#------------------------------------------------------------------------------
#$Date: 2015-10-09 10:55:22 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161211 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/63/7036353.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_7036353
loop_
_publ_author_name
'Chang, Ting-Wei'
'Ho, Pei-Yun'
'Mao, Kuo-Chung'
'Hong, Fung-E'
_publ_section_title
;
 Developing five-membered heterocycle substituted phosphinous acids as
 ligands for palladium-catalyzed Suzuki-Miyaura and Catellani reactions.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17129
_journal_page_last               17142
_journal_paper_doi               10.1039/c5dt02611c
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C18 H20 N O2 P'
_chemical_formula_sum            'C18 H20 N O2 P'
_chemical_formula_weight         313.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-27 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                67.278(7)
_cell_angle_beta                 87.525(6)
_cell_angle_gamma                62.600(8)
_cell_formula_units_Z            2
_cell_length_a                   9.4916(8)
_cell_length_b                   9.9475(8)
_cell_length_c                   10.6719(8)
_cell_measurement_temperature    150(2)
_cell_volume                     813.93(14)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6469
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                2920
_reflns_number_total             3760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt02611c2.cif
_cod_data_source_block           ctw05
_cod_depositor_comments
'Adding full bibliography for 7036349--7036358.cif.'
_cod_original_cell_volume        813.93(11)
_cod_database_code               7036353
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P P 0.02419(7) 0.15567(6) 0.31711(5) 0.02571(17) Uani 1 1 d .
O1 O -0.1306(2) 0.2268(2) 0.37989(18) 0.0396(4) Uani 1 1 d .
H1A H -0.1148 0.1637 0.4635 0.18(2) Uiso 1 1 calc R
O2 O 0.12694(19) -0.02896(18) 0.38641(16) 0.0355(4) Uani 1 1 d .
N N 0.2808(2) 0.2367(2) 0.29774(17) 0.0234(4) Uani 1 1 d .
C1 C 0.1257(3) 0.2670(2) 0.3248(2) 0.0246(5) Uani 1 1 d .
C2 C 0.0531(3) 0.4116(3) 0.3447(2) 0.0275(5) Uani 1 1 d .
H2B H -0.0529 0.4610 0.3641 0.033 Uiso 1 1 calc R
C3 C 0.1624(3) 0.4740(2) 0.3313(2) 0.0270(5) Uani 1 1 d .
C4 C 0.1576(3) 0.6133(3) 0.3420(2) 0.0345(6) Uani 1 1 d .
H4A H 0.0626 0.6918 0.3590 0.041 Uiso 1 1 calc R
C5 C 0.2914(3) 0.6334(3) 0.3277(3) 0.0393(6) Uani 1 1 d .
H5A H 0.2887 0.7268 0.3348 0.047 Uiso 1 1 calc R
C6 C 0.4333(3) 0.5182(3) 0.3024(3) 0.0411(6) Uani 1 1 d .
H6A H 0.5248 0.5347 0.2939 0.049 Uiso 1 1 calc R
C7 C 0.4417(3) 0.3818(3) 0.2899(2) 0.0324(5) Uani 1 1 d .
H7A H 0.5374 0.3040 0.2731 0.039 Uiso 1 1 calc R
C8 C 0.3053(3) 0.3623(2) 0.3027(2) 0.0260(5) Uani 1 1 d .
C9 C 0.4036(2) 0.0988(2) 0.2748(2) 0.0236(4) Uani 1 1 d .
C10 C 0.4688(3) 0.1291(3) 0.1554(2) 0.0271(5) Uani 1 1 d .
H10A H 0.4321 0.2400 0.0894 0.032 Uiso 1 1 calc R
C11 C 0.5879(3) -0.0026(3) 0.1319(2) 0.0326(5) Uani 1 1 d .
H11A H 0.6336 0.0182 0.0502 0.039 Uiso 1 1 calc R
C12 C 0.6402(3) -0.1640(3) 0.2274(3) 0.0379(6) Uani 1 1 d .
