#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:15:23 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179960 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/54/7025431.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_7025431
loop_
_publ_author_name
'Li, Fuwei'
'Hu, Jian Jin'
'Koh, Lip Lin'
'Hor, T. S. Andy'
_publ_section_title
;
 Substituent-dependent structures and catalysis of benzimidazole-tethered
 N-heterocyclic carbene complexes of Ag(I), Ni(II) and Pd(II).
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5231
_journal_page_last               5241
_journal_paper_doi               10.1039/c000722f
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C22 H29 Cl N4 O2'
_chemical_formula_weight         416.94
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8680(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2268(7)
_cell_length_b                   9.7074(5)
_cell_length_c                   16.0600(8)
_cell_measurement_reflns_used    3289
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.46
_cell_volume                     2202.05(19)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15263
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.9108
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0492
_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)+(0.0621P)²+0.4346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                3965
_reflns_number_total             5046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000722f.txt
_cod_data_source_block           1b
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7025431
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
N1 N 0.73417(10) 0.60438(14) 0.05483(9) 0.0421(3) Uani 1 1 d .
N2 N 0.83221(10) 0.42780(13) 0.09108(9) 0.0374(3) Uani 1 1 d .
N3 N 0.82280(10) 0.75742(13) 0.19616(9) 0.0378(3) Uani 1 1 d .
N4 N 0.74211(10) 0.93465(14) 0.22547(8) 0.0364(3) Uani 1 1 d .
C1 C 0.81375(12) 0.56546(16) 0.09828(11) 0.0379(4) Uani 1 1 d .
C2 C 0.69697(13) 0.48499(17) 0.01617(11) 0.0398(4) Uani 1 1 d .
C3 C 0.61260(14) 0.4642(2) -0.03582(13) 0.0490(5) Uani 1 1 d .
H3 H 0.5708 0.5375 -0.0509 0.059 Uiso 1 1 calc R
C4 C 0.59250(15) 0.3322(2) -0.06439(13) 0.0551(5) Uani 1 1 d .
H4 H 0.5359 0.3154 -0.0995 0.066 Uiso 1 1 calc R
C5 C 0.65429(15) 0.2232(2) -0.04233(12) 0.0509(5) Uani 1 1 d .
H5 H 0.6383 0.1347 -0.0632 0.061 Uiso 1 1 calc R
C6 C 0.73754(14) 0.24114(18) 0.00869(11) 0.0452(4) Uani 1 1 d .
H6 H 0.7791 0.1675 0.0233 0.054 Uiso 1 1 calc R
C7 C 0.75741(12) 0.37461(17) 0.03789(10) 0.0374(4) Uani 1 1 d .
C8 C 0.91455(13) 0.34879(18) 0.12776(11) 0.0446(4) Uani 1 1 d .
H8A H 0.8945 0.2549 0.1394 0.054 Uiso 1 1 calc R
H8B H 0.9399 0.3909 0.1812 0.054 Uiso 1 1 calc R
C9 C 0.99126(14) 0.3425(2) 0.07138(14) 0.0592(5) Uani 1 1 d .
H9A H 0.9656 0.3059 0.0172 0.089 Uiso 1 1 calc R
H9B H 1.0419 0.2833 0.0963 0.089 Uiso 1 1 calc R
H9C H 1.0159 0.4344 0.0642 0.089 Uiso 1 1 calc R
C10 C 0.87826(13) 0.66177(17) 0.15046(12) 0.0431(4) Uani 1 1 d .
H10A H 0.9215 0.6089 0.1905 0.052 Uiso 1 1 calc R
H10B H 0.9162 0.7140 0.1143 0.052 Uiso 1 1 calc R
C11 C 0.79193(12) 0.87996(17) 0.16924(10) 0.0365(4) Uani 1 1 d .
H11 H 0.8035 0.9214 0.1185 0.044 Uiso 1 1 calc R
C12 C 0.79077(14) 0.73184(18) 0.27199(11) 0.0451(4) Uani 1 1 d .
H12 H 0.8019 0.6519 0.3047 0.054 Uiso 1 1 calc R
C13 C 0.74050(14) 0.84237(18) 0.29061(11) 0.0458(4) Uani 1 1 d .
H13 H 0.7100 0.8546 0.3389 0.055 Uiso 1 1 calc R
C14 C 0.70312(11) 1.07337(16) 0.22151(10) 0.0356(4) Uani 1 1 d .
C15 C 0.75531(12) 1.17560(17) 0.26694(10) 0.0374(4) Uani 1 1 d .
C16 C 0.71762(12) 1.30760(18) 0.26298(11) 0.0410(4) Uani 1 1 d .
H16 H 0.7518 1.3791 0.2921 0.049 Uiso 1 1 calc R
C17 C 0.63069(12) 1.33721(18) 0.21712(11) 0.0413(4) Uani 1 1 d .
C18 C 0.58189(13) 1.23168(19) 0.17343(11) 0.0448(4) Uani 1 1 d .
