#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:19:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179917 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/12/7021285.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_7021285
loop_
_publ_author_name
'Huynh, Han Vinh'
'Lee, Chen-Shiang'
_publ_section_title
;
 Pincer-type di(1,2,4-triazolin-5-ylidene)Pd(ii) complexes and their
 catalytic activities towards Cu- and amine-free Sonogashira reaction.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6803
_journal_page_last               6809
_journal_paper_doi               10.1039/c3dt50237f
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C13 H15 Br2 N7 Pd'
_chemical_formula_weight         535.54
_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                 101.113(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1277(10)
_cell_length_b                   12.8390(17)
_cell_length_c                   15.837(2)
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.62
_cell_volume                     1621.6(4)
_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      100(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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11182
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    6.082
_exptl_absorpt_correction_T_max  0.2181
_exptl_absorpt_correction_T_min  0.1750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, Sheldrick 2008)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    2.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_refine_diff_density_max         1.239
_refine_diff_density_min         -1.375
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0343
_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)+(0.0371P)²+6.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                3241
_reflns_number_total             3720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt50237f.txt
_cod_data_source_block           c264
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_cell_volume        1621.7(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7021285
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 0.38457(4) 0.32618(2) 0.201572(17) 0.00997(9) Uani 1 1 d .
Br1 Br 0.41410(6) 0.17855(3) 0.29850(3) 0.01881(11) Uani 1 1 d .
Br2 Br 0.62286(7) 0.83036(4) 0.27182(3) 0.02953(14) Uani 1 1 d .
N1 N 0.3524(4) 0.4500(3) 0.3690(2) 0.0146(7) Uani 1 1 d .
N2 N 0.4881(4) 0.5247(3) 0.2856(2) 0.0134(7) Uani 1 1 d .
N3 N 0.3943(4) 0.5468(3) 0.4044(2) 0.0187(7) Uani 1 1 d .
N4 N 0.3482(4) 0.4495(2) 0.1144(2) 0.0109(6) Uani 1 1 d .
N5 N 0.4466(4) 0.1504(3) 0.0753(2) 0.0121(6) Uani 1 1 d .
N6 N 0.2462(4) 0.2524(2) 0.02763(19) 0.0103(6) Uani 1 1 d .
N7 N 0.3877(4) 0.1202(3) -0.0091(2) 0.0144(7) Uani 1 1 d .
C1 C 0.4069(5) 0.4345(3) 0.2958(2) 0.0139(8) Uani 1 1 d .
C2 C 0.4751(5) 0.5901(3) 0.3514(3) 0.0180(8) Uani 1 1 d .
H2 H 0.5196 0.6587 0.3575 0.022 Uiso 1 1 calc R
C3 C 0.2539(6) 0.3801(4) 0.4110(3) 0.0209(9) Uani 1 1 d .
H3A H 0.1903 0.3327 0.3684 0.031 Uiso 1 1 calc R
H3B H 0.1760 0.4207 0.4381 0.031 Uiso 1 1 calc R
H3C H 0.3286 0.3398 0.4550 0.031 Uiso 1 1 calc R
C4 C 0.5671(5) 0.5459(3) 0.2114(2) 0.0150(8) Uani 1 1 d .
H4A H 0.6590 0.4954 0.2108 0.018 Uiso 1 1 calc R
H4B H 0.6160 0.6167 0.2166 0.018 Uiso 1 1 calc R
C5 C 0.4404(5) 0.5374(3) 0.1288(2) 0.0127(7) Uani 1 1 d .
C6 C 0.4246(5) 0.6171(3) 0.0688(3) 0.0165(8) Uani 1 1 d .
H6 H 0.4896 0.6787 0.0809 0.020 Uiso 1 1 calc R
C7 C 0.3135(5) 0.6066(3) -0.0090(3) 0.0181(8) Uani 1 1 d .
H7 H 0.3036 0.6597 -0.0514 0.022 Uiso 1 1 calc R
C8 C 0.2168(5) 0.5168(3) -0.0236(2) 0.0144(8) Uani 1 1 d .
