#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/75/4327571.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_4327571
loop_
_publ_author_name
'Joel T. Mague'
'Jamin L. Krinsky'
_publ_section_title
;
 Synthetic and Structural Studies of the Coordination Behavior of
 2-Pyridylbis(diphenylphosphino)methane
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1962
_journal_page_last               1971
_journal_paper_doi               10.1021/ic001266+
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C34 H27 N O3 P2'
_chemical_formula_weight         559.51
_chemical_name_systematic
; 
 1,1,3,3-tetraphenyl-1,3-diphospha-2-(2-pyridyl)-4-keto-5-
 carboxymethylcyclopentadiene
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.806(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1970(6)
_cell_length_b                   16.7520(15)
_cell_length_c                   9.3600(7)
_cell_measurement_reflns_used    5932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     1400.42(19)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius 1999)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS 1997)'
_computing_publication_material  'SHELXTL (Bruker AXS 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD (with Oxford Cryostream)'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.043
_diffrn_reflns_av_sigmaI/netI    0.1228
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11962
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       Plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4505
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.821
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2701
_reflns_number_total             4505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0012662B_05.cif
_cod_data_source_block           5
_cod_database_code               4327571
loop_
_symmetry_equiv_pos_as_xyz
'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
P1 P 0.05058(9) 0.39331(6) 0.57965(10) 0.0332(2) Uani 1 1 d .
C1 C -0.0613(3) 0.4731(2) 0.4815(4) 0.0294(9) Uani 1 1 d .
C2 C -0.0670(4) 0.4873(3) 0.3334(4) 0.0528(12) Uani 1 1 d .
H2 H -0.0059 0.4575 0.2840 0.058 Uiso 1 1 calc R
C3 C -0.1626(4) 0.5455(3) 0.2596(5) 0.0601(13) Uani 1 1 d .
H3 H -0.1669 0.5553 0.1587 0.066 Uiso 1 1 calc R
C4 C -0.2510(4) 0.5892(3) 0.3288(5) 0.0555(11) Uani 1 1 d .
H4 H -0.3177 0.6282 0.2761 0.061 Uiso 1 1 calc R
C5 C -0.2423(4) 0.5762(3) 0.4733(5) 0.0540(11) Uani 1 1 d .
H5 H -0.3004 0.6079 0.5231 0.059 Uiso 1 1 calc R
C6 C -0.1507(4) 0.5179(2) 0.5486(4) 0.0424(10) Uani 1 1 d .
H6 H -0.1490 0.5084 0.6490 0.047 Uiso 1 1 calc R
C7 C 0.2174(3) 0.3867(3) 0.5111(4) 0.0388(9) Uani 1 1 d .
C8 C 0.2645(4) 0.3134(3) 0.4705(4) 0.0571(11) Uani 1 1 d .
H8 H 0.2071 0.2669 0.4763 0.063 Uiso 1 1 calc R
C9 C 0.3939(4) 0.3076(4) 0.4219(5) 0.0733(14) Uani 1 1 d .
H9 H 0.4255 0.2571 0.3944 0.081 Uiso 1 1 calc R
C10 C 0.4770(5) 0.3741(4) 0.4129(4) 0.0688(16) Uani 1 1 d .
H10 H 0.5666 0.3695 0.3797 0.076 Uiso 1 1 calc R
C11 C 0.4325(4) 0.4473(3) 0.4512(4) 0.0624(13) Uani 1 1 d .
H11 H 0.4911 0.4932 0.4444 0.069 Uiso 1 1 calc R
C12 C 0.2992(4) 0.4549(3) 0.5012(4) 0.0501(11) Uani 1 1 d .
H12 H 0.2670 0.5056 0.5272 0.055 Uiso 1 1 calc R
C13 C 0.0688(3) 0.3920(2) 0.7666(3) 0.0279(8) Uani 1 1 d .
C14 C 0.1461(3) 0.4543(2) 0.8613(4) 0.0296(8) Uani 1 1 d .
C15 C 0.1650(3) 0.4556(2) 1.0149(4) 0.0353(9) Uani 1 1 d .
H15 H 0.1224 0.4148 1.0624 0.039 Uiso 1 1 calc R
C16 C 0.2449(4) 0.5158(2) 1.0952(4) 0.0461(11) Uani 1 1 d .
