#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:01:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178734 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/45/4084578.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_4084578
loop_
_publ_author_name
'Oliva-Madrid, María-José'
'García-López, José-Antonio'
'Saura-Llamas, Isabel'
'Bautista, Delia'
'Vicente, José'
_publ_section_title
;
 Insertion Reactions on Carbopalladated Benzyne: From Eight- to Nine- and
 Ten-Membered Palladacycles. Applications to the Synthesis of
 N-Heterocycles
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6420
_journal_paper_doi               10.1021/om500772p
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety
'C34 H36 Cl N3 Pd, 0.72(C4 H10 O), 0.28(C H Cl3)'
_chemical_formula_sum            'C37.17 H43.49 Cl1.83 N3 O0.72 Pd'
_chemical_formula_weight         715.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.563(2)
_cell_angle_beta                 96.146(2)
_cell_angle_gamma                106.521(2)
_cell_formula_units_Z            2
_cell_length_a                   11.3846(11)
_cell_length_b                   11.6512(11)
_cell_length_c                   14.2219(13)
_cell_measurement_reflns_used    5624
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.58
_cell_measurement_theta_min      2.57
_cell_volume                     1727.3(3)
_computing_cell_refinement       'Bruker SAINT'
_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_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20030
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_correction_T_min  0.5564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             741
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment
'NH2 free, ordered methyls rigid, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         7528
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0372
_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)+(0.0376P)²+2.2348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                6954
_reflns_number_total             7528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500772p_si_002.cif
_cod_data_source_block           jaj761bs
_cod_depositor_comments
'Adding full bibliography for 4084578--4084580.cif.'
_cod_database_code               4084578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.972880(17) 0.680514(17) 0.174374(13) 0.01821(6) Uani 1 1 d . . .
Cl1 Cl 0.93902(6) 0.45534(6) 0.13483(4) 0.02424(13) Uani 1 1 d . . .
N1 N 0.9062(2) 0.6752(2) 0.02741(16) 0.0229(4) Uani 1 1 d D . .
H01A H 0.950(2) 0.641(2) -0.0057(19) 0.015(7) Uiso 1 1 d D . .
H01B H 0.933(3) 0.749(2) 0.024(2) 0.023(8) Uiso 1 1 d D . .
C1 C 0.9520(3) 0.9385(2) 0.18362(18) 0.0247(5) Uani 1 1 d . . .
C2 C 0.8258(3) 0.9027(2) 0.18982(19) 0.0251(5) Uani 1 1 d . . .
C3 C 0.7631(2) 0.7863(3) 0.2162(2) 0.0257(5) Uani 1 1 d . . .
C4 C 0.6935(2) 0.6774(3) 0.1417(2) 0.0282(6) Uani 1 1 d . . .
C5 C 0.6866(3) 0.6764(3) 0.0348(2) 0.0278(6) Uani 1 1 d . . .
H5A H 0.7057 0.7637 0.0319 0.033 Uiso 1 1 calc R . .
H5B H 0.5992 0.6316 0.0007 0.033 Uiso 1 1 calc R . .
C6 C 0.7713(3) 0.6180(3) -0.0244(2) 0.0280(6) Uani 1 1 d . . .
C7 C 0.7537(3) 0.9761(3) 0.1689(2) 0.0324(6) Uani 1 1 d . . .
H7 H 0.6686 0.9538 0.1754 0.039 Uiso 1 1 calc R . .
C8 C 0.8054(3) 1.0811(3) 0.1386(2) 0.0371(7) Uani 1 1 d . . .
H8 H 0.7554 1.1298 0.1239 0.045 Uiso 1 1 calc R . .
C9 C 0.9294(3) 1.1152(3) 0.1300(2) 0.0356(7) Uani 1 1 d . . .
H9 H 0.9645 1.1866 0.1084 0.043 Uiso 1 1 calc R . .
C10 C 1.0022(3) 1.0452(3) 0.1528(2) 0.0309(6) Uani 1 1 d . . .
H10 H 1.0877 1.0697 0.1475 0.037 Uiso 1 1 calc R . .
C11 C 0.6304(3) 0.5733(3) 0.1697(2) 0.0336(6) Uani 1 1 d . . .
H11 H 0.5826 0.4993 0.1201 0.040 Uiso 1 1 calc R . .
