#------------------------------------------------------------------------------
#$Date: 2015-10-09 12:21:01 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161461 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/61/7036187.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_7036187
loop_
_publ_author_name
'Chapman, Michael R.'
'Lake, Benjamin R. M.'
'Pask, Christopher M.'
'Nguyen, Bao N.'
'Willans, Charlotte E.'
_publ_section_title
;
 Solid-state structure, solution-state behaviour and catalytic activity of
 electronically divergent C,N-chelating palladium-N-heterocyclic carbene
 complexes.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15938
_journal_page_last               15948
_journal_paper_doi               10.1039/c5dt02194d
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C12 H13 Br2 N3 O Pd'
_chemical_formula_sum            'C12 H13 Br2 N3 O Pd'
_chemical_formula_weight         481.47
_chemical_name_systematic        4d
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_audit_update_record
;
2015-06-09 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.376(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5090(8)
_cell_length_b                   7.9393(3)
_cell_length_c                   13.9341(9)
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    120.01(11)
_cell_measurement_theta_max      26.6150
_cell_measurement_theta_min      3.6600
_cell_volume                     1418.25(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0350740000
_diffrn_orient_matrix_UB_12      0.0077306000
_diffrn_orient_matrix_UB_13      -0.0283626000
_diffrn_orient_matrix_UB_21      -0.0145629000
_diffrn_orient_matrix_UB_22      0.0856391000
_diffrn_orient_matrix_UB_23      -0.0100380000
_diffrn_orient_matrix_UB_31      0.0401992000
_diffrn_orient_matrix_UB_32      0.0244159000
_diffrn_orient_matrix_UB_33      0.0444159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8045
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.937
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.451
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+8.5887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2195
_reflns_number_total             2885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt02194d2.cif
_cod_data_source_block           mrc99_mo
_cod_depositor_comments
'Adding full bibliography for 7036182--7036191.cif.'
_cod_database_code               7036187
_chemical_oxdiff_formula         'C48 H52 Br8 N12 O4 Pd4'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_refinement_flags_posn
Pd1 Pd 0.00146(5) 0.07337(7) 0.31932(4) 0.01615(19) Uani 1 d .
Br2 Br 0.02868(8) -0.04365(13) 0.16944(7) 0.0349(3) Uani 1 d .
Br3 Br -0.18015(7) -0.02997(11) 0.25715(7) 0.0287(3) Uani 1 d .
C4 C 0.1469(6) 0.1519(10) 0.3893(6) 0.0163(16) Uani 1 d .
N5 N 0.2437(5) 0.1510(8) 0.3838(5) 0.0184(15) Uani 1 d .
C6 C 0.3108(7) 0.2368(11) 0.4640(6) 0.027(2) Uani 1 d .
H6 H 0.3816 0.2535 0.4750 0.033 Uiso 1 calc R
C7 C 0.2565(6) 0.2927(10) 0.5241(6) 0.0213(18) Uani 1 d .
H7 H 0.2818 0.3534 0.5839 0.026 Uiso 1 calc R
N8 N 0.1534(5) 0.2392(8) 0.4767(5) 0.0184(15) Uani 1 d .
C9 C 0.2826(6) 0.0643(11) 0.3099(6) 0.0238(19) Uani 1 d .
H9A H 0.3298 0.1385 0.2900 0.029 Uiso 1 calc R
H9B H 0.2244 0.0390 0.2500 0.029 Uiso 1 calc R
C10 C 0.3393(6) -0.0979(11) 0.3516(7) 0.0235(19) Uani 1 d .
H10 H 0.3633 -0.1613 0.3073 0.028 Uiso 1 calc R
C11 C 0.3583(7) -0.1589(12) 0.4438(7) 0.034(2) Uani 1 d .
H11A H 0.3360 -0.1005 0.4911 0.041 Uiso 1 calc R
H11B H 0.3939 -0.2602 0.4615 0.041 Uiso 1 calc R
C12 C 0.0650(6) 0.2647(9) 0.5065(6) 0.0149(16) Uani 1 d .
