#------------------------------------------------------------------------------
#$Date: 2018-08-19 15:10:01 +0300 (Sun, 19 Aug 2018) $
#$Revision: 209933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/09/4060979.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_4060979
loop_
_publ_author_name
'Hölscher, Markus'
'Franciò, Giancarlo'
'Leitner, Walter'
_publ_section_title
;
 Origin of Enantioselectivity in Asymmetric Hydrovinylations Catalyzed by
 Phosphoramidite Nickel Catalysts: An Experimentally Supported Density
 Functional Study
;
_journal_coden_ASTM              ORGND7
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              5606
_journal_page_last               5617
_journal_paper_doi               10.1021/om040107l
_journal_volume                  23
_journal_year                    2004
_chemical_formula_weight         624.51
_chemical_name_common            ((C10H6)O)2PNCH((Me)(Ph))2
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.49(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.594(4)
_cell_length_b                   15.841(10)
_cell_length_c                   10.786(5)
_cell_measurement_temperature    243(2)
_cell_volume                     1572.0(14)
_diffrn_ambient_temperature      243(2)
_exptl_crystal_density_diffrn    1.319
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4060979
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C14 C -0.5046(4) 0.1301(2) -0.3173(4) 0.0418(8) Uani 1 d . . .
H14 H -0.4304 0.1707 -0.2923 0.050 Uiso 1 calc R . .
C20 C -0.5964(4) 0.1987(2) -0.5314(4) 0.0439(9) Uani 1 d . . .
H20 H -0.5218 0.2392 -0.5082 0.053 Uiso 1 calc R . .
C32 C -0.6453(5) -0.0548(3) 0.2250(4) 0.0521(10) Uani 1 d . . .
H32 H -0.5988 -0.0028 0.2504 0.063 Uiso 1 calc R . .
C13 C -0.5106(4) 0.0664(2) -0.2352(3) 0.0379(7) Uani 1 d . . .
H13 H -0.4394 0.0619 -0.1551 0.045 Uiso 1 calc R . .
C34 C -0.6765(5) -0.1061(3) 0.3159(4) 0.0437(9) Uani 1 d . . .
H34 H -0.6513 -0.0896 0.4032 0.052 Uiso 1 calc R . .
C15 C -0.6081(4) 0.1366(2) -0.4397(4) 0.0345(7) Uani 1 d . . .
C19 C -0.6913(5) 0.2005(3) -0.6518(4) 0.0500(10) Uani 1 d . . .
H19 H -0.6830 0.2425 -0.7110 0.060 Uiso 1 calc R . .
C25 C -0.2419(5) -0.2169(4) 0.1850(4) 0.0649(14) Uani 1 d . . .
H25 H -0.2155 -0.1745 0.2483 0.078 Uiso 1 calc R . .
C26 C -0.1418(5) -0.2758(5) 0.1733(5) 0.0728(17) Uani 1 d . . .
H26 H -0.0476 -0.2754 0.2308 0.087 Uiso 1 calc R . .
C30 C -0.6812(5) -0.0784(3) 0.0964(4) 0.0437(9) Uani 1 d . . .
H30 H -0.6599 -0.0420 0.0354 0.052 Uiso 1 calc R . .
C12 C -0.6238(4) 0.0070(2) -0.2704(3) 0.0296(6) Uani 1 d . . .
C33 C -0.7447(5) -0.1815(3) 0.2782(4) 0.0440(9) Uani 1 d . . .
H33 H -0.7673 -0.2166 0.3400 0.053 Uiso 1 calc R . .
C24 C -0.3816(5) -0.2201(3) 0.1036(4) 0.0510(10) Uani 1 d . . .
H24 H -0.4499 -0.1798 0.1130 0.061 Uiso 1 calc R . .
C16 C -0.7234(4) 0.0768(2) -0.4751(3) 0.0304(6) Uani 1 d . . .
C18 C -0.8011(5) 0.1400(3) -0.6876(4) 0.0452(9) Uani 1 d . . .
H18 H -0.8636 0.1401 -0.7724 0.054 Uiso 1 calc R . .
