#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:17:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178601 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/12/4071283.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_4071283
loop_
_publ_author_name
'Chitanda, Jackson M.'
'Prokopchuk, Demyan E.'
'Quail, J. Wilson'
'Foley, Stephen R.'
_publ_section_title
;
 From Pyrroles to Isoindolines: Synthesis of a γ-Diimine Ligand for
 Applications in Palladium Coordination Chemistry and Catalysis
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              2337
_journal_paper_doi               10.1021/om800080e
_journal_volume                  27
_journal_year                    2008
_chemical_formula_moiety         'C32 H41 N2, C H Cl3, Cl'
_chemical_formula_sum            'C33 H42 Cl4 N2'
_chemical_formula_weight         608.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/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                 106.04(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.983(2)
_cell_length_b                   14.196(3)
_cell_length_c                   11.017(2)
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      0.998
_cell_volume                     1650.8(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25584
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0637
_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)+(0.0696P)²+2.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                3188
_reflns_number_total             3926
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om800080e-file001.cif
_cod_data_source_block           306
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4071283
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
N1 N 0.8854(2) 0.2500 0.1617(2) 0.0129(5) Uani 1 2 d S
N2 N 0.7814(2) 0.2500 -0.0537(2) 0.0135(5) Uani 1 2 d S
H2 H 0.7073 0.2500 -0.0376 0.016 Uiso 1 2 calc SR
C1 C 0.8849(3) 0.2500 0.0394(2) 0.0110(5) Uani 1 2 d S
C2 C 1.0185(2) 0.2500 0.0348(2) 0.0117(5) Uani 1 2 d S
C3 C 1.0730(3) 0.2500 -0.0659(3) 0.0166(6) Uani 1 2 d S
H3 H 1.0218 0.2500 -0.1509 0.020 Uiso 1 2 calc SR
C4 C 1.2044(3) 0.2500 -0.0375(3) 0.0217(6) Uani 1 2 d S
H4 H 1.2434 0.2500 -0.1045 0.026 Uiso 1 2 calc SR
C5 C 1.2799(3) 0.2500 0.0865(3) 0.0246(7) Uani 1 2 d S
H5 H 1.3695 0.2500 0.1032 0.030 Uiso 1 2 calc SR
C6 C 1.2256(3) 0.2500 0.1867(3) 0.0223(6) Uani 1 2 d S
H6 H 1.2770 0.2500 0.2716 0.027 Uiso 1 2 calc SR
C7 C 1.0950(3) 0.2500 0.1592(3) 0.0157(6) Uani 1 2 d S
C8 C 1.0138(3) 0.2500 0.2485(3) 0.0175(6) Uani 1 2 d S
H8A H 1.0290 0.1931 0.3027 0.021 Uiso 0.50 1 calc PR
H8B H 1.0290 0.3069 0.3027 0.021 Uiso 0.50 1 calc PR
C9 C 0.7753(3) 0.2500 0.2089(3) 0.0171(6) Uani 1 2 d S
C10 C 0.7257(2) 0.16318(17) 0.2331(2) 0.0245(5) Uani 1 1 d .
C11 C 0.6247(2) 0.1657(2) 0.2874(2) 0.0358(6) Uani 1 1 d .
H11 H 0.5891 0.1083 0.3059 0.043 Uiso 1 1 calc R
C12 C 0.5761(3) 0.2500 0.3146(3) 0.0392(10) Uani 1 2 d S
H12 H 0.5082 0.2500 0.3525 0.047 Uiso 1 2 calc SR
C13 C 0.7796(3) 0.06989(18) 0.2066(3) 0.0358(6) Uani 1 1 d .
H13 H 0.8436 0.0833 0.1596 0.043 Uiso 1 1 calc R
C14 C 0.6771(4) 0.0071(3) 0.1225(4) 0.0670(11) Uani 1 1 d .
H14A H 0.6205 -0.0156 0.1710 0.100 Uiso 1 1 calc R
H14B H 0.7170 -0.0468 0.0931 0.100 Uiso 1 1 calc R
H14C H 0.6283 0.0434 0.0497 0.100 Uiso 1 1 calc R
C15 C 0.8487(4) 0.0204(2) 0.3308(3) 0.0573(9) Uani 1 1 d .
H15A H 0.9165 0.0613 0.3799 0.086 Uiso 1 1 calc R
H15B H 0.8853 -0.0389 0.3118 0.086 Uiso 1 1 calc R
H15C H 0.7885 0.0073 0.3797 0.086 Uiso 1 1 calc R
C16 C 0.7874(3) 0.2500 -0.1827(3) 0.0144(5) Uani 1 2 d S
C17 C 0.7920(2) 0.16342(16) -0.2419(2) 0.0215(5) Uani 1 1 d .