H16 H 0.2590 0.5163 1.1991 0.051 Uiso 1 1 calc R
C17 C 0.3048(4) 0.5755(3) 1.0279(5) 0.0507(11) Uani 1 1 d .
H17 H 0.3609 0.6176 1.0830 0.056 Uiso 1 1 calc R
C18 C 0.2809(4) 0.5722(2) 0.8778(4) 0.0489(11) Uani 1 1 d .
H18 H 0.3215 0.6137 0.8299 0.054 Uiso 1 1 calc R
N N 0.2033(3) 0.51384(18) 0.7942(3) 0.0380(8) Uani 1 1 d .
P2 P -0.01950(10) 0.30982(6) 0.81599(10) 0.0354(3) Uani 1 1 d .
C19 C 0.1038(4) 0.2457(2) 0.9459(4) 0.0364(9) Uani 1 1 d .
C20 C 0.2582(4) 0.2542(2) 0.9644(4) 0.0453(10) Uani 1 1 d .
H20 H 0.2971 0.2949 0.9134 0.050 Uiso 1 1 calc R
C21 C 0.3539(4) 0.2029(3) 1.0576(4) 0.0550(12) Uani 1 1 d .
H21 H 0.4590 0.2090 1.0713 0.061 Uiso 1 1 calc R
C22 C 0.2993(6) 0.1435(3) 1.1302(5) 0.0668(13) Uani 1 1 d .
H22 H 0.3665 0.1086 1.1940 0.074 Uiso 1 1 calc R
C23 C 0.1501(6) 0.1342(3) 1.1115(5) 0.0706(14) Uani 1 1 d .
H23 H 0.1126 0.0919 1.1599 0.078 Uiso 1 1 calc R
C24 C 0.0511(5) 0.1864(3) 1.0217(5) 0.0573(12) Uani 1 1 d .
H24 H -0.0535 0.1810 1.0126 0.063 Uiso 1 1 calc R
C25 C -0.1773(3) 0.3337(2) 0.8931(4) 0.0379(10) Uani 1 1 d .
C26 C -0.3063(4) 0.3608(2) 0.7961(4) 0.0559(13) Uani 1 1 d .
H26 H -0.3124 0.3604 0.6933 0.061 Uiso 1 1 calc R
C27 C -0.4272(4) 0.3887(3) 0.8481(4) 0.0669(12) Uani 1 1 d .
H27 H -0.5140 0.4088 0.7815 0.074 Uiso 1 1 calc R
C28 C -0.4195(4) 0.3869(3) 0.9959(5) 0.0672(13) Uani 1 1 d .
H28 H -0.5019 0.4052 1.0316 0.074 Uiso 1 1 calc R
C29 C -0.2936(4) 0.3588(3) 1.0930(5) 0.0699(16) Uani 1 1 d .
H29 H -0.2896 0.3570 1.1953 0.077 Uiso 1 1 calc R
C30 C -0.1720(4) 0.3329(2) 1.0413(4) 0.0557(12) Uani 1 1 d .
H30 H -0.0843 0.3145 1.1089 0.061 Uiso 1 1 calc R
C31 C -0.0516(3) 0.2994(2) 0.5289(4) 0.0359(9) Uani 1 1 d .
O3 O -0.0885(3) 0.27835(14) 0.3921(3) 0.0456(7) Uani 1 1 d .
C32 C -0.0823(4) 0.2607(2) 0.6461(4) 0.0382(9) Uani 1 1 d .
C33 C -0.1538(4) 0.1792(2) 0.6349(4) 0.0549(12) Uani 1 1 d .
H33A H -0.1642 0.1633 0.7338 0.060 Uiso 1 1 calc R
H33B H -0.0855 0.1405 0.6046 0.060 Uiso 1 1 calc R
C34 C -0.3061(5) 0.1731(3) 0.5283(6) 0.0604(13) Uani 1 1 d .
O1 O -0.3195(3) 0.19977(17) 0.3951(3) 0.0515(7) Uani 1 1 d .
H34 H -0.227(4) 0.224(2) 0.374(4) 0.067(13) Uiso 1 1 d .
O2 O -0.4111(4) 0.1432(2) 0.5662(4) 0.0902(11) Uani 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'
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'
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_publ_flag
C13 P1 C1 115.80(17) ?
C13 P1 C7 118.52(15) ?
C1 P1 C7 107.17(17) ?
C13 P1 C31 99.87(18) y
C1 P1 C31 108.01(15) ?