O2 O -0.6267(3) -0.05689(15) -0.1837(2) 0.0326(5) Uani 1 d . . .
C27 C -0.1788(6) -0.3341(5) 0.0794(7) 0.0795(18) Uani 1 d . . .
H27 H -0.1082 -0.3725 0.0692 0.095 Uiso 1 calc R . .
C11 C -0.7330(4) 0.01265(19) -0.3840(3) 0.0282(6) Uani 1 d . . .
C31 C -0.7493(3) -0.1561(2) 0.0561(3) 0.0309(6) Uani 1 d . . .
C17 C -0.8197(4) 0.0802(2) -0.6017(3) 0.0368(7) Uani 1 d . . .
H17 H -0.8967 0.0414 -0.6269 0.044 Uiso 1 calc R . .
C29 C -0.7814(4) -0.2071(2) 0.1479(3) 0.0381(7) Uani 1 d . . .
H29 H -0.8280 -0.2592 0.1234 0.046 Uiso 1 calc R . .
C72 C -1.1321(11) -0.0729(5) -0.0096(8) 0.103(3) Uani 1 d . . .
H72A H -1.0452 -0.1058 0.0327 0.123 Uiso 1 calc R . .
H72B H -1.2154 -0.1115 -0.0305 0.123 Uiso 1 calc R . .
C23 C -0.4238(4) -0.2808(2) 0.0088(3) 0.0367(7) Uani 1 d . . .
C7 C -1.0495(4) 0.0557(2) -0.4387(4) 0.0379(7) Uani 1 d . . .
H7 H -0.9809 0.0993 -0.4140 0.045 Uiso 1 calc R . .
Cl1 Cl -1.1125(3) -0.0313(2) -0.1498(2) 0.1254(8) Uani 1 d . . .
P1 P -0.57097(8) -0.15189(5) -0.21435(7) 0.0292(2) Uani 1 d . . .
C28 C -0.3212(5) -0.3391(3) -0.0044(5) 0.0543(10) Uani 1 d . . .
H28 H -0.3461 -0.3813 -0.0682 0.065 Uiso 1 calc R . .
C8 C -1.1959(4) 0.0735(3) -0.4680(4) 0.0452(9) Uani 1 d . . .
H8 H -1.2255 0.1296 -0.4626 0.054 Uiso 1 calc R . .
N1 N -0.6478(3) -0.20442(17) -0.1180(2) 0.0274(5) Uani 1 d . . .
C35 C -0.7843(3) -0.1802(2) -0.0857(3) 0.0314(6) Uani 1 d . . .
H35 H -0.8221 -0.1288 -0.1363 0.038 Uiso 1 calc R . .
C6 C -0.8524(4) -0.0514(2) -0.4139(3) 0.0289(6) Uani 1 d . . .
C5 C -1.0025(4) -0.0289(2) -0.4459(3) 0.0307(6) Uani 1 d . . .
C21 C -0.5830(4) -0.2874(2) -0.0711(3) 0.0319(7) Uani 1 d . . .
H21 H -0.6363 -0.3080 -0.0109 0.038 Uiso 1 calc R . .
O1 O -0.6728(2) -0.16061(16) -0.3669(2) 0.0326(5) Uani 1 d . . .
C9 C -1.3006(5) 0.0110(3) -0.5052(5) 0.0537(11) Uani 1 d . . .
H9 H -1.3997 0.0249 -0.5246 0.064 Uiso 1 calc R . .
C1 C -0.8176(3) -0.1360(2) -0.4070(3) 0.0303(7) Uani 1 d . . .
C36 C -0.9016(4) -0.2470(3) -0.1263(3) 0.0413(8) Uani 1 d . . .
H36A H -0.9172 -0.2604 -0.2170 0.062 Uiso 1 calc R . .
H36B H -0.9912 -0.2259 -0.1131 0.062 Uiso 1 calc R . .
H36C H -0.8713 -0.2975 -0.0747 0.062 Uiso 1 calc R . .
