#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:22:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178561 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/69/4066977.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_4066977
loop_
_publ_author_name
'Xu, Xiangya'
'Xu, Baochang'
'Li, Yongxin'
'Hong, Soon Hyeok'
_publ_section_title
;
 Abnormal N-Heterocyclic Carbene Promoted Suzuki−Miyaura Coupling
 Reaction: A Comparative Study
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6343
_journal_paper_doi               10.1021/om100746r
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C24 H28 I2 N4 Pd'
_chemical_formula_sum            'C24 H28 I2 N4 Pd'
_chemical_formula_weight         732.70
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                102.880(3)
_cell_angle_beta                 92.338(3)
_cell_angle_gamma                118.385(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6567(4)
_cell_length_b                   8.7067(4)
_cell_length_c                   10.3222(8)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.27
_cell_measurement_theta_min      2.71
_cell_volume                     657.40(7)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11966
_diffrn_reflns_theta_full        31.32
_diffrn_reflns_theta_max         31.32
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    3.071
_exptl_absorpt_correction_T_max  0.7487
_exptl_absorpt_correction_T_min  0.3882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         4.553
_refine_diff_density_min         -1.989
_refine_diff_density_rms         0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0592
_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)+(0.1120P)²+2.7925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                3575
_reflns_number_total             4170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100746r_si_001.cif
_cod_data_source_block           compound7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4066977
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
Pd1 Pd 1.0000 1.0000 0.5000 0.01707(15) Uani 1 2 d S
C1 C 0.9052(7) 0.7403(7) 0.5041(5) 0.0206(9) Uani 1 1 d .
C2 C 0.8281(8) 0.4882(7) 0.5752(6) 0.0258(10) Uani 1 1 d .
H2 H 0.8217 0.4121 0.6304 0.031 Uiso 1 1 calc R
C3 C 0.7407(7) 0.4366(7) 0.4482(6) 0.0246(10) Uani 1 1 d .
H3 H 0.6595 0.3155 0.3969 0.030 Uiso 1 1 calc R
C4 C 1.0447(7) 0.7887(8) 0.7348(5) 0.0239(10) Uani 1 1 d .
C5 C 1.2154(8) 0.9211(9) 0.7377(7) 0.0301(11) Uani 1 1 d .
H5 H 1.2598 0.9391 0.6565 0.036 Uiso 1 1 calc R
C6 C 1.3193(11) 1.0258(9) 0.8594(7) 0.0380(14) Uani 1 1 d .
H6 H 1.4342 1.1244 0.8620 0.046 Uiso 1 1 calc R
C7 C 1.2646(10) 0.9947(11) 0.9820(7) 0.0420(16) Uani 1 1 d .
H7 H 1.3430 1.0648 1.0657 0.050 Uiso 1 1 calc R
C8 C 1.0923(11) 0.8583(13) 0.9763(7) 0.0440(17) Uani 1 1 d .
H8 H 1.0505 0.8350 1.0573 0.053 Uiso 1 1 calc R
C9 C 0.9793(9) 0.7546(10) 0.8523(6) 0.0322(12) Uani 1 1 d .
H9 H 0.8603 0.6626 0.8483 0.039 Uiso 1 1 calc R
C10 C 0.7229(8) 0.5952(8) 0.2743(6) 0.0259(10) Uani 1 1 d .
H10 H 0.7873 0.7240 0.2700 0.031 Uiso 1 1 calc R
C11 C 0.5271(10) 0.5351(13) 0.2635(9) 0.0460(18) Uani 1 1 d .
H11A H 0.4672 0.4295 0.2989 0.069 Uiso 1 1 calc R
H11B H 0.4749 0.5024 0.1687 0.069 Uiso 1 1 calc R
H11C H 0.5121 0.6344 0.3158 0.069 Uiso 1 1 calc R
C12 C 0.7629(12) 0.4823(12) 0.1597(7) 0.0434(17) Uani 1 1 d .
H12A H 0.8919 0.5304 0.1690 0.065 Uiso 1 1 calc R
H12B H 0.7184 0.4881 0.0731 0.065 Uiso 1 1 calc R
H12C H 0.7040 0.3558 0.1633 0.065 Uiso 1 1 calc R
I1 I 1.24741(5) 0.98894(5) 0.36698(4) 0.02730(15) Uani 1 1 d .
N1 N 0.9300(6) 0.6774(6) 0.6078(5) 0.0224(8) Uani 1 1 d .
N2 N 0.7902(6) 0.5906(6) 0.4064(5) 0.0213(8) Uani 1 1 d .
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Pd1 C1 180.000(1) . 2_776
C1 Pd1 I1 89.18(14) . 2_776
C1 Pd1 I1 90.82(14) 2_776 2_776
C1 Pd1 I1 90.82(14) . .
C1 Pd1 I1 89.18(14) 2_776 .
I1 Pd1 I1 180.0 2_776 .
N2 C1 N1 104.8(4) . .
N2 C1 Pd1 126.6(4) . .
N1 C1 Pd1 128.5(4) . .
C3 C2 N1 105.2(5) . .
C3 C2 H2 127.4 . .
N1 C2 H2 127.4 . .
C2 C3 N2 107.9(5) . .
C2 C3 H3 126.1 . .
N2 C3 H3 126.1 . .
C5 C4 C9 121.8(6) . .
C5 C4 N1 119.8(5) . .
C9 C4 N1 118.4(5) . .
C6 C5 C4 118.3(6) . .
C6 C5 H5 120.8 . .
C4 C5 H5 120.8 . .
C5 C6 C7 122.9(7) . .
C5 C6 H6 118.6 . .
C7 C6 H6 118.6 . .
C8 C7 C6 117.6(6) . .
C8 C7 H7 121.2 . .
C6 C7 H7 121.2 . .
C7 C8 C9 120.6(7) . .
C7 C8 H8 119.7 . .
C9 C8 H8 119.7 . .
C4 C9 C8 118.7(6) . .
C4 C9 H9 120.7 . .
C8 C9 H9 120.7 . .
N2 C10 C11 109.7(5) . .
N2 C10 C12 110.7(5) . .
C11 C10 C12 112.7(6) . .
N2 C10 H10 107.8 . .
C11 C10 H10 107.8 . .
C12 C10 H10 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 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C1 N1 C2 111.1(5) . .
C1 N1 C4 125.1(5) . .
C2 N1 C4 123.8(5) . .
C1 N2 C3 111.0(5) . .
C1 N2 C10 123.5(4) . .
C3 N2 C10 125.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.017(5) .
Pd1 C1 2.017(5) 2_776
Pd1 I1 2.6189(4) 2_776
Pd1 I1 2.6189(4) .
C1 N2 1.344(7) .
C1 N1 1.359(7) .
C2 C3 1.351(9) .
C2 N1 1.398(7) .
C2 H2 0.9500 .
C3 N2 1.376(6) .
C3 H3 0.9500 .
C4 C5 1.369(8) .
C4 C9 1.391(8) .
C4 N1 1.434(7) .
C5 C6 1.354(10) .
C5 H5 0.9500 .
C6 C7 1.407(11) .
C6 H6 0.9500 .
C7 C8 1.384(12) .
C7 H7 0.9500 .
C8 C9 1.397(10) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 N2 1.477(7) .
C10 C11 1.508(9) .
C10 C12 1.525(9) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
