#------------------------------------------------------------------------------
#$Date: 2016-03-22 22:09:21 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179033 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/31/4123135.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_4123135
loop_
_publ_author_name
'Zhang, Shu-Yu'
'Li, Qiong'
'He, Gang'
'Nack, William A.'
'Chen, Gong'
_publ_section_title
;
 Pd-Catalyzed Monoselective ortho-C-H Alkylation of N-Quinolyl Benzamides:
 Evidence for Stereoretentive Coupling of Secondary Alkyl Iodides.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              531
_journal_page_last               539
_journal_paper_doi               10.1021/ja511557h
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C26 H27 N3 O2 Pd'
_chemical_formula_sum            'C26 H27 N3 O2 Pd'
_chemical_formula_weight         519.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 126.7910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.663(2)
_cell_length_b                   6.7979(7)
_cell_length_c                   17.5827(18)
_cell_measurement_reflns_used    7560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.278
_cell_measurement_theta_min      2.354
_cell_volume                     2265.0(4)
_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      293(2)
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10973
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.9051
_exptl_absorpt_correction_T_min  0.8555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0269
_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)+(0.0435P)²+1.4469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                2872
_reflns_number_total             3038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja511557h_si_004.cif
_cod_data_source_block           suz12s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4123135--4123137.cif.
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4123135
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -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
C1 C 0.11001(13) 0.0000 0.40770(19) 0.0421(5) Uani 1 2 d S
C2 C 0.13309(14) 0.0000 0.34442(18) 0.0394(5) Uani 1 2 d S
C3 C 0.08569(15) 0.0000 0.24446(19) 0.0456(6) Uani 1 2 d S
C4 C 0.11515(18) 0.0000 0.1956(2) 0.0550(7) Uani 1 2 d S
H4 H 0.0852 0.0000 0.1295 0.066 Uiso 1 2 calc SR
C5 C 0.18700(18) 0.0000 0.2415(2) 0.0532(7) Uani 1 2 d S
H5 H 0.2045 0.0000 0.2063 0.064 Uiso 1 2 calc SR
C6 C 0.23302(14) 0.0000 0.3391(2) 0.0426(5) Uani 1 2 d S
C7 C 0.20667(14) 0.0000 0.39347(19) 0.0388(5) Uani 1 2 d S
C8 C 0.33285(19) 0.0000 0.3369(3) 0.0578(8) Uani 1 2 d S
H8A H 0.3823 -0.0301 0.3790 0.087 Uiso 0.50 1 calc PR
H8B H 0.3264 0.1274 0.3092 0.087 Uiso 0.50 1 calc PR
H8C H 0.3091 -0.0973 0.2876 0.087 Uiso 0.50 1 calc PR
C9 C 0.00542(15) 0.0000 0.1877(2) 0.0498(6) Uani 1 2 d S
H9 H -0.0040 0.0000 0.2349 0.060 Uiso 1 2 calc SR
C10 C -0.02862(14) 0.1822(5) 0.1299(3) 0.1009(11) Uani 1 1 d .
H10A H -0.0187 0.1934 0.0840 0.121 Uiso 1 1 calc R
H10B H -0.0086 0.2962 0.1713 0.121 Uiso 1 1 calc R
C11 C -0.10892(14) 0.1803(5) 0.0775(3) 0.1023(12) Uani 1 1 d .
