#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513201.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_1513201
loop_
_publ_author_name
'Yong-Joo Kim'
'Hyun-Kyung Kim'
'Jung-Hyun Lee'
'Zhen Nu Zheng'
'Soon W. Lee'
_publ_section_title
;
 Synthesis and structures of n1-allenyl and/or -propargyl Pd(II) complexes
 and their reactivity toward trimethylsilyl pseudohalides, organic thiols,
 and N-heterocyclic carbene ligands
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              54
_journal_page_last               63
_journal_paper_doi               10.1016/j.ica.2012.12.011
_journal_volume                  398
_journal_year                    2013
_chemical_formula_moiety         'C21 H37 Cl P2 Pd'
_chemical_formula_sum            'C21 H37 Cl P2 Pd'
_chemical_formula_weight         493.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.889(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1748(5)
_cell_length_b                   14.5911(6)
_cell_length_c                   14.2045(6)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.46
_cell_volume                     2477.91(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42303
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.8906
_exptl_absorpt_correction_T_min  0.7427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         6110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0267P)²+0.2739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0583
_reflns_number_gt                4820
_reflns_number_total             6110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-398-54-63-2.cif
_cod_data_source_block           p21c
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               1513201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd1 Pd 0.733429(10) 0.072112(9) 0.701558(9) 0.04231(5) Uani 1 1 d .
Cl1 Cl 0.58820(4) -0.00774(4) 0.75982(4) 0.06292(13) Uani 1 1 d .
P1 P 0.77794(4) -0.06574(3) 0.63640(4) 0.05090(12) Uani 1 1 d .
P2 P 0.69031(4) 0.20196(3) 0.78126(4) 0.05514(13) Uani 1 1 d .
C1 C 0.85746(15) 0.14066(13) 0.64821(13) 0.0531(4) Uani 1 1 d .
H1A H 0.8632 0.1165 0.5857 0.064 Uiso 1 1 calc R
H1B H 0.8397 0.2054 0.6414 0.064 Uiso 1 1 calc R
C2 C 0.96235(17) 0.12791(13) 0.71464(14) 0.0550(5) Uani 1 1 d .
C3 C 1.04773(18) 0.11492(14) 0.76986(15) 0.0588(5) Uani 1 1 d .
C4 C 1.15050(16) 0.09816(13) 0.83667(15) 0.0555(5) Uani 1 1 d .
C5 C 1.25036(19) 0.08641(17) 0.80596(18) 0.0767(7) Uani 1 1 d .
H5 H 1.2525 0.0903 0.7410 0.092 Uiso 1 1 calc R
C6 C 1.3485(2) 0.06866(18) 0.8721(2) 0.0912(8) Uani 1 1 d .
H6 H 1.4150 0.0589 0.8504 0.109 Uiso 1 1 calc R
C7 C 1.3481(2) 0.06554(17) 0.9666(2) 0.0848(7) Uani 1 1 d .
H7 H 1.4141 0.0546 1.0100 0.102 Uiso 1 1 calc R
C8 C 1.2516(2) 0.07833(17) 0.9982(2) 0.0862(7) Uani 1 1 d .
H8 H 1.2514 0.0763 1.0636 0.103 Uiso 1 1 calc R
C9 C 1.15275(19) 0.09442(16) 0.93435(17) 0.0712(6) Uani 1 1 d .
H9 H 1.0869 0.1029 0.9574 0.085 Uiso 1 1 calc R
C10 C 0.6585(2) -0.11848(16) 0.55849(16) 0.0754(6) Uani 1 1 d .
H10A H 0.6784 -0.1802 0.5426 0.090 Uiso 1 1 calc R
H10B H 0.5969 -0.1229 0.5928 0.090 Uiso 1 1 calc R
C11 C 0.6203(3) -0.0651(2) 0.4667(2) 0.1115(10) Uani 1 1 d .
H11A H 0.5575 -0.0955 0.4283 0.167 Uiso 1 1 calc R
H11B H 0.6804 -0.0616 0.4317 0.167 Uiso 1 1 calc R
H11C H 0.5989 -0.0044 0.4819 0.167 Uiso 1 1 calc R
C12 C 0.8887(2) -0.06778(14) 0.56533(18) 0.0722(6) Uani 1 1 d .
H12A H 0.8677 -0.0265 0.5114 0.087 Uiso 1 1 calc R
H12B H 0.9565 -0.0439 0.6045 0.087 Uiso 1 1 calc R
C13 C 0.9150(3) -0.16146(18) 0.5268(2) 0.1033(9) Uani 1 1 d .
H13A H 0.9740 -0.1552 0.4909 0.155 Uiso 1 1 calc R
H13B H 0.8494 -0.1852 0.4858 0.155 Uiso 1 1 calc R
H13C H 0.9382 -0.2028 0.5793 0.155 Uiso 1 1 calc R
C14 C 0.8206(2) -0.14963(14) 0.73121(16) 0.0712(6) Uani 1 1 d .
H14A H 0.7593 -0.1590 0.7649 0.085 Uiso 1 1 calc R
H14B H 0.8349 -0.2076 0.7023 0.085 Uiso 1 1 calc R
C15 C 0.9239(2) -0.12256(19) 0.80323(18) 0.0930(8) Uani 1 1 d .
H15A H 0.9410 -0.1696 0.8510 0.139 Uiso 1 1 calc R
H15B H 0.9102 -0.0659 0.8333 0.139 Uiso 1 1 calc R
H15C H 0.9858 -0.1151 0.7709 0.139 Uiso 1 1 calc R
C16 C 0.5485(2) 0.24303(18) 0.73917(19) 0.0887(8) Uani 1 1 d .
