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#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/54/4075426.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.
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data_4075426
loop_
_publ_author_name
'Doherty, Simon'
'Knight, Julian G.'
'Smyth, Catherine H.'
'Sore, Nicholas T.'
'Rath, Rakesh K.'
'McFarlane, William'
'Harrington, Ross W.'
'Clegg, William'
_publ_section_title
;
 Modular Synthesis of a New Class of Bis(amino-oxazoline) Using
 Palladium-Catalyzed Buchwald−Hartwig Amination Methodology
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4341
_journal_paper_doi               10.1021/om0602714
_journal_volume                  25
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C36 H38 N4 O2'
_chemical_formula_sum            'C36 H38 N4 O2'
_chemical_formula_weight         558.70
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.120(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.5149(16)
_cell_length_b                   9.3288(7)
_cell_length_c                   10.5748(10)
_cell_measurement_reflns_used    108
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1539.3(2)
_computing_cell_refinement       EvalCCD
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14339
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.132(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         1662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0552
_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)+(0.0852P)²+0.2937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                1495
_reflns_number_total             1662
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om0602714si20060328_094232.cif
_cod_data_source_block           sd188_compound6a
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4075426
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'
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
O O 0.59274(16) 0.8835(4) 0.6377(3) 0.0757(9) Uani 1 1 d .
N1 N 0.45131(15) 0.6500(3) 0.8368(2) 0.0414(6) Uani 1 1 d .
N2 N 0.57277(15) 0.6661(3) 0.7177(2) 0.0484(6) Uani 1 1 d .
C1 C 0.40541(16) 0.5559(3) 0.8920(2) 0.0362(6) Uani 1 1 d .
H1 H 0.495(2) 0.616(4) 0.809(3) 0.048(8) Uiso 1 1 d .
C2 C 0.45203(14) 0.4479(3) 0.9796(2) 0.0349(6) Uani 1 1 d .
C3 C 0.40708(16) 0.3465(3) 1.0279(3) 0.0425(6) Uani 1 1 d .
H3 H 0.4378 0.2723 1.0853 0.051 Uiso 1 1 calc R
C4 C 0.31798(18) 0.3520(3) 0.9935(3) 0.0492(7) Uani 1 1 d .
H4 H 0.2885 0.2826 1.0278 0.059 Uiso 1 1 calc R
C5 C 0.27306(16) 0.4590(3) 0.9094(3) 0.0451(7) Uani 1 1 d .
H5 H 0.2125 0.4642 0.8871 0.054 Uiso 1 1 calc R
C6 C 0.31574(16) 0.5593(3) 0.8570(3) 0.0426(6) Uani 1 1 d .
H6 H 0.2840 0.6307 0.7971 0.051 Uiso 1 1 calc R
C7 C 0.43997(15) 0.7963(3) 0.8185(2) 0.0371(6) Uani 1 1 d .
C8 C 0.38560(17) 0.8745(3) 0.8724(3) 0.0447(7) Uani 1 1 d .
H8 H 0.3560 0.8258 0.9230 0.054 Uiso 1 1 calc R
C9 C 0.3748(2) 1.0200(3) 0.8526(4) 0.0564(8) Uani 1 1 d .
H9 H 0.3385 1.0706 0.8905 0.068 Uiso 1 1 calc R
C10 C 0.4162(2) 1.0929(4) 0.7784(4) 0.0673(10) Uani 1 1 d .
H10 H 0.4063 1.1925 0.7618 0.081 Uiso 1 1 calc R
C11 C 0.4728(2) 1.0199(4) 0.7277(3) 0.0608(9) Uani 1 1 d .
H11 H 0.5023 1.0713 0.6785 0.073 Uiso 1 1 calc R
C12 C 0.48685(17) 0.8717(3) 0.7481(2) 0.0427(7) Uani 1 1 d .
C13 C 0.55086(17) 0.7989(4) 0.7010(2) 0.0471(8) Uani 1 1 d .
