#------------------------------------------------------------------------------
#$Date: 2018-08-16 18:56:10 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/49/4074992.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_4074992
loop_
_publ_author_name
'Ionkin, Alex S.'
'Marshall, William J.'
'Fish, Brian M.'
_publ_section_title
;
 Synthesis and Structural Characterization of a Series of Novel
 Polyaromatic Ligands Containing Pyrene and Related Biscyclometalated
 Iridium(III) Complexes
;
_journal_coden_ASTM              ORGND7
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1461
_journal_page_last               1471
_journal_paper_doi               10.1021/om0510775
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C24 H26 Br P Pd'
_chemical_formula_weight         531.73
_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                 108.464(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.327(3)
_cell_length_b                   12.964(3)
_cell_length_c                   16.075(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2436.7(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0732
_diffrn_reflns_av_sigmaI/netI    0.1248
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18540
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    2.473
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ireg.block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.173
_refine_diff_density_min         -1.530
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0502
_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)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                4026
_reflns_number_total             6888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0510775si20060112_022917.cif
_cod_data_source_block           04242
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4074992
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
Pd1 Pd 0.04156(3) 0.41252(2) 0.41777(2) 0.02465(10) Uani 1 1 d .
Br1 Br -0.12277(4) 0.43464(3) 0.48159(3) 0.03399(13) Uani 1 1 d .
P1 P -0.02629(9) 0.27803(8) 0.32683(8) 0.0254(2) Uani 1 1 d .
C1 C 0.1720(4) 0.4063(3) 0.3664(3) 0.0274(9) Uani 1 1 d .
C2 C 0.1622(3) 0.3391(3) 0.2925(3) 0.0247(9) Uani 1 1 d .
C3 C 0.2476(4) 0.3416(3) 0.2506(3) 0.0275(9) Uani 1 1 d .
C4 C 0.3424(4) 0.4091(3) 0.2803(3) 0.0319(10) Uani 1 1 d .
C5 C 0.3537(4) 0.4704(3) 0.3554(3) 0.0324(10) Uani 1 1 d .
C6 C 0.2670(4) 0.4661(3) 0.3976(3) 0.0283(9) Uani 1 1 d .
H6A H 0.2761 0.5053 0.4478 0.034 Uiso 1 1 calc R
C7 C 0.0710(3) 0.2695(3) 0.2632(3) 0.0266(9) Uani 1 1 d .
C8 C 0.0680(4) 0.2005(3) 0.1956(3) 0.0332(10) Uani 1 1 d .
H8A H 0.0100 0.1516 0.1789 0.040 Uiso 1 1 calc R
C9 C 0.1493(4) 0.2035(3) 0.1533(3) 0.0326(10) Uani 1 1 d .
H9A H 0.1444 0.1573 0.1080 0.039 Uiso 1 1 calc R
C10 C 0.2399(4) 0.2755(3) 0.1777(3) 0.0319(10) Uani 1 1 d .
C11 C 0.3241(4) 0.2840(4) 0.1334(3) 0.0376(11) Uani 1 1 d .
H11A H 0.3181 0.2426 0.0849 0.045 Uiso 1 1 calc R
C12 C 0.4113(4) 0.3507(4) 0.1610(3) 0.0395(12) Uani 1 1 d .
H12A H 0.4638 0.3555 0.1304 0.047 Uiso 1 1 calc R
C13 C 0.4258(4) 0.4148(3) 0.2363(3) 0.0370(11) Uani 1 1 d .
C14 C 0.5194(4) 0.4806(4) 0.2703(4) 0.0467(14) Uani 1 1 d .
H14A H 0.5745 0.4850 0.2421 0.056 Uiso 1 1 calc R
C15 C 0.5323(4) 0.5386(4) 0.3438(4) 0.0510(14) Uani 1 1 d .
H15A H 0.5961 0.5806 0.3656 0.061 Uiso 1 1 calc R
C16 C 0.4496(4) 0.5346(4) 0.3860(4) 0.0447(13) Uani 1 1 d .
