#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:15:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178695 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/06/4080628.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_4080628
loop_
_publ_author_name
'Chen, Wen-Ching'
'Hsu, Yu-Chen'
'Lee, Ching-Yu'
'Yap, Glenn P. A.'
'Ong, Tiow-Gan'
_publ_section_title
;
 Synthetic Modification of Acyclic Bent Allenes (Carbodicarbenes) and
 Further Studies on Their Structural Implications and Reactivities
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2435
_journal_paper_doi               10.1021/om400139s
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C27 H35 Cl3 N4 Pd'
_chemical_formula_weight         628.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 117.9890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0883(7)
_cell_length_b                   9.3309(3)
_cell_length_c                   18.8260(8)
_cell_measurement_reflns_used    6564
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.45
_cell_volume                     2805.81(19)
_computing_cell_refinement       'SHELXTL, Sheldrick (2001)'
_computing_data_collection       'SMART, Bruker (2002)'
_computing_data_reduction        'SHELXTL, Sheldrick (2001)'
_computing_molecular_graphics    'SHELXTL, Sheldrick (2001)'
_computing_publication_material  'SHELXTL, Sheldrick (2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24148
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.29
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.9092
_exptl_absorpt_correction_T_min  0.7596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         6440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+1.1825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                4160
_reflns_number_total             6440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400139s_si_003.cif
_cod_data_source_block           i13557
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2805.81(18)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4080628
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.43167(2) 0.93512(3) 0.15935(2) 0.01607(10) Uani 1 1 d .
Cl1 Cl 0.28638(7) 0.88668(10) 0.11818(7) 0.0210(3) Uani 1 1 d .
Cl2 Cl 0.76994(9) 0.40558(16) 0.11059(10) 0.0540(4) Uani 1 1 d .
Cl3 Cl 0.62759(10) 0.21978(16) 0.07168(11) 0.0605(5) Uani 1 1 d .
N1 N 0.4183(2) 0.9674(3) 0.3300(2) 0.0135(8) Uani 1 1 d .
N2 N 0.3841(2) 0.7391(3) 0.3234(2) 0.0140(8) Uani 1 1 d .
N3 N 0.5526(2) 0.6146(3) 0.2334(2) 0.0162(8) Uani 1 1 d .
N4 N 0.5676(2) 0.6221(3) 0.3577(2) 0.0146(8) Uani 1 1 d .
C1 C 0.4175(3) 1.0930(4) 0.0665(3) 0.0276(12) Uani 1 1 d .
H1A H 0.3767 1.0697 0.0103 0.033 Uiso 1 1 calc R
H1B H 0.4180 1.1954 0.0804 0.033 Uiso 1 1 calc R
C2 C 0.4931(4) 1.0251(6) 0.0977(4) 0.0446(15) Uani 1 1 d .
H2 H 0.5066 0.9628 0.0620 0.054 Uiso 1 1 calc R
C3 C 0.5475(3) 1.0241(5) 0.1829(3) 0.0268(12) Uani 1 1 d .
H3A H 0.5613 1.1185 0.2101 0.032 Uiso 1 1 calc R
H3B H 0.5957 0.9575 0.2028 0.032 Uiso 1 1 calc R
C4 C 0.4748(3) 0.8057(4) 0.2625(3) 0.0140(9) Uani 1 1 d .
C5 C 0.4307(3) 0.8346(4) 0.3054(2) 0.0127(9) Uani 1 1 d .
C6 C 0.4709(3) 1.0934(4) 0.3369(3) 0.0170(10) Uani 1 1 d .
H6 H 0.5128 1.0620 0.3195 0.020 Uiso 1 1 calc R
C7 C 0.4198(3) 1.2128(4) 0.2805(3) 0.0228(11) Uani 1 1 d .
H7A H 0.3877 1.1746 0.2259 0.034 Uiso 1 1 calc R
H7B H 0.4574 1.2885 0.2806 0.034 Uiso 1 1 calc R
H7C H 0.3812 1.2524 0.2985 0.034 Uiso 1 1 calc R
C8 C 0.5204(3) 1.1410(5) 0.4253(3) 0.0229(11) Uani 1 1 d .