H12A H 0.7211 -0.2542 0.2109 0.045 Uiso 1 1 calc R
C13 C 0.5752(3) -0.1943(3) 0.3466(2) 0.0345(6) Uani 1 1 d .
H13A H 0.6112 -0.3055 0.4118 0.041 Uiso 1 1 calc R
C14 C 0.4566(3) -0.0627(3) 0.3724(2) 0.0291(5) Uani 1 1 d .
H14A H 0.4130 -0.0833 0.4553 0.035 Uiso 1 1 calc R
C15 C -0.0500(3) 0.2211(3) 0.1384(2) 0.0271(5) Uani 1 1 d .
C16 C -0.1682(3) 0.4088(3) 0.0734(2) 0.0389(6) Uani 1 1 d .
H16A H -0.2079 0.4432 -0.0230 0.058 Uiso 1 1 calc R
H16B H -0.1131 0.4697 0.0779 0.058 Uiso 1 1 calc R
H16C H -0.2590 0.4330 0.1239 0.058 Uiso 1 1 calc R
C17 C 0.0898(3) 0.1804(3) 0.0584(2) 0.0339(5) Uani 1 1 d .
H17A H 0.0481 0.2165 -0.0379 0.051 Uiso 1 1 calc R
H17B H 0.1627 0.0602 0.0990 0.051 Uiso 1 1 calc R
H17C H 0.1483 0.2384 0.0626 0.051 Uiso 1 1 calc R
C18 C -0.1358(3) 0.1241(3) 0.1355(3) 0.0445(6) Uani 1 1 d .
H18A H -0.1775 0.1573 0.0399 0.067 Uiso 1 1 calc R
H18B H -0.2252 0.1483 0.1875 0.067 Uiso 1 1 calc R
H18C H -0.0597 0.0047 0.1771 0.067 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'
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
O2 P O1 114.57(9)
O2 P C1 113.24(10)
O1 P C1 104.04(10)
O2 P C15 110.93(10)
O1 P C15 104.42(10)
C1 P C15 109.04(10)
C8 N C1 108.50(17)
C8 N C9 122.65(18)
C1 N C9 128.78(18)
C2 C1 N 108.20(19)
C2 C1 P 123.79(17)
N C1 P 127.66(15)
C1 C2 C3 108.66(19)
C4 C3 C2 134.6(2)
C4 C3 C8 118.4(2)
C2 C3 C8 106.98(19)
C5 C4 C3 119.1(2)
C4 C5 C6 121.2(2)
C7 C6 C5 121.2(3)
C6 C7 C8 117.7(2)
C7 C8 N 129.9(2)
C7 C8 C3 122.3(2)
N C8 C3 107.6(2)
C10 C9 C14 120.61(19)
C10 C9 N 119.21(18)
C14 C9 N 120.17(19)
C9 C10 C11 119.9(2)
C12 C11 C10 120.0(2)
C13 C12 C11 120.1(2)
C12 C13 C14 120.5(2)
C9 C14 C13 118.8(2)
C17 C15 C18 108.7(2)
C17 C15 C16 110.16(19)
C18 C15 C16 110.0(2)
C17 C15 P 110.29(15)
C18 C15 P 107.71(16)
C16 C15 P 109.92(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P O2 1.4952(15)
P O1 1.5595(17)
P C1 1.795(2)
P C15 1.814(2)
N C8 1.392(3)
N C1 1.402(3)
N C9 1.436(2)
C1 C2 1.377(3)
C2 C3 1.412(3)
C3 C4 1.414(3)
C3 C8 1.417(3)
C4 C5 1.368(4)
C5 C6 1.409(3)
C6 C7 1.380(3)
C7 C8 1.388(3)
C9 C10 1.379(3)
C9 C14 1.389(3)
C10 C11 1.387(3)
C11 C12 1.382(3)
C12 C13 1.377(4)
C13 C14 1.397(3)
C15 C17 1.526(3)
C15 C18 1.531(3)
C15 C16 1.538(3)
