#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:19:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178503 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/50/4065002.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_4065002
loop_
_publ_author_name
'Kumar, P. Vijaya'
'Lin, Wu-Shien'
'Shen, Jiun-Shian'
'Nandi, Debkumar'
'Lee, Hon Man'
_publ_section_title
;
 Direct C5-Arylation Reaction between Imidazoles and Aryl Chlorides
 Catalyzed by Palladium Complexes with Phosphines and N-Heterocyclic
 Carbenes
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5160
_journal_paper_doi               10.1021/om200490k
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         '2(C13 H14 N2 O), H2 O'
_chemical_formula_sum            'C26 H30 N4 O3'
_chemical_formula_weight         446.54
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 120.125(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.0207(17)
_cell_length_b                   6.7826(5)
_cell_length_c                   14.2251(9)
_cell_measurement_reflns_used    2970
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.9
_cell_volume                     2254.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15005
_diffrn_reflns_theta_full        28.79
_diffrn_reflns_theta_max         28.79
_diffrn_reflns_theta_min         1.74
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0401
_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)+(0.0388P)²+1.8014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                2197
_reflns_number_total             2933
_reflns_threshold_expression     I>2σ
_cod_data_source_file            om200490k_si_002.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4065002
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.50468(5) 0.6871(2) 0.88672(11) 0.0277(3) Uani 1 1 d .
H1A H 0.5263 0.6079 0.8620 0.041 Uiso 1 1 calc R
H1B H 0.5285 0.7129 0.9648 0.041 Uiso 1 1 calc R
H1C H 0.4936 0.8124 0.8471 0.041 Uiso 1 1 calc R
C2 C 0.42241(6) 0.8259(2) 0.95836(11) 0.0272(3) Uani 1 1 d .
H2A H 0.4486 0.8072 1.0364 0.041 Uiso 1 1 calc R
H2B H 0.3849 0.8672 0.9461 0.041 Uiso 1 1 calc R
H2C H 0.4377 0.9275 0.9308 0.041 Uiso 1 1 calc R
C3 C 0.45232(5) 0.5776(2) 0.86587(10) 0.0223(3) Uani 1 1 d .
C4 C 0.38413(5) 0.3666(2) 0.80990(11) 0.0249(3) Uani 1 1 d .
H4 H 0.3610 0.2544 0.7754 0.030 Uiso 1 1 calc R
C5 C 0.37226(5) 0.50472(19) 0.86542(10) 0.0204(3) Uani 1 1 d .
C6 C 0.32499(5) 0.50615(18) 0.88835(10) 0.0199(3) Uani 1 1 d .
C7 C 0.33248(5) 0.55007(19) 0.99097(10) 0.0216(3) Uani 1 1 d .
H7 H 0.3688 0.5923 1.0477 0.026 Uiso 1 1 calc R
C8 C 0.28732(5) 0.53235(19) 1.01024(10) 0.0213(3) Uani 1 1 d .
H8 H 0.2930 0.5624 1.0802 0.026 Uiso 1 1 calc R
C9 C 0.23342(5) 0.47075(18) 0.92809(10) 0.0197(3) Uani 1 1 d .
C10 C 0.22596(5) 0.4286(2) 0.82593(10) 0.0225(3) Uani 1 1 d .
H10 H 0.1896 0.3866 0.7692 0.027 Uiso 1 1 calc R
C11 C 0.27094(5) 0.4472(2) 0.80599(10) 0.0224(3) Uani 1 1 d .
H11 H 0.2649 0.4194 0.7355 0.027 Uiso 1 1 calc R
C12 C 0.18614(5) 0.45042(18) 0.95305(10) 0.0218(3) Uani 1 1 d .
C13 C 0.12730(5) 0.3933(2) 0.86308(11) 0.0291(3) Uani 1 1 d .
H13A H 0.1025 0.3679 0.8936 0.044 Uiso 1 1 calc R
H13B H 0.1300 0.2740 0.8270 0.044 Uiso 1 1 calc R
H13C H 0.1112 0.5009 0.8101 0.044 Uiso 1 1 calc R
H3B H 0.4795(8) 0.241(3) 0.7682(15) 0.061(6) Uiso 1 1 d .
N1 N 0.41653(4) 0.64061(16) 0.90126(8) 0.0203(2) Uani 1 1 d .
N2 N 0.43400(5) 0.41116(18) 0.81027(9) 0.0264(3) Uani 1 1 d .
O1 O 0.19467(4) 0.48203(15) 1.04423(8) 0.0286(2) Uani 1 1 d .
O3 O 0.5000 0.1606(2) 0.7500 0.0343(3) Uani 1 2 d S
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C1 H1A 109.5
C3 C1 H1B 109.5
H1A C1 H1B 109.5
C3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N2 C3 N1 111.47(11)
N2 C3 C1 125.24(12)
N1 C3 C1 123.28(12)
C5 C4 N2 111.17(12)
C5 C4 H4 124.4
N2 C4 H4 124.4
C4 C5 N1 105.01(11)
C4 C5 C6 128.10(12)
N1 C5 C6 126.81(11)
C11 C6 C7 118.59(11)
C11 C6 C5 118.16(11)
C7 C6 C5 123.08(11)
C8 C7 C6 120.48(11)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C9 120.87(11)
C7 C8 H8 119.6
C9 C8 H8 119.6
C10 C9 C8 118.56(11)
C10 C9 C12 122.39(11)
C8 C9 C12 119.05(11)
C11 C10 C9 120.83(11)
C11 C10 H10 119.6
C9 C10 H10 119.6
C10 C11 C6 120.66(11)
C10 C11 H11 119.7
C6 C11 H11 119.7
O1 C12 C9 120.65(11)
O1 C12 C13 120.31(11)
C9 C12 C13 119.03(11)
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
C3 N1 C5 107.23(10)
C3 N1 C2 125.13(11)
C5 N1 C2 127.46(10)
C3 N2 C4 105.12(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C3 1.4899(18)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 N1 1.4609(17)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 N2 1.3236(18)
C3 N1 1.3638(16)
C4 C5 1.3630(18)
C4 N2 1.3786(16)
C4 H4 0.9500
C5 N1 1.3887(16)
C5 C6 1.4685(16)
C6 C11 1.3958(17)
C6 C7 1.4014(17)
C7 C8 1.3834(17)
C7 H7 0.9500
C8 C9 1.3975(17)
C8 H8 0.9500
C9 C10 1.3929(17)
C9 C12 1.4940(17)
C10 C11 1.3854(17)
C10 H10 0.9500
C11 H11 0.9500
C12 O1 1.2171(15)
C12 C13 1.5079(18)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
O3 H3B 0.903(19)