H8A H 0.4816 1.1782 0.4436 0.034 Uiso 1 1 calc R
H8B H 0.5602 1.2163 0.4298 0.034 Uiso 1 1 calc R
H8C H 0.5510 1.0589 0.4586 0.034 Uiso 1 1 calc R
C9 C 0.3607(2) 0.9565(4) 0.3597(3) 0.0131(9) Uani 1 1 d .
C10 C 0.3241(3) 1.0578(4) 0.3869(3) 0.0165(9) Uani 1 1 d .
H10 H 0.3365 1.1568 0.3875 0.020 Uiso 1 1 calc R
C11 C 0.2685(3) 1.0095(4) 0.4133(3) 0.0210(10) Uani 1 1 d .
H11 H 0.2428 1.0766 0.4328 0.025 Uiso 1 1 calc R
C12 C 0.2498(3) 0.8644(4) 0.4115(3) 0.0198(10) Uani 1 1 d .
H12 H 0.2122 0.8346 0.4308 0.024 Uiso 1 1 calc R
C13 C 0.2846(3) 0.7622(4) 0.3826(3) 0.0159(9) Uani 1 1 d .
H13 H 0.2709 0.6634 0.3807 0.019 Uiso 1 1 calc R
C14 C 0.3401(3) 0.8107(4) 0.3565(3) 0.0139(9) Uani 1 1 d .
C15 C 0.3714(3) 0.5893(4) 0.2988(3) 0.0178(10) Uani 1 1 d .
H15A H 0.4140 0.5302 0.3413 0.027 Uiso 1 1 calc R
H15B H 0.3760 0.5782 0.2492 0.027 Uiso 1 1 calc R
H15C H 0.3156 0.5587 0.2891 0.027 Uiso 1 1 calc R
C16 C 0.5268(3) 0.6881(4) 0.2824(3) 0.0142(9) Uani 1 1 d .
C17 C 0.5125(3) 0.6254(4) 0.1449(3) 0.0197(10) Uani 1 1 d .
H17 H 0.4729 0.7083 0.1293 0.024 Uiso 1 1 calc R
C18 C 0.5764(3) 0.6599(5) 0.1154(3) 0.0262(11) Uani 1 1 d .
H18A H 0.6089 0.7447 0.1438 0.039 Uiso 1 1 calc R
H18B H 0.5470 0.6790 0.0575 0.039 Uiso 1 1 calc R
H18C H 0.6143 0.5782 0.1262 0.039 Uiso 1 1 calc R
C19 C 0.4604(3) 0.4934(5) 0.1055(3) 0.0280(12) Uani 1 1 d .
H19A H 0.4972 0.4097 0.1181 0.042 Uiso 1 1 calc R
H19B H 0.4303 0.5071 0.0471 0.042 Uiso 1 1 calc R
H19C H 0.4201 0.4781 0.1258 0.042 Uiso 1 1 calc R
C20 C 0.6067(3) 0.5026(4) 0.2772(3) 0.0175(10) Uani 1 1 d .
C21 C 0.6478(3) 0.3994(4) 0.2557(3) 0.0238(11) Uani 1 1 d .
H21 H 0.6421 0.3956 0.2029 0.029 Uiso 1 1 calc R
C22 C 0.6981(3) 0.3013(5) 0.3149(3) 0.0269(12) Uani 1 1 d .
H22 H 0.7260 0.2281 0.3016 0.032 Uiso 1 1 calc R
C23 C 0.7083(3) 0.3079(4) 0.3917(3) 0.0276(12) Uani 1 1 d .
H23 H 0.7436 0.2403 0.4305 0.033 Uiso 1 1 calc R
C24 C 0.6673(3) 0.4132(4) 0.4142(3) 0.0210(10) Uani 1 1 d .
H24 H 0.6743 0.4188 0.4674 0.025 Uiso 1 1 calc R
C25 C 0.6161(3) 0.5081(4) 0.3547(3) 0.0148(9) Uani 1 1 d .
C26 C 0.5782(3) 0.6843(4) 0.4324(3) 0.0191(10) Uani 1 1 d .
H26A H 0.5788 0.7891 0.4288 0.029 Uiso 1 1 calc R
H26B H 0.6311 0.6514 0.4768 0.029 Uiso 1 1 calc R
H26C H 0.5317 0.6547 0.4421 0.029 Uiso 1 1 calc R
C27 C 0.7193(3) 0.2443(5) 0.0676(4) 0.0447(16) Uani 1 1 d .