C12 C 0.6352(3) 0.5745(3) 0.2678(3) 0.0387(7) Uani 1 1 d . . .
H12 H 0.5909 0.5024 0.2850 0.046 Uiso 1 1 calc R . .
C13 C 0.7050(3) 0.6818(3) 0.3403(2) 0.0365(7) Uani 1 1 d . . .
H13 H 0.7097 0.6833 0.4077 0.044 Uiso 1 1 calc R . .
C14 C 0.7680(3) 0.7870(3) 0.3147(2) 0.0316(6) Uani 1 1 d . . .
H14 H 0.8152 0.8606 0.3649 0.038 Uiso 1 1 calc R . .
C15 C 1.0365(2) 0.8687(2) 0.20993(18) 0.0218(5) Uani 1 1 d . . .
N2 N 1.1485(2) 0.9355(2) 0.24748(16) 0.0253(5) Uani 1 1 d . . .
C16 C 0.7615(3) 0.6468(3) -0.1239(2) 0.0366(7) Uani 1 1 d . . .
H16A H 0.7839 0.7372 -0.1133 0.055 Uiso 1 1 calc R . .
H16B H 0.6758 0.6065 -0.1606 0.055 Uiso 1 1 calc R . .
H16C H 0.8186 0.6154 -0.1615 0.055 Uiso 1 1 calc R . .
C17 C 0.7330(3) 0.4780(3) -0.0408(2) 0.0359(7) Uani 1 1 d . . .
H17A H 0.7887 0.4445 -0.0787 0.054 Uiso 1 1 calc R . .
H17B H 0.6470 0.4397 -0.0772 0.054 Uiso 1 1 calc R . .
H17C H 0.7387 0.4595 0.0230 0.054 Uiso 1 1 calc R . .
C21 C 1.2459(2) 0.8909(2) 0.2756(2) 0.0263(6) Uani 1 1 d . . .
C22 C 1.3074(3) 0.8405(3) 0.2047(2) 0.0314(6) Uani 1 1 d . . .
C23 C 1.4096(3) 0.8069(3) 0.2370(3) 0.0404(8) Uani 1 1 d . . .
H23 H 1.4529 0.7726 0.1903 0.049 Uiso 1 1 calc R . .
C24 C 1.4486(3) 0.8228(3) 0.3361(3) 0.0452(8) Uani 1 1 d . . .
H24 H 1.5171 0.7975 0.3567 0.054 Uiso 1 1 calc R . .
C25 C 1.3886(3) 0.8752(3) 0.4051(2) 0.0384(7) Uani 1 1 d . . .
H25 H 1.4161 0.8857 0.4730 0.046 Uiso 1 1 calc R . .
C26 C 1.2882(3) 0.9127(2) 0.3765(2) 0.0293(6) Uani 1 1 d . . .
C27 C 1.2289(3) 0.9787(3) 0.4516(2) 0.0366(7) Uani 1 1 d . . .
H27A H 1.2671 0.9820 0.5177 0.055 Uiso 1 1 calc R . .
H27B H 1.1393 0.9337 0.4396 0.055 Uiso 1 1 calc R . .
H27C H 1.2415 1.0637 0.4466 0.055 Uiso 1 1 calc R . .
C28 C 1.2674(3) 0.8286(3) 0.0974(2) 0.0380(7) Uani 1 1 d . . .
H28A H 1.1872 0.7623 0.0715 0.057 Uiso 1 1 calc R . .
H28B H 1.3303 0.8082 0.0606 0.057 Uiso 1 1 calc R . .
H28C H 1.2589 0.9077 0.0903 0.057 Uiso 1 1 calc R . .
C31 C 1.0292(2) 0.6860(2) 0.30867(19) 0.0235(5) Uani 1 1 d . . .
N3 N 1.0548(2) 0.6777(2) 0.38686(16) 0.0252(5) Uani 1 1 d . . .
C32 C 1.0990(3) 0.6532(2) 0.47382(18) 0.0253(5) Uani 1 1 d . . .
C33 C 1.1776(3) 0.5803(3) 0.4665(2) 0.0283(6) Uani 1 1 d . . .
C34 C 1.2177(3) 0.5524(3) 0.5514(2) 0.0317(6) Uani 1 1 d . . .
H34 H 1.2720 0.5035 0.5495 0.038 Uiso 1 1 calc R . .