H16A H 0.4582 0.5752 0.4353 0.054 Uiso 1 1 calc R
C17 C -0.1751(4) 0.2989(3) 0.2477(3) 0.0303(10) Uani 1 1 d .
C18 C -0.1989(4) 0.2380(4) 0.1623(3) 0.0360(11) Uani 1 1 d .
H18A H -0.2771 0.2479 0.1269 0.054 Uiso 1 1 calc R
H18B H -0.1852 0.1660 0.1755 0.054 Uiso 1 1 calc R
H18C H -0.1492 0.2618 0.1308 0.054 Uiso 1 1 calc R
C19 C -0.2663(4) 0.2747(3) 0.2907(3) 0.0371(11) Uani 1 1 d .
H19A H -0.3402 0.2934 0.2516 0.056 Uiso 1 1 calc R
H19B H -0.2509 0.3132 0.3442 0.056 Uiso 1 1 calc R
H19C H -0.2651 0.2023 0.3034 0.056 Uiso 1 1 calc R
C20 C -0.1805(4) 0.4142(3) 0.2239(3) 0.0379(11) Uani 1 1 d .
H20A H -0.2524 0.4290 0.1801 0.057 Uiso 1 1 calc R
H20B H -0.1192 0.4308 0.2014 0.057 Uiso 1 1 calc R
H20C H -0.1733 0.4548 0.2753 0.057 Uiso 1 1 calc R
C21 C -0.0127(4) 0.1517(3) 0.3871(3) 0.0304(10) Uani 1 1 d .
C22 C -0.0614(4) 0.1629(3) 0.4634(3) 0.0375(11) Uani 1 1 d .
H22A H -0.0505 0.0996 0.4960 0.056 Uiso 1 1 calc R
H22B H -0.1416 0.1782 0.4407 0.056 Uiso 1 1 calc R
H22C H -0.0226 0.2178 0.5012 0.056 Uiso 1 1 calc R
C23 C -0.0702(4) 0.0617(3) 0.3291(3) 0.0401(12) Uani 1 1 d .
H23A H -0.0572 -0.0005 0.3633 0.060 Uiso 1 1 calc R
H23B H -0.0388 0.0544 0.2819 0.060 Uiso 1 1 calc R
H23C H -0.1509 0.0744 0.3056 0.060 Uiso 1 1 calc R
C24 C 0.1159(4) 0.1310(3) 0.4247(3) 0.0349(11) Uani 1 1 d .
H24A H 0.1287 0.0707 0.4613 0.052 Uiso 1 1 calc R
H24B H 0.1529 0.1892 0.4590 0.052 Uiso 1 1 calc R
H24C H 0.1468 0.1200 0.3776 0.052 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Pd1 P1 83.38(12) . .
C1 Pd1 Br1 94.96(12) . 3_566
P1 Pd1 Br1 178.32(3) . 3_566
C1 Pd1 Br1 175.85(11) . .
P1 Pd1 Br1 99.67(3) . .
Br1 Pd1 Br1 81.97(2) 3_566 .
Pd1 Br1 Pd1 98.03(2) 3_566 .
C7 P1 C21 105.73(19) . .
C7 P1 C17 107.7(2) . .
C21 P1 C17 112.3(2) . .
C7 P1 Pd1 103.71(14) . .
C21 P1 Pd1 112.59(15) . .
C17 P1 Pd1 113.96(13) . .
C6 C1 C2 118.9(4) . .
C6 C1 Pd1 121.9(3) . .
C2 C1 Pd1 119.2(3) . .
C7 C2 C3 119.4(4) . .
C7 C2 C1 120.9(4) . .
C3 C2 C1 119.7(4) . .
C4 C3 C2 120.7(4) . .
C4 C3 C10 118.7(4) . .
C2 C3 C10 120.6(4) . .
C5 C4 C3 118.8(4) . .
