#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/04/4320411.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_4320411
loop_
_publ_author_name
'Jun Ho Shin'
'Brian M. Bridgewater'
'David G. Churchill'
'Gerard Parkin'
_publ_section_title
;
 Synthesis and Structural Characterization of PhP[(C5Me4)2], a Monodentate
 Chiral Phosphine Derived from Intramolecular C-C Coupling of
 Tetramethylcyclopentadienyl Groups: An Evaluation of Steric and
 Electronic Properties
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5626
_journal_page_last               5635
_journal_paper_doi               10.1021/ic010443j
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C24 H29 P'
_chemical_formula_weight         348.44
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0432(13)
_cell_length_b                   8.8035(10)
_cell_length_c                   16.4069(18)
_cell_measurement_temperature    223(2)
_cell_volume                     2028.4(4)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_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  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10291
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(12)
_refine_ls_extinction_coef       0.0000(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.105
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                2661
_reflns_number_total             3893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010443j_01.cif
_cod_data_source_block           nbs10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4320411
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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.34050(6) 0.32922(9) 0.56082(5) 0.0359(2) Uani 1 1 d . . .
C11 C 0.2912(2) 0.2379(4) 0.6515(2) 0.0357(8) Uani 1 1 d . . .
C12 C 0.2585(2) 0.1016(3) 0.6739(2) 0.0396(9) Uani 1 1 d . . .
C13 C 0.2475(2) 0.0986(3) 0.7632(2) 0.0397(9) Uani 1 1 d . . .
C14 C 0.2739(2) 0.2329(4) 0.7951(2) 0.0378(8) Uani 1 1 d . . .
C15 C 0.3001(2) 0.3420(3) 0.7261(2) 0.0345(7) Uani 1 1 d . . .
C21 C 0.4099(2) 0.4492(3) 0.6284(2) 0.0333(8) Uani 1 1 d . . .
C22 C 0.4393(2) 0.5916(3) 0.6184(2) 0.0352(8) Uani 1 1 d . . .
C23 C 0.4511(2) 0.6631(3) 0.6990(2) 0.0386(8) Uani 1 1 d . . .
C24 C 0.4256(2) 0.5642(3) 0.7578(2) 0.0377(8) Uani 1 1 d . . .
C25 C 0.4021(2) 0.4104(3) 0.71869(19) 0.0342(7) Uani 1 1 d . . .
C32 C 0.2354(3) -0.0316(4) 0.6205(3) 0.0613(11) Uani 1 1 d . . .
H32A H 0.2744 -0.1177 0.6362 0.092 Uiso 1 1 calc R . .
H32B H 0.2482 -0.0056 0.5641 0.092 Uiso 1 1 calc R . .
H32C H 0.1687 -0.0577 0.6266 0.092 Uiso 1 1 calc R . .
C33 C 0.2119(3) -0.0397(4) 0.8078(3) 0.0603(11) Uani 1 1 d . . .
H33A H 0.2102 -0.0190 0.8658 0.090 Uiso 1 1 calc R . .
H33B H 0.2543 -0.1246 0.7974 0.090 Uiso 1 1 calc R . .
H33C H 0.1484 -0.0647 0.7889 0.090 Uiso 1 1 calc R . .
C34 C 0.2705(3) 0.2793(4) 0.8831(2) 0.0474(10) Uani 1 1 d . . .
H34A H 0.2451 0.1965 0.9155 0.071 Uiso 1 1 calc R . .
H34B H 0.2299 0.3678 0.8890 0.071 Uiso 1 1 calc R . .
H34C H 0.3342 0.3037 0.9017 0.071 Uiso 1 1 calc R . .
C42 C 0.4529(3) 0.6747(4) 0.5392(2) 0.0529(10) Uani 1 1 d . . .
H42A H 0.4259 0.6153 0.4951 0.079 Uiso 1 1 calc R . .
H42B H 0.5203 0.6900 0.5295 0.079 Uiso 1 1 calc R . .
H42C H 0.4211 0.7724 0.5419 0.079 Uiso 1 1 calc R . .
C43 C 0.4889(3) 0.8214(3) 0.7102(3) 0.0590(11) Uani 1 1 d . . .
H43A H 0.5537 0.8266 0.6899 0.088 Uiso 1 1 calc R . .
H43B H 0.4881 0.8472 0.7677 0.088 Uiso 1 1 calc R . .
H43C H 0.4494 0.8925 0.6804 0.088 Uiso 1 1 calc R . .
C44 C 0.4288(3) 0.5893(4) 0.8482(2) 0.0535(10) Uani 1 1 d . . .
H44A H 0.3645 0.6012 0.8688 0.080 Uiso 1 1 calc R . .
H44B H 0.4653 0.6802 0.8599 0.080 Uiso 1 1 calc R . .
H44C H 0.4586 0.5026 0.8743 0.080 Uiso 1 1 calc R . .
C51 C 0.4235(2) 0.1929(3) 0.51617(18) 0.0283(7) Uani 1 1 d . . .
C52 C 0.5187(2) 0.1782(4) 0.53820(19) 0.0393(8) Uani 1 1 d . . .
H52A H 0.5423 0.2346 0.5824 0.047 Uiso 1 1 calc R . .
