#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021002.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_4021002
loop_
_publ_author_name
'Tanasri Bunlaksananusorn'
'Paul Knochel'
_publ_section_title
;
 t-BuOK-Mediated Hydrophosphination of Functionalized Alkenes:
 A Novel Synthesis of Chiral P,N- and P,P-Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4595
_journal_page_last               4601
_journal_paper_doi               10.1021/jo030383u
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C32 H32 N O P'
_chemical_formula_weight         477.56
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                105.86(2)
_cell_angle_beta                 92.166(15)
_cell_angle_gamma                113.13(2)
_cell_formula_units_Z            2
_cell_length_a                   10.856(2)
_cell_length_b                   11.450(2)
_cell_length_c                   12.027(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1304.6(4)
_diffrn_ambient_temperature      295(2)
_exptl_crystal_density_diffrn    1.216
_refine_ls_R_factor_obs          0.0509
_refine_ls_wR_factor_obs         0.1054
_cod_database_code               4021002
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
P1 P 0.10655(7) 0.18703(7) 0.80949(6) 0.0460(2) Uani 1 d . .
O1 O 0.0276(2) 0.0395(2) 0.7690(2) 0.0590(5) Uani 1 d . .
N1 N 0.2206(2) 0.4527(2) 0.6505(2) 0.0521(6) Uani 1 d . .
C1 C -0.0029(3) 0.2716(3) 0.8107(2) 0.0523(7) Uani 1 d . .
C2 C 0.0442(3) 0.4086(3) 0.8475(3) 0.0653(8) Uani 1 d . .
H2 H 0.1367(3) 0.4614(3) 0.8724(3) 0.078 Uiso 1 calc R .
C3 C -0.0437(5) 0.4689(4) 0.8481(3) 0.0837(11) Uani 1 d . .
H3 H -0.0111(5) 0.5616(4) 0.8730(3) 0.100 Uiso 1 calc R .
C4 C -0.1785(5) 0.3910(6) 0.8119(4) 0.1064(15) Uani 1 d . .
H4 H -0.2382(5) 0.4310(6) 0.8109(4) 0.128 Uiso 1 calc R .
C5 C -0.2276(4) 0.2556(6) 0.7772(4) 0.122(2) Uani 1 d . .
H5 H -0.3205(4) 0.2035(6) 0.7540(4) 0.146 Uiso 1 calc R .
C6 C -0.1394(3) 0.1953(4) 0.7762(3) 0.0864(11) Uani 1 d . .
H6 H -0.1730(3) 0.1025(4) 0.7521(3) 0.104 Uiso 1 calc R .
C7 C 0.1934(3) 0.2469(2) 0.9580(2) 0.0446(6) Uani 1 d . .
C8 C 0.1377(4) 0.1737(3) 1.0303(3) 0.0819(11) Uani 1 d . .
H8 H 0.0566(4) 0.0974(3) 1.0015(3) 0.098 Uiso 1 calc R .
C9 C 0.1977(4) 0.2093(4) 1.1443(3) 0.0953(13) Uani 1 d . .
H9 H 0.1573(4) 0.1570(4) 1.1912(3) 0.114 Uiso 1 calc R .
C10 C 0.3157(4) 0.3205(3) 1.1889(3) 0.0695(9) Uani 1 d . .
H10 H 0.3572(4) 0.3445(3) 1.2657(3) 0.083 Uiso 1 calc R .
C11 C 0.3721(3) 0.3961(3) 1.1192(3) 0.0620(8) Uani 1 d . .
H11 H 0.4522(3) 0.4733(3) 1.1492(3) 0.074 Uiso 1 calc R .
C12 C 0.3126(3) 0.3602(3) 1.0053(2) 0.0565(7) Uani 1 d . .
H12 H 0.3533(3) 0.4133(3) 0.9591(2) 0.068 Uiso 1 calc R .
C13 C 0.2364(2) 0.2476(2) 0.7232(2) 0.0427(6) Uani 1 d . .
H13 H 0.2803(2) 0.3452(2) 0.7565(2) 0.051 Uiso 1 calc R .
C14 C 0.3473(3) 0.1959(3) 0.7376(2) 0.0521(7) Uani 1 d . .
H14A H 0.4330(3) 0.2717(3) 0.7748(2) 0.062 Uiso 1 calc R .
H14B H 0.3224(3) 0.1405(3) 0.7885(2) 0.062 Uiso 1 calc R .
C15 C 0.3658(3) 0.1157(3) 0.6218(3) 0.0566(7) Uani 1 d . .
H15 H 0.4305(3) 0.0765(3) 0.6279(3) 0.068 Uiso 1 calc R .
C16 C 0.2250(3) 0.0162(3) 0.5512(3) 0.0617(8) Uani 1 d . .
H16A H 0.2251(3) -0.0598(3) 0.4908(3) 0.074 Uiso 1 calc R .
H16B H 0.1555(3) -0.0116(3) 0.5987(3) 0.074 Uiso 1 calc R .
C17 C 0.2273(3) 0.1309(3) 0.5070(2) 0.0535(7) Uani 1 d . .