N13 N -0.0217(5) 0.1959(8) 0.4405(5) 0.0191(15) Uani 1 d .
C14 C -0.1126(6) 0.2237(10) 0.4603(6) 0.0223(19) Uani 1 d .
H14 H -0.1741 0.1827 0.4149 0.027 Uiso 1 calc R
C15 C -0.1180(6) 0.3095(11) 0.5440(6) 0.0241(19) Uani 1 d .
H15 H -0.1819 0.3250 0.5548 0.029 Uiso 1 calc R
C16 C -0.0264(6) 0.3735(10) 0.6131(6) 0.0182(17) Uani 1 d .
C17 C 0.0676(6) 0.3520(10) 0.5932(6) 0.0164(16) Uani 1 d .
H17 H 0.1298 0.3947 0.6365 0.020 Uiso 1 calc R
O18 O -0.0364(4) 0.4537(7) 0.6937(4) 0.0243(13) Uani 1 d .
C19 C 0.0580(6) 0.4955(12) 0.7727(6) 0.0248(19) Uani 1 d .
H19A H 0.0913 0.5890 0.7517 0.037 Uiso 1 calc GR
H19B H 0.1040 0.4002 0.7864 0.037 Uiso 1 calc GR
H19C H 0.0417 0.5254 0.8327 0.037 Uiso 1 calc GR
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'
Br Br -0.2901 2.4595 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
15 -2 7 0.0426 14.9910 -2.0013 7.0042 0.3117 -0.4600 0.8649
-15 2 -7 0.0426 -14.9910 2.0013 -7.0042 -0.3117 0.4600 -0.8649
6 11 -3 0.0594 5.9878 11.0069 -2.9997 0.3802 0.8855 0.3762
-6 -11 3 0.0594 -5.9878 -11.0069 2.9997 -0.3802 -0.8855 -0.3762
17 -1 -13 0.0214 16.9771 -0.9987 -12.9941 0.9563 -0.2023 0.0809
-17 1 13 0.0214 -16.9771 0.9987 12.9941 -0.9563 0.2023 -0.0809
0 7 14 0.0506 0.0050 7.0027 13.9981 -0.3427 0.4591 0.7929
-2 -2 -18 0.0459 -2.0077 -1.9995 -17.9992 0.4246 0.0387 -0.9290
2 3 17 0.0311 2.0067 3.0002 16.9991 -0.3886 0.0571 0.9089
2 -11 -1 0.0477 2.0025 -11.0062 -0.9977 0.0134 -0.9617 -0.2325
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
Br2 Pd1 Br3 88.52(4)
C4 Pd1 Br2 98.5(2)
C4 Pd1 Br3 171.9(2)
C4 Pd1 N13 80.3(3)
N13 Pd1 Br2 174.36(18)
N13 Pd1 Br3 93.08(18)
N5 C4 Pd1 143.3(6)
N5 C4 N8 105.3(6)
N8 C4 Pd1 111.5(5)
C4 N5 C6 110.9(7)
C4 N5 C9 128.1(6)
C6 N5 C9 120.8(7)
N5 C6 H6 125.7
C7 C6 N5 108.6(7)
C7 C6 H6 125.7
C6 C7 H7 127.4
C6 C7 N8 105.2(7)
N8 C7 H7 127.4
C4 N8 C7 110.1(7)
C4 N8 C12 120.9(6)
C12 N8 C7 129.1(7)
N5 C9 H9A 109.2
N5 C9 H9B 109.2
N5 C9 C10 112.3(7)
H9A C9 H9B 107.9
C10 C9 H9A 109.2
C10 C9 H9B 109.2
C9 C10 H10 116.4
C11 C10 C9 127.1(8)
C11 C10 H10 116.4
C10 C11 H11A 120.0
C10 C11 H11B 120.0
H11A C11 H11B 120.0