C35 C 1.1801(3) 0.5944(3) 0.6388(2) 0.0331(6) Uani 1 1 d . . .
H35 H 1.2075 0.5732 0.6959 0.040 Uiso 1 1 calc R . .
C36 C 1.1030(3) 0.6669(3) 0.6433(2) 0.0324(6) Uani 1 1 d . . .
H36 H 1.0781 0.6952 0.7038 0.039 Uiso 1 1 calc R . .
C37 C 1.0608(3) 0.6997(3) 0.56102(19) 0.0279(6) Uani 1 1 d . . .
C38 C 0.9764(3) 0.7785(3) 0.5664(2) 0.0367(7) Uani 1 1 d . . .
H38A H 0.9695 0.8051 0.5061 0.055 Uiso 1 1 calc R . .
H38B H 1.0111 0.8521 0.6234 0.055 Uiso 1 1 calc R . .
H38C H 0.8936 0.7299 0.5732 0.055 Uiso 1 1 calc R . .
C39 C 1.2141(3) 0.5328(3) 0.3699(2) 0.0342(6) Uani 1 1 d . . .
H39A H 1.2655 0.4797 0.3779 0.051 Uiso 1 1 calc R . .
H39B H 1.2618 0.6034 0.3487 0.051 Uiso 1 1 calc R . .
H39C H 1.1389 0.4842 0.3202 0.051 Uiso 1 1 calc R . .
C81 C 0.5652(6) 0.6837(6) 0.5786(5) 0.0726(18) Uiso 0.721(2) 1 d P A 1
H81A H 0.5653 0.6957 0.5126 0.109 Uiso 0.721(2) 1 calc PR A 1
H81B H 0.5122 0.5990 0.5733 0.109 Uiso 0.721(2) 1 calc PR A 1
H81C H 0.6505 0.6959 0.6099 0.109 Uiso 0.721(2) 1 calc PR A 1
C82 C 0.5166(5) 0.7738(5) 0.6380(4) 0.0540(13) Uiso 0.721(2) 1 d P A 1
H82A H 0.5695 0.8598 0.6437 0.065 Uiso 0.721(2) 1 calc PR A 1
H82B H 0.4307 0.7627 0.6067 0.065 Uiso 0.721(2) 1 calc PR A 1
O83 O 0.5173(3) 0.7536(3) 0.7319(3) 0.0504(9) Uiso 0.721(2) 1 d P A 1
C84 C 0.4751(5) 0.8420(5) 0.7949(3) 0.0429(11) Uiso 0.721(2) 1 d P A 1
H84A H 0.3877 0.8314 0.7680 0.052 Uiso 0.721(2) 1 calc PR A 1
H84B H 0.5270 0.9276 0.7986 0.052 Uiso 0.721(2) 1 calc PR A 1
C85 C 0.4838(6) 0.8231(6) 0.8946(5) 0.0693(17) Uiso 0.721(2) 1 d P A 1
H85A H 0.4549 0.8838 0.9379 0.104 Uiso 0.721(2) 1 calc PR A 1
H85B H 0.5707 0.8344 0.9211 0.104 Uiso 0.721(2) 1 calc PR A 1
H85C H 0.4316 0.7385 0.8906 0.104 Uiso 0.721(2) 1 calc PR A 1
C99 C 0.5671(11) 0.8300(11) 0.7293(7) 0.041(3) Uiso 0.279(2) 1 d PD A 2
H99 H 0.6441 0.9040 0.7450 0.050 Uiso 0.279(2) 1 calc PR A 2
Cl2 Cl 0.5305(4) 0.7979(4) 0.8386(3) 0.0685(12) Uiso 0.279(2) 1 d PD A 2
Cl3 Cl 0.5931(4) 0.7011(4) 0.6513(3) 0.0590(11) Uiso 0.279(2) 1 d PD A 2
Cl4 Cl 0.4414(3) 0.8644(3) 0.6700(2) 0.0466(9) Uiso 0.279(2) 1 d PD A 2
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C31 Pd1 C15 90.22(10)
C31 Pd1 N1 178.44(10)
C15 Pd1 N1 89.64(9)
C31 Pd1 Cl1 86.40(8)
C15 Pd1 Cl1 168.76(8)
N1 Pd1 Cl1 94.03(6)