H17 H 0.1860(3) 0.1032(3) 0.4248(2) 0.064 Uiso 1 calc R .
C18 C 0.1708(3) 0.2144(3) 0.5944(2) 0.0475(6) Uani 1 d . .
H18 H 0.0743(3) 0.1571(3) 0.5880(2) 0.057 Uiso 1 calc R .
C19 C 0.3851(3) 0.1901(3) 0.5292(3) 0.0566(7) Uani 1 d . .
C20 C 0.4396(3) 0.1271(3) 0.4250(3) 0.0805(10) Uani 1 d . .
H20A H 0.4262(18) 0.1574(16) 0.3605(6) 0.097 Uiso 1 calc R .
H20B H 0.3920(14) 0.0314(4) 0.4023(11) 0.097 Uiso 1 calc R .
H20C H 0.5347(6) 0.1528(17) 0.4470(6) 0.097 Uiso 1 calc R .
C21 C 0.4687(3) 0.3405(3) 0.5695(3) 0.0632(8) Uani 1 d . .
H21A H 0.4647(15) 0.3745(4) 0.5055(5) 0.076 Uiso 1 calc R .
H21B H 0.5613(5) 0.3601(3) 0.5959(14) 0.076 Uiso 1 calc R .
H21C H 0.4330(11) 0.3818(3) 0.6327(10) 0.076 Uiso 1 calc R .
C22 C 0.1766(3) 0.3371(3) 0.5643(2) 0.0508(7) Uani 1 d . .
C23 C 0.1306(3) 0.3247(3) 0.4510(3) 0.0659(8) Uani 1 d . .
H23 H 0.0974(3) 0.2423(3) 0.3925(3) 0.079 Uiso 1 calc R .
C24 C 0.1352(4) 0.4365(4) 0.4268(3) 0.0808(10) Uani 1 d . .
H24 H 0.1080(4) 0.4315(4) 0.3507(3) 0.097 Uiso 1 calc R .
C25 C 0.1801(3) 0.5559(4) 0.5155(3) 0.0746(10) Uani 1 d . .
H25 H 0.1839(3) 0.6324(4) 0.5000(3) 0.089 Uiso 1 calc R .
C26 C 0.2197(3) 0.5612(3) 0.6279(3) 0.0587(8) Uani 1 d . .
C27 C 0.2563(3) 0.6806(3) 0.7316(3) 0.0671(9) Uani 1 d . .
C28 C 0.2032(4) 0.7733(4) 0.7351(4) 0.0859(11) Uani 1 d . .
H28 H 0.1503(4) 0.7651(4) 0.6684(4) 0.103 Uiso 1 calc R .
C29 C 0.2274(5) 0.8769(4) 0.8354(5) 0.1073(15) Uani 1 d . .
H29 H 0.1889(5) 0.9367(4) 0.8363(5) 0.129 Uiso 1 calc R .
C30 C 0.3067(5) 0.8934(4) 0.9335(5) 0.122(2) Uani 1 d . .
H30 H 0.3217(5) 0.9634(4) 1.0013(5) 0.146 Uiso 1 calc R .
C31 C 0.3651(5) 0.8051(4) 0.9317(4) 0.116(2) Uani 1 d . .
H31 H 0.4219(5) 0.8168(4) 0.9975(4) 0.139 Uiso 1 calc R .
C32 C 0.3383(4) 0.6998(3) 0.8315(4) 0.0860(11) Uani 1 d . .
H32 H 0.3764(4) 0.6399(3) 0.8312(4) 0.103 Uiso 1 calc R .
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
P1 O1 1.486(2) . ?
P1 C7 1.802(3) . ?
P1 C1 1.803(3) . ?
P1 C13 1.812(3) . ?
N1 C22 1.330(3) . ?
N1 C26 1.345(3) . ?
C1 C6 1.367(4) . ?
C1 C2 1.375(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.357(6) . ?
C4 C5 1.357(6) . ?
C5 C6 1.382(5) . ?
C7 C8 1.364(4) . ?
C7 C12 1.380(4) . ?
C8 C9 1.375(5) . ?
C9 C10 1.358(5) . ?
C10 C11 1.358(4) . ?
C11 C12 1.371(4) . ?
C13 C18 1.561(3) . ?
C13 C14 1.559(3) . ?
C14 C15 1.513(4) . ?
C15 C16 1.536(4) . ?
C15 C19 1.552(4) . ?
C16 C17 1.538(4) . ?
C17 C18 1.535(4) . ?
C17 C19 1.555(4) . ?
C18 C22 1.523(4) . ?
C19 C21 1.518(4) . ?
C19 C20 1.529(4) . ?
C22 C23 1.384(4) . ?
C23 C24 1.372(4) . ?
C24 C25 1.373(5) . ?
C25 C26 1.381(4) . ?
C26 C27 1.479(4) . ?
C27 C28 1.385(4) . ?
C27 C32 1.380(5) . ?
C28 C29 1.372(6) . ?
C29 C30 1.358(6) . ?
C30 C31 1.384(6) . ?
C31 C32 1.376(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11294518