H16A H 0.4965 0.1931 0.7418 0.106 Uiso 1 1 calc R
H16B H 0.5322 0.2910 0.7818 0.106 Uiso 1 1 calc R
C17 C 0.5303(3) 0.2800(2) 0.6380(2) 0.1201(11) Uani 1 1 d .
H17A H 0.4541 0.2999 0.6192 0.180 Uiso 1 1 calc R
H17B H 0.5455 0.2327 0.5953 0.180 Uiso 1 1 calc R
H17C H 0.5796 0.3309 0.6354 0.180 Uiso 1 1 calc R
C18 C 0.7780(2) 0.30357(15) 0.78149(17) 0.0792(7) Uani 1 1 d .
H18A H 0.8555 0.2854 0.8017 0.095 Uiso 1 1 calc R
H18B H 0.7694 0.3259 0.7162 0.095 Uiso 1 1 calc R
C19 C 0.7542(3) 0.38263(17) 0.8451(2) 0.1099(10) Uani 1 1 d .
H19A H 0.8045 0.4324 0.8402 0.165 Uiso 1 1 calc R
H19B H 0.7649 0.3623 0.9105 0.165 Uiso 1 1 calc R
H19C H 0.6785 0.4029 0.8247 0.165 Uiso 1 1 calc R
C20 C 0.6984(2) 0.17703(17) 0.90860(15) 0.0798(7) Uani 1 1 d .
H20A H 0.6731 0.2302 0.9395 0.096 Uiso 1 1 calc R
H20B H 0.6485 0.1266 0.9150 0.096 Uiso 1 1 calc R
C21 C 0.8165(3) 0.15226(19) 0.95943(17) 0.1004(9) Uani 1 1 d .
H21A H 0.8164 0.1397 1.0257 0.151 Uiso 1 1 calc R
H21B H 0.8660 0.2026 0.9546 0.151 Uiso 1 1 calc R
H21C H 0.8415 0.0990 0.9299 0.151 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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
C1 Pd1 P2 91.83(6)
C1 Pd1 P1 91.80(6)
P2 Pd1 P1 174.187(18)
C1 Pd1 Cl1 178.80(5)
P2 Pd1 Cl1 88.783(19)
P1 Pd1 Cl1 87.668(18)
C14 P1 C10 104.40(11)
C14 P1 C12 105.07(11)
C10 P1 C12 104.16(12)
C14 P1 Pd1 110.06(7)
C10 P1 Pd1 112.84(8)
C12 P1 Pd1 119.06(7)
C16 P2 C18 104.56(13)
C16 P2 C20 105.11(12)
C18 P2 C20 103.74(11)
C16 P2 Pd1 113.41(8)
C18 P2 Pd1 118.57(8)
C20 P2 Pd1 110.22(8)
C2 C1 Pd1 108.28(12)
C2 C1 H1A 110.0
Pd1 C1 H1A 110.0
C2 C1 H1B 110.0
Pd1 C1 H1B 110.0
H1A C1 H1B 108.4
C3 C2 C1 178.1(2)
C2 C3 C4 179.3(2)
C5 C4 C9 117.5(2)
C5 C4 C3 121.4(2)
C9 C4 C3 121.14(18)
C4 C5 C6 120.3(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C5 120.9(2)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 119.7(3)
C6 C7 H7 120.1
C8 C7 H7 120.1
C7 C8 C9 120.7(3)
C7 C8 H8 119.7
C9 C8 H8 119.7
C8 C9 C4 121.0(2)
C8 C9 H9 119.5
C4 C9 H9 119.5
C11 C10 P1 112.67(18)
C11 C10 H10A 109.1
P1 C10 H10A 109.1
C11 C10 H10B 109.1
P1 C10 H10B 109.1
H10A C10 H10B 107.8
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 P1 115.99(17)
C13 C12 H12A 108.3
P1 C12 H12A 108.3
C13 C12 H12B 108.3
P1 C12 H12B 108.3
H12A C12 H12B 107.4
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 P1 114.10(17)
C15 C14 H14A 108.7
P1 C14 H14A 108.7
C15 C14 H14B 108.7
P1 C14 H14B 108.7
H14A C14 H14B 107.6
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C17 C16 P2 112.9(2)
C17 C16 H16A 109.0
P2 C16 H16A 109.0
C17 C16 H16B 109.0
P2 C16 H16B 109.0
H16A C16 H16B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 P2 116.0(2)
C19 C18 H18A 108.3
P2 C18 H18A 108.3
C19 C18 H18B 108.3
P2 C18 H18B 108.3
H18A C18 H18B 107.4
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C21 C20 P2 112.62(18)
C21 C20 H20A 109.1
P2 C20 H20A 109.1
C21 C20 H20B 109.1
P2 C20 H20B 109.1
H20A C20 H20B 107.8
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 2.0705(18)
Pd1 P2 2.3176(5)
Pd1 P1 2.3207(5)
Pd1 Cl1 2.3919(5)
P1 C14 1.821(2)
P1 C10 1.823(2)
P1 C12 1.831(2)
P2 C16 1.819(2)
P2 C18 1.827(2)
P2 C20 1.829(2)
C1 C2 1.449(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.193(3)
C3 C4 1.441(3)
C4 C5 1.378(3)
C4 C9 1.384(3)
C5 C6 1.397(3)
C5 H5 0.9300
C6 C7 1.345(4)
C6 H6 0.9300
C7 C8 1.347(4)
C7 H7 0.9300
C8 C9 1.383(3)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.514(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.529(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.516(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.511(4)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.526(3)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 C21 1.526(4)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