H11A H -0.1189 0.1830 0.1235 0.123 Uiso 1 1 calc R
H11B H -0.1294 0.2971 0.0383 0.123 Uiso 1 1 calc R
C12 C -0.1422(2) 0.0000 0.0159(3) 0.0936(17) Uani 1 2 d S
H12 H -0.1324 0.0000 -0.0309 0.112 Uiso 1 2 calc SR
C13 C -0.2224(2) 0.0000 -0.0373(3) 0.1085(19) Uani 1 2 d S
H13A H -0.2329 -0.0160 0.0073 0.163 Uiso 0.50 1 calc PR
H13B H -0.2429 -0.1064 -0.0821 0.163 Uiso 0.50 1 calc PR
H13C H -0.2416 0.1225 -0.0704 0.163 Uiso 0.50 1 calc PR
C14 C 0.16269(14) 0.0000 0.57671(18) 0.0392(5) Uani 1 2 d S
C15 C 0.10287(15) 0.0000 0.5741(2) 0.0468(6) Uani 1 2 d S
H15 H 0.0586 0.0000 0.5156 0.056 Uiso 1 2 calc SR
C16 C 0.10763(16) 0.0000 0.6575(2) 0.0515(6) Uani 1 2 d S
H16 H 0.0665 0.0000 0.6532 0.062 Uiso 1 2 calc SR
C17 C 0.17172(17) 0.0000 0.7453(2) 0.0518(7) Uani 1 2 d S
H17 H 0.1738 0.0000 0.7998 0.062 Uiso 1 2 calc SR
C18 C 0.23451(16) 0.0000 0.75279(19) 0.0457(6) Uani 1 2 d S
C19 C 0.22985(14) 0.0000 0.66844(19) 0.0391(5) Uani 1 2 d S
C20 C 0.30236(18) 0.0000 0.8396(2) 0.0553(7) Uani 1 2 d S
H20 H 0.3075 0.0000 0.8964 0.066 Uiso 1 2 calc SR
C21 C 0.36011(18) 0.0000 0.8412(2) 0.0595(8) Uani 1 2 d S
H21 H 0.4050 0.0000 0.8989 0.071 Uiso 1 2 calc SR
C22 C 0.35212(15) 0.0000 0.7555(2) 0.0495(6) Uani 1 2 d S
H22 H 0.3922 0.0000 0.7573 0.059 Uiso 1 2 calc SR
C23 C 0.41804(16) 0.0000 0.6004(2) 0.0550(7) Uani 1 2 d S
C24 C 0.4899(2) 0.0000 0.6282(4) 0.0923(14) Uani 1 2 d S
H24A H 0.4909 -0.0696 0.5814 0.138 Uiso 0.50 1 calc PR
H24B H 0.5209 -0.0635 0.6887 0.138 Uiso 0.50 1 calc PR
H24C H 0.5052 0.1331 0.6326 0.138 Uiso 0.50 1 calc PR
N1 N 0.16649(11) 0.0000 0.50081(16) 0.0379(4) Uani 1 2 d S
N2 N 0.28902(12) 0.0000 0.67191(16) 0.0413(5) Uani 1 2 d S
N3 N 0.36171(13) 0.0000 0.57538(19) 0.0487(5) Uani 1 2 d S
O1 O 0.04877(11) 0.0000 0.37992(15) 0.0711(7) Uani 1 2 d S
O2 O 0.30449(11) 0.0000 0.38849(16) 0.0567(5) Uani 1 2 d S
Pd1 Pd 0.261543(9) 0.0000 0.534084(12) 0.03639(8) Uani 1 2 d S
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N1 123.9(2) . .
O1 C1 C2 125.0(2) . .
N1 C1 C2 111.1(2) . .
C7 C2 C3 122.2(2) . .
C7 C2 C1 114.3(2) . .
C3 C2 C1 123.5(2) . .
C4 C3 C2 116.8(3) . .
C4 C3 C9 118.9(3) . .
C2 C3 C9 124.3(2) . .
C5 C4 C3 122.4(3) . .
C5 C4 H4 118.8 . .
C3 C4 H4 118.8 . .
C6 C5 C4 120.6(3) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
O2 C6 C5 123.3(2) . .
O2 C6 C7 116.6(2) . .
C5 C6 C7 120.1(3) . .
C2 C7 C6 117.9(2) . .
C2 C7 Pd1 114.16(18) . .
C6 C7 Pd1 127.9(2) . .
O2 C8 H8A 109.5 . .
O2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C10 111.9(3) 6 .
C10 C9 C3 113.39(17) 6 .
C10 C9 C3 113.39(17) . .
C10 C9 H9 105.8 6 .
C10 C9 H9 105.8 . .
C3 C9 H9 105.8 . .
C9 C10 C11 111.7(3) . .
C9 C10 H10A 109.3 . .
C11 C10 H10A 109.3 . .