N13 C12 N8 112.2(6)
N13 C12 C17 125.0(7)
C17 C12 N8 122.9(7)
C12 N13 Pd1 115.2(5)
C12 N13 C14 116.1(7)
C14 N13 Pd1 128.6(5)
N13 C14 H14 118.4
N13 C14 C15 123.1(8)
C15 C14 H14 118.4
C14 C15 H15 120.3
C14 C15 C16 119.4(8)
C16 C15 H15 120.3
C17 C16 C15 118.8(7)
O18 C16 C15 116.7(7)
O18 C16 C17 124.5(7)
C12 C17 C16 117.5(7)
C12 C17 H17 121.3
C16 C17 H17 121.3
C16 O18 C19 117.0(6)
O18 C19 H19A 109.5
O18 C19 H19B 109.5
O18 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 Br2 2.4175(11)
Pd1 Br3 2.4703(10)
Pd1 C4 1.998(8)
Pd1 N13 2.057(7)
C4 N5 1.334(10)
C4 N8 1.380(10)
N5 C6 1.377(10)
N5 C9 1.467(10)
C6 H6 0.9300
C6 C7 1.350(12)
C7 H7 0.9300
C7 N8 1.406(10)
N8 C12 1.396(10)
C9 H9A 0.9700
C9 H9B 0.9700
C9 C10 1.517(12)
C10 H10 0.9300
C10 C11 1.321(12)
C11 H11A 0.9300
C11 H11B 0.9300
C12 N13 1.355(10)
C12 C17 1.384(11)
N13 C14 1.359(10)
C14 H14 0.9300
C14 C15 1.372(12)
C15 H15 0.9300
C15 C16 1.403(11)
C16 C17 1.393(11)
C16 O18 1.334(10)
C17 H17 0.9300
O18 C19 1.436(10)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Pd1 C4 N5 C6 179.8(8)
Pd1 C4 N5 C9 -4.4(15)
Pd1 C4 N8 C7 180.0(5)
Pd1 C4 N8 C12 -0.5(8)
Pd1 N13 C14 C15 -179.3(6)
Br2 Pd1 C4 N5 -5.6(10)
Br2 Pd1 C4 N8 175.1(5)
Br2 Pd1 N13 C12 -79.3(19)
Br2 Pd1 N13 C14 97.1(18)
Br3 Pd1 C4 N5 143.4(11)
Br3 Pd1 C4 N8 -35.9(19)
Br3 Pd1 N13 C12 174.3(5)
Br3 Pd1 N13 C14 -9.3(7)
C4 Pd1 N13 C12 -0.8(5)
C4 Pd1 N13 C14 175.6(7)
C4 N5 C6 C7 1.0(10)
C4 N5 C9 C10 -100.6(9)
C4 N8 C12 N13 -0.2(10)
C4 N8 C12 C17 -179.7(7)
N5 C4 N8 C7 0.4(8)
N5 C4 N8 C12 180.0(7)
N5 C6 C7 N8 -0.6(9)
N5 C9 C10 C11 -2.6(12)
C6 N5 C9 C10 74.8(9)
C6 C7 N8 C4 0.1(9)
C6 C7 N8 C12 -179.4(7)
C7 N8 C12 N13 179.2(7)
C7 N8 C12 C17 -0.3(12)
N8 C4 N5 C6 -0.8(9)
N8 C4 N5 C9 174.9(7)
N8 C12 N13 Pd1 0.8(8)
N8 C12 N13 C14 -176.1(6)
N8 C12 C17 C16 178.1(7)
C9 N5 C6 C7 -175.2(7)
C12 N13 C14 C15 -2.9(11)
N13 Pd1 C4 N5 180.0(10)
N13 Pd1 C4 N8 0.7(5)
N13 C12 C17 C16 -1.3(11)
N13 C14 C15 C16 0.5(12)
C14 C15 C16 C17 1.7(12)
C14 C15 C16 O18 -179.1(7)
C15 C16 C17 C12 -1.3(11)
C15 C16 O18 C19 170.2(7)
C17 C12 N13 Pd1 -179.7(6)
C17 C12 N13 C14 3.4(11)
C17 C16 O18 C19 -10.8(11)
O18 C16 C17 C12 179.6(7)