C5 C4 C13 120.3(4) . .
C3 C4 C13 120.9(4) . .
C16 C5 C4 118.4(4) . .
C16 C5 C6 122.0(4) . .
C4 C5 C6 119.6(4) . .
C1 C6 C5 122.1(4) . .
C8 C7 C2 119.6(4) . .
C8 C7 P1 128.2(3) . .
C2 C7 P1 112.0(3) . .
C9 C8 C7 121.4(4) . .
C8 C9 C10 121.1(4) . .
C9 C10 C3 117.7(4) . .
C9 C10 C11 123.1(4) . .
C3 C10 C11 119.3(4) . .
C12 C11 C10 121.0(4) . .
C11 C12 C13 121.7(4) . .
C14 C13 C4 118.3(5) . .
C14 C13 C12 123.4(5) . .
C4 C13 C12 118.3(4) . .
C15 C14 C13 121.9(5) . .
C14 C15 C16 119.9(5) . .
C15 C16 C5 121.2(5) . .
C19 C17 C18 109.9(4) . .
C19 C17 C20 109.4(4) . .
C18 C17 C20 107.3(4) . .
C19 C17 P1 111.3(3) . .
C18 C17 P1 113.5(3) . .
C20 C17 P1 105.2(3) . .
C23 C21 C24 109.3(4) . .
C23 C21 C22 109.7(4) . .
C24 C21 C22 108.6(4) . .
C23 C21 P1 113.8(3) . .
C24 C21 P1 105.6(3) . .
C22 C21 P1 109.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.028(4) .
Pd1 P1 2.2587(11) .
Pd1 Br1 2.5533(7) 3_566
Pd1 Br1 2.5603(7) .
Br1 Pd1 2.5534(7) 3_566
P1 C7 1.810(4) .
P1 C21 1.883(4) .
P1 C17 1.891(4) .
C1 C6 1.361(6) .
C1 C2 1.447(6) .
C2 C7 1.401(6) .
C2 C3 1.418(6) .
C3 C4 1.417(6) .
C3 C10 1.431(6) .
C4 C5 1.416(6) .
C4 C13 1.423(6) .
C5 C16 1.401(6) .
C5 C6 1.436(6) .
C7 C8 1.398(6) .
C8 C9 1.378(6) .
C9 C10 1.412(6) .
C10 C11 1.437(6) .
C11 C12 1.341(7) .
C12 C13 1.432(7) .
C13 C14 1.400(7) .
C14 C15 1.366(7) .
C15 C16 1.393(7) .
C17 C19 1.527(6) .
C17 C18 1.531(6) .
C17 C20 1.539(6) .
C21 C23 1.521(6) .
C21 C24 1.532(6) .
C21 C22 1.533(6) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 Pd1 Br1 Pd1 -42.6(17) . 3_566
P1 Pd1 Br1 Pd1 -179.64(3) . 3_566
Br1 Pd1 Br1 Pd1 0.0 3_566 3_566
C1 Pd1 P1 C7 -6.95(17) . .
Br1 Pd1 P1 C7 2.3(12) 3_566 .
Br1 Pd1 P1 C7 170.21(14) . .
C1 Pd1 P1 C21 106.9(2) . .
Br1 Pd1 P1 C21 116.1(11) 3_566 .
Br1 Pd1 P1 C21 -75.98(16) . .
C1 Pd1 P1 C17 -123.7(2) . .
Br1 Pd1 P1 C17 -114.5(12) 3_566 .
Br1 Pd1 P1 C17 53.43(16) . .
P1 Pd1 C1 C6 -173.5(4) . .
Br1 Pd1 C1 C6 6.8(4) 3_566 .
Br1 Pd1 C1 C6 49.0(19) . .
P1 Pd1 C1 C2 8.8(3) . .
Br1 Pd1 C1 C2 -171.0(3) 3_566 .
Br1 Pd1 C1 C2 -128.7(15) . .