C7 P1 C31 106.40(18) ?
C6 C1 C2 118.5(3) ?
C6 C1 P1 120.3(3) ?
C2 C1 P1 121.1(3) ?
C3 C2 C1 119.1(4) ?
C4 C3 C2 121.4(4) ?
C5 C4 C3 119.2(4) ?
C4 C5 C6 120.7(4) ?
C5 C6 C1 121.2(4) ?
C12 C7 C8 120.2(3) ?
C12 C7 P1 119.8(3) ?
C8 C7 P1 120.0(3) ?
C9 C8 C7 120.4(5) ?
C10 C9 C8 120.3(5) ?
C9 C10 C11 120.5(4) ?
C10 C11 C12 120.3(4) ?
C7 C12 C11 118.3(4) ?
C14 C13 P2 127.6(2) y
C14 C13 P1 122.0(3) y
P2 C13 P1 110.33(19) y
N C14 C15 119.8(3) ?
N C14 C13 116.0(3) ?
C15 C14 C13 124.2(3) ?
C16 C15 C14 119.6(3) ?
C15 C16 C17 120.7(4) ?
C16 C17 C18 117.4(4) ?
N C18 C17 123.9(4) ?
C18 N C14 118.5(3) ?
C13 P2 C32 101.88(17) y
C13 P2 C19 113.35(17) ?
C32 P2 C19 110.39(16) ?
C13 P2 C25 113.92(16) ?
C32 P2 C25 109.96(17) ?
C19 P2 C25 107.27(16) ?
C24 C19 C20 118.9(3) ?
C24 C19 P2 122.4(3) ?
C20 C19 P2 118.7(3) ?
C21 C20 C19 119.4(4) ?
C22 C21 C20 120.9(4) ?
C23 C22 C21 120.1(4) ?
C22 C23 C24 120.3(4) ?
C19 C24 C23 120.4(4) ?
C30 C25 C26 118.9(3) ?
C30 C25 P2 124.0(3) ?
C26 C25 P2 116.9(3) ?
C25 C26 C27 120.6(4) ?
C28 C27 C26 119.5(4) ?
C27 C28 C29 120.6(4) ?
C28 C29 C30 119.9(4) ?
C25 C30 C29 120.6(4) ?
O3 C31 C32 127.8(3) y
O3 C31 P1 119.1(3) y
C32 C31 P1 113.1(3) y
C31 C32 C33 123.1(3) y
C31 C32 P2 114.8(3) y
C33 C32 P2 122.0(3) y
C32 C33 C34 115.2(3) ?
O2 C34 O1 121.4(4) ?
O2 C34 C33 120.7(5) ?
O1 C34 C33 117.9(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C13 1.718(3) y
P1 C1 1.799(3) y
P1 C7 1.802(3) y
P1 C31 1.836(4) y
C1 C6 1.371(4) ?
C1 C2 1.395(4) ?
C2 C3 1.382(5) ?
C3 C4 1.367(5) ?
C4 C5 1.354(5) ?
C5 C6 1.370(5) ?
C7 C12 1.383(5) ?
C7 C8 1.385(5) ?
C8 C9 1.375(5) ?
C9 C10 1.364(6) ?
C10 C11 1.368(6) ?
C11 C12 1.418(5) ?
C13 C14 1.443(4) y
C13 P2 1.716(3) y
C14 N 1.351(4) ?
C14 C15 1.406(4) ?
C15 C16 1.363(5) ?
C16 C17 1.365(5) ?
C17 C18 1.371(5) ?
C18 N 1.346(4) ?
P2 C32 1.761(3) y
P2 C19 1.805(3) y
P2 C25 1.814(3) y
C19 C24 1.375(5) ?
C19 C20 1.396(4) ?
C20 C21 1.381(5) ?
C21 C22 1.367(6) ?
C22 C23 1.350(6) ?
C23 C24 1.390(6) ?
C25 C30 1.376(5) ?
C25 C26 1.387(5) ?
C26 C27 1.397(5) ?
C27 C28 1.368(5) ?
C28 C29 1.373(5) ?
C29 C30 1.389(5) ?
C31 O3 1.294(4) y
C31 C32 1.360(4) y
C32 C33 1.508(5) y
C33 C34 1.517(5) ?
C34 O2 1.214(5) y
C34 O1 1.303(5) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H34 O3 1.01(4) 1.54(4) 2.505(4) 159(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15901411