C14 C 0.6499(2) 0.7896(6) 0.5989(3) 0.0817(15) Uani 1 1 d .
H14A H 0.7095 0.8253 0.6342 0.098 Uiso 1 1 calc R
H14B H 0.6329 0.7833 0.5001 0.098 Uiso 1 1 calc R
C15 C 0.64233(17) 0.6419(5) 0.6591(3) 0.0628(11) Uani 1 1 d .
H15 H 0.6969 0.6210 0.7331 0.075 Uiso 1 1 calc R
C16 C 0.6222(2) 0.5163(6) 0.5603(3) 0.0756(14) Uani 1 1 d .
H16 H 0.5682 0.5396 0.4861 0.091 Uiso 1 1 calc R
C17 C 0.6076(3) 0.3772(6) 0.6253(4) 0.0910(16) Uani 1 1 d .
H17A H 0.6586 0.3551 0.7019 0.136 Uiso 1 1 calc R
H17B H 0.5970 0.2991 0.5599 0.136 Uiso 1 1 calc R
H17C H 0.5580 0.3881 0.6558 0.136 Uiso 1 1 calc R
C18 C 0.6949(2) 0.5002(10) 0.4991(4) 0.126(3) Uani 1 1 d .
H18A H 0.6777 0.4306 0.4256 0.189 Uiso 1 1 calc R
H18B H 0.7471 0.4666 0.5680 0.189 Uiso 1 1 calc R
H18C H 0.7060 0.5931 0.4648 0.189 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C13 O C14 105.8(3) . .
C1 N1 H1 120(2) . .
C1 N1 C7 127.4(2) . .
H1 N1 C7 112(2) . .
C13 N2 C15 108.0(3) . .
N1 C1 C2 117.7(2) . .
N1 C1 C6 122.9(2) . .
C2 C1 C6 119.3(2) . .
C1 C2 C2 119.03(18) . 2_657
C1 C2 C3 118.8(2) . .
C2 C2 C3 122.2(2) 2_657 .
C2 C3 H3 119.3 . .
C2 C3 C4 121.4(3) . .
H3 C3 C4 119.3 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.5(3) . .
H4 C4 C5 120.3 . .
C4 C5 H5 119.7 . .
C4 C5 C6 120.5(2) . .
H5 C5 C6 119.7 . .
C1 C6 C5 120.5(2) . .
C1 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
N1 C7 C8 121.8(3) . .
N1 C7 C12 119.3(2) . .
C8 C7 C12 118.8(2) . .
C7 C8 H8 119.5 . .
C7 C8 C9 121.0(3) . .
H8 C8 C9 119.5 . .
C8 C9 H9 119.7 . .
C8 C9 C10 120.7(3) . .
H9 C9 C10 119.7 . .
C9 C10 H10 120.1 . .
C9 C10 C11 119.8(3) . .
H10 C10 C11 120.1 . .
C10 C11 H11 119.4 . .
C10 C11 C12 121.1(3) . .
H11 C11 C12 119.4 . .
C7 C12 C11 118.4(3) . .
C7 C12 C13 121.5(2) . .
C11 C12 C13 120.1(3) . .
O C13 N2 117.4(3) . .
O C13 C12 115.8(3) . .
N2 C13 C12 126.7(2) . .
O C14 H14A 110.5 . .
O C14 H14B 110.5 . .
O C14 C15 106.1(2) . .
H14A C14 H14B 108.7 . .
H14A C14 C15 110.5 . .
H14B C14 C15 110.5 . .
N2 C15 C14 102.4(3) . .
N2 C15 H15 108.9 . .
N2 C15 C16 112.0(3) . .
C14 C15 H15 108.9 . .
C14 C15 C16 115.5(3) . .
H15 C15 C16 108.9 . .
C15 C16 H16 107.9 . .
C15 C16 C17 112.0(3) . .
C15 C16 C18 109.6(4) . .
H16 C16 C17 107.9 . .