H18 H 0.5231 1.2511 0.1424 0.054 Uiso 1 1 calc R
C19 C 0.61669(12) 1.09763(18) 0.17363(10) 0.0399(4) Uani 1 1 d .
C20 C 0.84807(13) 1.14506(19) 0.31933(12) 0.0471(4) Uani 1 1 d .
H20A H 0.8798 1.2309 0.3360 0.071 Uiso 1 1 calc R
H20B H 0.8878 1.0908 0.2868 0.071 Uiso 1 1 calc R
H20C H 0.8363 1.0938 0.3689 0.071 Uiso 1 1 calc R
C21 C 0.59210(15) 1.48222(19) 0.21494(14) 0.0548(5) Uani 1 1 d .
H21A H 0.6152 1.5327 0.1693 0.082 Uiso 1 1 calc R
H21B H 0.6129 1.5278 0.2677 0.082 Uiso 1 1 calc R
H21C H 0.5235 1.4793 0.2064 0.082 Uiso 1 1 calc R
C22 C 0.56378(15) 0.9853(2) 0.12312(14) 0.0542(5) Uani 1 1 d .
H22A H 0.5974 0.9612 0.0761 0.081 Uiso 1 1 calc R
H22B H 0.5007 1.0174 0.1025 0.081 Uiso 1 1 calc R
H22C H 0.5592 0.9049 0.1583 0.081 Uiso 1 1 calc R
O1W O 0.68898(12) 0.85114(17) -0.04867(10) 0.0647(4) Uani 1 1 d D
H1W H 0.6954(18) 0.781(2) -0.0161(14) 0.080 Uiso 1 1 d D
H2W H 0.7465(13) 0.883(3) -0.0379(16) 0.080 Uiso 1 1 d D
O2W O 0.87669(11) 0.95761(19) -0.00363(10) 0.0656(4) Uani 1 1 d D
H3W H 0.9004(18) 0.974(3) -0.0494(13) 0.080 Uiso 1 1 d D
H4W H 0.9235(15) 0.967(3) 0.0345(14) 0.080 Uiso 1 1 d D
Cl1 Cl 1.01740(4) 0.98717(5) 0.16028(3) 0.05048(15) 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C2 104.82(14)
C1 N2 C7 105.98(13)
C1 N2 C8 129.03(14)
C7 N2 C8 124.95(14)
C11 N3 C12 108.66(14)
C11 N3 C10 125.59(15)
C12 N3 C10 125.69(14)
C11 N4 C13 108.40(14)
C11 N4 C14 125.01(13)
C13 N4 C14 126.39(14)
N1 C1 N2 113.46(15)
N1 C1 C10 123.42(14)
N2 C1 C10 123.12(15)
N1 C2 C7 109.84(15)
N1 C2 C3 130.08(16)
C7 C2 C3 120.07(16)
C4 C3 C2 117.62(18)
C3 C4 C5 121.41(18)
C6 C5 C4 122.01(17)
C5 C6 C7 116.45(18)
N2 C7 C2 105.91(14)
N2 C7 C6 131.65(16)
C2 C7 C6 122.43(16)
N2 C8 C9 112.53(14)
N3 C10 C1 110.16(14)
N3 C11 N4 108.77(14)
C13 C12 N3 107.17(15)
C12 C13 N4 106.99(16)
C19 C14 C15 123.37(15)
C19 C14 N4 119.23(15)
C15 C14 N4 117.40(14)
C16 C15 C14 117.08(16)
C16 C15 C20 120.99(16)
C14 C15 C20 121.92(15)
C15 C16 C17 121.94(16)
C18 C17 C16 118.47(16)
C18 C17 C21 121.36(17)
C16 C17 C21 120.17(17)
C17 C18 C19 122.35(16)
C14 C19 C18 116.77(16)
C14 C19 C22 121.82(16)
C18 C19 C22 121.40(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.312(2)
N1 C2 1.389(2)
N2 C1 1.369(2)
N2 C7 1.383(2)
N2 C8 1.464(2)
N3 C11 1.323(2)
N3 C12 1.373(2)
N3 C10 1.470(2)
N4 C11 1.324(2)
N4 C13 1.380(2)
N4 C14 1.455(2)
C1 C10 1.495(2)
C2 C7 1.392(2)
C2 C3 1.393(3)
C3 C4 1.379(3)
C4 C5 1.394(3)
C5 C6 1.368(3)
C6 C7 1.395(2)
C8 C9 1.500(3)
C12 C13 1.343(3)
C14 C19 1.390(2)
C14 C15 1.392(2)
C15 C16 1.388(2)
C15 C20 1.507(2)
C16 C17 1.392(2)
C17 C18 1.381(2)
C17 C21 1.510(2)
C18 C19 1.392(2)
C19 C22 1.506(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H2W O2W 0.874(16) 2.002(17) 2.874(2) 175(2) .
O1W H1W N1 0.856(16) 2.097(17) 2.943(2) 170(2) .
O2W H3W Cl1 0.859(17) 2.276(17) 3.1295(16) 172(2) 3_775
O2W H4W Cl1 0.855(17) 2.292(18) 3.1239(17) 164(2) .
