#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:51:05 +0100 (lun 21 de mar de 2016) $
#$Revision: 178726 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/37/4083780.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_4083780
loop_
_publ_author_name
'Bernhammer, Jan C.'
'Chong, Ning Xi'
'Jothibasu, Ramasamy'
'Zhou, Binbin'
'Huynh, Han Vinh'
_publ_section_title
;
 Palladium(II) Complexes Bearing an Indazole-Derived N-Heterocyclic
 Carbene and Phosphine Coligands as Catalysts for the Sonogashira
 Coupling and the Hydroamination of Alkynes
;
_journal_name_full               Organometallics
_journal_page_first              140627160434001
_journal_paper_doi               10.1021/om500566n
_journal_year                    2014
_chemical_formula_sum            'C12 H13 Br2 N3 Pd'
_chemical_formula_weight         465.47
_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                 90.10(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4099(17)
_cell_length_b                   12.173(3)
_cell_length_c                   12.280(2)
_cell_measurement_reflns_used    4429
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.36
_cell_volume                     1406.6(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9583
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    6.985
_exptl_absorpt_correction_T_max  0.5418
_exptl_absorpt_correction_T_min  0.2284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    2.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0243
_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)+(0.0271P)²+0.9366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0585
_reflns_number_gt                2901
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500566n_si_002.cif
_cod_data_source_block           9418
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/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
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z 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)/n
_cod_database_code               4083780
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 0.55664(2) 0.348908(16) 0.747943(16) 0.01243(7) Uani 1 1 d .
Br1 Br 0.42938(3) 0.26200(2) 0.59825(2) 0.01986(8) Uani 1 1 d .
Br2 Br 0.69923(3) 0.43481(2) 0.89051(2) 0.02043(8) Uani 1 1 d .
N1 N 0.8329(2) 0.25265(18) 0.70419(19) 0.0158(5) Uani 1 1 d .
N2 N 0.9491(3) 0.24993(19) 0.6362(2) 0.0190(5) Uani 1 1 d .
N3 N 0.3640(3) 0.38236(19) 0.82654(19) 0.0170(5) Uani 1 1 d .
C1 C 0.7331(3) 0.3211(2) 0.6705(2) 0.0136(5) Uani 1 1 d .
C2 C 0.7869(3) 0.3667(2) 0.5709(2) 0.0149(5) Uani 1 1 d .
C3 C 0.7342(3) 0.4450(2) 0.4975(2) 0.0188(6) Uani 1 1 d .
H3 H 0.6458 0.4805 0.5099 0.023 Uiso 1 1 calc R
C4 C 0.8145(3) 0.4691(2) 0.4068(2) 0.0204(6) Uani 1 1 d .
H4 H 0.7804 0.5216 0.3558 0.025 Uiso 1 1 calc R
C5 C 0.9464(3) 0.4173(2) 0.3881(2) 0.0207(6) Uani 1 1 d .
H5 H 0.9979 0.4354 0.3241 0.025 Uiso 1 1 calc R
C6 C 1.0031(3) 0.3416(2) 0.4588(2) 0.0199(6) Uani 1 1 d .
H6 H 1.0924 0.3076 0.4461 0.024 Uiso 1 1 calc R
C7 C 0.9206(3) 0.3177(2) 0.5513(2) 0.0166(6) Uani 1 1 d .
C8 C 1.0485(3) 0.1627(2) 0.6656(2) 0.0204(6) Uani 1 1 d .
H8A H 1.1484 0.1874 0.6592 0.024 Uiso 1 1 calc R
H8B H 1.0341 0.0963 0.6203 0.024 Uiso 1 1 calc R
C9 C 1.0064(3) 0.1421(2) 0.7857(2) 0.0190(6) Uani 1 1 d .
H9A H 1.0196 0.0637 0.8050 0.023 Uiso 1 1 calc R
H9B H 1.0652 0.1875 0.8353 0.023 Uiso 1 1 calc R
C10 C 0.8501(3) 0.1743(2) 0.7941(2) 0.0177(6) Uani 1 1 d .
H10A H 0.7874 0.1097 0.7845 0.021 Uiso 1 1 calc R
H10B H 0.8293 0.2092 0.8651 0.021 Uiso 1 1 calc R
C12 C 0.2551(3) 0.4030(2) 0.8605(2) 0.0153(5) Uani 1 1 d .
C13 C 0.1126(3) 0.4304(3) 0.8990(3) 0.0232(6) Uani 1 1 d .