H16 C16 C18 107.9 . .
C17 C16 C18 111.4(5) . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O C13 1.361(3) .
O C14 1.443(6) .
N1 C1 1.405(3) .
N1 H1 0.92(4) .
N1 C7 1.383(3) .
N2 C13 1.287(4) .
N2 C15 1.490(3) .
C1 C2 1.415(4) .
C1 C6 1.404(3) .
C2 C2 1.500(4) 2_657
C2 C3 1.398(3) .
C3 H3 0.950 .
C3 C4 1.396(4) .
C4 H4 0.950 .
C4 C5 1.380(5) .
C5 H5 0.950 .
C5 C6 1.391(4) .
C6 H6 0.950 .
C7 C8 1.414(4) .
C7 C12 1.424(4) .
C8 H8 0.950 .
C8 C9 1.376(4) .
C9 H9 0.950 .
C9 C10 1.377(6) .
C10 H10 0.950 .
C10 C11 1.398(6) .
C11 H11 0.950 .
C11 C12 1.407(5) .
C12 C13 1.473(4) .
C14 H14A 0.990 .
C14 H14B 0.990 .
C14 C15 1.540(6) .
C15 H15 1.000 .
C15 C16 1.532(6) .
C16 H16 1.000 .
C16 C17 1.523(7) .
C16 C18 1.547(4) .
C17 H17A 0.980 .
C17 H17B 0.980 .
C17 H17C 0.980 .
C18 H18A 0.980 .
C18 H18B 0.980 .
C18 H18C 0.980 .
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
N1 H1 N2 0.92(4) 1.90(4) 2.700(3) 144(3)
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
C7 N1 C1 C2 -139.2(3) . .
C7 N1 C1 C6 45.0(4) . .
N1 C1 C2 C2 6.2(3) . 2_657
N1 C1 C2 C3 -175.3(2) . .
C6 C1 C2 C2 -177.9(2) . 2_657
C6 C1 C2 C3 0.6(3) . .
C1 C2 C3 C4 -1.3(4) . .
C2 C2 C3 C4 177.1(3) 2_657 .
C2 C3 C4 C5 0.5(4) . .
C3 C4 C5 C6 1.2(4) . .
C4 C5 C6 C1 -1.9(4) . .
N1 C1 C6 C5 176.6(2) . .
C2 C1 C6 C5 1.0(4) . .
C1 N1 C7 C8 9.0(4) . .
C1 N1 C7 C12 -173.6(2) . .
N1 C7 C8 C9 -179.7(3) . .
C12 C7 C8 C9 2.9(4) . .
C7 C8 C9 C10 0.7(4) . .
C8 C9 C10 C11 -2.9(5) . .
C9 C10 C11 C12 1.6(5) . .
C10 C11 C12 C7 1.9(4) . .
C10 C11 C12 C13 -176.1(3) . .
N1 C7 C12 C11 178.5(3) . .
N1 C7 C12 C13 -3.6(3) . .
C8 C7 C12 C11 -4.0(3) . .
C8 C7 C12 C13 173.9(2) . .
C15 N2 C13 O 0.0(3) . .
C15 N2 C13 C12 -177.4(2) . .
C14 O C13 N2 3.5(3) . .
C14 O C13 C12 -178.8(2) . .
C7 C12 C13 O -178.5(2) . .
C7 C12 C13 N2 -1.1(4) . .
C11 C12 C13 O -0.6(3) . .
C11 C12 C13 N2 176.8(3) . .
C13 O C14 C15 -5.2(3) . .
C13 N2 C15 C14 -3.3(3) . .
C13 N2 C15 C16 -127.6(3) . .
O C14 C15 N2 5.1(3) . .
O C14 C15 C16 127.1(3) . .
N2 C15 C16 C17 -58.0(4) . .
N2 C15 C16 C18 177.9(4) . .
C14 C15 C16 C17 -174.6(3) . .
C14 C15 C16 C18 61.2(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101406556