C9 C10 H10B 109.3 . .
C11 C10 H10B 109.3 . .
H10A C10 H10B 107.9 . .
C12 C11 C10 111.4(3) . .
C12 C11 H11A 109.4 . .
C10 C11 H11A 109.4 . .
C12 C11 H11B 109.4 . .
C10 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
C11 C12 C11 108.7(3) . 6
C11 C12 C13 111.2(2) . .
C11 C12 C13 111.2(2) 6 .
C11 C12 H12 108.5 . .
C11 C12 H12 108.5 6 .
C13 C12 H12 108.5 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 N1 128.2(2) . .
C15 C14 C19 117.3(2) . .
N1 C14 C19 114.5(2) . .
C14 C15 C16 121.6(3) . .
C14 C15 H15 119.2 . .
C16 C15 H15 119.2 . .
C17 C16 C15 121.3(3) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C16 C17 C18 119.9(3) . .
C16 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
C20 C18 C17 123.8(3) . .
C20 C18 C19 117.3(3) . .
C17 C18 C19 118.9(3) . .
N2 C19 C18 121.2(2) . .
N2 C19 C14 117.8(2) . .
C18 C19 C14 121.0(2) . .
C21 C20 C18 120.4(3) . .
C21 C20 H20 119.8 . .
C18 C20 H20 119.8 . .
C20 C21 C22 119.6(3) . .
C20 C21 H21 120.2 . .
C22 C21 H21 120.2 . .
N2 C22 C21 121.9(3) . .
N2 C22 H22 119.0 . .
C21 C22 H22 119.0 . .
N3 C23 C24 177.2(4) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C1 N1 C14 125.1(2) . .
C1 N1 Pd1 119.04(17) . .
C14 N1 Pd1 115.89(17) . .
C22 N2 C19 119.6(2) . .
C22 N2 Pd1 130.1(2) . .
C19 N2 Pd1 110.38(17) . .
C23 N3 Pd1 178.5(3) . .
C6 O2 C8 118.4(3) . .
N1 Pd1 C7 81.40(10) . .
N1 Pd1 N3 177.14(9) . .
C7 Pd1 N3 101.46(11) . .
N1 Pd1 N2 81.43(9) . .
C7 Pd1 N2 162.83(10) . .
N3 Pd1 N2 95.71(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.221(3) .
C1 N1 1.359(3) .
C1 C2 1.505(4) .
C2 C7 1.406(4) .
C2 C3 1.409(4) .
C3 C4 1.394(4) .
C3 C9 1.527(4) .
C4 C5 1.378(5) .
C4 H4 0.9300 .
C5 C6 1.375(4) .
C5 H5 0.9300 .
C6 O2 1.362(3) .
C6 C7 1.420(3) .
C7 Pd1 1.988(3) .
C8 O2 1.415(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C10 1.495(3) 6
C9 C10 1.495(3) .
C9 H9 0.9800 .
C10 C11 1.537(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.508(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C11 1.508(4) 6
C12 C13 1.532(5) .
C12 H12 0.9800 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.388(4) .
C14 N1 1.390(3) .
C14 C19 1.434(4) .
C15 C16 1.403(4) .
C15 H15 0.9300 .
C16 C17 1.370(5) .
C16 H16 0.9300 .
C17 C18 1.411(4) .
C17 H17 0.9300 .
C18 C20 1.405(4) .
C18 C19 1.420(4) .
C19 N2 1.365(3) .
C20 C21 1.350(5) .
C20 H20 0.9300 .
C21 C22 1.402(5) .
C21 H21 0.9300 .
C22 N2 1.327(4) .
C22 H22 0.9300 .
C23 N3 1.126(4) .
C23 C24 1.462(4) .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
N1 Pd1 1.956(2) .
N2 Pd1 2.100(2) .
N3 Pd1 2.021(2) .
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
O1 C1 C2 C7 180.0 . .
N1 C1 C2 C7 0.0 . .
O1 C1 C2 C3 0.0 . .
N1 C1 C2 C3 180.0 . .
C7 C2 C3 C4 0.0 . .
C1 C2 C3 C4 180.0 . .
