0.054(6) Uiso 1 1 d .
C15 C 0.56058(13) 0.6106(2) 0.65627(10) 0.0476(5) Uani 1 1 d .
H15B H 0.5649(13) 0.528(2) 0.6254(9) 0.055(6) Uiso 1 1 d .
H15A H 0.5578(14) 0.699(2) 0.6345(10) 0.064(6) Uiso 1 1 d .
C16 C 0.41193(13) 0.5684(2) 0.61531(9) 0.0424(4) Uani 1 1 d .
H16C H 0.4058(13) 0.658(2) 0.5902(9) 0.048(5) Uiso 1 1 d .
H16B H 0.3605(13) 0.550(2) 0.6290(9) 0.047(5) Uiso 1 1 d .
H16A H 0.4224(14) 0.484(2) 0.5906(9) 0.055(6) Uiso 1 1 d .
C17 C 0.67724(12) 0.3649(2) 0.73358(10) 0.0411(4) Uani 1 1 d .
H17B H 0.6743(13) 0.277(2) 0.7593(9) 0.049(5) Uiso 1 1 d .
H17A H 0.6543(12) 0.3467(18) 0.6890(9) 0.035(4) Uiso 1 1 d .
H17C H 0.7357(15) 0.395(2) 0.7407(10) 0.058(6) Uiso 1 1 d .
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'
Li Li -0.0003 0.0001 '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'
P P 0.1023 0.0942 '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
O2 Li O2 102.03(15) 2_656 .
O2 Li O1 88.19(8) 2_656 .
O2 Li O1 80.43(7) . .
O2 Li O1 80.43(7) 2_656 2_656
O2 Li O1 88.19(8) . 2_656
O1 Li O1 161.91(19) . 2_656
O2 Li P1 99.15(5) 2_656 2_656
O2 Li P1 158.22(11) . 2_656
O1 Li P1 95.33(8) . 2_656
O1 Li P1 100.31(8) 2_656 2_656
O2 Li P1 158.22(11) 2_656 .
O2 Li P1 99.15(5) . .
O1 Li P1 100.31(8) . .
O1 Li P1 95.33(8) 2_656 .
P1 Li P1 60.35(7) 2_656 .
C1 P1 C8 107.82(6) . .
C1 P1 C2 106.82(6) . .
C8 P1 C2 97.22(6) . .
C1 P1 Li 92.59(7) . .
C8 P1 Li 121.22(4) . .
C2 P1 Li 129.15(4) . .
C14 O1 C17 113.31(14) . .
C14 O1 Li 105.63(13) . .
C17 O1 Li 119.27(13) . .
C16 O2 C15 111.59(14) . .
C16 O2 Li 120.93(11) . .
C15 O2 Li 110.82(10) . .
P1 C1 P1 114.46(11) 2_656 .
P1 C1 H1 122.77(6) 2_656 .
P1 C1 H1 122.77(5) . .
C3 C2 C7 117.12(13) . .
C3 C2 P1 120.98(11) . .
C7 C2 P1 121.85(11) . .
C2 C3 C4 121.63(14) . .
C2 C3 H3 118.2(12) . .
C4 C3 H3 120.2(11) . .
C5 C4 C3 120.06(15) . .
C5 C4 H4 121.4(13) . .
C3 C4 H4 118.6(13) . .
C4 C5 C6 119.38(15) . .
C4 C5 H5 122.4(11) . .
C6 C5 H5 118.2(11) . .
C5 C6 C7 120.58(15) . .
C5 C6 H6 119.9(13) . .
C7 C6 H6 119.5(13) . .
C6 C7 C2 121.22(15) . .
C6 C7 H7 121.3(11) . .
C2 C7 H7 117.5(11) . .
C9 C8 C13 117.76(13) . .
C9 C8 P1 120.81(11) . .
C13 C8 P1 121.26(12) . .
C8 C9 C10 121.27(16) . .
C8 C9 H9 119.9(11) . .
C10 C9 H9 118.8(11) . .
C11 C10 C9 120.35(18) . .
C11 C10 H10 122.3(12) . .
C9 C10 H10 117.2(12) . .
C10 C11 C12 119.40(15) . .
C10 C11 H11 121.3(13) . .
C12 C11 H11 119.3(13) . .
C11 C12 C13 120.62(16) . .
C11 C12 H12 122.8(13) . .
C13 C12 H12 116.5(13) . .
C12 C13 C8 120.59(16) . .
C12 C13 H13 119.2(10) . .
C8 C13 H13 120.2(10) . .
O1 C14 C15 111.05(14) . .
O1 C14 H14B 109.9(11) . .
C15 C14 H14B 109.2(12) . .
O1 C14 H14A 104.9(11) . .
C15 C14 H14A 108.9(12) . .
H14B C14 H14A 112.8(17) . .
O2 C15 C14 106.89(15) . .
O2 C15 H15B 105.4(12) . .
C14 C15 H15B 114.3(11) . .
O2 C15 H15A 109.6(14) . .
C14 C15 H15A 111.7(14) . .
H15B C15 H15A 108.7(17) . .
O2 C16 H16C 107.9(11) . .
O2 C16 H16B 107.6(11) . .
H16C C16 H16B 111.0(16) . .
O2 C16 H16A 109.9(12) . .
H16C C16 H16A 112.0(15) . .
H16B C16 H16A 108.4(16) . .
O1 C17 H17B 109.1(11) . .
O1 C17 H17A 109.6(11) . .
H17B C17 H17A 110.9(15) . .
O1 C17 H17C 109.2(12) . .
H17B C17 H17C 110.5(16) . .
H17A C17 H17C 107.5(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li O2 2.114(2) 2_656
Li O2 2.114(2) .
Li O1 2.1184(12) .
Li O1 2.1185(12) 2_656
Li P1 2.895(3) 2_656
Li P1 2.896(3) .
P1 C1 1.7308(11) .
P1 C8 1.8509(14) .
P1 C2 1.8553(14) .
O1 C14 1.431(2) .
O1 C17 1.431(2) .
O2 C16 1.424(2) .
O2 C15 1.426(2) .
C1 P1 1.7307(11) 2_656
C1 H1 0.96(3) .
C2 C3 1.388(2) .
C2 C7 1.398(2) .
C3 C4 1.393(2) .
C3 H3 0.92(2) .
C4 C5 1.374(2) .
C4 H4 0.92(2) .
C5 C6 1.379(2) .
C5 H5 0.942(19) .
C6 C7 1.383(2) .
C6 H6 0.91(2) .
C7 H7 0.952(18) .
C8 C9 1.384(2) .
C8 C13 1.401(2) .
C9 C10 1.396(2) .
C9 H9 0.968(18) .
C10 C11 1.372(3) .
C10 H10 0.97(2) .
C11 C12 1.379(3) .
C11 H11 0.93(2) .
C12 C13 1.392(2) .
C12 H12 0.93(2) .
C13 H13 0.946(18) .
C14 C15 1.488(3) .
C14 H14B 0.98(2) .
C14 H14A 0.98(2) .
C15 H15B 1.03(2) .
C15 H15A 0.94(2) .
C16 H16C 0.98(2) .
C16 H16B 0.98(2) .
C16 H16A 0.99(2) .
C17 H17B 1.00(2) .
C17 H17A 0.949(18) .
C17 H17C 0.96(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139161986