C53 C 0.5797(2) 0.0814(4) 0.4959(2) 0.0450(9) Uani 1 1 d . . .
H53A H 0.6435 0.0711 0.5122 0.054 Uiso 1 1 calc R . .
C54 C 0.5457(3) 0.0010(4) 0.4301(2) 0.0433(9) Uani 1 1 d . . .
H54A H 0.5869 -0.0623 0.4004 0.052 Uiso 1 1 calc R . .
C55 C 0.4527(2) 0.0128(3) 0.4078(2) 0.0392(8) Uani 1 1 d . . .
H55A H 0.4294 -0.0458 0.3643 0.047 Uiso 1 1 calc R . .
C56 C 0.3916(2) 0.1106(3) 0.44895(19) 0.0351(8) Uani 1 1 d . . .
H56A H 0.3283 0.1213 0.4313 0.042 Uiso 1 1 calc R . .
C35 C 0.2248(2) 0.4714(3) 0.7213(2) 0.0391(8) Uani 1 1 d . . .
H35A H 0.2270 0.5313 0.7709 0.059 Uiso 1 1 calc R . .
H35B H 0.1619 0.4277 0.7150 0.059 Uiso 1 1 calc R . .
H35C H 0.2387 0.5361 0.6749 0.059 Uiso 1 1 calc R . .
C45 C 0.4758(2) 0.2916(3) 0.7458(2) 0.0371(8) Uani 1 1 d . . .
H45A H 0.4745 0.2823 0.8047 0.056 Uiso 1 1 calc R . .
H45B H 0.5388 0.3233 0.7285 0.056 Uiso 1 1 calc R . .
H45C H 0.4607 0.1943 0.7214 0.056 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'
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
_geom_angle_publ_flag
C21 P C51 106.51(14) . . ?
C21 P C11 87.83(14) . . ?
C51 P C11 106.24(14) . . ?
C12 C11 C15 110.2(3) . . ?
C12 C11 P 138.5(3) . . ?
C15 C11 P 110.9(2) . . ?
C11 C12 C13 108.9(3) . . ?
C11 C12 C32 128.0(4) . . ?
C13 C12 C32 123.0(3) . . ?
C14 C13 C12 110.0(3) . . ?
C14 C13 C33 127.8(3) . . ?
C12 C13 C33 122.1(3) . . ?
C13 C14 C34 127.2(3) . . ?
C13 C14 C15 109.3(3) . . ?
C34 C14 C15 123.2(3) . . ?
C14 C15 C11 101.3(2) . . ?
C14 C15 C35 109.6(3) . . ?
C11 C15 C35 110.0(3) . . ?
C14 C15 C25 121.4(3) . . ?
C11 C15 C25 104.1(2) . . ?
C35 C15 C25 109.7(2) . . ?
C22 C21 C25 110.6(3) . . ?
C22 C21 P 129.8(3) . . ?
C25 C21 P 115.1(2) . . ?
C21 C22 C23 109.1(3) . . ?
C21 C22 C42 127.1(3) . . ?
C23 C22 C42 123.6(3) . . ?
C24 C23 C22 109.7(3) . . ?
C24 C23 C43 127.2(3) . . ?
C22 C23 C43 123.1(3) . . ?
C23 C24 C44 127.2(3) . . ?
C23 C24 C25 109.1(3) . . ?
C44 C24 C25 123.4(3) . . ?
C21 C25 C24 101.2(2) . . ?
C21 C25 C45 112.6(3) . . ?
C24 C25 C45 109.5(3) . . ?
C21 C25 C15 103.2(3) . . ?
C24 C25 C15 120.4(3) . . ?
C45 C25 C15 109.5(2) . . ?
C52 C51 C56 117.8(3) . . ?
C52 C51 P 124.8(2) . . ?
C56 C51 P 117.0(2) . . ?
C51 C52 C53 121.2(3) . . ?
C54 C53 C52 119.5(3) . . ?
C55 C54 C53 120.3(3) . . ?
C54 C55 C56 120.6(3) . . ?
C55 C56 C51 120.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P C21 1.815(3) . ?
P C51 1.827(3) . ?
P C11 1.828(3) . ?
C11 C12 1.337(4) . ?
C11 C15 1.534(4) . ?
C12 C13 1.474(4) . ?
C12 C32 1.499(5) . ?
C13 C14 1.344(4) . ?
C13 C33 1.506(5) . ?
C14 C34 1.502(5) . ?
C14 C15 1.529(5) . ?
C15 C35 1.556(4) . ?
C15 C25 1.559(4) . ?
C21 C22 1.330(4) . ?
C21 C25 1.525(5) . ?
C22 C23 1.473(4) . ?
C22 C42 1.503(5) . ?
C23 C24 1.348(4) . ?
C23 C43 1.503(4) . ?
C24 C44 1.500(5) . ?
C24 C25 1.534(4) . ?
C25 C45 1.538(4) . ?
C51 C52 1.390(4) . ?
C51 C56 1.394(4) . ?
C52 C53 1.393(4) . ?
C53 C54 1.377(5) . ?
C54 C55 1.360(5) . ?
C55 C56 1.389(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102572253