C7 C2 C3 C9 180.0 . .
C1 C2 C3 C9 0.0 . .
C2 C3 C4 C5 0.0 . .
C9 C3 C4 C5 180.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 O2 180.0 . .
C4 C5 C6 C7 0.0 . .
C3 C2 C7 C6 0.0 . .
C1 C2 C7 C6 180.0 . .
C3 C2 C7 Pd1 180.0 . .
C1 C2 C7 Pd1 0.0 . .
O2 C6 C7 C2 180.0 . .
C5 C6 C7 C2 0.0 . .
O2 C6 C7 Pd1 0.0 . .
C5 C6 C7 Pd1 180.0 . .
C4 C3 C9 C10 64.5(2) . 6
C2 C3 C9 C10 -115.5(2) . 6
C4 C3 C9 C10 -64.5(2) . .
C2 C3 C9 C10 115.5(2) . .
C10 C9 C10 C11 52.7(5) 6 .
C3 C9 C10 C11 -177.5(3) . .
C9 C10 C11 C12 -56.1(4) . .
C10 C11 C12 C11 58.0(5) . 6
C10 C11 C12 C13 -179.2(3) . .
N1 C14 C15 C16 180.0 . .
C19 C14 C15 C16 0.0 . .
C14 C15 C16 C17 0.0 . .
C15 C16 C17 C18 0.000(1) . .
C16 C17 C18 C20 180.000(2) . .
C16 C17 C18 C19 0.0 . .
C20 C18 C19 N2 0.0 . .
C17 C18 C19 N2 180.0 . .
C20 C18 C19 C14 180.000(1) . .
C17 C18 C19 C14 0.000(1) . .
C15 C14 C19 N2 180.000(1) . .
N1 C14 C19 N2 0.0 . .
C15 C14 C19 C18 0.0 . .
N1 C14 C19 C18 180.000(1) . .
C17 C18 C20 C21 180.0 . .
C19 C18 C20 C21 0.000(2) . .
C18 C20 C21 C22 0.000(1) . .
C20 C21 C22 N2 0.000(1) . .
O1 C1 N1 C14 0.0 . .
C2 C1 N1 C14 180.0 . .
O1 C1 N1 Pd1 180.0 . .
C2 C1 N1 Pd1 0.0 . .
C15 C14 N1 C1 0.000(1) . .
C19 C14 N1 C1 180.000(1) . .
C15 C14 N1 Pd1 180.0 . .
C19 C14 N1 Pd1 0.0 . .
C21 C22 N2 C19 0.000(1) . .
C21 C22 N2 Pd1 180.0 . .
C18 C19 N2 C22 0.0 . .
C14 C19 N2 C22 180.000(1) . .
C18 C19 N2 Pd1 180.0 . .
C14 C19 N2 Pd1 0.0 . .
C24 C23 N3 Pd1 180.000(16) . .
C5 C6 O2 C8 0.0 . .
C7 C6 O2 C8 180.0 . .
C1 N1 Pd1 C7 0.0 . .
C14 N1 Pd1 C7 180.0 . .
C1 N1 Pd1 N3 180.000(5) . .
C14 N1 Pd1 N3 0.000(5) . .
C1 N1 Pd1 N2 180.0 . .
C14 N1 Pd1 N2 0.0 . .
C2 C7 Pd1 N1 0.0 . .
C6 C7 Pd1 N1 180.0 . .
C2 C7 Pd1 N3 180.0 . .
C6 C7 Pd1 N3 0.0 . .
C2 C7 Pd1 N2 0.0 . .
C6 C7 Pd1 N2 180.000(2) . .
C23 N3 Pd1 N1 0.00(2) . .
C23 N3 Pd1 C7 180.00(2) . .
C23 N3 Pd1 N2 0.00(2) . .
C22 N2 Pd1 N1 180.0 . .
C19 N2 Pd1 N1 0.0 . .
C22 N2 Pd1 C7 180.000(1) . .
C19 N2 Pd1 C7 0.0 . .
C22 N2 Pd1 N3 0.0 . .
C19 N2 Pd1 N3 180.0 . .
