#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:17:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178742 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/53/4085313.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_4085313
loop_
_publ_author_name
'Serrano, J. Luis'
'Pérez, José'
'García, Luis'
'Sánchez, Gregorio'
'García, Joaquín'
'Lozano, Pedro'
'Zende, Vidya'
'Kapdi, Anant'
_publ_section_title
;
 N-Heterocyclic-Carbene Complexes Readily Prepared from
 Di-μ-hydroxopalladacycles Catalyze the Suzuki Arylation of
 9-Bromophenanthrene
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              522
_journal_paper_doi               10.1021/om501160n
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C27 H26 N4 O2 Pd'
_chemical_formula_sum            'C27 H26 N4 O2 Pd'
_chemical_formula_weight         544.92
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 96.2630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6655(6)
_cell_length_b                   11.2625(5)
_cell_length_c                   15.8256(7)
_cell_measurement_temperature    100(2)
_cell_volume                     2421.14(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            78179
_diffrn_reflns_theta_full        0.50
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.8897
_exptl_absorpt_correction_T_min  0.7676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         7441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.002
_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+2.9869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                6414
_reflns_number_total             7441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om501160n_si_002.cif
_cod_data_source_block           IIe
_cod_depositor_comments
'Adding full bibliography for 4085310--4085313.cif.'
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4085313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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 0.100413(9) 0.896082(11) 0.187770(8) 0.01622(4) Uani 1 1 d .
O1 O 0.03229(15) 0.95979(17) 0.38200(11) 0.0445(4) Uani 1 1 d .
O2 O 0.23922(12) 1.13826(14) 0.21280(11) 0.0327(3) Uani 1 1 d .
N1 N -0.02544(11) 0.98373(13) 0.13665(10) 0.0198(3) Uani 1 1 d .
N2 N 0.13420(12) 1.02288(15) 0.28291(10) 0.0243(3) Uani 1 1 d .
N3 N 0.21828(11) 0.70791(15) 0.28904(10) 0.0232(3) Uani 1 1 d .
N4 N 0.30623(11) 0.80137(14) 0.20708(10) 0.0200(3) Uani 1 1 d .
C1 C -0.06549(14) 1.07873(17) 0.17035(14) 0.0251(4) Uani 1 1 d .
H1 H -0.0305 1.1157 0.2185 0.030 Uiso 1 1 calc R
C2 C -0.15571(15) 1.12560(19) 0.13812(16) 0.0314(5) Uani 1 1 d .
H2 H -0.1827 1.1928 0.1636 0.038 Uiso 1 1 calc R
C3 C -0.20494(15) 1.0713(2) 0.06779(16) 0.0337(5) Uani 1 1 d .
H3 H -0.2673 1.1005 0.0445 0.040 Uiso 1 1 calc R
C4 C -0.16392(14) 0.97445(19) 0.03113(14) 0.0281(4) Uani 1 1 d .
H4 H -0.1971 0.9380 -0.0181 0.034 Uiso 1 1 calc R
C5 C -0.07341(13) 0.93091(17) 0.06714(12) 0.0206(3) Uani 1 1 d .
C6 C -0.02329(12) 0.82583(16) 0.03790(12) 0.0195(3) Uani 1 1 d .
C7 C 0.06194(12) 0.78779(15) 0.09013(11) 0.0185(3) Uani 1 1 d .
C8 C 0.10845(14) 0.68528(17) 0.06486(13) 0.0229(3) Uani 1 1 d .
H8 H 0.1654 0.6567 0.0986 0.027 Uiso 1 1 calc R
C9 C 0.07319(16) 0.62396(18) -0.00869(14) 0.0281(4) Uani 1 1 d .
H9 H 0.1062 0.5544 -0.0243 0.034 Uiso 1 1 calc R
C10 C -0.00998(16) 0.66371(19) -0.05949(14) 0.0289(4) Uani 1 1 d .
H10 H -0.0337 0.6216 -0.1096 0.035 Uiso 1 1 calc R
C11 C -0.05779(14) 0.76483(18) -0.03642(12) 0.0246(4) Uani 1 1 d .
H11 H -0.1142 0.7930 -0.0711 0.029 Uiso 1 1 calc R
C12 C 0.09251(17) 1.0289(2) 0.35894(13) 0.0307(4) Uani 1 1 d .
C13 C 0.13410(19) 1.1371(2) 0.40554(14) 0.0333(5) Uani 1 1 d .
C14 C 0.1162(2) 1.1854(2) 0.48295(15) 0.0445(6) Uani 1 1 d .
H14 H 0.0711 1.1502 0.5171 0.053 Uiso 1 1 calc R
C15 C 0.1681(3) 1.2887(2) 0.50807(16) 0.0535(8) Uani 1 1 d .
H15 H 0.1574 1.3247 0.5606 0.064 Uiso 1 1 calc R
C16 C 0.2345(2) 1.3403(2) 0.45926(18) 0.0501(7) Uani 1 1 d .
H16 H 0.2696 1.4092 0.4794 0.060 Uiso 1 1 calc R
C17 C 0.2506(2) 1.2916(2) 0.37976(16) 0.0393(5) Uani 1 1 d .
H17 H 0.2946 1.3273 0.3448 0.047 Uiso 1 1 calc R
C18 C 0.19912(17) 1.18956(19) 0.35530(14) 0.0314(4) Uani 1 1 d .
C19 C 0.19614(15) 1.11678(17) 0.27501(13) 0.0254(4) Uani 1 1 d .
C20 C 0.21428(12) 0.79651(16) 0.23105(11) 0.0189(3) Uani 1 1 d .
C21 C 0.31109(14) 0.65687(18) 0.29957(13) 0.0262(4) Uani 1 1 d .