C4 C -1.1096(4) -0.0934(2) -0.4822(3) 0.0362(7) Uani 1 d . . .
C22 C -0.6115(5) -0.3519(3) -0.1804(4) 0.0489(9) Uani 1 d . . .
H22A H -0.7117 -0.3475 -0.2328 0.073 Uiso 1 calc R . .
H22B H -0.5934 -0.4082 -0.1443 0.073 Uiso 1 calc R . .
H22C H -0.5473 -0.3408 -0.2338 0.073 Uiso 1 calc R . .
C10 C -1.2591(4) -0.0712(3) -0.5137(4) 0.0476(9) Uani 1 d . . .
H10 H -1.3304 -0.1133 -0.5407 0.057 Uiso 1 calc R . .
C2 C -0.9232(4) -0.1991(2) -0.4446(3) 0.0350(7) Uani 1 d . . .
H2 H -0.8947 -0.2560 -0.4430 0.042 Uiso 1 calc R . .
C3 C -1.0658(4) -0.1790(2) -0.4832(3) 0.0384(8) Uani 1 d . . .
H3 H -1.1360 -0.2216 -0.5106 0.046 Uiso 1 calc R . .
Cl2 Cl -1.1581(4) 0.00321(17) 0.0970(3) 0.1429(11) Uani 1 d . . .
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
C14 C13 1.355(5) . ?
C14 C15 1.413(6) . ?
C14 H14 0.9400 . ?
C20 C19 1.359(6) . ?
C20 C15 1.422(5) . ?
C20 H20 0.9400 . ?
C32 C34 1.371(6) . ?
C32 C30 1.382(5) . ?
C32 H32 0.9400 . ?
C13 C12 1.405(5) . ?
C13 H13 0.9400 . ?
C34 C33 1.366(6) . ?
C34 H34 0.9400 . ?
C15 C16 1.424(5) . ?
C19 C18 1.396(7) . ?
C19 H19 0.9400 . ?
C25 C26 1.371(9) . ?
C25 C24 1.379(6) . ?
C25 H25 0.9400 . ?
C26 C27 1.342(11) . ?
C26 H26 0.9400 . ?
C30 C31 1.404(5) . ?
C30 H30 0.9400 . ?
C12 C11 1.371(5) . ?
C12 O2 1.383(4) . ?
C33 C29 1.409(5) . ?
C33 H33 0.9400 . ?
C24 C23 1.378(6) . ?
C24 H24 0.9400 . ?
C16 C17 1.416(5) . ?
C16 C11 1.434(4) . ?
C18 C17 1.371(5) . ?
C18 H18 0.9400 . ?
O2 P1 1.661(3) . ?
C27 C28 1.410(8) . ?
C27 H27 0.9400 . ?
C11 C6 1.496(4) . ?
C31 C29 1.379(5) . ?
C31 C35 1.519(4) . ?
C17 H17 0.9400 . ?
C29 H29 0.9400 . ?
C72 Cl1 1.708(8) . ?
C72 Cl2 1.732(8) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C23 C28 1.387(6) . ?
C23 C21 1.530(5) . ?
C7 C8 1.378(5) . ?
C7 C5 1.423(5) . ?
C7 H7 0.9400 . ?
P1 N1 1.658(3) . ?
P1 O1 1.664(2) . ?
C28 H28 0.9400 . ?
C8 C9 1.386(7) . ?
C8 H8 0.9400 . ?
N1 C21 1.480(4) . ?
N1 C35 1.498(4) . ?
C35 C36 1.516(5) . ?
C35 H35 0.9900 . ?
C6 C1 1.378(5) . ?
C6 C5 1.428(5) . ?
C5 C4 1.422(5) . ?
C21 C22 1.525(5) . ?
C21 H21 0.9900 . ?
O1 C1 1.389(4) . ?
C9 C10 1.372(7) . ?
C9 H9 0.9400 . ?
C1 C2 1.399(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?
C4 C3 1.421(6) . ?
C4 C10 1.421(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C10 H10 0.9400 . ?
C2 C3 1.350(5) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21192832