H27A H 0.7073 0.2416 0.0106 0.054 Uiso 1 1 calc R
H27B H 0.7575 0.1637 0.0958 0.054 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'
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
C3 Pd1 C4 97.50(17)
C3 Pd1 C2 39.8(2)
C4 Pd1 C2 132.1(2)
C3 Pd1 C1 68.69(19)
C4 Pd1 C1 165.95(17)
C2 Pd1 C1 36.68(19)
C3 Pd1 Cl1 166.60(14)
C4 Pd1 Cl1 93.77(11)
C2 Pd1 Cl1 132.15(18)
C1 Pd1 Cl1 99.62(13)
C5 N1 C9 109.8(3)
C5 N1 C6 123.1(3)
C9 N1 C6 126.2(3)
C5 N2 C14 110.2(3)
C5 N2 C15 124.5(3)
C14 N2 C15 124.5(3)
C16 N3 C20 109.6(4)
C16 N3 C17 125.0(3)
C20 N3 C17 123.5(3)
C25 N4 C16 109.7(3)
C25 N4 C26 123.1(4)
C16 N4 C26 125.0(3)
C2 C1 Pd1 68.3(3)
C1 C2 C3 120.4(5)
C1 C2 Pd1 75.0(3)
C3 C2 Pd1 69.2(3)
C2 C3 Pd1 71.0(3)
C16 C4 C5 119.7(4)
C16 C4 Pd1 128.4(3)
C5 C4 Pd1 110.9(3)
N2 C5 N1 106.6(3)
N2 C5 C4 126.7(3)
N1 C5 C4 126.3(3)
N1 C6 C7 111.5(3)
N1 C6 C8 110.4(3)
C7 C6 C8 113.5(3)
C10 C9 N1 132.4(3)
C10 C9 C14 121.0(3)
N1 C9 C14 106.6(3)
C9 C10 C11 117.6(4)
C10 C11 C12 121.0(4)
C13 C12 C11 121.9(4)
C14 C13 C12 116.9(4)
C13 C14 N2 131.7(3)
C13 C14 C9 121.6(3)
N2 C14 C9 106.7(3)
C4 C16 N3 127.5(4)
C4 C16 N4 126.6(4)
N3 C16 N4 105.8(3)
N3 C17 C19 111.1(3)
N3 C17 C18 111.6(4)
C19 C17 C18 113.3(4)
C25 C20 C21 120.9(4)
C25 C20 N3 107.3(3)
C21 C20 N3 131.8(4)
C20 C21 C22 117.3(4)
C23 C22 C21 121.7(4)
C22 C23 C24 121.3(4)
C25 C24 C23 116.6(4)
C24 C25 C20 122.1(4)
C24 C25 N4 130.3(4)
C20 C25 N4 107.6(4)
Cl3 C27 Cl2 113.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C3 2.098(4)
Pd1 C4 2.101(4)
Pd1 C2 2.122(5)
Pd1 C1 2.207(4)
Pd1 Cl1 2.4083(11)
Cl2 C27 1.751(5)
Cl3 C27 1.711(5)
N1 C5 1.376(5)
N1 C9 1.400(5)
N1 C6 1.479(5)
N2 C5 1.374(5)
N2 C14 1.391(5)
N2 C15 1.457(4)
N3 C16 1.395(5)
N3 C20 1.404(5)
N3 C17 1.476(6)
N4 C25 1.397(5)
N4 C16 1.397(5)
N4 C26 1.449(5)
C1 C2 1.364(7)
C2 C3 1.436(7)
C4 C16 1.377(5)
C4 C5 1.404(5)
C6 C7 1.518(6)
C6 C8 1.539(6)
C9 C10 1.382(5)
C9 C14 1.405(5)
C10 C11 1.389(5)
C11 C12 1.392(6)
C12 C13 1.388(5)
C13 C14 1.383(5)
C17 C19 1.516(6)
C17 C18 1.532(5)
C20 C25 1.388(6)
C20 C21 1.388(5)
C21 C22 1.399(6)
C22 C23 1.370(7)
C23 C24 1.410(6)
C24 C25 1.386(6)