C6 N1 Pd1 124.77(18)
C2 C1 C10 118.8(2)
C2 C1 C15 122.6(2)
C10 C1 C15 118.6(3)
C1 C2 C7 119.5(3)
C1 C2 C3 122.3(2)
C7 C2 C3 118.2(3)
C14 C3 C4 119.7(3)
C14 C3 C2 120.2(2)
C4 C3 C2 120.0(2)
C11 C4 C3 118.2(3)
C11 C4 C5 121.8(3)
C3 C4 C5 120.0(3)
C4 C5 C6 118.3(2)
N1 C6 C17 108.8(2)
N1 C6 C16 107.9(2)
C17 C6 C16 109.4(2)
N1 C6 C5 110.9(2)
C17 C6 C5 111.9(2)
C16 C6 C5 107.7(2)
C8 C7 C2 120.6(3)
C9 C8 C7 120.1(3)
C8 C9 C10 119.8(3)
C9 C10 C1 121.1(3)
C12 C11 C4 121.9(3)
C13 C12 C11 119.3(3)
C12 C13 C14 120.0(3)
C13 C14 C3 120.8(3)
N2 C15 C1 114.9(2)
N2 C15 Pd1 124.94(19)
C1 C15 Pd1 119.90(18)
C15 N2 C21 125.5(2)
C22 C21 C26 121.5(3)
C22 C21 N2 120.0(3)
C26 C21 N2 118.0(2)
C23 C22 C21 118.0(3)
C23 C22 C28 121.3(3)
C21 C22 C28 120.7(3)
C24 C23 C22 120.9(3)
C25 C24 C23 120.3(3)
C24 C25 C26 120.7(3)
C25 C26 C21 118.4(3)
C25 C26 C27 121.0(3)
C21 C26 C27 120.6(3)
N3 C31 Pd1 173.3(2)
C31 N3 C32 169.0(3)
C33 C32 C37 123.8(2)
C33 C32 N3 116.8(2)
C37 C32 N3 119.4(2)
C34 C33 C32 116.9(3)
C34 C33 C39 122.2(3)
C32 C33 C39 120.9(2)
C35 C34 C33 121.1(3)
C36 C35 C34 120.3(3)
C35 C36 C37 121.4(3)
C36 C37 C32 116.4(3)
C36 C37 C38 121.1(3)
C32 C37 C38 122.4(2)
O83 C82 C81 107.9(5)
C82 O83 C84 110.6(4)
O83 C84 C85 109.4(4)
Cl2 C99 Cl3 110.5(6)
Cl2 C99 Cl4 108.6(6)
Cl3 C99 Cl4 110.0(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C31 1.929(3)
Pd1 C15 2.021(2)
Pd1 N1 2.126(2)
Pd1 Cl1 2.4565(7)
N1 C6 1.513(3)
C1 C2 1.397(4)
C1 C10 1.403(4)
C1 C15 1.496(4)
C2 C7 1.401(4)
C2 C3 1.495(4)
C3 C14 1.394(4)
C3 C4 1.407(4)
C4 C11 1.392(4)
C4 C5 1.510(4)
C5 C6 1.543(4)
C6 C17 1.516(4)
C6 C16 1.529(4)
C7 C8 1.385(4)
C8 C9 1.381(5)
C9 C10 1.382(4)
C11 C12 1.388(4)
C12 C13 1.383(5)
C13 C14 1.383(4)
C15 N2 1.269(3)
N2 C21 1.411(3)
C21 C22 1.400(4)
C21 C26 1.402(4)
C22 C23 1.395(4)
C22 C28 1.508(4)
C23 C24 1.384(5)
C24 C25 1.380(5)
C25 C26 1.389(4)
C26 C27 1.501(4)
C31 N3 1.152(3)
N3 C32 1.406(3)
C32 C33 1.394(4)
C32 C37 1.398(4)
C33 C34 1.387(4)
C33 C39 1.504(4)
C34 C35 1.384(4)
C35 C36 1.377(4)
C36 C37 1.393(4)
C37 C38 1.502(4)
C81 C82 1.462(8)
C82 O83 1.410(6)
O83 C84 1.426(6)
C84 C85 1.482(8)
C99 Cl2 1.747(10)
C99 Cl3 1.765(10)
C99 Cl4 1.773(9)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H01A Cl1 0.84(2) 2.56(2) 3.390(2) 169(2) 2_765