C6 C1 C2 C7 174.3(4) . .
Pd1 C1 C2 C7 -7.9(5) . .
C6 C1 C2 C3 -4.0(6) . .
Pd1 C1 C2 C3 173.8(3) . .
C7 C2 C3 C4 -178.3(4) . .
C1 C2 C3 C4 0.0(6) . .
C7 C2 C3 C10 1.4(6) . .
C1 C2 C3 C10 179.7(4) . .
C2 C3 C4 C5 3.3(6) . .
C10 C3 C4 C5 -176.5(4) . .
C2 C3 C4 C13 -177.5(4) . .
C10 C3 C4 C13 2.7(6) . .
C3 C4 C5 C16 178.0(4) . .
C13 C4 C5 C16 -1.3(7) . .
C3 C4 C5 C6 -2.5(6) . .
C13 C4 C5 C6 178.2(4) . .
C2 C1 C6 C5 4.8(6) . .
Pd1 C1 C6 C5 -172.9(3) . .
C16 C5 C6 C1 177.9(4) . .
C4 C5 C6 C1 -1.6(6) . .
C3 C2 C7 C8 2.8(6) . .
C1 C2 C7 C8 -175.5(4) . .
C3 C2 C7 P1 179.1(3) . .
C1 C2 C7 P1 0.8(5) . .
C21 P1 C7 C8 62.5(4) . .
C17 P1 C7 C8 -57.7(4) . .
Pd1 P1 C7 C8 -178.8(4) . .
C21 P1 C7 C2 -113.3(3) . .
C17 P1 C7 C2 126.4(3) . .
Pd1 P1 C7 C2 5.3(3) . .
C2 C7 C8 C9 -4.1(6) . .
P1 C7 C8 C9 -179.7(3) . .
C7 C8 C9 C10 1.0(7) . .
C8 C9 C10 C3 3.2(6) . .
C8 C9 C10 C11 -177.6(4) . .
C4 C3 C10 C9 175.4(4) . .
C2 C3 C10 C9 -4.3(6) . .
C4 C3 C10 C11 -3.8(6) . .
C2 C3 C10 C11 176.4(4) . .
C9 C10 C11 C12 -177.3(4) . .
C3 C10 C11 C12 1.9(6) . .
C10 C11 C12 C13 1.2(7) . .
C5 C4 C13 C14 1.2(7) . .
C3 C4 C13 C14 -178.0(4) . .
C5 C4 C13 C12 179.5(4) . .
C3 C4 C13 C12 0.2(6) . .
C11 C12 C13 C14 175.9(5) . .
C11 C12 C13 C4 -2.3(7) . .
C4 C13 C14 C15 0.1(7) . .
C12 C13 C14 C15 -178.1(5) . .
C13 C14 C15 C16 -1.3(8) . .
C14 C15 C16 C5 1.2(8) . .
C4 C5 C16 C15 0.1(7) . .
C6 C5 C16 C15 -179.4(5) . .
C7 P1 C17 C19 162.7(3) . .
C21 P1 C17 C19 46.7(4) . .
Pd1 P1 C17 C19 -82.8(3) . .
C7 P1 C17 C18 38.1(4) . .
C21 P1 C17 C18 -77.9(4) . .
Pd1 P1 C17 C18 152.6(3) . .
C7 P1 C17 C20 -78.9(3) . .
C21 P1 C17 C20 165.1(3) . .
Pd1 P1 C17 C20 35.6(3) . .
C7 P1 C21 C23 -74.3(4) . .
C17 P1 C21 C23 42.9(4) . .
Pd1 P1 C21 C23 173.2(3) . .
C7 P1 C21 C24 45.6(3) . .
C17 P1 C21 C24 162.8(3) . .
Pd1 P1 C21 C24 -66.9(3) . .
C7 P1 C21 C22 162.4(3) . .
C17 P1 C21 C22 -80.4(4) . .
Pd1 P1 C21 C22 49.8(3) . .