C18 C 0.8092(2) 0.1656(2) -0.3629(2) 0.0324(6) Uani 1 1 d .
H18 H 0.8137 0.1081 -0.4056 0.039 Uiso 1 1 calc R
C19 C 0.8197(4) 0.2500 -0.4214(3) 0.0368(9) Uani 1 2 d S
H19 H 0.8342 0.2500 -0.5025 0.044 Uiso 1 2 calc SR
C20 C 0.7799(3) 0.07065(16) -0.1784(3) 0.0318(6) Uani 1 1 d .
H20 H 0.7793 0.0850 -0.0897 0.038 Uiso 1 1 calc R
C21 C 0.8917(4) 0.0055(2) -0.1719(5) 0.0713(12) Uani 1 1 d .
H21A H 0.8863 -0.0495 -0.1198 0.107 Uiso 1 1 calc R
H21B H 0.9709 0.0393 -0.1343 0.107 Uiso 1 1 calc R
H21C H 0.8897 -0.0152 -0.2572 0.107 Uiso 1 1 calc R
C22 C 0.6565(3) 0.0220(2) -0.2422(4) 0.0598(10) Uani 1 1 d .
H22A H 0.5856 0.0640 -0.2425 0.090 Uiso 1 1 calc R
H22B H 0.6492 -0.0358 -0.1961 0.090 Uiso 1 1 calc R
H22C H 0.6545 0.0062 -0.3293 0.090 Uiso 1 1 calc R
Cl1 Cl 0.50440(9) 0.2500 0.90776(10) 0.0576(4) Uani 1 2 d S
Cl2 Cl 0.17082(12) 0.2500 0.60628(11) 0.0538(3) Uani 1 2 d S
Cl3 Cl 0.36507(12) 0.14814(7) 0.53022(10) 0.0712(4) Uani 1 1 d .
C23 C 0.3314(5) 0.2500 0.6076(4) 0.0485(11) Uani 1 2 d S
H23 H 0.3854 0.2500 0.6970 0.058 Uiso 1 2 calc SR
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'
Cl Cl 0.1484 0.1585 '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'
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 N1 C9 126.1(2) . .
C1 N1 C8 112.9(2) . .
C9 N1 C8 121.0(2) . .
C1 N2 C16 120.6(2) . .
C1 N2 H2 119.7 . .
C16 N2 H2 119.7 . .
N2 C1 N1 123.3(2) . .
N2 C1 C2 129.0(2) . .
N1 C1 C2 107.7(2) . .
C7 C2 C3 120.4(2) . .
C7 C2 C1 107.4(2) . .
C3 C2 C1 132.2(2) . .
C4 C3 C2 117.9(3) . .
C4 C3 H3 121.1 . .
C2 C3 H3 121.1 . .
C5 C4 C3 121.5(3) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 120.7(3) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C7 C6 C5 118.2(3) . .
C7 C6 H6 120.9 . .
C5 C6 H6 120.9 . .
C6 C7 C2 121.4(3) . .
C6 C7 C8 128.8(3) . .
C2 C7 C8 109.8(2) . .
N1 C8 C7 102.2(2) . .
N1 C8 H8A 111.3 . .
C7 C8 H8A 111.3 . .
N1 C8 H8B 111.3 . .
C7 C8 H8B 111.3 . .
H8A C8 H8B 109.2 . .
C10 C9 C10 123.0(3) 4_565 .
C10 C9 N1 118.48(13) 4_565 .
C10 C9 N1 118.48(13) . .
C11 C10 C9 117.0(2) . .
C11 C10 C13 120.3(2) . .
C9 C10 C13 122.68(19) . .
C12 C11 C10 121.1(3) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C11 120.8(3) 4_565 .
C11 C12 H12 119.6 4_565 .
C11 C12 H12 119.6 . .
C10 C13 C14 111.4(3) . .
C10 C13 C15 110.6(2) . .
C14 C13 C15 111.8(3) . .
C10 C13 H13 107.6 . .
C14 C13 H13 107.6 . .
C15 C13 H13 107.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 C17 123.0(3) 4_565 .
C17 C16 N2 118.49(13) 4_565 .
C17 C16 N2 118.49(13) . .
C18 C17 C16 117.2(2) . .
C18 C17 C20 120.8(2) . .
C16 C17 C20 122.0(2) . .
C19 C18 C17 121.0(2) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C18 C19 C18 120.5(3) 4_565 .
C18 C19 H19 119.8 4_565 .
C18 C19 H19 119.8 . .
C22 C20 C17 111.4(2) . .
C22 C20 C21 110.7(3) . .
C17 C20 C21 112.2(2) . .
C22 C20 H20 107.4 . .
C17 C20 H20 107.4 . .