H8 H 0.1389 0.5080 -0.0762 0.017 Uiso 1 1 calc R
C9 C 0.2347(5) 0.4402(3) 0.0389(2) 0.0128(8) Uani 1 1 d .
C10 C 0.1333(5) 0.3413(3) 0.0253(2) 0.0118(7) Uani 1 1 d .
H10A H 0.0663 0.3340 0.0710 0.014 Uiso 1 1 calc R
H10B H 0.0552 0.3439 -0.0309 0.014 Uiso 1 1 calc R
C11 C 0.3636(5) 0.2306(3) 0.0989(2) 0.0104(7) Uani 1 1 d .
C12 C 0.2661(5) 0.1843(3) -0.0357(2) 0.0135(8) Uani 1 1 d .
H12 H 0.1995 0.1841 -0.0920 0.016 Uiso 1 1 calc R
C13 C 0.5864(5) 0.0941(3) 0.1274(3) 0.0169(8) Uani 1 1 d .
H13A H 0.6532 0.1422 0.1683 0.025 Uiso 1 1 calc R
H13B H 0.6568 0.0643 0.0898 0.025 Uiso 1 1 calc R
H13C H 0.5429 0.0381 0.1589 0.025 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'
Br Br -0.2901 2.4595 '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
C11 Pd1 C1 173.95(15)
C11 Pd1 N4 87.05(13)
C1 Pd1 N4 87.02(14)
C11 Pd1 Br1 91.01(10)
C1 Pd1 Br1 94.97(11)
N4 Pd1 Br1 177.01(9)
C1 N1 N3 113.1(3)
C1 N1 C3 127.8(4)
N3 N1 C3 119.1(3)
C1 N2 C2 109.0(3)
C1 N2 C4 123.4(3)
C2 N2 C4 127.6(3)
C2 N3 N1 103.9(3)
C5 N4 C9 118.7(3)
C5 N4 Pd1 121.3(3)
C9 N4 Pd1 119.9(3)
C11 N5 N7 113.0(3)
C11 N5 C13 127.5(3)
N7 N5 C13 119.5(3)
C11 N6 C12 108.4(3)
C11 N6 C10 121.2(3)
C12 N6 C10 130.2(3)
C12 N7 N5 103.7(3)
N1 C1 N2 103.1(3)
N1 C1 Pd1 138.3(3)
N2 C1 Pd1 118.4(3)
N3 C2 N2 111.0(4)
N2 C4 C5 110.5(3)
N4 C5 C6 121.7(4)
N4 C5 C4 118.2(3)
C6 C5 C4 120.1(4)
C5 C6 C7 119.8(4)
C6 C7 C8 118.6(4)
C9 C8 C7 119.5(4)
N4 C9 C8 121.7(4)
N4 C9 C10 117.2(3)
C8 C9 C10 121.1(4)
N6 C10 C9 109.3(3)
N5 C11 N6 103.8(3)
N5 C11 Pd1 137.1(3)
N6 C11 Pd1 118.8(3)
N7 C12 N6 111.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C11 2.017(4)
Pd1 C1 2.022(4)
Pd1 N4 2.084(3)
Pd1 Br1 2.4217(5)
N1 C1 1.334(5)
N1 N3 1.379(5)
N1 C3 1.447(5)
N2 C1 1.358(5)
N2 C2 1.358(5)
N2 C4 1.468(5)
N3 C2 1.288(6)
N4 C5 1.351(5)
N4 C9 1.366(5)
N5 C11 1.324(5)
N5 N7 1.386(4)
N5 C13 1.460(5)
N6 C11 1.359(5)
N6 C12 1.363(5)
N6 C10 1.462(5)
N7 C12 1.293(5)
C4 C5 1.505(5)
C5 C6 1.385(5)
C6 C7 1.387(6)
C7 C8 1.390(6)
C8 C9 1.383(5)
C9 C10 1.507(5)