H13A H 0.1061 0.5097 0.9116 0.035 Uiso 1 1 calc R
H13B H 0.0938 0.3912 0.9672 0.035 Uiso 1 1 calc R
H13C H 0.0424 0.4086 0.8441 0.035 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pd1 0.00938(11) 0.01426(11) 0.01365(11) 0.00003(7) 0.00327(8) 0.00146(7)
Br1 0.01497(15) 0.02402(16) 0.02059(15) -0.00491(11) 0.00169(11) -0.00205(11)
Br2 0.01855(15) 0.02346(16) 0.01929(15) -0.00414(11) -0.00061(11) 0.00155(11)
N1 0.0123(11) 0.0179(11) 0.0172(11) 0.0008(9) 0.0054(9) 0.0017(9)
N2 0.0131(12) 0.0192(12) 0.0246(13) 0.0006(10) 0.0080(10) 0.0050(10)
N3 0.0159(12) 0.0183(12) 0.0169(11) 0.0014(9) 0.0017(9) 0.0006(10)
C1 0.0110(12) 0.0145(13) 0.0154(12) -0.0027(10) 0.0039(10) 0.0010(10)
C2 0.0129(13) 0.0155(13) 0.0162(13) -0.0027(10) 0.0022(10) -0.0032(10)
C3 0.0159(14) 0.0196(14) 0.0209(14) -0.0008(11) -0.0008(11) -0.0009(11)
C4 0.0227(15) 0.0230(15) 0.0156(13) 0.0019(11) -0.0022(12) -0.0052(12)
C5 0.0208(14) 0.0231(15) 0.0182(13) -0.0023(11) 0.0064(11) -0.0076(12)
C6 0.0175(14) 0.0196(14) 0.0227(14) -0.0073(11) 0.0079(12) -0.0049(12)
C7 0.0150(13) 0.0145(13) 0.0203(14) -0.0025(11) 0.0039(11) -0.0035(11)
C8 0.0153(14) 0.0166(14) 0.0293(15) 0.0018(12) 0.0040(12) 0.0060(11)
C9 0.0155(14) 0.0177(14) 0.0239(15) 0.0024(11) 0.0023(12) 0.0034(11)
C10 0.0160(14) 0.0183(13) 0.0189(13) 0.0034(11) 0.0039(11) 0.0032(11)
C12 0.0163(14) 0.0141(13) 0.0154(12) 0.0013(10) 0.0033(11) 0.0009(11)
C13 0.0146(14) 0.0254(15) 0.0296(16) -0.0036(12) 0.0091(12) 0.0015(12)
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
C1 Pd1 N3 177.89(10)
C1 Pd1 Br1 88.54(8)
N3 Pd1 Br1 90.43(7)
C1 Pd1 Br2 87.50(8)
N3 Pd1 Br2 93.52(7)
Br1 Pd1 Br2 176.020(12)
C1 N1 N2 112.9(2)
C1 N1 C10 136.3(2)
N2 N1 C10 110.7(2)
C7 N2 N1 107.2(2)
C7 N2 C8 139.3(2)
N1 N2 C8 112.1(2)
C12 N3 Pd1 174.0(2)
N1 C1 C2 105.0(2)
N1 C1 Pd1 124.3(2)
C2 C1 Pd1 130.7(2)
C3 C2 C7 119.4(3)
C3 C2 C1 133.3(3)
C7 C2 C1 107.3(2)
C4 C3 C2 118.1(3)
C3 C4 C5 121.3(3)
C6 C5 C4 122.5(3)
C5 C6 C7 115.8(3)
N2 C7 C6 129.7(3)
N2 C7 C2 107.5(2)
C6 C7 C2 122.8(3)
N2 C8 C9 100.9(2)
C10 C9 C8 105.7(2)
N1 C10 C9 102.8(2)
N3 C12 C13 177.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 1.945(3)
Pd1 N3 2.095(2)
Pd1 Br1 2.4341(6)
Pd1 Br2 2.4395(6)
N1 C1 1.322(3)
N1 N2 1.377(3)
N1 C10 1.468(3)
N2 C7 1.356(4)
N2 C8 1.460(4)
N3 C12 1.135(3)
C1 C2 1.436(4)
C2 C3 1.402(4)
C2 C7 1.414(4)
C3 C4 1.378(4)
C4 C5 1.412(4)
C5 C6 1.373(4)
C6 C7 1.407(4)
C8 C9 1.549(4)
C9 C10 1.526(4)
C12 C13 1.461(4)