H21 H 0.3317 0.5925 0.3361 0.031 Uiso 1 1 calc R
C22 C 0.36624(13) 0.71562(18) 0.24843(12) 0.0237(4) Uani 1 1 d .
H22 H 0.4335 0.7012 0.2418 0.028 Uiso 1 1 calc R
C23 C 0.33682(15) 0.88523(19) 0.14491(14) 0.0293(4) Uani 1 1 d .
H23A H 0.4064 0.8722 0.1378 0.044 Uiso 1 1 calc R
H23B H 0.3279 0.9665 0.1648 0.044 Uiso 1 1 calc R
H23C H 0.2968 0.8734 0.0903 0.044 Uiso 1 1 calc R
C24 C 0.13633(16) 0.6695(2) 0.33421(15) 0.0335(5) Uani 1 1 d .
H24A H 0.0860 0.7331 0.3312 0.040 Uiso 1 1 calc R
H24B H 0.1603 0.6566 0.3948 0.040 Uiso 1 1 calc R
C25 C 0.08941(17) 0.5561(2) 0.29750(19) 0.0434(6) Uani 1 1 d .
H25A H 0.1408 0.4944 0.2960 0.052 Uiso 1 1 calc R
H25B H 0.0603 0.5709 0.2384 0.052 Uiso 1 1 calc R
C26 C 0.00952(16) 0.5108(2) 0.3496(2) 0.0636(10) Uani 1 1 d .
H26A H 0.0368 0.5058 0.4101 0.076 Uiso 1 1 calc R
H26B H -0.0453 0.5686 0.3454 0.076 Uiso 1 1 calc R
C27 C -0.03041(16) 0.3902(2) 0.3209(2) 0.0885(16) Uani 1 1 d R
H27A H -0.0813 0.3659 0.3564 0.133 Uiso 1 1 calc R
H27B H 0.0232 0.3319 0.3263 0.133 Uiso 1 1 calc R
H27C H -0.0589 0.3948 0.2614 0.133 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'
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 Pd1 C7 93.01(7)
C20 Pd1 N1 173.82(7)
C7 Pd1 N1 81.44(7)
C20 Pd1 N2 91.96(7)
C7 Pd1 N2 174.43(7)
N1 Pd1 N2 93.70(6)
C1 N1 C5 119.45(16)
C1 N1 Pd1 125.72(14)
C5 N1 Pd1 114.56(12)
C19 N2 C12 110.96(17)
C19 N2 Pd1 123.53(13)
C12 N2 Pd1 125.35(14)
C20 N3 C21 110.87(16)
C20 N3 C24 125.09(16)
C21 N3 C24 124.04(17)
C20 N4 C22 111.09(16)
C20 N4 C23 123.99(16)
C22 N4 C23 124.91(16)
N1 C1 C2 122.9(2)
C3 C2 C1 117.6(2)
C2 C3 C4 120.28(19)
C3 C4 C5 119.2(2)
N1 C5 C4 120.45(18)
N1 C5 C6 114.14(15)
C4 C5 C6 125.38(19)
C11 C6 C7 121.43(17)
C11 C6 C5 122.36(17)
C7 C6 C5 116.20(16)
C8 C7 C6 116.93(17)
C8 C7 Pd1 129.61(14)
C6 C7 Pd1 113.40(13)
C9 C8 C7 121.46(18)
C10 C9 C8 120.60(19)
C11 C10 C9 119.48(19)
C10 C11 C6 120.08(18)
O1 C12 N2 125.7(2)
O1 C12 C13 127.1(2)
N2 C12 C13 107.22(19)
C14 C13 C18 121.6(2)
C14 C13 C12 131.2(2)
C18 C13 C12 107.20(18)
C13 C14 C15 116.5(3)
C16 C15 C14 122.3(2)
C15 C16 C17 120.7(2)
C18 C17 C16 116.7(3)
C17 C18 C13 122.2(2)
C17 C18 C19 130.9(2)
C13 C18 C19 106.91(19)
O2 C19 N2 125.60(18)
O2 C19 C18 126.7(2)
N2 C19 C18 107.64(18)
N4 C20 N3 104.48(15)
N4 C20 Pd1 126.84(13)
N3 C20 Pd1 128.67(13)
C22 C21 N3 106.88(17)
C21 C22 N4 106.67(16)
N3 C24 C25 112.2(2)
C24 C25 C26 111.9(2)
C27 C26 C25 113.16(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C20 1.9788(17)
Pd1 C7 1.9936(18)
Pd1 N1 2.0696(15)
Pd1 N2 2.0899(16)
O1 C12 1.217(3)
O2 C19 1.225(3)
N1 C1 1.339(2)
N1 C5 1.355(3)
N2 C19 1.369(3)
N2 C12 1.388(3)
N3 C20 1.353(2)
N3 C21 1.386(2)
N3 C24 1.458(3)
N4 C20 1.353(2)
N4 C22 1.384(2)
N4 C23 1.458(3)
C1 C2 1.386(3)
C2 C3 1.379(4)
C3 C4 1.382(3)
C4 C5 1.393(3)
C5 C6 1.467(3)
C6 C11 1.399(3)
C6 C7 1.419(2)
C7 C8 1.397(2)
C8 C9 1.393(3)
C9 C10 1.393(3)
C10 C11 1.382(3)
C12 C13 1.503(3)
C13 C14 1.386(3)
C13 C18 1.388(3)
C14 C15 1.397(4)
C15 C16 1.382(5)
C16 C17 1.411(4)
C17 C18 1.380(3)
C18 C19 1.509(3)
C21 C22 1.339(3)
C24 C25 1.517(4)
C25 C26 1.526(3)
C26 C27 1.5148