C21 C20 H20 107.4 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
Cl2 C23 Cl3 109.80(19) . 4_565
Cl2 C23 Cl3 109.80(19) . .
Cl3 C23 Cl3 109.7(2) 4_565 .
Cl2 C23 H23 109.2 . .
Cl3 C23 H23 109.2 4_565 .
Cl3 C23 H23 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.345(3) .
N1 C9 1.442(3) .
N1 C8 1.469(4) .
N2 C1 1.304(4) .
N2 C16 1.441(3) .
N2 H2 0.8800 .
C1 C2 1.482(4) .
C2 C7 1.396(4) .
C2 C3 1.399(4) .
C3 C4 1.389(4) .
C3 H3 0.9500 .
C4 C5 1.389(5) .
C4 H4 0.9500 .
C5 C6 1.391(4) .
C5 H5 0.9500 .
C6 C7 1.382(4) .
C6 H6 0.9500 .
C7 C8 1.499(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.402(3) 4_565
C9 C10 1.402(3) .
C10 C11 1.399(3) .
C10 C13 1.512(4) .
C11 C12 1.376(3) .
C11 H11 0.9500 .
C12 C11 1.376(3) 4_565
C12 H12 0.9500 .
C13 C14 1.531(4) .
C13 C15 1.539(4) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.399(2) 4_565
C16 C17 1.399(2) .
C17 C18 1.398(3) .
C17 C20 1.514(3) .
C18 C19 1.380(3) .
C18 H18 0.9500 .
C19 C18 1.380(3) 4_565
C19 H19 0.9500 .
C20 C22 1.511(4) .
C20 C21 1.522(4) .
C20 H20 1.0000 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
Cl2 C23 1.760(5) .
Cl3 C23 1.769(3) .
C23 Cl3 1.769(3) 4_565
C23 H23 1.0000 .
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
C23 H23 Cl1 1.00 2.33 3.328(5) 177.9 .
C20 H20 N2 1.00 2.38 2.891(3) 111.2 .
C13 H13 N1 1.00 2.41 2.907(3) 109.9 .
N2 H2 Cl1 0.88 2.14 2.954(3) 153.2 1_554
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
C16 N2 C1 N1 180.0 . .
C16 N2 C1 C2 0.0 . .
C9 N1 C1 N2 0.0 . .
C8 N1 C1 N2 180.0 . .
C9 N1 C1 C2 180.0 . .
C8 N1 C1 C2 0.0 . .
N2 C1 C2 C7 180.0 . .
N1 C1 C2 C7 0.0 . .
N2 C1 C2 C3 0.0 . .
N1 C1 C2 C3 180.0 . .
C7 C2 C3 C4 0.0 . .
C1 C2 C3 C4 180.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C7 0.0 . .
C5 C6 C7 C2 0.0 . .
C5 C6 C7 C8 180.0 . .
C3 C2 C7 C6 0.0 . .
C1 C2 C7 C6 180.0 . .
C3 C2 C7 C8 180.0 . .
C1 C2 C7 C8 0.0 . .
C1 N1 C8 C7 0.0 . .
C9 N1 C8 C7 180.0 . .
C6 C7 C8 N1 180.0 . .
C2 C7 C8 N1 0.0 . .
C1 N1 C9 C10 -91.2(2) . 4_565
C8 N1 C9 C10 88.8(2) . 4_565
C1 N1 C9 C10 91.2(2) . .
C8 N1 C9 C10 -88.8(2) . .
C10 C9 C10 C11 -2.0(4) 4_565 .
N1 C9 C10 C11 175.5(2) . .
C10 C9 C10 C13 179.91(19) 4_565 .
N1 C9 C10 C13 -2.6(4) . .
C9 C10 C11 C12 0.5(4) . .
C13 C10 C11 C12 178.7(3) . .
C10 C11 C12 C11 0.8(5) . 4_565
C11 C10 C13 C14 56.1(3) . .
C9 C10 C13 C14 -125.8(3) . .
C11 C10 C13 C15 -68.9(3) . .
C9 C10 C13 C15 109.2(3) . .
C1 N2 C16 C17 -89.1(2) . 4_565
C1 N2 C16 C17 89.1(2) . .
C17 C16 C17 C18 3.7(4) 4_565 .
N2 C16 C17 C18 -174.4(2) . .
C17 C16 C17 C20 -176.69(18) 4_565 .
N2 C16 C17 C20 5.2(4) . .
C16 C17 C18 C19 -0.7(4) . .
C20 C17 C18 C19 179.7(3) . .
C17 C18 C19 C18 -2.1(5) . 4_565
C18 C17 C20 C22 -69.5(3) . .
C16 C17 C20 C22 110.9(3) . .
C18 C17 C20 C21 55.2(4) . .
C16 C17 C20 C21 -124.4(3) . .
